Molecules

7177 KiB

Open AccessArticle

Efficient Approach to Carbinol Derivatives through Palladium-Catalyzed Base-Free Addition of Aryltriolborates to Aldehydes

by Kun Hu, Pengqing Ye, Qianqian Zhen, Xinrong Yao, Tong Xu, Yinlin Shao and Jiuxi Chen

Molecules 2017, 22(9), 1580; https://doi.org/10.3390/molecules22091580 - 20 Sep 2017

Cited by 7 | Viewed by 4477

Abstract

Palladium-catalyzed base-free addition of aryltriolborates to aldehydes has been developed, leading to a wide range of carbinol derivatives in good to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The present synthetic route [...] Read more.

Palladium-catalyzed base-free addition of aryltriolborates to aldehydes has been developed, leading to a wide range of carbinol derivatives in good to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The present synthetic route to carbinol derivatives could be readily scaled up to gram quantity without difficulty. Thus, this method represents a simple and practical procedure to access carbinol derivatives. Full article

(This article belongs to the Section Organic Chemistry)

► Show Figures

Graphical abstract

4414 KiB

Open AccessArticle

The Effect of Copper Addition on the Activity and Stability of Iron-Based CO₂ Hydrogenation Catalysts

by Matthew J. Bradley, Ramagopal Ananth, Heather D. Willauer, Jeffrey W. Baldwin, Dennis R. Hardy and Frederick W. Williams

Molecules 2017, 22(9), 1579; https://doi.org/10.3390/molecules22091579 - 20 Sep 2017

Cited by 25 | Viewed by 5903

Abstract

Iron-based CO₂ catalysts have shown promise as a viable route to the production of olefins from CO₂ and H₂ gas. However, these catalysts can suffer from low conversion and high methane selectivity, as well as being particularly vulnerable to water [...] Read more.

Iron-based CO₂ catalysts have shown promise as a viable route to the production of olefins from CO₂ and H₂ gas. However, these catalysts can suffer from low conversion and high methane selectivity, as well as being particularly vulnerable to water produced during the reaction. In an effort to improve both the activity and durability of iron-based catalysts on an alumina support, copper (10–30%) has been added to the catalyst matrix. In this paper, the effects of copper addition on the catalyst activity and morphology are examined. The addition of 10% copper significantly increases the CO₂ conversion, and decreases methane and carbon monoxide selectivity, without significantly altering the crystallinity and structure of the catalyst itself. The FeCu/K catalysts form an inverse spinel crystal phase that is independent of copper content and a metallic phase that increases in abundance with copper loading (>10% Cu). At higher loadings, copper separates from the iron oxide phase and produces metallic copper as shown by SEM-EDS. An addition of copper appears to increase the rate of the Fischer–Tropsch reaction step, as shown by modeling of the chemical kinetics and the inter- and intra-particle transport of mass and energy. Full article

(This article belongs to the Special Issue Hydrofunctionalization and Hydrogenation with Earth Abundant Metals)

► Show Figures

Graphical abstract

4578 KiB

Open AccessFeature PaperArticle

Cytotoxic and Apoptotic Activities of Prunus spinosa Trigno Ecotype Extract on Human Cancer Cells

by Stefania Meschini, Evelin Pellegrini, Maria Condello, Giovanni Occhionero, Sebastiano Delfine, Giancarlo Condello and Franco Mastrodonato

Molecules 2017, 22(9), 1578; https://doi.org/10.3390/molecules22091578 - 20 Sep 2017

Cited by 23 | Viewed by 7098

Abstract

The aim of this work was to demonstrate that a natural compound, not-toxic to normal cells, has cytotoxic and sensitizing effects on carcinoma cells, with the final goal of combining it with chemotherapeutic drugs to reduce the overall dose. Prunus spinosa Trigno ecotype [...] Read more.

The aim of this work was to demonstrate that a natural compound, not-toxic to normal cells, has cytotoxic and sensitizing effects on carcinoma cells, with the final goal of combining it with chemotherapeutic drugs to reduce the overall dose. Prunus spinosa Trigno ecotype (PsT) drupe extract with a nutraceutical activator complex (NAC) made of amino acids, vitamins and mineral salt blends, has shown in vitro anticancer activity. The cytotoxic effect of (PsT + NAC)^® has been evaluated on human cancer cells, with an initial screening with colorectal, uterine cervical, and bronchoalveolar cells, and a subsequent focus on colon carcinoma cells HCT116 and SW480. The viability reduction of HCT116 and SW480 after treatment with (PsT 10 mg/mL + NAC)^® was about 40% (p < 0.05), compared to control cells. The cell’s survival reduction was ineffective when the drug vehicle (NAC) was replaced with a phosphate buffer saline (PBS) or physiological solution (PS). The flow cytometry evaluation of cancer cells’ mitochondrial membrane potential showed an increase of 20% depolarized mitochondria. Cell cycle analysis showed a sub G1 (Gap 1 phase) peak appearance (HCT116: 35.1%; SW480: 11.6%), indicating apoptotic cell death induction that was confirmed by Annexin V assay (HCT116: 86%; SW480: 96%). Normal cells were not altered by (PsT + NAC)^® treatments. Full article

(This article belongs to the Collection Natural Products: Anticancer Potential and Beyond)

► Show Figures

Graphical abstract

121 KiB

Open AccessEditorial

Molecules New Aims and Scope

by Derek J. McPhee

Molecules 2017, 22(9), 1510; https://doi.org/10.3390/molecules22091510 - 20 Sep 2017

Viewed by 4299

Abstract

As we approach the end of our 22nd year as the pioneering and preeminent Open Access journal in the field of organic chemistry and natural products, time has come to formally announce what has been the de facto reality of the journal for [...] Read more.

As we approach the end of our 22nd year as the pioneering and preeminent Open Access journal in the field of organic chemistry and natural products, time has come to formally announce what has been the de facto reality of the journal for the past few years, the expansion of the range of topics we cover.[...] Full article

2935 KiB

Open AccessArticle

Improving the Efficiency of New Automatic Dishwashing Detergent Formulation by Addition of Thermostable Lipase, Protease and Amylase

by Ashwini Naganthran, Malihe Masomian, Raja Noor Zaliha Raja Abd. Rahman, Mohd Shukuri Mohamad Ali and Hisham Mohd Nooh

Molecules 2017, 22(9), 1577; https://doi.org/10.3390/molecules22091577 - 19 Sep 2017

Cited by 40 | Viewed by 10730

Abstract

The use of T1 lipase in automatic dishwashing detergent (ADD) is well established, but efficiency in hard water is very low. A new enzymatic environmentally-friendly dishwashing was formulated to be efficient in both soft and hard water. Thermostable enzymes such as T1 lipase [...] Read more.

The use of T1 lipase in automatic dishwashing detergent (ADD) is well established, but efficiency in hard water is very low. A new enzymatic environmentally-friendly dishwashing was formulated to be efficient in both soft and hard water. Thermostable enzymes such as T1 lipase from Geobacillus strain T1, Rand protease from Bacillus subtilis strain Rand, and Maltogenic amylase from Geobacillus sp. SK70 were produced and evaluated for an automatic dishwashing detergent formulation. The components of the new ADD were optimized for compatibility with these three enzymes. In compatibility tests of the enzymes with different components, several criteria were considered. The enzymes were mostly stable in non-ionic surfactants, especially polyhydric alcohols, Glucopon UP 600, and in a mixture of sodium carbonate and glycine (30:70) buffer at a pH of 9.25. Sodium polyacrylate and sodium citrate were used in the ADD formulation as a dispersing agent and a builder, respectively. Dishwashing performance of the formulated ADDs was evaluated in terms of percent of soil removed using the Leenert‘s Improved Detergency Tester. The results showed that the combination of different hydrolysis enzymes could improve the washing efficiency of formulated ADD compared to the commercial ADD “Finish” at 40 and 50 C. Full article

(This article belongs to the Special Issue Lipases and Lipases Modification)

► Show Figures

Figure 1

2698 KiB

Open AccessArticle

Quantitative Structure–Activity Relationship Modeling of Kinase Selectivity Profiles

by Sandeepkumar Kothiwale, Corina Borza, Ambra Pozzi and Jens Meiler

Molecules 2017, 22(9), 1576; https://doi.org/10.3390/molecules22091576 - 19 Sep 2017

Cited by 10 | Viewed by 5661

Abstract

The discovery of selective inhibitors of biological target proteins is the primary goal of many drug discovery campaigns. However, this goal has proven elusive, especially for inhibitors targeting the well-conserved orthosteric adenosine triphosphate (ATP) binding pocket of kinase enzymes. The human kinome is [...] Read more.

The discovery of selective inhibitors of biological target proteins is the primary goal of many drug discovery campaigns. However, this goal has proven elusive, especially for inhibitors targeting the well-conserved orthosteric adenosine triphosphate (ATP) binding pocket of kinase enzymes. The human kinome is large and it is rather difficult to profile early lead compounds against around 500 targets to gain an upfront knowledge on selectivity. Further, selectivity can change drastically during derivatization of an initial lead compound. Here, we have introduced a computational model to support the profiling of compounds early in the drug discovery pipeline. On the basis of the extensive profiled activity of 70 kinase inhibitors against 379 kinases, including 81 tyrosine kinases, we developed a quantitative structure–activity relation (QSAR) model using artificial neural networks, to predict the activity of these kinase inhibitors against the panel of 379 kinases. The model’s performance in predicting activity ranges from 0.6 to 0.8 depending on the kinase, from the area under the curve (AUC) of the receiver operating characteristics (ROC). The profiler is available online at http://www.meilerlab.org/index.php/servers/show?s_id=23. Full article

► Show Figures

Figure 1

1461 KiB

Open AccessFeature PaperPerspective

Covalent Organic Frameworks—Organic Chemistry Beyond the Molecule

by Christian S. Diercks, Markus J. Kalmutzki and Omar M. Yaghi

Molecules 2017, 22(9), 1575; https://doi.org/10.3390/molecules22091575 - 19 Sep 2017

Cited by 35 | Viewed by 10292

Abstract

The synthesis of organic molecules has at its core, purity, definitiveness of structure, and the ability to access specific atoms through chemical reactions. When considering extended organic structures, covalent organic frameworks (COFs) stand out as a true extension of molecular organic chemistry to [...] Read more.

The synthesis of organic molecules has at its core, purity, definitiveness of structure, and the ability to access specific atoms through chemical reactions. When considering extended organic structures, covalent organic frameworks (COFs) stand out as a true extension of molecular organic chemistry to the solid state, because these three fundamental attributes of molecular organic chemistry are preserved. The fact that COFs are porous provides confined space within which molecules can be further modified and controlled. Full article

(This article belongs to the Special Issue Covalent Organic Frameworks and Related Porous Organic Materials)

► Show Figures

Figure 1

1033 KiB

Open AccessArticle

Sulfadiazine Salicylaldehyde-Based Schiff Bases: Synthesis, Antimicrobial Activity and Cytotoxicity

by Martin Krátký, Magdaléna Dzurková, Jiří Janoušek, Klára Konečná, František Trejtnar, Jiřina Stolaříková and Jarmila Vinšová

Molecules 2017, 22(9), 1573; https://doi.org/10.3390/molecules22091573 - 19 Sep 2017

Cited by 76 | Viewed by 10737

Abstract

The resistance among microbes has brought an urgent need for new drugs. Thus, we synthesized a series of Schiff bases derived from the sulfa drug sulfadiazine and various salicylaldehydes. The resulting 4-[(2-hydroxybenzylidene)amino]-N-(pyrimidin-2-yl)benzene-sulfonamides were characterized and evaluated against Gram-positive and Gram-negative bacteria, [...] Read more.

The resistance among microbes has brought an urgent need for new drugs. Thus, we synthesized a series of Schiff bases derived from the sulfa drug sulfadiazine and various salicylaldehydes. The resulting 4-[(2-hydroxybenzylidene)amino]-N-(pyrimidin-2-yl)benzene-sulfonamides were characterized and evaluated against Gram-positive and Gram-negative bacteria, yeasts, moulds, Mycobacterium tuberculosis, nontuberculous mycobacteria (M. kansasii, M. avium) and their cytotoxicity was determined. Among bacteria, the genus Staphylococcus, including methicillin-resistant S. aureus, showed the highest susceptibility, with minimum inhibitory concentration values from 7.81 µM. The growth of Candida sp. and Trichophyton interdigitale was inhibited at concentrations starting from 1.95 µM. 4-[(2,5-Dihydroxybenzylidene)amino]-N-(pyrimidin-2-yl)-benzenesulfonamide was identified as the most selective Schiff base for these strains with no apparent cytotoxicity and a selectivity index higher than 16. With respect to M. tuberculosis and M. kansasii that were inhibited within the range of 8 to 250 µM, unsubstituted 4-[(2-hydroxy-benzylidene)amino]-N-(pyrimidin-2-yl)benzenesulfonamide meets the selectivity requirement. In general, dihalogenation of the salicylic moiety improved the antibacterial and antifungal activity but also increased the cytotoxicity, especially with an increasing atomic mass. Some derivatives offer more advantageous properties than the parent sulfadiazine, thus constituting promising hits for further antimicrobial drug development. Full article

(This article belongs to the Special Issue Medicinal Chemistry in Europe)

► Show Figures

Graphical abstract

2828 KiB

Open AccessFeature PaperArticle

Studying the Structural Significance of Galectin Design by Playing a Modular Puzzle: Homodimer Generation from Human Tandem-Repeat-Type (Heterodimeric) Galectin-8 by Domain Shuffling

by Anna-Kristin Ludwig, Malwina Michalak, Nadya Shilova, Sabine André, Herbert Kaltner, Nicolai V. Bovin, Jürgen Kopitz and Hans-Joachim Gabius

Molecules 2017, 22(9), 1572; https://doi.org/10.3390/molecules22091572 - 19 Sep 2017

Cited by 13 | Viewed by 4954

Abstract

Tissue lectins are emerging (patho)physiological effectors with broad significance. The capacity of adhesion/growth-regulatory galectins to form functional complexes with distinct cellular glycoconjugates is based on molecular selection of matching partners. Engineering of variants by changing the topological display of carbohydrate recognition domains (CRDs) [...] Read more.

Tissue lectins are emerging (patho)physiological effectors with broad significance. The capacity of adhesion/growth-regulatory galectins to form functional complexes with distinct cellular glycoconjugates is based on molecular selection of matching partners. Engineering of variants by changing the topological display of carbohydrate recognition domains (CRDs) provides tools to understand the inherent specificity of the functional pairing. We here illustrate its practical implementation in the case of human tandem-repeat-type galectin-8 (Gal-8). It is termed Gal-8 (NC) due to presence of two different CRDs at the N- and C-terminal positions. Gal-8N exhibits exceptionally high affinity for 3′-sialylated/sulfated β-galactosides. This protein is turned into a new homodimer, i.e., Gal-8 (NN), by engineering. The product maintained activity for lactose-inhibitable binding of glycans and glycoproteins. Preferential association with 3′-sialylated/sulfated (and 6-sulfated) β-galactosides was seen by glycan-array analysis when compared to the wild-type protein, which also strongly bound to ABH-type epitopes. Agglutination of erythrocytes documented functional bivalency. This result substantiates the potential for comparative functional studies between the variant and natural Gal-8 (NC)/Gal-8N. Full article

► Show Figures

Figure 1

37028 KiB

Open AccessArticle

Chemoinformatic Database Building and in Silico Hit-Identification of Potential Multi-Targeting Bioactive Compounds Extracted from Mushroom Species

by Annalisa Maruca, Federica Moraca, Roberta Rocca, Fulvia Molisani, Francesca Alcaro, Maria Concetta Gidaro, Stefano Alcaro, Giosuè Costa and Francesco Ortuso

Molecules 2017, 22(9), 1571; https://doi.org/10.3390/molecules22091571 - 19 Sep 2017

Cited by 26 | Viewed by 8987

Abstract

Mushrooms are widely-consumed fungi which contain natural compounds that can be used both for their nutritive and medicinal properties, i.e., taking advantage of their antimicrobial, antiviral, antitumor, anti-allergic, immunomodulation, anti-inflammatory, anti-atherogenic, hypoglycemic, hepatoprotective and antioxidant effects. Currently, scientific interest in natural compounds extracted [...] Read more.

Mushrooms are widely-consumed fungi which contain natural compounds that can be used both for their nutritive and medicinal properties, i.e., taking advantage of their antimicrobial, antiviral, antitumor, anti-allergic, immunomodulation, anti-inflammatory, anti-atherogenic, hypoglycemic, hepatoprotective and antioxidant effects. Currently, scientific interest in natural compounds extracted from the fungal species is increasing because these compounds are also known to have pharmacological/biological activity. Unfortunately, however, their mechanisms of action are often unknown, not well understood or have not been investigated in their entirety. Given the poly-pharmacological properties of bioactive fungal compounds, it was decided to carry out a multi-targeted approach to predict possible interactions occurring among bioactive natural fungal extracts and several macromolecular targets that are therapeutically interesting, i.e., proteins, enzymes and nucleic acids. A chemical database of compounds extracted from both edible and no-edible mushrooms was created. This database was virtually screened against 43 macromolecular targets downloaded from the Protein Data Bank website. The aim of this work is to provide a molecular description of the main interactions involving ligand/multi-target recognition in order to understand the polypharmacological profile of the most interesting fungal extracts and to suggest a design strategy of new multi-target agents. Full article

(This article belongs to the Special Issue Medicinal Chemistry in Europe)

► Show Figures

Graphical abstract

3564 KiB

Open AccessArticle

Preventing Surgical Site Infections Using a Natural, Biodegradable, Antibacterial Coating on Surgical Sutures

by Jochen Reinbold, Ann-Kristin Uhde, Ingrid Müller, Tobias Weindl, Jürgen Geis-Gerstorfer, Christian Schlensak, Hans-Peter Wendel and Stefanie Krajewski

Molecules 2017, 22(9), 1570; https://doi.org/10.3390/molecules22091570 - 19 Sep 2017

Cited by 43 | Viewed by 9337

Abstract

Surgical site infections (SSIs) are one of the most common nosocomial infections, which can result in serious complications after surgical interventions. Foreign materials such as implants or surgical sutures are optimal surfaces for the adherence of bacteria and subsequent colonization and biofilm formation. [...] Read more.

Surgical site infections (SSIs) are one of the most common nosocomial infections, which can result in serious complications after surgical interventions. Foreign materials such as implants or surgical sutures are optimal surfaces for the adherence of bacteria and subsequent colonization and biofilm formation. Due to a significant increase in antibiotic-resistant bacterial strains, naturally occurring agents exhibiting antibacterial properties have great potential in prophylactic therapies. The aim of this study was to develop a coating for surgical sutures consisting of the antibacterial substance totarol, a naturally occurring diterpenoid isolated from Podocarpus totara in combination with poly(lactide-co-glycolide acid) (PLGA) as a biodegradable drug delivery system. Hence, non-absorbable monofilament and multifilament sutures were coated with solutions containing different amounts and ratios of totarol and PLGA, resulting in a smooth, crystalline coating. Using an agar diffusion test (ADT), it became evident that the PLGA/totarol-coated sutures inhibited the growth of Staphylococcus aureus over a period of 15 days. A 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay showed that the coated sutures were not cytotoxic to murine fibroblasts. Overall, the data indicates that our innovative, biodegradable suture coating has the potential to reduce the risk of SSIs and postoperative biofilm-formation on suture material without adverse effects on tissue. Full article

(This article belongs to the Special Issue Biomedical Applications of Polylactide (PLA) and its Copolymers)

► Show Figures

Graphical abstract

5292 KiB

Open AccessArticle

Spiropyran-Isoquinoline Dyad as a Dual Chemosensor for Co(II) and In(III) Detection

by Yong-Min Kho and Eun Ju Shin

Molecules 2017, 22(9), 1569; https://doi.org/10.3390/molecules22091569 - 19 Sep 2017

Cited by 24 | Viewed by 6322

Abstract

Spiropyran derivatives have been studied as light-regulated chemosensors for a variety of metal cations and anions, but there is little research on chemosensors that simultaneously detect multiple metal cations. In this study, a spiropyran derivative with isoquinoline, SP-IQ, was prepared and it [...] Read more.

Spiropyran derivatives have been studied as light-regulated chemosensors for a variety of metal cations and anions, but there is little research on chemosensors that simultaneously detect multiple metal cations. In this study, a spiropyran derivative with isoquinoline, SP-IQ, was prepared and it functions investigated as a light-regulated sensor for both Co²⁺ and In³⁺ cations. A colorless nonfluorescent SP-IQ converts to a pink-colored fluorescent MC-IQ by UV irradiation or standing in the dark, and MC-IQ returns to SP-IQ with visible light. Upon UV irradiation with the Co²⁺ cation for 7 min, the stronger absorption at 540 nm and the similar fluorescence intensity at 640 nm are observed, compared to when no metal cation is added, due to the formation of a Co²⁺ complex with pink color and pink fluorescence. When placed in the dark with the In³⁺ cation for 7 h, the colorless solution of SP-IQ changes to the In³⁺ complex with yellow color and pink fluorescence, which shows strong absorption at 410 nm and strong fluorescence at 640 nm. Selective detection of the Co²⁺ cation with UV irradiation and the In³⁺ cation in the dark could be possible with SP-IQ by both absorption and fluorescence spectroscopy or by the naked eye. Full article

(This article belongs to the Special Issue Advances in Spiro Compounds)

► Show Figures

Graphical abstract

3501 KiB

Open AccessArticle

Transesterification Synthesis of Chloramphenicol Esters with the Lipase from Bacillus amyloliquefaciens

by Fengying Dong, Lingmeng Li, Lin Lin, Dannong He, Jingwen Chen, Wei Wei and Dongzhi Wei

Molecules 2017, 22(9), 1523; https://doi.org/10.3390/molecules22091523 - 19 Sep 2017

Cited by 11 | Viewed by 6560

Abstract

This work presents a synthetic route to produce chloramphenicol esters by taking advantage the high enantio- and regio-selectivity of lipases. A series of chloramphenicol esters were synthesized using chloramphenicol, acyl donors of different carbon chain length and lipase Lip_BA (lipase cloned from [...] Read more.

This work presents a synthetic route to produce chloramphenicol esters by taking advantage the high enantio- and regio-selectivity of lipases. A series of chloramphenicol esters were synthesized using chloramphenicol, acyl donors of different carbon chain length and lipase Lip_BA (lipase cloned from Bacillus amyloliquefaciens). Among acyl donors with different carbon chain lengths, vinyl propionate was found to be the best. The influences of different organic solvents, reaction temperature, reaction time, enzyme loading and water content on the synthesis of the chloramphenicol esters were studied. The synthesis of chloramphenicol propionate (0.25 M) with 4.0 g L⁻¹ of Lip_BA loading gave a conversion of ~98% and a purity of ~99% within 8 h at 50 °C in 1,4-dioxane as solvent. The optimum mole ratio of vinyl propionate to chloramphenicol was increased to 5:1. This is the first report of B. amyloliquefaciens lipase being used in chloramphenicol ester synthesis and a detailed study of the synthesis of chloramphenicol propionate using this reaction. The high enzyme activity and selectivity make lipase Lip_BA an attractive catalyst for green chemical synthesis of molecules with complex structures. Full article

(This article belongs to the Special Issue Lipases and Lipases Modification)

► Show Figures

Graphical abstract

667 KiB

Open AccessArticle

Nematicidal Activity of 3-Acyltetramic Acid Analogues Against Pine Wood Nematode, Bursaphelenchus xylophilus

by Hyo-Rim Lee, Sung-Chan Lee, Ji-Eun Lee, Seon-Mi Seo, Yong-Chul Jeong, Chan-Sik Jung, Mark G. Moloney and Il-Kwon Park

Molecules 2017, 22(9), 1568; https://doi.org/10.3390/molecules22091568 - 18 Sep 2017

Cited by 8 | Viewed by 4851

Abstract

Among 98 3-acyltetramic acid analogues, compounds 1c, 2c, 2f and 2g, showed >90% nematicidal activity against the pine wood nematode Bursaphelenchus xylophilus at a 10 μg/mL concentration. The nematicidal activities of compounds 1d, 1h, and 2k were a [...] Read more.

Among 98 3-acyltetramic acid analogues, compounds 1c, 2c, 2f and 2g, showed >90% nematicidal activity against the pine wood nematode Bursaphelenchus xylophilus at a 10 μg/mL concentration. The nematicidal activities of compounds 1d, 1h, and 2k were a little lower at 88.0%, 85.8%, and 57.2% at a 10 μg/mL concentration, respectively. The nematicidal activity of emamection benzoate, widely used in Korea for the prevention of pine wilt disease, was 32.3% at a 10 μg/mL concentration. Other 3-acyltetramic acid analogues showed less than 30% nematicidal activity. A structure-activity relationship study indicated that the chain length of the C-acyl substituent was very important for high nematicidal activity. All active compounds had C₁₃H₂₇ or C₁₁H₂₃ acyl substituents, in two closely related groups with the common physicochemical properties of a polar surface area 57.6A², PSA (polar surface area) 7.8–8.6% and ClogP (calculated partition coefficient) 5.1–5.9 and a polar surface area 75–84A², PSA 11.1–11.6% and ClogP 4.7–5.1, respectively. Our study indicates that active 3-acyltetramic acid analogues could have potential as lead compounds for developing novel pine wood nematode control agents. Full article

► Show Figures

Figure 1

2485 KiB

Open AccessArticle

Stable Carbon Isotope Composition of the Lipids in Natural Ophiocordyceps sinensis from Major Habitats in China and Its Substitutes

by Lian-Xian Guo, Xiao-Ming Xu, Yue-Hui Hong, Yan Li and Jiang-Hai Wang

Molecules 2017, 22(9), 1567; https://doi.org/10.3390/molecules22091567 - 18 Sep 2017

Cited by 9 | Viewed by 5096

Abstract

Ophiocordyceps sinensis is one rare medicinal fungus produced in the Qinghai-Tibetan Plateau. Its quality and price varies hugely with different habitat, and its numerous substitutes have sprung up in functional food markets. This paper aims to discriminate the geographic origin of wild O. [...] Read more.

Ophiocordyceps sinensis is one rare medicinal fungus produced in the Qinghai-Tibetan Plateau. Its quality and price varies hugely with different habitat, and its numerous substitutes have sprung up in functional food markets. This paper aims to discriminate the geographic origin of wild O. sinensis and its substitutes via element analyzer–isotope ratio mass spectrometry and gas chromatography–isotope ratio mass spectrometry. The δ¹³C values of major fatty acids in the lipids of O. sinensis are characterized unanimously by the variation relation C_18:0 < C_18:2 ≈ C_16:0 < C_18:1, while their fluctuation intervals are notably different between those of neutral and polar lipids. The comparative analysis of the δ¹³C ratios of major fatty acids in lipids of O. sinensis suggests that the δ¹³C patterns may be sensitive potential indicators to discriminate its geographical origin. The δ¹³C values of individual major fatty acids of lipids from the cultivated stromata of Cordyceps militaris (SCM), the fermented mycelia of Hirsurella sinensis (FM_H) and Paecilomyces epiali (FM_P) range from −31.2‰ to −29.7‰, −16.9‰ to −14.3‰, and −26.5‰ to −23.9‰, respectively. Their δ¹³C pattern of individual major fatty acids may be used as a potential indicator to discriminate the products of natural O. sinensis and its substitutes. Full article

► Show Figures

Figure 1

1053 KiB

Open AccessArticle

Anti-Inflammatory and Anti-Oxidative Activities of Phenolic Compounds from Alnus sibirica Stems Fermented by Lactobacillus plantarum subsp. argentoratensis

by Thi Tam Le, Jun Yin and MinWon Lee

Molecules 2017, 22(9), 1566; https://doi.org/10.3390/molecules22091566 - 18 Sep 2017

Cited by 11 | Viewed by 5616

Abstract

Fermentation of Alnus sibirica (AS) stems using Lactobacillus plantarum subsp. argentoratensis was conducted and three compounds isolated from the Alnus species were identified for the first time, 7-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-heptan-3-one, 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-heptan-3-one and 4-(3,4-dihydroxyphenyl)-butan-2-one, along with 14 known compounds. The anti-oxidative and anti-inflammatory abilities of AS [...] Read more.

Fermentation of Alnus sibirica (AS) stems using Lactobacillus plantarum subsp. argentoratensis was conducted and three compounds isolated from the Alnus species were identified for the first time, 7-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-heptan-3-one, 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-heptan-3-one and 4-(3,4-dihydroxyphenyl)-butan-2-one, along with 14 known compounds. The anti-oxidative and anti-inflammatory abilities of AS and fermented AS (FAS) as well as the isolated phenolic compounds from FAS were investigated. FAS showed stronger anti-oxidative and anti-inflammatory activities than non-fermented AS. Full article

(This article belongs to the Collection Phytochemicals: Biosynthesis, Metabolism and Biological Activities)

► Show Figures

Figure 1

1464 KiB

Open AccessArticle

The Native Fruit Geoffroea decorticans from Arid Northern Chile: Phenolic Composition, Antioxidant Activities and In Vitro Inhibition of Pro-Inflammatory and Metabolic Syndrome-Associated Enzymes

by Felipe Jiménez-Aspee, Cristina Theoduloz, Maria Del Pilar C. Soriano, Maider Ugalde-Arbizu, Maria Rosa Alberto, Iris Catiana Zampini, Maria Inés Isla, Mario J. Simirgiotis and Guillermo Schmeda-Hirschmann

Molecules 2017, 22(9), 1565; https://doi.org/10.3390/molecules22091565 - 18 Sep 2017

Cited by 31 | Viewed by 6629

Abstract

The native tree Geoffroea decorticans (chañar) grows in the arid lands of northern Chile. It has been used as a food plant since prehistoric times. Phenolic-enriched extracts (PEEs) of Chilean chañar fruits were assessed for their chemical composition, antioxidant properties and inhibition of [...] Read more.

The native tree Geoffroea decorticans (chañar) grows in the arid lands of northern Chile. It has been used as a food plant since prehistoric times. Phenolic-enriched extracts (PEEs) of Chilean chañar fruits were assessed for their chemical composition, antioxidant properties and inhibition of pro-inflammatory and metabolic syndrome-associated enzymes. Phenolic profiles were determined by HPLC-DAD-MS/MS. The PEEs of G. decorticans showed a strong effect towards the enzymes COX-1/COX-2, with inhibition percentages ranging from inactive to 92.1% and inactive to 76.0% at 50 µg PEE/mL, respectively. The IC₅₀ values of the PEEs towards lipoxygenase and phospholipase A2 inhibitory activity were between 43.6–96.8 and 98.9–156.0 μg PEE/mL, respectively. Samples inhibited α-glucosidase (IC₅₀ 0.8–7.3 μg PEE/mL) and lipase (9.9 to >100 μg PEE/mL). However, samples did not inhibit α-amylase. The HPLC-DAD-MS analysis of the PEEs allowed the tentative identification of 53 compounds, mainly flavonol glycosides and procyanidins. The procyanidin content of the Chilean G. decorticans pulp was positively correlated with the antioxidant activity and the inhibition of the enzyme α-glucosidase. These results indicate that the Chilean chañar fruit contains bioactive polyphenols with functional properties. Full article

(This article belongs to the Section Natural Products Chemistry)

► Show Figures

Figure 1

12400 KiB

Open AccessFeature PaperArticle

Brush Polymer of Donor-Accepter Dyads via Adduct Formation between Lewis Base Polymer Donor and All Carbon Lewis Acid Acceptor

by Yang Wang, Miao Hong, Travis S. Bailey and Eugene Y.-X. Chen

Molecules 2017, 22(9), 1564; https://doi.org/10.3390/molecules22091564 - 18 Sep 2017

Cited by 6 | Viewed by 6255

Abstract

A synthetic method that taps into the facile Lewis base (LB)→Lewis acid (LA) adduct forming reaction between the semiconducting polymeric LB and all carbon LA C₆₀ for the construction of covalently linked donor-acceptor dyads and brush polymer of dyads is reported. The [...] Read more.

A synthetic method that taps into the facile Lewis base (LB)→Lewis acid (LA) adduct forming reaction between the semiconducting polymeric LB and all carbon LA C₆₀ for the construction of covalently linked donor-acceptor dyads and brush polymer of dyads is reported. The polymeric LB is built on poly(3-hexylthiophene) (P3HT) macromers containing either an alkyl or vinyl imidazolium end group that can be readily converted into the N-heterocyclic carbene (NHC) LB site, while the brush polymer architecture is conveniently constructed via radical polymerization of the macromer P3HT with the vinyl imidazolium chain end. Simply mixing of such donor polymeric LB with C₆₀ rapidly creates linked P3HT-C₆₀ dyads and brush polymer of dyads in which C₆₀ is covalently linked to the NHC junction connecting the vinyl polymer main chain and the brush P3HT side chains. Thermal behaviors, electronic absorption and emission properties of the resulting P3HT-C₆₀ dyads and brush polymer of dyads have been investigated. The results show that a change of the topology of the P3HT-C₆₀ dyad from linear to brush architecture enhances the crystallinity and T_m of the P3HT domain and, along with other findings, they indicate that the brush polymer architecture of donor-acceptor domains provides a promising approach to improve performances of polymer-based solar cells. Full article

(This article belongs to the Special Issue Lewis Pair Polymerization for New Reactivity and Structure in Polymer Synthesis)

► Show Figures

Graphical abstract

2582 KiB

Open AccessArticle

Indexing Natural Products for Their Potential Anti-Diabetic Activity: Filtering and Mapping Discriminative Physicochemical Properties

by Mouhammad Zeidan, Mahmoud Rayan, Nuha Zeidan, Mizied Falah and Anwar Rayan

Molecules 2017, 22(9), 1563; https://doi.org/10.3390/molecules22091563 - 17 Sep 2017

Cited by 20 | Viewed by 6213

Abstract

Diabetes mellitus (DM) poses a major health problem, for which there is an unmet need to develop novel drugs. The application of in silico techniques and optimization algorithms is instrumental to achieving this goal. A set of 97 approved anti-diabetic drugs, representing the [...] Read more.

Diabetes mellitus (DM) poses a major health problem, for which there is an unmet need to develop novel drugs. The application of in silico techniques and optimization algorithms is instrumental to achieving this goal. A set of 97 approved anti-diabetic drugs, representing the active domain, and a set of 2892 natural products, representing the inactive domain, were used to construct predictive models and to index anti-diabetic bioactivity. Our recently-developed approach of ‘iterative stochastic elimination’ was utilized. This article describes a highly discriminative and robust model, with an area under the curve above 0.96. Using the indexing model and a mix ratio of 1:1000 (active/inactive), 65% of the anti-diabetic drugs in the sample were captured in the top 1% of the screened compounds, compared to 1% in the random model. Some of the natural products that scored highly as potential anti-diabetic drug candidates are disclosed. One of those natural products is caffeine, which is noted in the scientific literature as having the capability to decrease blood glucose levels. The other nine phytochemicals await evaluation in a wet lab for their anti-diabetic activity. The indexing model proposed herein is useful for the virtual screening of large chemical databases and for the construction of anti-diabetes focused libraries. Full article

► Show Figures

Figure 1

402 KiB

Open AccessArticle

Chemical Composition, Antibacterial Activity, and Synergistic Effects with Conventional Antibiotics and Nitric Oxide Production Inhibitory Activity of Essential Oil from Geophila repens (L.) I.M. Johnst

by Huijuanzi Rao, Pengxiang Lai and Yang Gao

Molecules 2017, 22(9), 1561; https://doi.org/10.3390/molecules22091561 - 17 Sep 2017

Cited by 24 | Viewed by 6032

Abstract

Geophila repens (L.) I.M. Johnst, a perennial herb, belongs to the Rubiaceae family. In this study, we identified the chemical composition of the Geophila repens essential oil (GR-EO) for the first time. Totally, seventy-seven compounds were identified according to GC and GC-MS, which [...] Read more.

Geophila repens (L.) I.M. Johnst, a perennial herb, belongs to the Rubiaceae family. In this study, we identified the chemical composition of the Geophila repens essential oil (GR-EO) for the first time. Totally, seventy-seven compounds were identified according to GC and GC-MS, which represent 98.0% of the oil. And the major components of GR-EO were β-caryophyllene (23.3%), β-elemene (8.0%), farnesyl butanoate (7.4%), myrcene (3.5%), and trans-nerolidol (3.3%). Then we evaluated the antibacterial activities of GR-EO and the synergistic effects of GR-EO in combination with commercial antibiotics using the microdilution and Checkerboard method. The results demonstrated that GR-EO possessed an excellent broad spectrum antibacterial activity, especially against Pseudomonas aeruginosa and Bacillus subtilis. It also showed that the combined application of GR-EO with antibiotics led to synergistic effects in most cases. And the most prominent synergistic effect was noticed when GR-EO was in combination with Streptomycin and tested against Escherichia coli (fractional inhibitory concentration indices (FICI) of 0.13). Additionally, the results of a Griess assay revealed that GR-EO exhibited a potent inhibitory effect on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 (murine macrophage) cells. In conclusion, the combination of GR-EO and the commercial antibiotics has significant potential for the development of new antimicrobial treatment and reduction of drug resistance. Full article

(This article belongs to the Special Issue Essential Oils as Antimicrobial and Anti-infectious Agents)

► Show Figures

Figure 1

3874 KiB

Open AccessArticle

The Influence of Accelerated UV-A and Q-SUN Irradiation on the Antimicrobial Properties of Coatings Containing ZnO Nanoparticles

by Małgorzata Mizielińska, Łukasz Łopusiewicz, Monika Mężyńska and Artur Bartkowiak

Molecules 2017, 22(9), 1556; https://doi.org/10.3390/molecules22091556 - 17 Sep 2017

Cited by 22 | Viewed by 6697

Abstract

The influence of accelerated UV-A and Q-SUN irradiation on the antimicrobial properties of coatings containing ZnO nanoparticles was investigated using a polyethylene (PE) film covering. The results of the study showed that Methyl Hydroxypropyl Celluloses (MHPC) coatings did not influence the growth of [...] Read more.

The influence of accelerated UV-A and Q-SUN irradiation on the antimicrobial properties of coatings containing ZnO nanoparticles was investigated using a polyethylene (PE) film covering. The results of the study showed that Methyl Hydroxypropyl Celluloses (MHPC) coatings did not influence the growth of S. aureus, B. cereus, E. coli, P. aeruginosa or C. albicans cells. MHPC coatings containing ZnO nanoparticles inhibited the growth of bacterial strains and reduced the number of C. albicans strains. Accelerated Q-SUN and UV-A irradiation had no influence on the antimicrobial effect of nano ZnO coatings against S. aureus, B. cereus and E. coli. Q-SUN irradiation decreased the activity of MHPC coatings containing nanoparticles against P. aeruginosa and C. albicans. An FT-IR analysis clearly showed that ZnO nanoparticles shielded the MHPC coating during Q-SUN irradiation. Full article

(This article belongs to the Special Issue Antibacterial Materials and Coatings)

► Show Figures

Figure 1

4338 KiB

Open AccessReview

Cardiovascular Activity of the Chemical Constituents of Essential Oils

by Tadeu Uggere De Andrade, Girlandia Alexandre Brasil, Denise Coutinho Endringer, Flávio Rogério Da Nóbrega and Damião Pergentino De Sousa

Molecules 2017, 22(9), 1539; https://doi.org/10.3390/molecules22091539 - 17 Sep 2017

Cited by 29 | Viewed by 8232

Abstract

Cardiovascular diseases are a leading cause of death in developed and developing countries and decrease the quality of life, which has enormous social and economic consequences for the population. Recent studies on essential oils have attracted attention and encouraged continued research of this [...] Read more.

Cardiovascular diseases are a leading cause of death in developed and developing countries and decrease the quality of life, which has enormous social and economic consequences for the population. Recent studies on essential oils have attracted attention and encouraged continued research of this group of natural products because of their effects on the cardiovascular system. The pharmacological data indicate a therapeutic potential for essential oils for use in the treatment of cardiovascular diseases. Therefore, this review reports the current studies of essential oils chemical constituents with cardiovascular activity, including a description of their mechanisms of action. Full article

(This article belongs to the Collection Bioactive Compounds)

1706 KiB

Open AccessArticle

Antibiofilm Activity and Mechanism of Action of the Disinfectant Chloramine T on Candida spp., and Its Toxicity against Human Cells

by Gabriela Lacet Silva Ferreira, Pedro Luiz Rosalen, Larissa Rangel Peixoto, Ana Luiza Alves de Lima Pérez, Fabíola Galbiatti de Carvalho Carlo, Lúcio Roberto Cançado Castellano, Jefferson Muniz de Lima, Irlan Almeida Freires, Edeltrudes De Oliveira Lima and Ricardo Dias de Castro

Molecules 2017, 22(9), 1527; https://doi.org/10.3390/molecules22091527 - 17 Sep 2017

Cited by 10 | Viewed by 5910

Abstract

We evaluated the antifungal and anti-biofilm activity, mechanism of action and cytotoxicity of chloramine T trihydrate (CAT) against Candida spp. The Minimum Inhibitory and Fungicidal Concentrations (MIC/MFC) of CAT were determined. Changes in CAT-treated C. albicans growth kinetics and micromorphology were evaluated, as [...] Read more.

We evaluated the antifungal and anti-biofilm activity, mechanism of action and cytotoxicity of chloramine T trihydrate (CAT) against Candida spp. The Minimum Inhibitory and Fungicidal Concentrations (MIC/MFC) of CAT were determined. Changes in CAT-treated C. albicans growth kinetics and micromorphology were evaluated, as well as the mechanism of action, and its effects on biofilm. Cytotoxicity was assessed by the hemolysis method. The data were analyzed by inferential statistics (p ≤ 0.05). CAT showed antifungal activity against all strains, with MIC values ranging between 1.38 and 5.54 mmol/L (MIC_75%: 2.77 mmol/L). CAT demonstrated an immediate and sustained action on C. albicans growth kinetics, particularly at 2 × MIC. This compound likely acts on the cell wall and membrane permeability simultaneously and was found to cause changes in C. albicans micromorphology. Tha antibiofilm activity of CAT was similar to that of sodium hypochlorite (p > 0.05) against mature biofilms. CAT was more effective than NaOCl in reducing mature biofilm upon 1-min exposure at 2 × MIC (24 h) and 4 × MIC (48 h) (p < 0.05). Toxicological analysis revealed that CAT had hemolytic activity between 61 and 67.7% as compared to 100% by NaOCl. CAT has antifungal and anti-biofilm properties, probably acting on both cell wall and membrane permeability, and showed low toxicity in vitro. Full article

(This article belongs to the Special Issue Emerging Drug Discovery Approaches against Infectious Diseases)

► Show Figures

Figure 1

5312 KiB

Open AccessArticle

Identification of Novel Bisbenzimidazole Derivatives as Anticancer Vacuolar (H⁺)-ATPase Inhibitors

by Renukadevi Patil, Arpita Kulshrestha, Anjali Tikoo, Sara Fleetwood, Gajendra Katara, Bala Kolli, William Seibel, Alice Gilman-Sachs, Shivaputra A. Patil and Kenneth D. Beaman

Molecules 2017, 22(9), 1559; https://doi.org/10.3390/molecules22091559 - 16 Sep 2017

Cited by 10 | Viewed by 6576

Abstract

The vacuolar (H⁺)-ATPases (V-ATPases) are a family of ATP-driven proton pumps and they have been associated with cancer invasion, metastasis, and drug resistance. Despite the clear involvement of V-ATPases in cancer, the therapeutic use of V-ATPase-targeting small molecules has not reached [...] Read more.

The vacuolar (H⁺)-ATPases (V-ATPases) are a family of ATP-driven proton pumps and they have been associated with cancer invasion, metastasis, and drug resistance. Despite the clear involvement of V-ATPases in cancer, the therapeutic use of V-ATPase-targeting small molecules has not reached human clinical trials to date. Thus, V-ATPases are emerging as important targets for the identification of potential novel therapeutic agents. We identified a bisbenzimidazole derivative (V) as an initial hit from a similarity search using four known V-ATPase inhibitors (I–IV). Based on the initial hit (V), we designed and synthesized a focused set of novel bisbenzimidazole analogs (2a–e). All newly prepared compounds have been screened for selected human breast cancer (MDA-MB-468, MDA-MB-231, and MCF7) and ovarian cancer (A2780, Cis-A2780, and PA-1) cell lines, along with the normal breast epithelial cell line, MCF10A. The bisbenzimidazole derivative (2e) is active against all cell lines tested. Remarkably, it demonstrated high cytotoxicity against the triple-negative breast cancer (TNBC) cell line, MDA-MB-468 (IC₅₀ = 0.04 ± 0.02 μM). Additionally, it has been shown to inhibit the V-ATPase pump that is mainly responsible for acidification. To the best of our knowledge the bisbenzimidazole pharmacophore has been identified as the first V-ATPase inhibitor in its class. These results strongly suggest that the compound 2e could be further developed as a potential anticancer V-ATPase inhibitor for breast cancer treatment. Full article

(This article belongs to the Collection Efficient Pharmaceutical and Chemical Approaches for Anticancer Therapy: Design, Preliminary Evaluations, and Further Developments)

► Show Figures

Figure 1

1643 KiB

Open AccessArticle

A New Erythrinan Alkaloid Glycoside from the Seeds of Erythrina crista-galli

by Qing-Wei Tan, Jian-Cheng Ni, Pei-Hua Fang and Qi-Jian Chen

Molecules 2017, 22(9), 1558; https://doi.org/10.3390/molecules22091558 - 16 Sep 2017

Cited by 15 | Viewed by 5830

Abstract

A new Erythrina alkaloid glycoside, named erythraline-11β-O-glucopyranoside, was isolated from the seeds of Erythrina crista-galli L., together with five known Erythrina alkaloids and an indole alkaloid. The structure of the new alkaloid glycoside was elucidated by spectroscopic methods, and all of [...] Read more.

A new Erythrina alkaloid glycoside, named erythraline-11β-O-glucopyranoside, was isolated from the seeds of Erythrina crista-galli L., together with five known Erythrina alkaloids and an indole alkaloid. The structure of the new alkaloid glycoside was elucidated by spectroscopic methods, and all of the compounds were evaluated for their antiviral activity against tobacco mosaic virus. Full article

(This article belongs to the Section Natural Products Chemistry)

► Show Figures

Figure 1

4027 KiB

Open AccessReview

Probing Gas Adsorption in Zeolites by Variable-Temperature IR Spectroscopy: An Overview of Current Research

by Edoardo Garrone, Montserrat R. Delgado, Barbara Bonelli and Carlos O. Arean

Molecules 2017, 22(9), 1557; https://doi.org/10.3390/molecules22091557 - 15 Sep 2017

Cited by 9 | Viewed by 6647

Abstract

The current state of the art in the application of variable-temperature IR (VTIR) spectroscopy to the study of (i) adsorption sites in zeolites, including dual cation sites; (ii) the structure of adsorption complexes and (iii) gas-solid interaction energy is reviewed. The main focus [...] Read more.

The current state of the art in the application of variable-temperature IR (VTIR) spectroscopy to the study of (i) adsorption sites in zeolites, including dual cation sites; (ii) the structure of adsorption complexes and (iii) gas-solid interaction energy is reviewed. The main focus is placed on the potential use of zeolites for gas separation, purification and transport, but possible extension to the field of heterogeneous catalysis is also envisaged. A critical comparison with classical IR spectroscopy and adsorption calorimetry shows that the main merits of VTIR spectroscopy are (i) its ability to provide simultaneously the spectroscopic signature of the adsorption complex and the standard enthalpy change involved in the adsorption process; and (ii) the enhanced potential of VTIR to be site specific in favorable cases. Full article

(This article belongs to the Special Issue Zeolites and Related Nanoporous Materials: Synthesis, Characterization and Applications in Catalysis and Green Chemistry)

► Show Figures

Figure 1

1547 KiB

Open AccessArticle

Synthesis, In Vitro α-Glucosidase Inhibitory Activity and Molecular Docking Studies of Novel Benzothiazole-Triazole Derivatives

by Zipeng Gong, Yaping Peng, Jie Qiu, Anbai Cao, Guangcheng Wang and Zhiyun Peng

Molecules 2017, 22(9), 1555; https://doi.org/10.3390/molecules22091555 - 15 Sep 2017

Cited by 51 | Viewed by 7150

Abstract

Benzothiazole-triazole derivatives 6a–6s have been synthesized and characterized by ¹HNMR and ¹³C-NMR. All synthetic compounds were screened for their in vitro α-glucosidase inhibitory activity by using Baker’s yeast α-glucosidase enzyme. The majority of compounds exhibited a varying degree of α-glucosidase inhibitory [...] Read more.

Benzothiazole-triazole derivatives 6a–6s have been synthesized and characterized by ¹HNMR and ¹³C-NMR. All synthetic compounds were screened for their in vitro α-glucosidase inhibitory activity by using Baker’s yeast α-glucosidase enzyme. The majority of compounds exhibited a varying degree of α-glucosidase inhibitory activity with IC50 values between 20.7 and 61.1 μM when compared with standard acarbose (IC₅₀ = 817.38 μM). Among the series, compound 6s (IC₅₀ = 20.7 μM) bearing a chlorine group at the 5-position of the benzothiazole ring and a tertbutyl group at the para position of the phenyl ring, was found to be the most active compound. Preliminary structure-activity relationships were established. Molecular docking studies were performed to predict the binding interaction of the compounds in the binding pocket of the enzyme. Full article

(This article belongs to the Section Medicinal Chemistry)

► Show Figures

Graphical abstract

2432 KiB

Open AccessArticle

Comparison of Two Components of Propolis: Caffeic Acid (CA) and Caffeic Acid Phenethyl Ester (CAPE) Induce Apoptosis and Cell Cycle Arrest of Breast Cancer Cells MDA-MB-231

by Agata Kabała-Dzik, Anna Rzepecka-Stojko, Robert Kubina, Żaneta Jastrzębska-Stojko, Rafał Stojko, Robert Dariusz Wojtyczka and Jerzy Stojko

Molecules 2017, 22(9), 1554; https://doi.org/10.3390/molecules22091554 - 15 Sep 2017

Cited by 68 | Viewed by 9055

Abstract

Studies show that caffeic acid (CA) and caffeic acid phenethyl ester (CAPE) are compounds with potent chemopreventive effects. Breast cancer is a common form of aggressive cancer among women worldwide. This study shows a comparison of CA and CAPE activity on triple-negative human [...] Read more.

Studies show that caffeic acid (CA) and caffeic acid phenethyl ester (CAPE) are compounds with potent chemopreventive effects. Breast cancer is a common form of aggressive cancer among women worldwide. This study shows a comparison of CA and CAPE activity on triple-negative human caucasian breast adenocarcinoma line cells (MDA-MB-231). MDA-MB-231 cells were treated by CA and CAPE with doses of from 10 to 100 µM, for periods of 24 h and 48 h. Cytotoxicity MTT tests, apoptosis by Annexin V, and cell cycle with Dead Cell Assays were performed. Cytotoxic activity was greater for CAPE compared to CA (both incubation times, same dosage). IC₅₀ values for CAPE were 27.84 µM (24 h) and 15.83 µM (48 h) and for CA > 10,000 µM (24 h) and > 1000 µM (48 h). Polyphenols induced apoptosis, while CAPE (dose dependently), induced a higher apoptotic effect. CAPE also induced cell cycle arrest in S phase (time and dose dependently), CA did it only for 50 and 100 µM. A dose dependent decline was seen for the G0/G1 phase (CAPE, 48 h), as well as elimination of phase G2/M by 100 µM of CAPE (only mild effect for CA). Comparing CA and CAPE activity on MDA-MB-231, CAPE clearly showed better activity for the same dosages and experiment times. Full article

(This article belongs to the Collection Phytochemicals: Biosynthesis, Metabolism and Biological Activities)

► Show Figures

Graphical abstract

4868 KiB

Open AccessArticle

Cytotoxic Evaluation of (2S)-5,7-Dihydroxy-6-prenylflavanone Derivatives Loaded PLGA Nanoparticles against MiaPaCa-2 Cells

by Berenice Andrade-Carrera, Beatriz Clares, Véronique Noé, Mireia Mallandrich, Ana C. Calpena, María Luisa García and María Luisa Garduño-Ramírez

Molecules 2017, 22(9), 1553; https://doi.org/10.3390/molecules22091553 - 15 Sep 2017

Cited by 18 | Viewed by 6159

Abstract

The search for new alternatives for the prevention and treatment of cancer is extremely important to minimize human mortality. Natural products are an alternative to chemical drugs, since they are a source of many potential compounds with anticancer properties. In the present study, [...] Read more.

The search for new alternatives for the prevention and treatment of cancer is extremely important to minimize human mortality. Natural products are an alternative to chemical drugs, since they are a source of many potential compounds with anticancer properties. In the present study, the (2S)-5,7-dihydroxy-6-prenylflavanone (semi-systematic name), also called (2S)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-Benzopyran-4-one (CAS Name registered) (1) was isolated from Eysenhardtia platycarpa leaves. This flavanone 1 was considered as the lead compound to generate new cytotoxic derivatives 1a, 1b, 1c and 1d. These compounds 1, 1a, 1b, 1c, and 1d were then loaded in nanosized drug delivery systems such as polymeric nanoparticles (NPs). Small homogeneous spherical shaped NPs were obtained. Cytotoxic activity of free compounds 1, 1a, 1b, 1c, and 1d and encapsulated in polymeric NPs (NPs1, NPs1a, NPs1b, NPs1c and NPs1d) were evaluated against the pancreatic cancer cell line MiaPaCa-2. The obtained results demonstrated that NPs1a and NPs1b exhibited optimal cytotoxicity, and an even higher improvement of the cytotoxic efficacy was exhibited with the encapsulation of 1a. Based on these results, NPs1a were proposed as promising anticancer agent candidates. Full article

(This article belongs to the Special Issue Synthesis and Modification of Natural Product)

► Show Figures

Figure 1

2912 KiB

Open AccessArticle

Development, Optimization and In Vitro/In Vivo Characterization of Collagen-Dextran Spongious Wound Dressings Loaded with Flufenamic Acid

by Mihaela Violeta Ghica, Mădălina Georgiana Albu Kaya, Cristina-Elena Dinu-Pîrvu, Dumitru Lupuleasa and Denisa Ioana Udeanu

Molecules 2017, 22(9), 1552; https://doi.org/10.3390/molecules22091552 - 15 Sep 2017

Cited by 46 | Viewed by 6790

Abstract

The aim of this study was the development and optimization of some topical collagen-dextran sponges with flufenamic acid, designed to be potential dressings for burn wounds healing. The sponges were obtained by lyophilization of hydrogels based on type I fibrillar collagen gel extracted [...] Read more.

The aim of this study was the development and optimization of some topical collagen-dextran sponges with flufenamic acid, designed to be potential dressings for burn wounds healing. The sponges were obtained by lyophilization of hydrogels based on type I fibrillar collagen gel extracted from calf hide, dextran and flufenamic acid, crosslinked and un-crosslinked, and designed according to a 3-factor, 3-level Box-Behnken experimental design. The sponges showed good fluid uptake ability quantified by a high swelling ratio. The flufenamic acid release profiles from sponges presented two stages—burst effect resulting in a rapid inflammation reduction, and gradual delivery ensuring the anti-inflammatory effect over a longer burn healing period. The resistance to enzymatic degradation was monitored through a weight loss parameter. The optimization of the sponge formulations was performed based on an experimental design technique combined with response surface methodology, followed by the Taguchi approach to select those formulations that are the least affected by the noise factors. The treatment of experimentally induced burns on animals with selected sponges accelerated the wound healing process and promoted a faster regeneration of the affected epithelial tissues compared to the control group. The results generated by the complex sponge characterization indicate that these formulations could be successfully used for burn dressing applications. Full article

(This article belongs to the Special Issue Natural Polymers and Biopolymers)

► Show Figures

Figure 1

Journal Menu

Journal Browser

Molecules, Volume 22, Issue 9 (September 2017) – 186 articles

Further Information

Guidelines

MDPI Initiatives

Follow MDPI