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New Trends in Developing Complexes as Biological Active Species

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Inorganic Chemistry".

Deadline for manuscript submissions: closed (31 October 2022) | Viewed by 38335

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Dr. Rodica Olar

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Department of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, 050663 Bucharest, Romania
Interests: coordination chemistry; biological active species (organic and inorganic); characterization methods (ESI-MS, NMR, IR, EPR)
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Prof. Dr. Carlo Santini

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School of Science and Technology, Chemistry Division, University of Camerino, Via Sant’Agostino 1, 62032 Camerino, Italy
Interests: metal-based drugs; coordination chemistry; functional metal complexes; hybrid materials; inorganic and organometallic chemistry; scorpionate ligands; phosphanes; N-heterocyclic carbenes
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Dr. Maura Pellei

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School of Science and Technology, Chemistry Division, University of Camerino, Via Sant’Agostino 1, 62032 Camerino, Italy
Interests: metal-based drugs; bioinorganic chemistry; coordination chemistry; inorganic materials; organometalllic chemistry; copper; scorpionate ligands; phosphanes N-heterocyclic carbenes
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Dear Colleagues,

It is well known that the evolution of diseases makes classical drugs ineffective. A viable strategy to overcome problems such as resistance, side effects, and microorganisms’ ability to develop biofilms is provided by complexes, especially by those bearing transition metal ions and multidentate ligands. Several species of this type were tested and proved to have valuable antitumor, antimicrobial, anti-inflammatory, anti-infective, or antiparasitic activity both in vitro and in vivo. Important aspects that need to be clarified in the development of these compounds as drugs are their interactions with serum and cytoplasmic peptides, as well as with the target sites, which most often are DNA and enzymes.

This Special Issue will cover the aspects concerning the design, synthesis, characterization, and in vitro or in vivo assay of various complexes as potential biological active species.

Dr. Rodica Olar
Prof. Dr. Carlo Santini
Prof. Dr. Maura Pellei
Guest Editors

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Keywords

coordination chemistry
multidentate ligands
in vitro assays
in vivo assays
antioxidant assay
antitumor activity
antimicrobial activity
anti-inflammatory activity
SOD-like activity;
metallonuclease-like activity
biofilm
multiresistant strains
molecular docking

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Published Papers (12 papers)

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7 pages, 937 KiB

Open AccessCommunication

Complex-Forming Properties of Ceftazidime with Fe(III) Ions in an Aqueous Solution

by Marek Pająk, Magdalena Woźniczka and Jakub Fichna

Molecules 2022, 27(21), 7226; https://doi.org/10.3390/molecules27217226 - 25 Oct 2022

Cited by 1 | Viewed by 1321

Abstract

In the present study, the complexing properties of ceftazidime with Fe(III) ions in aqueous solutions were characterized by UV-vis spectrophotometric and potentiometric methods. Using the UV-vis spectrophotometric method, the absorbance values for Fe(III) ions, a third-generation cephalosporin antibiotic (ceftazidime), and the Fe(III)-ceftazidime system [...] Read more.

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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16 pages, 5703 KiB

Open AccessArticle

BSA Interaction, Molecular Docking, and Antibacterial Activity of Zinc(II) Complexes Containing the Sterically Demanding Biomimetic N₃S₂ Ligand: The Effect of Structure Flexibility

by Eman Soliman, Mohamed M. Ibrahim, Mohamed E. El-Khouly, Ibrahim El-Mehasseb, Abd El-Motaleb M. Ramadan, Magdy E. Mahfouz, Shaban Y. Shaban and Rudi van Eldik

Molecules 2022, 27(11), 3543; https://doi.org/10.3390/molecules27113543 - 31 May 2022

Cited by 7 | Viewed by 2566

Abstract

Two zinc(II) complexes, DBZ and DBZH₄, that have (ZnN₃S₂) cores and differ in the bridging mode of the ligating backbone, effectively bind to BSA. The binding affinity varies as DBZ > DBZH₄ and depends on the ligand structure. At low concentrations, both complexes exhibit dynamic quenching, whereas at higher concentrations they exhibit mixed (static and dynamic) quenching. The energy transfer mechanism from the BSA singlet excited state to DBZ and DBZH₄, is highly likely according to steady-state fluorescence and time-correlated singlet photon counting. Molecular docking was used to support the mode of interaction of the complexes with BSA and showed that DBZ had more energy for binding. Furthermore, antibacterial testing revealed that both complexes were active but to a lesser extent than chloramphenicol. In comparison to DBZH₄, DBZ has higher antibacterial activity, which is consistent with the binding constants, molecular docking, and particle size of adducts. These findings may have an impact on biomedicine. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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27 pages, 5212 KiB

Open AccessArticle

Insights into Structure and Biological Activity of Copper(II) and Zinc(II) Complexes with Triazolopyrimidine Ligands

by Aura Argăseală, Cătălin Maxim, Mihaela Badea, Larisa Ioniță, Mariana Carmen Chifiriuc, Arpad Mihai Rostas, Mihaela Bacalum, Mina Răileanu, Lavinia L. Ruţă, Ileana C. Farcaşanu, Emilia Elena Iorgulescu and Rodica Olar

Molecules 2022, 27(3), 765; https://doi.org/10.3390/molecules27030765 - 24 Jan 2022

Cited by 2 | Viewed by 2938

Abstract

In an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-a]pyrimidine scaffold through complexation with essential metal ions, the complexes trans-[Cu(mptp)₂Cl₂] (1), [Zn(mptp)Cl₂(DMSO)] (2) (mptp: 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidine), [Cu₂(dmtp)₄Cl₄]·2H₂O (3) and [Zn(dmtp)₂Cl₂] (4) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine), were synthesized and characterized as new antiproliferative and antimicrobial species. Both complexes (1) and (2) crystallize in the P2₁/n monoclinic space group, with the tetrahedral surroundings generating a square-planar stereochemistry in the Cu(II) complex and a tetrahedral stereochemistry in the Zn(II) species. The mononuclear units are interconnected in a supramolecular network through π–π interactions between the pyrimidine moiety and the phenyl ring in (1) while supramolecular chains resulting from C-H∙∙∙π interactions were observed in (2). All complexes exhibit an antiproliferative effect against B16 tumor cells and improved antibacterial and antifungal activities compared to the free ligands. Complex (3) displays the best antimicrobial activity against all four tested strains, both in the planktonic and biofilm-embedded states, which can be correlated to its stronger DNA-binding and nuclease-activity traits. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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15 pages, 1973 KiB

Open AccessArticle

Tris-(2-pyridyl)-pyrazolyl Borate Zinc(II) Complexes: Synthesis, DNA/Protein Binding and In Vitro Cytotoxicity Studies

by Manmath Narwane, Dorothy Priyanka Dorairaj, Yu-Lun Chang, Ramasamy Karvembu, Yu-Han Huang, Hsueh-Wei Chang and Sodio C. N. Hsu

Molecules 2021, 26(23), 7341; https://doi.org/10.3390/molecules26237341 - 3 Dec 2021

Cited by 7 | Viewed by 2702

Abstract

Zn(II) complexes bearing tris[3-(2-pyridyl)-pyrazolyl] borate (Tp^py) ligand (1–3) was synthesized and examined by spectroscopic and analytical tools. Mononuclear [Tp^pyZnCl] (1) has a Zn(II) centre with one arm (pyrazolyl-pyridyl) dangling outside the coordination sphere which is a novel finding in Tp^pyZn(II) chemistry. In complex [Tp^pyZn(H₂O)][BF₄] (2) hydrogen bonding interaction of aqua moiety stabilizes the dangling arm. In addition, solution state behaviour of complex 1 confirms the tridentate binding mode and reactivity studies show the exogenous axial substituents used to form the [Tp^pyZnN₃] (3). The complexes (1–3) were tested for their ability to bind with Calf thymus (CT) DNA and Bovine serum albumin (BSA) wherein they revealed to exhibit good binding constant values with both the biomolecules in the order of 10⁴–10⁵ M⁻¹. The intercalative binding mode with CT DNA was confirmed from the UV-Visible absorption, viscosity, and ethidium bromide (EB) DNA displacement studies. Further, the complexes were tested for in vitro cytotoxic ability on four triple-negative breast cancer (TNBC) cell lines (MDA-MB-231, MDA-MB-468, HCC1937, and Hs 578T). All three complexes (1–3) exhibited good IC₅₀ values (6.81 to 16.87 μM for 24 h as seen from the MTS assay) results which indicated that these complexes were found to be potential anticancer agents against the TNBC cells. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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18 pages, 3235 KiB

Open AccessFeature PaperArticle

Bioactive Co(II), Ni(II), and Cu(II) Complexes Containing a Tridentate Sulfathiazole-Based (ONN) Schiff Base

by Aurora Reiss, Nicoleta Cioateră, Aurelian Dobrițescu, Mihaela Rotaru, Alice Carla Carabet, Filippo Parisi, Anca Gănescu, Irina Dăbuleanu, Cezar Ionuț Spînu and Petre Rotaru

Molecules 2021, 26(10), 3062; https://doi.org/10.3390/molecules26103062 - 20 May 2021

Cited by 27 | Viewed by 3981

Abstract

New Co(II), Ni(II), and Cu(II) complexes were synthesized with the Schiff base ligand obtained by the condensation of sulfathiazole with salicylaldehyde. Their characterization was performed by elemental analysis, molar conductance, spectroscopic techniques (IR, diffuse reflectance and UV–Vis–NIR), magnetic moments, thermal analysis, and calorimetry (thermogravimetry/derivative thermogravimetry/differential scanning calorimetry), while their morphological and crystal systems were explained on the basis of powder X-ray diffraction results. The IR data indicated that the Schiff base ligand is tridentate coordinated to the metallic ion with two N atoms from azomethine group and thiazole ring and one O atom from phenolic group. The composition of the complexes was found to be of the [ML₂]∙nH₂O (M = Co, n = 1.5 (1); M = Ni, n = 1 (2); M = Cu, n = 4.5 (3)) type, having an octahedral geometry for the Co(II) and Ni(II) complexes and a tetragonally distorted octahedral geometry for the Cu(II) complex. The presence of lattice water molecules was confirmed by thermal analysis. XRD analysis evidenced the polycrystalline nature of the powders, with a monoclinic structure. The unit cell volume of the complexes was found to increase in the order of (2) < (1) < (3). SEM evidenced hard agglomerates with micrometric-range sizes for all the investigated samples (ligand and complexes). EDS analysis showed that the N:S and N:M atomic ratios were close to the theoretical ones (1.5 and 6.0, respectively). The geometric and electronic structures of the Schiff base ligand 4-((2-hydroxybenzylidene) amino)-N-(thiazol-2-yl) benzenesulfonamide (HL) was computationally investigated by the density functional theory (DFT) method. The predictive molecular properties of the chemical reactivity of the HL and Cu(II) complex were determined by a DFT calculation. The Schiff base and its metal complexes were tested against some bacterial strains (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Bacillus subtilis). The results indicated that the antibacterial activity of all metal complexes is better than that of the Schiff base. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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15 pages, 2784 KiB

Open AccessArticle

New Cobalt (II) Complexes with Imidazole Derivatives: Antimicrobial Efficiency against Planktonic and Adherent Microbes and In Vitro Cytotoxicity Features

by Alina Fudulu, Rodica Olar, Cătălin Maxim, Gina Vasile Scăeţeanu, Coralia Bleotu, Lilia Matei, Mariana Carmen Chifiriuc and Mihaela Badea

Molecules 2021, 26(1), 55; https://doi.org/10.3390/molecules26010055 - 24 Dec 2020

Cited by 17 | Viewed by 3615

Abstract

Three novel Co(II) complexes of the type [Co(C₄H₅O₂)₂L₂] (where C₄H₅O₂ is methacrylate anion; L = C₃H₄N₂ (imidazole; HIm) (1), C₄ [...] Read more.

Three novel Co(II) complexes of the type [Co(C₄H₅O₂)₂L₂] (where C₄H₅O₂ is methacrylate anion; L = C₃H₄N₂ (imidazole; HIm) (1), C₄H₆N₂ (2-methylimidazole; 2-MeIm) (2), C₅H₈N₂ (2-ethylimidazole; 2-EtIm) (3)) have been synthesized and characterized by elemental analysis, IR and UV-Vis spectroscopic techniques, thermal analysis and single crystal X-ray diffraction. X-ray crystallography revealed for complexes (1) and (2) distorted trigonal bipyramid stereochemistry for Co(II), meanwhile for complex (3) evidenced that the unit cell comprises three molecular units with interesting structural features. In each unit, both stereochemistry adopted by metallic ion and coordination modes of carboxylate anions are different. The screening of antimicrobial activity revealed that Candida albicans planktonic cells were the most susceptible, with minimal inhibitory concentration (MIC) values of 7.8 μg/mL for complexes (1) and (2) and 15.6 μg/mL for complex (3). Complexes (1) and (2) proved to be more active than complex (3) against the tested bacterial strains, both in planktonic and biofilm growth state, with MIC and minimal biofilm eradication concentration (MBEC) values ranging from 15.6 to 62.5 μg/mL, the best antibacterial effects being noticed against Staphylococcus aureus and Pseudomonas aeruginosa. Remarkably, the MBEC values obtained for the four tested bacterial strains were either identical or even lower than the MIC ones. The cytotoxicity assay indicated that the tested complexes affected the cellular cycle of HeLa, HCT-8, and MG63 cells, probably by inhibiting the expression of vimentin and transient receptor potential canonical 1 (TRPC1). The obtained biological results recommend these complexes as potential candidates for the development of novel anti-biofilm agents. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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9 pages, 1159 KiB

Open AccessFeature PaperArticle

Design, Preparation, and Evaluation of a Novel ^99mTcN Complex of Ciprofloxacin Xanthate as a Potential Bacterial Infection Imaging Agent

by Si’an Fang, Yuhao Jiang, Qianqian Gan, Qing Ruan, Di Xiao and Junbo Zhang

Molecules 2020, 25(24), 5837; https://doi.org/10.3390/molecules25245837 - 10 Dec 2020

Cited by 8 | Viewed by 2256

Abstract

In order to seek novel technetium-99m bacterial infection imaging agents, a ciprofloxacin xanthate (CPF2XT) was synthesized and radiolabeled with [^99mTcN]²⁺ core to obtain the ^99mTcN-CPF2XT complex, which exhibited high radiochemical purity, hydrophilicity, and good stability in vitro. The bacteria binding assay indicated that ^99mTcN-CPF2XT had specificity to bacteria. A study of biodistribution in mice showed that ^99mTcN-CPF2XT had a higher uptake in bacterial infection tissues than in turpentine-induced abscesses, indicating that it could distinguish bacterial infection from sterile inflammation. Compared to ^99mTcN-CPFXDTC, the abscess/blood and abscess/muscle ratios of ^99mTcN-CPF2XT were higher and the uptakes of ^99mTcN-CPF2XT in the liver and lung were obviously decreased. The results suggested that ^99mTcN-CPF2XT would be a potential bacterial infection imaging agent. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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27 pages, 2440 KiB

Open AccessArticle

Rare-Earth Metal Complexes of the Antibacterial Drug Oxolinic Acid: Synthesis, Characterization, DNA/Protein Binding and Cytotoxicity Studies

by Ana-Madalina Maciuca, Alexandra-Cristina Munteanu, Mirela Mihaila, Mihaela Badea, Rodica Olar, George Mihai Nitulescu, Cristian V. A. Munteanu, Marinela Bostan and Valentina Uivarosi

Molecules 2020, 25(22), 5418; https://doi.org/10.3390/molecules25225418 - 19 Nov 2020

Cited by 15 | Viewed by 3810

Abstract

“Drug repositioning” is a current trend which proved useful in the search for new applications for existing, failed, no longer in use or abandoned drugs, particularly when addressing issues such as bacterial or cancer cells resistance to current therapeutic approaches. In this context, six new complexes of the first-generation quinolone oxolinic acid with rare-earth metal cations (Y³⁺, La³⁺, Sm³⁺, Eu³⁺, Gd³⁺, Tb³⁺) have been synthesized and characterized. The experimental data suggest that the quinolone acts as a bidentate ligand, binding to the metal ion via the keto and carboxylate oxygen atoms; these findings are supported by DFT (density functional theory) calculations for the Sm³⁺ complex. The cytotoxic activity of the complexes, as well as the ligand, has been studied on MDA-MB 231 (human breast adenocarcinoma), LoVo (human colon adenocarcinoma) and HUVEC (normal human umbilical vein endothelial cells) cell lines. UV-Vis spectroscopy and competitive binding studies show that the complexes display binding affinities (K_b) towards double stranded DNA in the range of 9.33 × 10⁴ − 10.72 × 10⁵. Major and minor groove-binding most likely play a significant role in the interactions of the complexes with DNA. Moreover, the complexes bind human serum albumin more avidly than apo-transferrin. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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9 pages, 1930 KiB

Open AccessCommunication

Mononuclear Perfluoroalkyl-Heterocyclic Complexes of Pd(II): Synthesis, Structural Characterization and Antimicrobial Activity

by Simona Rubino, Rosa Alduina, Patrizia Cancemi, Maria Assunta Girasolo, Vita Di Stefano, Santino Orecchio, Silvestre Buscemi and Ivana Pibiri

Molecules 2020, 25(19), 4487; https://doi.org/10.3390/molecules25194487 - 30 Sep 2020

Cited by 2 | Viewed by 2056

Abstract

Two mononuclear Pd(II) complexes [PdCl₂(pfptp)] (1) and [PdCl₂(pfhtp)] (2), with ligands 2-(3-perfluoropropyl-1-methyl-1,2,4-triazole-5yl)-pyridine (pfptp) and 2-(3-perfluoroheptyl-1-methyl-1,2,4-triazole-5yl)-pyridine (pfhtp), were synthesized and structurally characterized. The two complexes showed a bidentate coordination of the ligand occurring through N atom of pyridine ring and N4 atom of 1,2,4-triazole. Both complexes showed antimicrobial activity when tested against both Gram-negative and Gram-positive bacterial strains. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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22 pages, 3893 KiB

Open AccessArticle

Copper(II) Complexes with Mixed Heterocycle Ligands as Promising Antibacterial and Antitumor Species

by Arpad Mihai Rostas, Mihaela Badea, Lavinia L. Ruta, Ileana C. Farcasanu, Catalin Maxim, Mariana Carmen Chifiriuc, Marcela Popa, Mirela Luca, Natasa Celan Korosin, Romana Cerc Korosec, Mihaela Bacalum, Mina Raileanu and Rodica Olar

Molecules 2020, 25(17), 3777; https://doi.org/10.3390/molecules25173777 - 19 Aug 2020

Cited by 19 | Viewed by 5548

Abstract

Complexes with mixed ligands [Cu(N-N)₂(pmtp)](ClO₄)₂ ((1) N-N: 2,2′-bipyridine; (2) L: 1,10-phenanthroline and pmpt: 5-phenyl-7-methyl-1,2,4-triazolo[1,5-a]pyrimidine) were synthesized and structurally and biologically characterized. Compound (1) crystallizes into space group Pa and (2) in P-1. Both complexes display an intermediate stereochemistry between the two five-coordinated ones. The biological tests indicated that the two compounds exhibited superoxide scavenging capacity, intercalative DNA properties, and metallonuclease activity. Tests on various cell systems indicated that the two complexes neither interfere with the proliferation of Saccharomyces cerevisiae or BJ healthy skin cells, nor cause hemolysis in the active concentration range. Nevertheless, the compounds showed antibacterial potential, with complex (2) being significantly more active than complex (1) against all tested bacterial strains, both in planktonic and biofilm growth state. Both complexes exhibited a very good activity against B16 melanoma cells, with a higher specificity being displayed by compound (1). Taken together, the results indicate that complexes (1) and (2) have specific biological relevance, with potential for the development of antitumor or antimicrobial drugs. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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17 pages, 3676 KiB

Open AccessArticle

Synthesis, Characterization and Biological Evaluation of Metal Adamantyl 2-Pyridylhydrazone Complexes

by Ihsan A. Shehadi, Fatima-Azzahra Delmani, Areej M. Jaber, Hana Hammad, Murad A. AlDamen, Raed A. Al-Qawasmeh and Monther A. Khanfar

Molecules 2020, 25(11), 2530; https://doi.org/10.3390/molecules25112530 - 29 May 2020

Cited by 12 | Viewed by 2691

Abstract

Four new complexes derived from adamantly containing hydrazone (APH) ligand with Cu(II) (1), Co(II) (2), Ni(II) (3) and Zn(II) (4), have been synthesized and characterized using different physicochemical methods. The structure of the ligand APH and its copper complex 1 have been established by single-crystal X-ray diffraction direct methods, which reveal that complex 1 has distorted square-pyramidal geometry. Complexes 1–4 are screened against seven human cancer cell lines namely, breast cancer cell lines (MCF7, T47D, MDA-MB-231), prostate cancer cell lines (PC3, DU145) and the colorectal cancer cell line Coco-2, for their antiproliferative activities. Complex 1 has shown a promising anticancer activity compared to the other ones. The structural and spectroscopic analysis of APH and its complexes are confirmed by DFT calculations. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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27 pages, 3166 KiB

Open AccessFeature PaperReview

Improvement in the Pharmacological Profile of Copper Biological Active Complexes by Their Incorporation into Organic or Inorganic Matrix

by Mihaela Badea, Valentina Uivarosi and Rodica Olar

Molecules 2020, 25(24), 5830; https://doi.org/10.3390/molecules25245830 - 10 Dec 2020

Cited by 21 | Viewed by 3672

Abstract

Every year, more Cu(II) complexes are proven to be biologically active species, but very few are developed as drugs or entered in clinical trials. This is due to their poor water solubility and lipophilicity, low stability as well as in vivo inactivation. The possibility to improve their pharmacological and/or oral administration profile by incorporation into inorganic or organic matrix was studied. Most of them are either physically encapsulated or conjugated to the matrix via a moiety able to coordinate Cu(II). As a result, a large variety of species were developed as delivery carriers. The organic carriers include liposomes, synthetic or natural polymers or dendrimers, while the inorganic ones are based on carbon nanotubes, hydrotalcite and silica. Some hybrid organic-inorganic materials based on alginate-carbonate, gold-PEG and magnetic mesoporous silica-Schiff base were also developed for this purpose. Full article

(This article belongs to the Special Issue New Trends in Developing Complexes as Biological Active Species)

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