International Journal of Molecular Sciences

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20 pages, 13626 KiB

Open AccessArticle

Synthesis, DFT, Biological and Molecular Docking Analysis of Novel Manganese(II), Iron(III), Cobalt(II), Nickel(II), and Copper(II) Chelate Complexes Ligated by 1-(4-Nitrophenylazo)-2-naphthol

by Yousef A. A. Alghuwainem, Hany M. Abd El-Lateef, Mai M. Khalaf, Amer A. Amer, Antar A. Abdelhamid, Ahmed A. Alzharani, Anas Alfarsi, Saad Shaaban, Mohamed Gouda and Aly Abdou

Int. J. Mol. Sci. 2022, 23(24), 15614; https://doi.org/10.3390/ijms232415614 - 9 Dec 2022

Cited by 41 | Viewed by 2727

Abstract

Novelmanganese(II), iron(III), cobalt(II), nickel(II), and copper(II) chelates were synthesized and studied using elemental analysis (EA), infrared spectroscopy, mass spectrometry, ultraviolet-visible spectroscopy, and conductivity, as well as magnetic measurements and thermogravimetric analysis (TG). The azo-ligand 1-[(4-nitrophenyl)diazenyl]-2-naphthol (HL) chelates to the metal ions via the [...] Read more.

Novelmanganese(II), iron(III), cobalt(II), nickel(II), and copper(II) chelates were synthesized and studied using elemental analysis (EA), infrared spectroscopy, mass spectrometry, ultraviolet-visible spectroscopy, and conductivity, as well as magnetic measurements and thermogravimetric analysis (TG). The azo-ligand 1-[(4-nitrophenyl)diazenyl]-2-naphthol (HL) chelates to the metal ions via the nitrogen and oxygen centers of the azo group and the hydroxyl, respectively. The amounts of H₂O present and its precise position were identified by thermal analysis. Density functional theory (DFT) was employed to theoretically elucidate the molecular structures of the ligand and the metal complexes. Furthermore, the quantum chemical parameters were also evaluated. The antimicrobial properties were evaluated against a group of fungal and bacterial microbes. Interestingly, the bioactivity of the complexes is enhanced compared to free ligands. Within this context, the CuL complex manifested the lowest activity, whereas the FeL complex had the greatest. Molecular docking was used to foretell the drugs’ binding affinity for the structure of Escherichia coli (PDB ID: 1hnj). Protein-substrate interactions were resolved, and binding energies were accordingly calculated. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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12 pages, 2857 KiB

Open AccessArticle

Coordination Chemistry of Phosphate Groups in Systems Including Copper(II) Ions, Phosphoethanolamine and Pyrimidine Nucleotides

by Malwina Gabryel-Skrodzka, Martyna Nowak, Anna Teubert and Renata Jastrzab

Int. J. Mol. Sci. 2022, 23(22), 13718; https://doi.org/10.3390/ijms232213718 - 8 Nov 2022

Cited by 5 | Viewed by 1627

Abstract

The activity of phosphate groups of phosphoethanolamine and pyrimidine nucleotides (thymidine 5-monophosphate, cytidine 5-monophosphate and uridine 5’monophosphate) in the process of complexation metal ions in aqueous solution was studied. Using the potentiometric method with computer calculation of the data and spectroscopic methods such [...] Read more.

The activity of phosphate groups of phosphoethanolamine and pyrimidine nucleotides (thymidine 5-monophosphate, cytidine 5-monophosphate and uridine 5’monophosphate) in the process of complexation metal ions in aqueous solution was studied. Using the potentiometric method with computer calculation of the data and spectroscopic methods such as UV-Vis, EPR, ¹³C and ³¹P NMR as well as FT-IR, the overall stability constants of the complexes as well as coordination modes were obtained. At lower pH, copper(II) ions are complexed only by phosphate groups, whereas the endocyclic nitrogen atom of nucleotides has been identified as a negative center interacting with the -NH₃⁺ groups of phosphoethanolamine. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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15 pages, 2441 KiB

Open AccessArticle

Synthesis and Biological Studies of Novel Aminophosphonates and Their Metal Carbonyl Complexes (Fe, Ru)

by Aneta Kosińska, David Virieux, Jean-Luc Pirat, Kamila Czarnecka, Małgorzata Girek, Paweł Szymański, Sławomir Wojtulewski, Saranya Vasudevan, Arkadiusz Chworos and Bogna Rudolf

Int. J. Mol. Sci. 2022, 23(15), 8091; https://doi.org/10.3390/ijms23158091 - 22 Jul 2022

Cited by 4 | Viewed by 2252

Abstract

The quest to find new inhibitors of biologically relevant targets is considered an important strategy to introduce new drug candidates for the treatment of neurodegenerative diseases. A series of (aminomethyl)benzylphosphonates 8a–c and their metallocarbonyl iron 9a–c and ruthenium 10a [...] Read more.

The quest to find new inhibitors of biologically relevant targets is considered an important strategy to introduce new drug candidates for the treatment of neurodegenerative diseases. A series of (aminomethyl)benzylphosphonates 8a–c and their metallocarbonyl iron 9a–c and ruthenium 10a–c complexes were designed, synthesized, and evaluated for their inhibitory potentials against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) by determination of IC₅₀. Metallocarbonyl derivatives, in general, did not show significant inhibition activity against these enzymes, the most potent inhibitor was the (aminomethyl)benzylphosphonate 8a (IC₅₀ = 1.215 µM against AChE). Molecular docking analysis of AChE and (aminomethyl)benzylphosphonates 8a–c showed the strongest interactions of 8a and AChE compared to isomers 8b and 8c. Cytotoxicity studies of synthesized compounds towards the V79 cell line were also performed and discussed. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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19 pages, 3943 KiB

Open AccessArticle

Zinc Coordination Compounds with Benzimidazole Derivatives: Synthesis, Structure, Antimicrobial Activity and Potential Anticancer Application

by Anita Raducka, Marcin Świątkowski, Izabela Korona-Głowniak, Barbara Kaproń, Tomasz Plech, Małgorzata Szczesio, Katarzyna Gobis, Małgorzata Iwona Szynkowska-Jóźwik and Agnieszka Czylkowska

Int. J. Mol. Sci. 2022, 23(12), 6595; https://doi.org/10.3390/ijms23126595 - 13 Jun 2022

Cited by 21 | Viewed by 3494

Abstract

Developing new, smart drugs with the anticancer activity is crucial, especially for cancers, which cause the highest mortality in humans. In this paper we describe a series of coordination compounds with the element of health, zinc, and bioactive ligands, benzimidazole derivatives. By way [...] Read more.

Developing new, smart drugs with the anticancer activity is crucial, especially for cancers, which cause the highest mortality in humans. In this paper we describe a series of coordination compounds with the element of health, zinc, and bioactive ligands, benzimidazole derivatives. By way of synthesis we have obtained four compounds named C1, C2, C4 and C4. Analytical analyses (elemental analysis (EA), flame atomic absorption spectrometry (FAAS)), spectroscopic (Fourier transform infrared spectroscopy (FT-IR), mass spectrometry (MS)) and thermogravimetric (TG) methods and the definition of crystal structures were used to explore the nature of bonding and to elucidate the chemical structures. The collected analytical data allowed the determination of the stoichiometry in coordination compounds, thermal stability, crystal structure and way of bonding. The cytotoxicity effect of the new compounds as a potential antitumor agent on the glioblastoma (T98G), neuroblastoma (SK-N-AS) and lung adenocarcinoma (A549) cell lines and human normal skin fibroblasts (CCD-1059Sk) was also determined. Cell viability was determined by the MTT assay. The results obtained confirmed that conversion of ligands into the respective metal complexes significantly improved their anticancer properties. The complexes were screened for antibacterial and antifungal activities. The ADME technique was used to determine the physicochemical and biological properties. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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30 pages, 29943 KiB

Open AccessArticle

Development of Metal Complexes for Treatment of Coronaviruses

by Hany M. Abd El-Lateef, Tarek El-Dabea, Mai M. Khalaf and Ahmed M. Abu-Dief

Int. J. Mol. Sci. 2022, 23(12), 6418; https://doi.org/10.3390/ijms23126418 - 8 Jun 2022

Cited by 34 | Viewed by 3020

Abstract

Coronavirus disease (SARS-CoV-2) is a global epidemic. This pandemic, which has been linked to high rates of death, has forced some countries throughout the world to implement complete lockdowns in order to contain the spread of infection. Because of the advent of new [...] Read more.

Coronavirus disease (SARS-CoV-2) is a global epidemic. This pandemic, which has been linked to high rates of death, has forced some countries throughout the world to implement complete lockdowns in order to contain the spread of infection. Because of the advent of new coronavirus variants, it is critical to find effective treatments and vaccines to prevent the virus’s rapid spread over the world. In this regard, metal complexes have attained immense interest as antibody modifiers and antiviral therapies, and they have a lot of promise towards SARS-CoV-2 and their suggested mechanisms of action are discussed, i.e., a new series of metal complexes’ medicinal vital role in treatment of specific proteins or SARS-CoV-2 are described. The structures of the obtained metal complexes were fully elucidated by different analytical and spectroscopic techniques also. Molecular docking and pharmacophore studies presented that most of complexes studied influenced good binding affinity to the main protease SARS-CoV-2, which also was attained as from the RCSB pdb (Protein Data Bank) data PDB ID: 6 W41, to expect the action of metal complexes in contradiction of COVID-19. Experimental research is required to determine the pharmacokinetics of most of the complexes analyzed for the treatment of SARS-CoV-2-related disease. Finally, the toxicity of a metal-containing inorganic complex will thus be discussed by its capability to transfer metals which may bind with targeted site. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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19 pages, 2112 KiB

Open AccessArticle

New Metallophthalocyanines Bearing 2-Methylimidazole Moieties—Potential Photosensitizers against Staphylococcus aureus

by Marcin Wierzchowski, Daniel Ziental, Dawid Łażewski, Artur Korzanski, Agnieszka Gielara-Korzanska, Ewa Tykarska, Jolanta Dlugaszewska and Lukasz Sobotta

Int. J. Mol. Sci. 2022, 23(11), 5910; https://doi.org/10.3390/ijms23115910 - 25 May 2022

Cited by 4 | Viewed by 1813

Abstract

Newly developed tetra- and octasubstituted methimazole-phthalocyanine conjugates as potential photosensitizers have been obtained. Synthesized intermediates and final products were characterized by the MALD-TOF technique and various NMR techniques, including 2D methods. Single-crystal X-ray diffraction was used to determine the crystal structures of dinitriles. [...] Read more.

Newly developed tetra- and octasubstituted methimazole-phthalocyanine conjugates as potential photosensitizers have been obtained. Synthesized intermediates and final products were characterized by the MALD-TOF technique and various NMR techniques, including 2D methods. Single-crystal X-ray diffraction was used to determine the crystal structures of dinitriles. The studied phthalocyanines revealed two typical absorption bands—the Soret band and the Q band. The most intense fluorescence was observed for octasubstituted magnesium(II) phthalocyanine in DMF (Φ_FL = 0.022). The best singlet oxygen generators were octasubstituted magnesium(II) and zinc(II) phthalocyanines (Φ_∆ 0.56 and 0.81, respectively). The studied compounds presented quantum yields of photodegradation at the level between 10⁻⁵ and 10⁻⁶. Due to their low solubility in a water environment, the liposomal formulations were prepared. Within the studied group, octasubstituted zinc(II) phthalocyanine at the concentration of 100 µM activated with red light showed the highest antibacterial activity against S. aureus equal to a 5.68 log reduction of bacterial growth. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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23 pages, 61700 KiB

Open AccessArticle

Fabrication, DFT Calculation, and Molecular Docking of Two Fe(III) Imine Chelates as Anti-COVID-19 and Pharmaceutical Drug Candidate

by Hany M. Abd El-Lateef, Mai M. Khalaf, Mohamed R. Shehata and Ahmed M. Abu-Dief

Int. J. Mol. Sci. 2022, 23(7), 3994; https://doi.org/10.3390/ijms23073994 - 3 Apr 2022

Cited by 45 | Viewed by 3472

Abstract

Two tetradentate dibasic chelating Schiff base iron (III) chelates were prepared from the reaction of 2,2′-((1E,1′E)-(1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromophenol) (PDBS) and 2,2′-((1E,1′E)-((4-chloro-1,2-phenylene)bis(azanylylidene))-bis(methanylylidene))bis(4-bromophenol) (CPBS) with Fe³⁺ ions. The prepared complexes were fully characterized with spectral and physicochemical tools such as IR, NMR, CHN analysis, TGA, UV-visible [...] Read more.

Two tetradentate dibasic chelating Schiff base iron (III) chelates were prepared from the reaction of 2,2′-((1E,1′E)-(1,2-phenylenebis(azanylylidene))bis(methanylylidene))bis(4-bromophenol) (PDBS) and 2,2′-((1E,1′E)-((4-chloro-1,2-phenylene)bis(azanylylidene))-bis(methanylylidene))bis(4-bromophenol) (CPBS) with Fe³⁺ ions. The prepared complexes were fully characterized with spectral and physicochemical tools such as IR, NMR, CHN analysis, TGA, UV-visible spectra, and magnetic moment measurements. Moreover, geometry optimizations for the synthesized ligands and complexes were conducted using the Gaussian09 program through the DFT approach, to find the best structures and key parameters. The prepared compounds were tested as antimicrobial agents against selected strains of bacteria and fungi. The results suggests that the CPBSFe complex has the highest activity, which is close to the reference. An MTT assay was used to screen the newly synthesized compounds against a variety of cell lines, including colon cancer cells, hepatic cellular carcinoma cells, and breast carcinoma cells. The results are expressed by IC50 value, in which the 48 µg/mL value of the CPBSFe complex indicates its success as a potential anticancer agent. The antioxidant behavior of the two imine chelates was studied by DPPH assay. All the tested imine complexes show potent antioxidant activity compared to the standard Vitamin C. Furthermore, the in vitro assay and the mechanism of binding and interaction efficiency of the tested samples with the receptor of COVID-19 core protease viral protein (PDB ID: 6lu7) and the receptor of Gram-negative bacteria (Escherichia coli, PDB ID: 1fj4) were investigated using molecular docking experiments. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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Review

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22 pages, 11363 KiB

Open AccessReview

NSAID-Based Coordination Compounds for Biomedical Applications: Recent Advances and Developments

by Ariana C. F. Santos, Luís P. G. Monteiro, Adriana C. C. Gomes, Fátima Martel, Teresa M. Santos and Bárbara J. M. Leite Ferreira

Int. J. Mol. Sci. 2022, 23(5), 2855; https://doi.org/10.3390/ijms23052855 - 5 Mar 2022

Cited by 22 | Viewed by 4789

Abstract

After the serendipitous discovery of cisplatin, a platinum-based drug with chemotherapeutic effects, an incredible amount of research in the area of coordination chemistry has been produced. Other transition metal compounds were studied, and several new relevant metallodrugs have been synthetized in the past [...] Read more.

After the serendipitous discovery of cisplatin, a platinum-based drug with chemotherapeutic effects, an incredible amount of research in the area of coordination chemistry has been produced. Other transition metal compounds were studied, and several new relevant metallodrugs have been synthetized in the past few years. This review is focused on coordination compounds with first-row transition metals, namely, copper, cobalt, nickel or manganese, or with zinc, which have potential or effective pharmacological properties. It is known that metal complexes, once bound to organic drugs, can enhance the drugs’ biological activities, such as anticancer, antimicrobial or anti-inflammatory ones. NSAIDs are a class of compounds with anti-inflammatory properties used to treat pain or fever. NSAIDs’ properties can be strongly improved when included in complexes using their compositional N and O donor atoms, which facilitate their coordination to metal ions. This review focuses on the research on this topic and on the promising or effective results that complexes of first-row transition metals and NSAIDs can exhibit. Full article

(This article belongs to the Special Issue Novel Metal Coordination Complexes for Biomedical Applications)

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