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Metal-Based Complex: Preparation and Medicinal Characteristics
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Metal-Based Complex: Preparation and Medicinal Characteristics

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

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 33837

Special Issue Editors

Prof. Dr. Saied Soliman

E-Mail Website
Guest Editor
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
Interests: X-ray crystallography; coordination compounds; metal-based drugs; DFT; Hirshfeld; pincer ligands
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Ayman El-Faham

E-Mail Website
Guest Editor
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
Interests: amino acids; peptide synthesis; small bioactive molecules; pincer ligands
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Assem Barakat

E-Mail Website1 Website2
Guest Editor
Department of Chemistry, King Saud University, Riyadh 11451, Saudi Arabia
Interests: drug discovery; protein–protein interaction inhibitor; organic synthesis of biological active compounds; asymmetric synthesis; X-ray single crystallography
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Metal complexes are receiving undue interest from researchers due to their diverse range of medicinal applications. Numerous metal-based drugs are proven to be highly effective as medicine, such as in the case of cisplatin, which is the most widely used anticancer drug. The successful application of cisplatin in chemotherapy has motivated researchers to synthesize more types of Pt(II) complexes and led to the research being extending to the construction of complexes based on other metals (such as palladium, silver, tin, antimony, rhodium, boron, etc.) for use as antitumor drugs. Moreover, silver sulfadiazine is being used to prevent and treat infections due to second- and third-degree burns. This is especially relevant where commercially available organic antibiotics cannot be used in treatment due to problems related to multidrug-resistant (MDR) microbes. Hence, a great deal of interest is focused on the synthesis of metal-based drugs as alternatives for the common organic antibiotics to address the issue of MDR microbes.

This Special Issue of Molecules, entitled “Metal-Based Complexes: Preparation and Medicinal Characteristics”, will cover a selection of recent research studies and review articles in the field of metal-based complexes, including their synthetic protocols and medicinal applications—including as diagnostic agents—in the context of numerous diseases, such as cancers, diabetes, and osteoporosis.

Prof. Dr. Saied Soliman
Prof. Dr. Ayman El-Faham
Prof. Dr. Assem Barakat
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • coordination chemistry
  • metals in medicine
  • organometallics
  • anticancer agents
  • antibacterial agents
  • chelation therapy
  • metalloantibiotics for MDR microbes

Published Papers (18 papers)

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Research

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14 pages, 4549 KiB  
Article
Exploring the Mechanisms behind the Anti-Tumoral Effects of Model C-Scorpionate Complexes
by Pedro M. G. Silva, Pedro F. Pinheiro, Sérgio P. Camões, Ana P. C. Ribeiro, Luísa M. D. R. S. Martins, Joana P. G. Miranda and Gonçalo C. Justino
Molecules 2023, 28(14), 5451; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28145451 - 17 Jul 2023
Viewed by 938
Abstract
The growing worldwide cancer incidence, coupled to the increasing occurrence of multidrug cancer resistance, requires a continuous effort towards the identification of new leads for cancer management. In this work, two C-scorpionate complexes, [FeCl2(κ3-Tpm)] (1) and [...] Read more.
The growing worldwide cancer incidence, coupled to the increasing occurrence of multidrug cancer resistance, requires a continuous effort towards the identification of new leads for cancer management. In this work, two C-scorpionate complexes, [FeCl2(κ3-Tpm)] (1) and [Co(κ3-TpmOH)2](NO3)2 (2), (Tpm = hydrotris(pyrazol-1-yl)methane and TpmOH = 2,2,2-tris(pyrazol-1-yl)ethanol), were studied as potential scaffolds for future anticancer drug development. Their cytotoxicity and cell migration inhibitory activity were analyzed, and an untargeted metabolomics approach was employed to elucidate the biological processes significantly affected by these two complexes, using two tumoral cell lines (B16 and HCT116) and a non-tumoral cell line (HaCaT). While [FeCl2(κ3-Tpm)] did not display a significant cytotoxicity, [Co(κ3-TpmOH)2](NO3)2 was particularly cytotoxic against the HCT116 cell line. While [Co(κ3-TpmOH)2](NO3)2 significantly inhibited cell migration in all tested cell lines, [FeCl2(κ3-Tpm)] displayed a mixed activity. From a metabolomics perspective, exposure to [FeCl2(κ3-Tpm)] was associated with changes in various metabolic pathways involving tyrosine, where iron-dependent enzymes are particularly relevant. On the other hand, [Co(κ3-TpmOH)2](NO3)2 was associated with dysregulation of cell adhesion and membrane structural pathways, suggesting that its antiproliferative and anti-migration properties could be due to changes in the overall cellular adhesion mechanisms. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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19 pages, 2099 KiB  
Article
Synthesis, Crystal Structure, Antibacterial and In Vitro Anticancer Activity of Novel Macroacyclic Schiff Bases and Their Cu (II) Complexes Derived from S-Methyl and S-Benzyl Dithiocarbazate
by Mohammed Khaled Bin Break, Tan Yew Fung, May Zie Koh, Wan Yong Ho, Mohamed Ibrahim Mohamed Tahir, Omar Ashraf Elfar, Rahamat Unissa Syed, Weam M. A. Khojali, Turki Mubarak Alluhaibi, Bader Huwaimel, Christophe Wiart and Teng-Jin Khoo
Molecules 2023, 28(13), 5009; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28135009 - 26 Jun 2023
Cited by 1 | Viewed by 1450
Abstract
A series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with S-methyl dithiocarbazate (SMDTC) and S-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were [...] Read more.
A series of novel macroacyclic Schiff base ligands and their Cu (II) complexes were synthesised via reacting dicarbonyls of varying chain lengths with S-methyl dithiocarbazate (SMDTC) and S-benzyl dithiocarbazate (SBDTC) followed by coordination with Cu (II) ions. X-ray crystal structures were obtained for compound 4, an SBDTC-diacetyl analogue, and Cu7, an SMDTC-hexanedione Cu (II) complex. Anticancer evaluation of the compounds showed that Cu1, an SMDTC-glyoxal complex, demonstrated the highest cytotoxic activity against MCF-7 and MDA-MB-231 breast cancer cells with IC50 values of 1.7 µM and 1.4 µM, respectively. There was no clear pattern observed between the effect of chain length and cytotoxic activity; however, SMDTC-derived analogues were more active than SBDTC-derived analogues against MDA-MB-231 cells. The antibacterial assay showed that K. rhizophila was the most susceptible bacteria to the compounds, followed by S. aureus. Compound 4 and the SMDTC-derived analogues 3, 5, Cu7 and Cu9 possessed the highest antibacterial activity. These active analogues were further assessed, whereby 3 possessed the highest antibacterial activity with an MIC of <24.4 µg/mL against K. rhizophila and S. aureus. Further antibacterial studies showed that at least compounds 4 and 5 were bactericidal. Thus, Cu1 and 3 were the most promising anticancer and antibacterial agents, respectively. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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18 pages, 5970 KiB  
Article
Antitumor and Antibacterial Activity of Ni(II), Cu(II), Ag(I), and Hg(II) Complexes with Ligand Derived from Thiosemicarbazones: Characterization and Theoretical Studies
by Heba Alshater, Ahlam I. Al-Sulami, Samar A. Aly, Ehab M. Abdalla, Mohamed A. Sakr and Safaa S. Hassan
Molecules 2023, 28(6), 2590; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28062590 - 13 Mar 2023
Cited by 10 | Viewed by 1663
Abstract
Four new complexes (Ni2+, Cu2+, Ag+, and Hg2+) were prepared from the ligand N-(4-chlorophenyl)-2-(phenylglycyl)hydrazine-1-carbothioamide (H2L). Analytical and spectroscopic techniques were used to clarify the structural composition of the new chelates. In addition, all [...] Read more.
Four new complexes (Ni2+, Cu2+, Ag+, and Hg2+) were prepared from the ligand N-(4-chlorophenyl)-2-(phenylglycyl)hydrazine-1-carbothioamide (H2L). Analytical and spectroscopic techniques were used to clarify the structural composition of the new chelates. In addition, all chelates were tested against bacterial strains and the HepG2 cell line to determine their antiseptic and carcinogenic properties. The Ni(II) complex was preferable to the other chelates. Molecular optimization revealed that H2L had the highest reactivity, followed by Hg-chelate, Ag-chelate, Ni-chelate, and Cu-chelate. Moreover, molecular docking was investigated against two different proteins: the ribosyltransferase enzyme (code: 3GEY) and the EGFR tyrosine kinase receptor (code: 1m17). Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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23 pages, 4521 KiB  
Article
Fabrication and Evaluation of Polyvinyl Alcohol/Corn Starch/Patchouli Oil Hydrogel Films Loaded with Silver Nanoparticles Biosynthesized in Pogostemon cablin Benth Leaves’ Extract
by Khairan Khairan, Miftahul Hasan, Rinaldi Idroes and Muhammad Diah
Molecules 2023, 28(5), 2020; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28052020 - 21 Feb 2023
Cited by 5 | Viewed by 2482
Abstract
Research on the manufacture of hydrogel films from polyvinyl alcohol, corn starch, patchouli oil, and silver nanoparticles, (PVA/CS/PO/AgNPs, respectively) was completed. The silver nanoparticles used in this study resulted from green synthesis using local patchouli plants (Pogostemon cablin Benth). Aqueous patchouli leaf [...] Read more.
Research on the manufacture of hydrogel films from polyvinyl alcohol, corn starch, patchouli oil, and silver nanoparticles, (PVA/CS/PO/AgNPs, respectively) was completed. The silver nanoparticles used in this study resulted from green synthesis using local patchouli plants (Pogostemon cablin Benth). Aqueous patchouli leaf extract (APLE) and methanol patchouli leaf extract (MPLE) are used in the synthesis of phytochemicals (green synthesis), which are then blended in the production of PVA/CS/PO/AgNPs hydrogel films, which are then cross linked with glutaraldehyde. The results demonstrated that the hydrogel film was flexible, easy to fold, and free of holes and air bubbles. The presence of hydrogen bonds between the functional groups of PVA, CS, and PO was revealed using FTIR spectroscopy. SEM analysis revealed that the hydrogel film was slightly agglomerated and did not exhibit cracking or pinholes. The analysis of pH, spreadability, gel fraction, and swelling index showed that the resulting PVA/CS/PO/AgNP hydrogel films met expected standards except for the organoleptic properties of the resulting colors, which tended to be slightly darker in color. The formula with silver nanoparticles synthesized in methanolic of patchouli leaf extract (AgMENPs) had the highest thermal stability compared to hydrogel films with silver nanoparticles synthesized in aqueous of patchouli leaf extract (AgAENPs). The hydrogel films can be safely used up to 200 °C. The antibacterial studies revealed that the films inhibited the growth of both Staphylococcus aureus and Staphylococcus epidermis, as determined by the disc diffusion method, with the best antibacterial activity being against Staphylococcus aureus. In conclusion, the hydrogel film F1, loaded with silver nanoparticles biosynthesized in aqueous of patchouli leave extract (AgAENPs) and light fraction of patchouli oil (LFoPO) performed the best activity against both Staphylococcus aureus and Staphylococcus epidermis. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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14 pages, 11578 KiB  
Article
Development of Wireless Power-Transmission-Based Photodynamic Therapy for the Induction of Cell Death in Cancer Cells by Cyclometalated Iridium(III) Complexes
by Kenta Yokoi, Yoshitaka Yasuda, Azusa Kanbe, Takehiro Imura and Shin Aoki
Molecules 2023, 28(3), 1433; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28031433 - 02 Feb 2023
Cited by 5 | Viewed by 1885
Abstract
Photodynamic therapy (PDT), a noninvasive method for cancer therapy, involves the generation of reactive oxygen species (ROS) by the photochemical excitation of photosensitizers (PSs) to induce cell death in cancer cells. A variety of PS including porphyrin derivatives and metal complexes such as [...] Read more.
Photodynamic therapy (PDT), a noninvasive method for cancer therapy, involves the generation of reactive oxygen species (ROS) by the photochemical excitation of photosensitizers (PSs) to induce cell death in cancer cells. A variety of PS including porphyrin derivatives and metal complexes such as iridium (Ir) complexes have been reported. In clinical trials, red-near infrared (NIR) light (650–900 nm) is preferred for the excitation of PSs due to its deeper penetration into tissues compared with visible light (400–500 nm). To overcome this limitation, we established a PDT system that uses cyclometalated iridium(III) (Ir(III)) complexes that are excited with blue light in the wireless power transmission (WPT) system. To achieve this, we developed a light-emitting diode (LED) light device equipped with a receiver coil that receives electricity from the transmitter coil through magnetic resonance coupling. The LEDs in the receiving device use blue light (470 nm) to irradiate a given Ir(III) complex and excite triplet oxygen (3O2) to singlet oxygen (1O2) which induces cell death in HeLa S3 cells (human cervical carcinoma cells). The results obtained in this study suggest that WPT-based PDT represents a potentially new method for the treatment of tumors by a non-battery LED, which are otherwise difficult to treat by previous PDT systems. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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14 pages, 3973 KiB  
Article
Green Synthesis of Flower-Like Carrageenan-Silver Nanoparticles and Elucidation of Its Physicochemical and Antibacterial Properties
by Syafiqah Syazwani Jaffar, Suryani Saallah, Mailin Misson, Shafiquzzaman Siddiquee, Jumardi Roslan and Wuled Lenggoro
Molecules 2023, 28(2), 907; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28020907 - 16 Jan 2023
Cited by 8 | Viewed by 2380
Abstract
Herein, we report the green synthesis of flower-like carrageenan-silver nanoparticles (c-AgNPs) through a facile hydrothermal reaction at 90 °C for 2 h. The reduction of silver nitrate (AgNO3) to c-AgNPs was evident by the colour change of the solution from colourless [...] Read more.
Herein, we report the green synthesis of flower-like carrageenan-silver nanoparticles (c-AgNPs) through a facile hydrothermal reaction at 90 °C for 2 h. The reduction of silver nitrate (AgNO3) to c-AgNPs was evident by the colour change of the solution from colourless to dark brown and further confirmed by a UV-Vis surface plasmon resonance (SPR) peak at ~420 nm. The FTIR spectra showed that the abundance of functional groups present in the carrageenan were responsible for the reduction and stabilisation of the c-AgNPs. The XRD pattern confirmed the crystalline nature and face-centred cubic structure of the c-AgNPs, while the EDX analysis showed the presence of a high composition of elemental silver (85.87 wt%). Interestingly, the morphological characterisations by SEM and FE-SEM revealed the formation of flower-like c-AgNPs composed of intercrossed and random lamellar petals of approximately 50 nm in thickness. The growth mechanism of flower-like c-AgNPs were elucidated based on the TEM and AFM analyses. The c-AgNPs displayed promising antibacterial properties against E. coli and S. aureus, with zones of inhibition ranging from 8.0 ± 0.0 to 11.7 ± 0.6 mm and 7.3 ± 0.6 to 9.7 ± 0.6 mm, respectively, as the concentration of c-AgNPs increased from 0.1 to 4 mg/mL. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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25 pages, 4686 KiB  
Article
Synthesis, Characterization and Biological Investigations of Half-Sandwich Ruthenium(II) Complexes Containing Benzimidazole Moiety
by Patrycja Rogala, Agnieszka Jabłońska-Wawrzycka, Grzegorz Czerwonka, Katarzyna Kazimierczuk, Katarzyna Gałczyńska, Sławomir Michałkiewicz, Justyna Kalinowska-Tłuścik, Marta Karpiel and Karel D. Klika
Molecules 2023, 28(1), 40; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28010040 - 21 Dec 2022
Cited by 4 | Viewed by 2289
Abstract
Half-sandwich Ru(II) complexes belong to group of biologically active metallo-compounds with promising antimicrobial and anticancer activity. Herein, we report the synthesis and characterization of arene ruthenium complexes containing benzimidazole moiety, namely, [(η6-p-cymene)RuCl(bimCOO)] (1) and [(η6- [...] Read more.
Half-sandwich Ru(II) complexes belong to group of biologically active metallo-compounds with promising antimicrobial and anticancer activity. Herein, we report the synthesis and characterization of arene ruthenium complexes containing benzimidazole moiety, namely, [(η6-p-cymene)RuCl(bimCOO)] (1) and [(η6-p-cymene)RuCl2(bim)] (2) (where bimCOO = benzimidazole-2-carboxylate and bim = 1-H-benzimidazole). The compounds were characterized by 1H NMR, 13C NMR, IR, UV–vis and CV. Molecular structures of the complexes were determined by SC-XRD analysis, and the results indicated the presence of a pseudo-tetrahedral (piano stool) geometry. Interactions in the crystals of the Ru complexes using the Hirshfeld surface analysis were also examined. In addition, the biological studies of the complexes, such as antimicrobial assays (against planktonic and adherent microbes), cytotoxicity and lipophilicity, were performed. Antibacterial activity of the complexes was evaluated against S. aureus, E. coli, P. aeruginosa PAO1 and LES B58. Cytotoxic activity was tested against primary human fibroblasts and adenocarcinoma human alveolar basal epithelial cells. Obtained biological results show that the ruthenium compounds have bacteriostatic activity toward Pseudomonas aeruginosa PAO1 strain and are not toxic to normal cells. A molecular docking study was applied as a predictive source of information about the plausibility of examined structures binding with HSA as a transporting system. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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18 pages, 3992 KiB  
Article
Copper(II) Complexes of 5–Fluoro–Salicylaldehyde: Synthesis, Characterization, Antioxidant Properties, Interaction with DNA and Serum Albumins
by Zisis Papadopoulos, Efstratia Doulopoulou, Ariadni Zianna, Antonios G. Hatzidimitriou and George Psomas
Molecules 2022, 27(24), 8929; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27248929 - 15 Dec 2022
Cited by 4 | Viewed by 1639
Abstract
The synthesis, characterization and biological profile (antioxidant capacity, interaction with calf-thymus DNA and serum albumins) of five neutral copper(II) complexes of 5–fluoro–salicylaldehyde in the absence or presence of the N,N’–donor co–ligands 2,2′–bipyridylamine, 2,9–dimethyl–1,10–phenanthroline, 1,10–phenanthroline and 2,2′–bipyridine are presented herein. The [...] Read more.
The synthesis, characterization and biological profile (antioxidant capacity, interaction with calf-thymus DNA and serum albumins) of five neutral copper(II) complexes of 5–fluoro–salicylaldehyde in the absence or presence of the N,N’–donor co–ligands 2,2′–bipyridylamine, 2,9–dimethyl–1,10–phenanthroline, 1,10–phenanthroline and 2,2′–bipyridine are presented herein. The compounds were characterized by physicochemical and spectroscopic techniques. The crystal structures of four complexes were determined by single-crystal X-ray crystallography. The ability of the complexes to scavenge 1,1–diphenyl–picrylhydrazyl and 2,2′–azinobis(3–ethylbenzothiazoline–6–sulfonic acid) radicals and to reduce H2O2 was investigated in order to evaluate their antioxidant activity. The interaction of the compounds with calf-thymus DNA possibly takes place via intercalation as suggested by UV–vis spectroscopy and DNA–viscosity titration studies and via competitive studies with ethidium bromide. The affinity of the complexes with bovine and human serum albumins was examined by fluorescence emission spectroscopy revealing the tight and reversible binding of the complexes with the albumins. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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12 pages, 1757 KiB  
Article
α-Diimine Cisplatin Derivatives: Synthesis, Structure, Cyclic Voltammetry and Cytotoxicity
by Dmitriy S. Yambulatov, Irina A. Lutsenko, Stanislav A. Nikolaevskii, Pavel A. Petrov, Ivan V. Smolyaninov, Irina K. Malyants, Victoria O. Shender, Mikhail A. Kiskin, Alexey A. Sidorov, Nadezhda T. Berberova and Igor L. Eremenko
Molecules 2022, 27(23), 8565; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27238565 - 05 Dec 2022
Cited by 5 | Viewed by 2168
Abstract
Three new Pt(II) complexes [(dpp-DAD)PtCl2] (I), [(Mes-DAD(Me)2)PtCl2] (II) and [(dpp-DAD(Me)2)PtCl2] (III) were synthesized by the direct reaction of [(CH3CN)2PtCl2] and corresponding [...] Read more.
Three new Pt(II) complexes [(dpp-DAD)PtCl2] (I), [(Mes-DAD(Me)2)PtCl2] (II) and [(dpp-DAD(Me)2)PtCl2] (III) were synthesized by the direct reaction of [(CH3CN)2PtCl2] and corresponding redox-active 1,4-diaza-1,3-butadienes (DAD). The compounds were isolated in a single crystal form and their molecular structures were determined by X-ray diffraction. The purity of the complexes and their stability in solution was confirmed by NMR analysis. The Pt(II) ions in all compounds are in a square planar environment. The electrochemical reduction of complexes I–III proceeds in two successive cathodic stages. The first quasi-reversible reduction leads to the relatively stable monoanionic complexes; the second cathodic stage is irreversible. The coordination of 1,4-diaza-1,3-butadienes ligands with PtCl2 increases the reduction potential and the electron acceptor ability of the DAD ligands. The synthesized compounds were tested in relation to an adenocarcinoma of the ovary (SKOV3). Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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12 pages, 3321 KiB  
Article
Antibacterial, Antioxidant, Larvicidal and Anticancer Activities of Silver Nanoparticles Synthesized Using Extracts from Fruits of Lagerstroemia speciose and Flowers of Couroupita guianensis
by Venkatadri Babu, Selvaraj Arokiyaraj, Swathi Pon Sakthi Sri, Mary George, Rameshkumar Marimuthu Ragavan, Dinesh Dharmalingam, Taehwan Oh, Subramaniyan Ramasundaram and Paul Agastian
Molecules 2022, 27(22), 7792; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27227792 - 12 Nov 2022
Cited by 2 | Viewed by 1539
Abstract
The present study aimed to analyze the in vitro antibacterial, antioxidant, larvicidal and cytotoxicity properties of green synthesized silver nanoparticles (Ag NPs) using aqueous extracts from fruits of Lagerstroemia speciosa and flowers of Couropita guinensis. Synthesized Ag NPs were characterized using UV-DRS, [...] Read more.
The present study aimed to analyze the in vitro antibacterial, antioxidant, larvicidal and cytotoxicity properties of green synthesized silver nanoparticles (Ag NPs) using aqueous extracts from fruits of Lagerstroemia speciosa and flowers of Couropita guinensis. Synthesized Ag NPs were characterized using UV-DRS, FTIR, XRD, DLS, and High-Resolution SEM and TEM analyses. Absorption wavelength was observed at 386 nm by UV-DRS analysis and energy band gap was calculated as 3.24 eV. FTIR analysis showed the existence of various functional groups in the aqueous extract and in the NPs. DLS analysis showed the stability and particle size of the synthesized Ag NPs. SEM analysis revealed that Ag NPs are in a face centered cubic symmetry and spherical shape with a size of 23.9 nm. TEM analysis showed particle size as 29.90 nm. Ag NPs showed antibacterial activity against both Gram-positive and Gram-negative bacteria. DPPH scavenging trait of Ag NPs was ranging from 20.0 ± 0.2% to 62.4 ± 0.3% and observed significant larvicidal activity (LC50 at 0.742 ppm and LC90 at 6.061 ppm) against Culex quinquefasciatus. In vitro cytotoxicity activity of Ag NPs was also tested against human breast cancer (MCF-7) and fibroblast cells (L-929) and found that cells viabilities are ranging (500 to 25 µg/mL) from 52.5 ± 0.4 to 94.0 ± 0.7% and 53.6 ± 0.5 to 90.1 ± 0.8%, respectively. The synthesized Ag NPs have the potential to be used in the various biomedical applications. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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18 pages, 7623 KiB  
Article
Ru(II)(ƞ6-p-cymene) Conjugates Loaded onto Graphene Oxide: An Effective pH-Responsive Anticancer Drug Delivery System
by Suffora Akhter, Farukh Arjmand, Claudio Pettinari and Sartaj Tabassum
Molecules 2022, 27(21), 7592; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27217592 - 05 Nov 2022
Cited by 3 | Viewed by 1388
Abstract
Graphene oxide-based nanodrug delivery systems are considered one of the most promising platforms to deliver therapeutic drugs at the target site. In this study, Ru(II)(ƞ6-p-cymene) complexes containing the benzothiazole ligand were covalently anchored on graphene oxide using the ultrasonication [...] Read more.
Graphene oxide-based nanodrug delivery systems are considered one of the most promising platforms to deliver therapeutic drugs at the target site. In this study, Ru(II)(ƞ6-p-cymene) complexes containing the benzothiazole ligand were covalently anchored on graphene oxide using the ultrasonication method. The nanoconjugates GO-NCD-1 and GO-NCD-2 were characterized by FT-IR, UV-visible, 1H NMR, TGA, SEM, and TEM techniques, which confirmed the successful loading of both the complexes (NCD 1 and NCD 2) on the carrier with average particle diameter sizes of 17 ± 6.9 nm and 25 ± 6.5 nm. In vitro DNA binding studies of the nanoconjugates were carried out by employing various biophysical methods to investigate the binding interaction with the therapeutic target biomolecule and to quantify the intrinsic binding constant values useful to understand their binding affinity. Our results suggest (i) high Kb and Ksv values of the graphene-loaded conjugates (ii) effective cleavage of plasmid DNA at a lower concentration of 7.5 µM and 10 µM via an oxidative pathway, and (iii) fast release of NCD 2 at an acidic pH that could have a good impact on the controlled delivery of drug. It was found that 90% of the drug was released in an acidic pH (5.8 pH) environment in 48 h, therefore suggesting pH-responsive behavior of the drug delivery system. Molecular docking, DFT studies, and cytotoxicity activity against three cancer cell lines by SRB assay were also performed. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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16 pages, 4168 KiB  
Article
A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of an Azomethine Ylide with an Electrophilic Ethylene Linked to Triazole and Ferrocene Units
by Luis R. Domingo, Mar Ríos-Gutiérrez and Assem Barakat
Molecules 2022, 27(19), 6532; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27196532 - 03 Oct 2022
Cited by 4 | Viewed by 1857
Abstract
The [3+2] cycloaddition (32CA) reaction of an azomethine ylide (AY) with an electrophilic ethylene linked to triazole and ferrocene units has been studied within the Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) level. The topology of the electron localization function (ELF) [...] Read more.
The [3+2] cycloaddition (32CA) reaction of an azomethine ylide (AY) with an electrophilic ethylene linked to triazole and ferrocene units has been studied within the Molecular Electron Density Theory (MEDT) at the ωB97X-D/6-311G(d,p) level. The topology of the electron localization function (ELF) of this AY allows classifying it as a pseudo(mono)radical species characterized by the presence of two monosynaptic basins, integrating a total of 0.76 e, at the C1 carbon. While the ferrocene ethylene has a strong electrophilic character, the AY is a supernucleophile, suggesting that the corresponding 32CA reaction has a high polar character and a low activation energy. The most favorable ortho/endo reaction path presents an activation enthalpy of 8.7 kcal·mol−1, with the 32CA reaction being exergonic by −42.1 kcal·mol−1. This reaction presents a total endo stereoselectivity and a total ortho regioselectivity. Analysis of the global electron density transfer (GEDT) at the most favorable TS-on (0.23 e) accounts for the high polar character of this 32CA reaction, classified as forward electron density flux (FEDF). The formation of two intermolecular hydrogen bonds between the two interacting frameworks at the most favorable TS-on accounts for the unexpected ortho regioselectivity experimentally observed. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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14 pages, 4142 KiB  
Article
Synthesis of a Novel Unexpected Cu(II)–Thiazolidine Complex—X-ray Structure, Hirshfeld Surface Analysis, and Biological Studies
by Mezna Saleh Altowyan, Samar M. S. M. Khalil, Dhuha Al-Wahaib, Assem Barakat, Saied M. Soliman, Ali Eldissouky Ali and Hemmat A. Elbadawy
Molecules 2022, 27(14), 4583; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27144583 - 18 Jul 2022
Cited by 4 | Viewed by 1512
Abstract
An unexpected trinuclear Cu(II)–thiazolidine complex has been synthesized by mixing CuCl2·2H2O with the Schiff base ligand, 1-(((4,5-dihydrothiazol-2-yl)ethylidene)hydrazono)methyl)phenol L, in ethanol. Unexpectedly, the reaction proceeded via the hydrolysis of the Schiff base L, followed by cyclization to afford [...] Read more.
An unexpected trinuclear Cu(II)–thiazolidine complex has been synthesized by mixing CuCl2·2H2O with the Schiff base ligand, 1-(((4,5-dihydrothiazol-2-yl)ethylidene)hydrazono)methyl)phenol L, in ethanol. Unexpectedly, the reaction proceeded via the hydrolysis of the Schiff base L, followed by cyclization to afford 3-methyl-5,6-dihydrothiazolo[3,2-c][1,2,3]triazole (La), then complexation with the Cu(II) salt, forming the trinuclear [Cu3(La)4(Cl)6] complex. The complex was characterized by means of FTIR spectra, elemental analysis, and X-ray crystallography. In the trinuclear [Cu3(La)4(Cl)6] complex, there are two crystallographically independent hexa- and penta-coordinated Cu(II) sites, where the thiazolidine ligand La units act as a monodentate ligand and a linker between the Cu(II) centers. The crystal packing of the [Cu3(La)4(Cl)6] complex is primarily affected by the weak non-covalent C-H∙∙∙Cl interactions. In accordance with Hirshfeld surface analysis, the Cl∙∙∙H, H∙∙∙H, S∙∙∙H, and N∙∙∙H percentages are 31.9%, 27.2%, 13.5%, and 9.9%, respectively. X-ray photoelectron spectroscopy confirmed the oxidation state of copper as Cu(II), as well as the presence of two different coordination environments around copper centers. The complex showed interesting antibacterial activity against the Gram-positive bacteria S. subtilis, with MIC = 9.7 µg/mL compared to MIC = 4.8 µg/mL for the control, gentamycin. Moreover, the Cu(II) complex showed an equal MIC (312.5 µg/mL) against C. albicans compared to ketoconazole. It also exhibits a very promising inhibitory activity against colon carcinoma (IC50 = 3.75 ± 0.43 µg/mL). Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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15 pages, 6013 KiB  
Article
Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3 + 2] Cycloaddition Reaction
by Mezna Saleh Altowyan, Saied M. Soliman, Matti Haukka, Nora Hamad Al-Shaalan, Aminah A. Alkharboush and Assem Barakat
Molecules 2022, 27(13), 4095; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27134095 - 25 Jun 2022
Cited by 4 | Viewed by 2034
Abstract
In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized via the attachment of ferrocene and triazole motifs into an azomethine ylide by [3 + 2] cycloaddition reaction protocol. The X-ray structure of the heterocyclic hybrid (1″R,2″ [...] Read more.
In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized via the attachment of ferrocene and triazole motifs into an azomethine ylide by [3 + 2] cycloaddition reaction protocol. The X-ray structure of the heterocyclic hybrid (1″R,2″S,3R)-2″-(1-(3-chloro-4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbonyl)-5-methyl-1″-(ferrocin-2-yl)-1″,2″,5″,6″,7″,7a″-hexahydrospiro[indoline-3,3″-pyrrolizin]-2-one revealed very well the expected structure, by using different analytical tools (FTIR and NMR spectroscopy). It crystallized in the triclinic-crystal system and the P-1-space group. The unit cell parameters are a = 9.1442(2) Å, b = 12.0872(3) Å, c = 14.1223(4) Å, α = 102.1700(10)°, β = 97.4190(10)°, γ = 99.1600(10)°, and V = 1484.81(7) Å3. There are two molecules per unit cell and one formula unit per asymmetric unit. Hirshfeld analysis was used to study the molecular packing of the heterocyclic hybrid. H···H (50.8%), H···C (14.2%), Cl···H (8.9%), O···H (7.3%), and N···H (5.1%) are the most dominant intermolecular contacts in the crystal structure. O···H, N···H, H···C, F···H, F···C, and O···O are the only contacts that have the characteristic features of short and significant interactions. AIM study indicated predominant covalent characters for the Fe–C interactions. Also, the electron density (ρ(r)) at the bond critical point correlated inversely with the Fe–C distances. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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12 pages, 3271 KiB  
Article
Synthesis, Structure and Biological Evaluations of Zn(II) Pincer Complexes Based on S-Triazine Type Chelator
by Heba M. Refaat, Atallh A. M. Alotaibi, Necmi Dege, Ayman El-Faham and Saied M. Soliman
Molecules 2022, 27(11), 3625; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27113625 - 05 Jun 2022
Cited by 8 | Viewed by 1500
Abstract
2,4-bis (3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,3,5-triazine (BPMT) pincer ligand was used to synthesize the new [Zn(BPMT)(NCS)2] (1) and [Zn(BPMT)(Br)2] (2) complexes by a reaction with Zn(NO3)2·6H2O in the [...] Read more.
2,4-bis (3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,3,5-triazine (BPMT) pincer ligand was used to synthesize the new [Zn(BPMT)(NCS)2] (1) and [Zn(BPMT)(Br)2] (2) complexes by a reaction with Zn(NO3)2·6H2O in the presence of either KSCN or KBr, respectively. The structure of complex 1 has been exclusively confirmed using single crystal X-ray diffraction. In this neutral heteroleptic complex, the BPMT is a pincer chelate coordinating the Zn(II) ion via three interactions with the two pyrazole moieties and the s-triazine core. Hence, BPMT is a tridentate NNN-chelate. The coordination environment of Zn(II) is completed by two strong interactions with two terminal SCN− ions via the N-atom. Hence, the Zn(II) is penta-coordinated with a distorted square pyramidal coordination geometry. Hirshfeld analysis indicated the predominance of H…H, H…C and N…H intermolecular interactions. Additionally, the S…H, S…C and S…N contacts are the most significant. The free ligand has no or weak antimicrobial, antioxidant and anticancer activities while the studied Zn(II) complexes showed interesting biological activity. Complex 1 has excellent antibacterial activity against B. subtilis (2.4 μg/mL) and P. vulgaris (4.8 μg/mL) compared to Gentamycin (4.8 μg/mL). Additionally, complex 1 (78.09 ± 4.23 µg/mL) has better antioxidant activity than 2 (365.60 ± 20.89 µg/mL). In addition, complex 1 (43.86 ± 3.12 µg/mL) and 2 (30.23 ± 1.26 µg/mL) have 8 and 12 times the anticancer activity of the free BPMT ligand (372.79 ± 13.64 µg/mL). Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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14 pages, 2033 KiB  
Article
Synthesis, Theoretical Calculation, and Biological Studies of Mono- and Diphenyltin(IV) Complexes of N-Methyl-N-hydroxyethyldithiocarbamate
by Jerry O. Adeyemi, Lukman O. Olasunkanmi, Adewale O. Fadaka, Nicole R. S. Sibuyi, Adebola O. Oyedeji and Damian C. Onwudiwe
Molecules 2022, 27(9), 2947; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27092947 - 05 May 2022
Cited by 4 | Viewed by 1662
Abstract
In this study, chlorophenyltin(IV) [(C6H5)(Cl)Sn(L)2] and diphenyltin(IV) [(C6H5)2Sn(L)2] of N-methyl-N-hydroxyethyldithiocarbamate were prepared and characterized using various spectroscopic methods (FTIR, 1H, 13C, and 119Sn NMR) and elemental analysis. The FTIR and NMR [...] Read more.
In this study, chlorophenyltin(IV) [(C6H5)(Cl)Sn(L)2] and diphenyltin(IV) [(C6H5)2Sn(L)2] of N-methyl-N-hydroxyethyldithiocarbamate were prepared and characterized using various spectroscopic methods (FTIR, 1H, 13C, and 119Sn NMR) and elemental analysis. The FTIR and NMR spectral data, used to establish the structure of the compounds, showed the formation of the complexes via coordination to the two sulfur atoms from the dithiocarbamate ligand and the respective phenyltin(IV) derivatives. This coordination mode was further explored by DFT calculations, which showed that the bonding around the Sn center in [(C6H5)2Sn(L)2] was more asymmetric compared to the bonding around [(C6H5)(Cl)Sn(L)2]. However, the Sn–S bonds in [(C6H5)(Cl)Sn(L)2] were found to be more covalent than those in [(C6H5)2Sn(L)2]. Furthermore, the charge density of the frontier orbitals showed that the Sn atom in the complexes is relatively electrophilic and the Sn atom in [(C6H5)2Sn(L)2] has a lower atomic dipole moment than that of [(C6H5)(Cl)Sn(L)2]. The cytotoxicity and anti-inflammatory study revealed that [(C6H5)2Sn(L)2], with the higher number of phenyl substituents, has a higher potency than [(C6H5)(Cl)Sn(L)2]. The bio-efficacy study of these complexes as cytotoxic and anti-inflammatory agents showed that the complexes possessed moderate to high activity in comparison to the camptothecin and diclofenac in each case. Nevertheless, the diphenyltin(IV) derivative [(C6H5)2Sn(L)2] was found to possess a better activity than its counterpart due to the number of phenyl rings attached to the Sn center. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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Review

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17 pages, 2253 KiB  
Review
A Comprehensive Survey on the Expediated Anti-COVID-19 Options Enabled by Metal Complexes—Tasks and Trials
by Judy Gopal, Manikandan Muthu and Iyyakkannu Sivanesan
Molecules 2023, 28(8), 3354; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28083354 - 10 Apr 2023
Cited by 4 | Viewed by 1947
Abstract
Contemporary pharmacology dating back to the late 19th/early 20th centuries has benefitted largely from the incorporation of metal complexes. Various biological attributes have been successfully realized using metal/metal complex-based drugs. Among anticancer, antimicrobial, and antiviral applications, anticancer applications have extracted the maximum benefit [...] Read more.
Contemporary pharmacology dating back to the late 19th/early 20th centuries has benefitted largely from the incorporation of metal complexes. Various biological attributes have been successfully realized using metal/metal complex-based drugs. Among anticancer, antimicrobial, and antiviral applications, anticancer applications have extracted the maximum benefit from the metal complex, Cisplatin. The following review has compiled the various antiviral benefits harnessed through inputs from metal complexes. As a result of exploiting the pharmacological aspects of metal complexes, the anti-COVID-19 deliverables have been summarized. The challenges ahead, the gaps in this research area, the need to improvise incorporating nanoaspects in metal complexes, and the need to test metal complex-based drugs in clinical trials have been discussed and deliberated. The pandemic shook the entire world and claimed quite a percentage of the global population. Metal complex-based drugs are already established for their antiviral property with respect to enveloped viruses and extrapolating them for COVID-19 can be an effective way to manipulate drug resistance and mutant issues that the current anti-COVID-19 drugs are facing. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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29 pages, 3532 KiB  
Review
Coordination Compounds of Cu, Zn, and Ni with Dicarboxylic Acids and N Donor Ligands, and Their Biological Activity: A Review
by Ivana Loubalová and Pavel Kopel
Molecules 2023, 28(3), 1445; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28031445 - 02 Feb 2023
Cited by 5 | Viewed by 2181
Abstract
Complexes of carboxylic acids are very often studied due to their interesting structural, spectral, and magnetic properties. This review is focused on complexes of four dicarboxylic acids, namely, 2,2′-thiodioacetic, 3,3′-thiodipropionic, 3,3′-dithiodipropionic, and fumaric acid. Many of the complexes were characterized by single crystal [...] Read more.
Complexes of carboxylic acids are very often studied due to their interesting structural, spectral, and magnetic properties. This review is focused on complexes of four dicarboxylic acids, namely, 2,2′-thiodioacetic, 3,3′-thiodipropionic, 3,3′-dithiodipropionic, and fumaric acid. Many of the complexes were characterized by single crystal X-ray analyses. Without the analyses, it is very difficult to predict the coordination mode of carboxylate groups or nitrogen ligands on central atoms. Thus, structural properties are also discussed, as well as potential applications. Full article
(This article belongs to the Special Issue Metal-Based Complex: Preparation and Medicinal Characteristics)
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