Design and Antitumor Activity of Platinum Complexes

Kritchenkov, Andreii S.; Stanishevskii, Ya. M.; Skorik, Yury А.

doi:10.1007/s11094-019-01947-8

Cited by 13 publications

(3 citation statements)

References 51 publications

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“…It is nearly impossible to think of a reaction series that does not utilize a transition metal-catalyzed route to make traditionally difficult carbon–carbon bonds, induce and control chirality, or control redox processes. Primary to this exploration has been the reaction chemistry of precious metals in the platinum group, such as rhodium, − iridium, ruthenium, − platinum, − and, in particular, palladium. − The prevalence of these metals in organic chemistry stems from their predictable two-electron transformations and stability under a variety of conditions. The high specific activities and relative stabilities of these metals and their organometallic complexes has resulted in utilization of catalysts based on noble metals being deployed on an industrial scale with highly specialized catalysts for nearly every synthesis-based chemical industry. − Nobel Prizes in Chemistry were awarded in 2005 and 2010 to recognize the impact that transition-metal catalysis has had on the field.…”

Section: Introductionmentioning

confidence: 99%

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

et al. 2020

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A critically important process in catalysis is the formation of an active catalyst from the combination of a metal precursor and a ligand, as the efficacy of this reaction governs the amount of active catalyst. This Review is a comprehensive overview of reactions catalyzed by nickel and an added bidentate phosphine, focusing on the steps transforming the combination of precatalyst and ligand into an active catalyst and the potential effects of this transformation on nickel catalysis. Reactions covered include common cross-coupling reactions, such as Suzuki, Heck, Kumada, and Negishi couplings, addition reactions, cycloadditions, C−H functionalizations, polymerizations, hydrogenations, and reductive couplings, among others. Overall, the most widely used nickel precatalyst with free bidentate phosphines is Ni(cod) 2 , which accounts for ∼50% of the reports surveyed, distantly followed by Ni(acac) 2 and Ni(OAc) 2 , which account for ∼10% each. By compiling the reports of these reactions, we have calculated statistics of the usage and efficacy of each ligand with Ni(cod) 2 and other nickel sources. The most common bidentate phosphines are simple, relatively inexpensive ligands, such as DPPE, DCPE, DPPP, and DPPB, along with others with more complex backbones, such as DPPF and Xantphos. The use of expensive chiral phosphines is more scattered, but the most common ligands include BINAP, Me-Duphos, Josiphos, and related analogs.

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Section: Introductionmentioning

confidence: 99%

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

et al. 2020

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“…To be different from Pt(II) complexes, Pt(IV) complexes have low antitumor activities, and exhibit relative inertness and consequent low systemic toxicity [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

QSPR study on Hydrophobicity of Pt(II) complexes with surface electrostatic potential-based descriptors

Cui¹,

Zou²,

Chen³

et al. 2022

Journal of Molecular Graphics and Modelling

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“…The discovery of cisplatin paved the way for the treatment of oncological diseases with metal-based compounds. Unfortunately, the use of cisplatin and other platinum derivatives for the treatment of malignant tumours causes a series of side effects such as nausea, vomiting, neurotoxicity, nephrotoxicity, and ototoxicity [ 5 , 6 ]. To reduce these side effects of metal-based cytotoxins, the focus of novel investigations shifted to non-platinum candidates [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Evaluation of Antiproliferative Properties of Novel Organotin(IV) Carboxylate Compounds with Propanoic Acid Derivatives on a Panel of Human Cancer Cell Lines

et al. 2021

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The synthesis of novel triphenyltin(IV) compounds, Ph3SnLn (n = 1–3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1, and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2, and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid, HL3, has been performed. The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC50 values ranging from 0.100 to 0.758 µM. According to the CV assay (IC50 = 0.218 ± 0.025 µM), complex Ph3SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph3SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph3SnL1 induces caspase-independent apoptosis in MCF-7 cells.

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Design and Antitumor Activity of Platinum Complexes

Cited by 13 publications

References 51 publications

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis

QSPR study on Hydrophobicity of Pt(II) complexes with surface electrostatic potential-based descriptors

In Vitro Evaluation of Antiproliferative Properties of Novel Organotin(IV) Carboxylate Compounds with Propanoic Acid Derivatives on a Panel of Human Cancer Cell Lines

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