Synthesis, characterization, structure, molecular modeling studies and biological activity of sterically crowded Pt(II) complexes containing bis(imidazole) ligands

Ravera, Mauro; Gabano, Elisabetta; Sardi, Manuele; Ermondi, Giuseppe; Caron, Giulia; McGlinchey, Michael J.; Müller‐Bunz, Helge; Monti, Elena; Gariboldi, Marzia Bruna; Osella, Domenico

doi:10.1016/j.jinorgbio.2010.12.002

Cited by 17 publications

(18 citation statements)

References 47 publications

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“…Clotrimazole platinum(II) supramolecular complex 47 was formed by two clotrimazole molecules and one platinum dichloride through coordination of nitrogen atom in imidazole ring. It was able to interact with the minor groove of DNA and effectively inhibit the growth of MCF‐7, SKBR‐3, HT‐29, and B16/BL6 . This result expanded the application of clotrimazole in cancer therapy and opened a novel space of using antifungal agents to develop metal‐based anticancer agents.…”

Section: Imidazoles As Anticancer Agentsmentioning

confidence: 88%

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

et al. 2013

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Imidazole ring is an important five-membered aromatic heterocycle widely present in natural products and synthetic molecules. The unique structural feature of imidazole ring with desirable electron-rich characteristic is beneficial for imidazole derivatives to readily bind with a variety of enzymes and receptors in biological systems through diverse weak interactions, thereby exhibiting broad bioactivities. The related research and developments of imidazole-based medicinal chemistry have become a rapidly developing and increasingly active topic. Particularly, numerous imidazole-based compounds as clinical drugs have been extensively used in the clinic to treat various types of diseases with high therapeutic potency, which have shown the enormous development value. This work systematically gives a comprehensive review in current developments of imidazole-based compounds in the whole range of medicinal chemistry as anticancer, antifungal, antibacterial, antitubercular, anti-inflammatory, antineuropathic, antihypertensive, antihistaminic, antiparasitic, antiobesity, antiviral, and other medicinal agents, together with their potential applications in diagnostics and pathology. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic imidazole-based medicinal drugs, as well as more effective diagnostic agents and pathologic probes.

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Section: Imidazoles As Anticancer Agentsmentioning

confidence: 88%

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

et al. 2013

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“…The inhibition of glycolysis was shown against breast cancer, MCF-7, MCF10A, MDA-MB-231, HeLa, B16-F10, and Lewis lung carcinoma cell lines [13,15-19]. Further research showed the cytotoxicity of derivative compounds when clotrimazole was used as a ligand in metal coordination complexes [20,21]. In each case, clotrimazole was a potent inhibitor of glycolysis, leading to cell-cycle arrest and apoptosis.…”

Section: Introductionmentioning

confidence: 99%

“…The nitrogen atom present in the imidazole ring of clotrimazole facilitates coordination with transition metal ions such as Pt, as well as Ru, Pd, Cu, Co, Zn and Ni. Ravera et al synthesized Pt(II) complexes containing bis(clotrimazole) ligands which were shown to effectively inhibit the growth of MCF-7, SKBR-3, HT-29, and B16/BL6 cell lines [21]. In another study, a series of Ru-clotrimazole compounds were synthesized which were shown to be active against multiple cancer cell lines [34].…”

Section: Introductionmentioning

confidence: 99%

Clotrimazole as a Cancer Drug:A Short Review

Kadavakollu

Stailey

et al. 2014

Med chem

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Although clotrimazole was first used against fungal infections, a body of research was later developed indicating that this drug has anticancer properties as well. The mechanism of action is based on the inhibition of mitochondrial-bound glycolytic enzymes and calmodulin, which starves cancer cells of energy. Clotrimazole and its derivatives have been shown to decrease rates of cancer cell proliferation, induce G1 phase arrest, and promote pro-apoptotic factors, which lead to cell death.

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“…Trans -orientation of planar pyridines seems to contribute to greater affinity of complexes for interstrand cross-link formation and DNA conformational distortion, comparing to cis -isomers, leading to activation of different DNA-repair mechanisms 19–21…”

Section: Introductionmentioning

confidence: 99%

“…Recent studies demonstrated that fine tuning of the biological activity of trans -platinum pyridines may be achieved by different positioning of the substituents such as: methyl-group and 3- or 4-hydroxymethyl-group, on the pyridine ring 19,20,22…”

Section: Introductionmentioning

confidence: 99%

Biological evaluation of transdichloridoplatinum( II) complexes with 3- and 4-acetylpyridine in comparison to cisplatin

Filipović¹,

Aranđelović²,

Gligorijević³

et al. 2013

Radiology and Oncology

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BackgroundIn our previous study we reported the synthesis and cytotoxicity of two trans-platinum(II) complexes: trans-[PtCl2(3-acetylpyridine)2] (1) and trans-[PtCl2(4-acetylpyridine)2] (2), revealing significant cytotoxic potential of 2. In order to evaluate the mechanism underlying biological activity of both trans-Pt(II) isomers, comparative studies versus cisplatin were performed in HeLa, MRC-5 and MS1 cells.Materials and methods.The cytotoxic activity of the investigated complexes was determined using SRB assay. The colagenolytic activity was determined using gelatin zymography, while the effect of platinum complexes on matrix metalloproteinases 2 and 9 mRNA expression was evaluated by quantitative real-time PCR. Apoptotic potential and cell cycle alterations were determined by FACS analyses. Western blot analysis was used to evaluate the effect on expression of DNA-repair enzyme ERCC1, and quantitative real-time PCR was used for the ERCC1 mRNA expression analysis. In vitro antiangiogenic potential was determined by tube formation assay. Platinum content in intracellular DNA and proteins was determined by inductively coupled plasma-optical emission spectrometry.ResultsCompound 2 displayed an apparent cytoselective profile, and flow cytometry analysis in HeLa cells indicated that 2 exerted antiproliferative effect through apoptosis induction, while 1 induced both apoptosis and necrosis. Action of 1 and 2, as analyzed by quantitative real-time PCR and Western blot, was associated with down-regulation of ERCC1. Both trans-complexes inhibited MMP-9 mRNA expression in HeLa, while 2 significantly abrogated in vitro tubulogenesis in MS1 cells.ConclusionsThe ability of 2 to induce multiple and selective in vitro cytotoxic effects encourages further investigations of trans-platinum(II) complexes with substituted pyridines.

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Synthesis, characterization, structure, molecular modeling studies and biological activity of sterically crowded Pt(II) complexes containing bis(imidazole) ligands

Cited by 17 publications

References 47 publications

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

Clotrimazole as a Cancer Drug:A Short Review

Biological evaluation of transdichloridoplatinum( II) complexes with 3- and 4-acetylpyridine in comparison to cisplatin

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