Platinum coordination compounds with potent anticancer activity

Deo, K.; Ang, Dale L.; McGhie, Brondwyn S.; Rajamanickam, Adeline; Dhiman, Ankita; Khoury, Aleen; Holland, J. Murray; Bjelosevic, Aleksandra; Pages, Benjamin J.; Gordon, Christopher P.

doi:10.1016/j.ccr.2017.11.014

Cited by 157 publications

(104 citation statements)

References 193 publications

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“…Different from the mechanism of action of cisplatin and its previously described derivatives, covalently binding Pt(II) complexes incorporating a planar aromatic ligand, such as 1,10‐phenanthroline, anthraquinone, acridine etc., may intercalate between two adjacent DNA base pairs stabilized through π–π stacking stabilization, and/or may subsequently coordinatively bind to DNA by losing a labile leaving group . Intercalation thus causes DNA to lose its regular helical structure .…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Ionescu

Caligiuri

Godbert

et al. 2020

Applied Organom Chemis

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The in vitro biological activity towards the MDA‐MB‐231 triple‐negative breast cancer cell line of two different series of anionic Pt(II) organometallic complexes was tested. For the first time, cytotoxic activity of anionic Pt(II) complexes has been observed. The anionic compounds of general formula NBu4[(C^N)Pt(O^O)], where (C^N) represents the cyclometalated form of 2‐phenylpyridine (H(PhPy)), 2‐thienylpyridine (H(Thpy)) or 2‐benzo[h]quinoline (H(Bzq)), feature two different (O^O) chelated ligands: tetrabromocatechol [BrCat]2− (1–3) or alizarine [Aliz]2− (4–6). Complexes 1–6 displayed a significant cytotoxic effect against the studied cell line (IC50 range of 1.9–52.8 μM). For BrCat‐containing complexes 1–3, the biological activity was independent of the nature of the coordinated (C^N) ligand. In contrast, in the case of 4–6, the cytotoxicity (significantly high for 4) was concomitantly induced by the presence of either the PhPy or the [Aliz]2− ligand. Since complexes 1–6 are emissive in solution, the potential use of 4 as a theranostic agent was investigated using confocal analysis. The fluorescence signal from MDA‐MB‐231 cells incubated with 4 indicated the localization of the compound into the cytosol region.

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Section: Introductionmentioning

confidence: 99%

“…Chemical structures of (a–c) positively charged Pt(II) complexes, (d) catecholate‐bearing Pt(II) complexes, (e) doxorubicin and (f) mitoxantrone…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Ionescu

Caligiuri

Godbert

et al. 2020

Applied Organom Chemis

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“…Organotin (IV) compounds have been receiving increasing attention over the past years [1][2][3][4][5][6] due to their possible use as biologically active non-platinum chemotherapeutic agents, that might have lower toxicity, better excretion properties and fewer side effects than platinum based drugs [7][8][9]. These compounds, even at low doses, present high anti-proliferative activity which, in some cases, is higher than that of cisplatin.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms

et al. 2020

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In this study cytotoxicity of organotin(IV) compounds with 1,2,4-triazolo[1,5-a]pyrimidines, Me3Sn(5tpO) (1), n-Bu3Sn(5tpO) (2), Me3Sn(mtpO) (3), n-Bu3Sn(mtpO) (4), n-Bu3Sn(HtpO2) (5), Ph3Sn(HtpO2) (6) where 5HtpO = 4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine, HmtpO = 4,7-dihydro-5-methyl-7-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine, and H2tpO2 = 4,5,6,7-tetrahydro-5,7- dioxo-[1,2,4]triazolo-[1,5-a]-pyrimidine, was assessed on three different human tumor cell lines: HCT-116 (colorectal carcinoma), HepG2 (hepatocarcinoma) and MCF-7 (breast cancer). While 1 and 3 were inactive, compounds 2, 4, 5 and 6 inhibited the growth of the three tumor cell lines with IC50 values in the submicromolar range and showed high selectivity indexes towards the tumor cells (SI > 90). The mechanism of cell death triggered by the organotin(IV) derivatives, investigated on HCT-116 cells, was apoptotic, as evident from the externalization of phosphatidylserine to the cell surface, and occurred via the intrinsic pathway with fall of mitochondrial inner membrane potential and production of reactive oxygen species. While compound 6 arrested the cell progression in the G2/M cell cycle phase and increased p53 and p21 levels, compounds 2, 4 and 5 blocked cell duplication in the G1 phase without affecting the expression of either of the two tumor suppressor proteins. Compounds 1 and 2 were also investigated using single crystal X-ray diffraction and found to be, in both cases, coordination polymers forming 1 D chains based on metal-ligand interactions. Interestingly, for n-Bu3Sn(5tpO)(2) H-bonding interactions between 5tpO− ligands belonging to adjacent chains were also detected that resemble the “base-pairing” assembly and could be responsible for the higher biological activity compared to compound 1. In addition, they are the first example of bidentate N(3), O coordination for the 5HtpO ligand on two adjacent metal atoms.

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“…Since Alfred Werner published his theory of the constitution of inorganic compounds in 1893 [1,2], coordination compounds have attracted much attention. During this time period, the synthesis and structural investigation of these compounds have gained wide acceptance in material science because of their functional architectures and potential applications in catalysis [3][4][5], gas storage [6,7], and medicine [8,9], and as luminescent materials [10] or scintillators [11][12][13]. Today, we are able to test the performance of scintillators with a tabletop device [14,15].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Architecture in a Ni(II) Complex with a Weakly Bonded N,N′-(1,4-phenylenedi- carbonyl)Diglycinate Counter-Anion: Crystal Structure Investigation and Hirshfeld Surface Analysis

Pook

2019

Crystals

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In this work, we describe the structural investigation of a Ni(II) complex, [Ni(C12H8N2)2(H2O)2]2·(C12H10N2O6)·(NO3)2·10H2O, with phenanthroline ligands, a deprotonated aromatic dicarboxylic acid, N,N′-(1,4-phenylenedicarbonyl)diglycine, and a nitrate as counter-anions, as well as water molecules. Noncovalent interactions, such as π–π stacking, lone-pair···π, and C–H···π between the phenanthrolines of the cationic complex, [Ni(C12H8N2)2(H2O)2]2+, and counter-anions are observed. Moreover, the solvated and noncoordinating counter-anion, N,N′-(1,4-phenylenedicarbonyl)diglycinate, is embedded in classical and nonclassical hydrogen-bonding interactions with water molecules and phenanthrolines. The two water molecules coordinated by the NiII atom and hydrogen bonded to the carboxylate of the N,N′-(1,4-phenylenedicarbonyl)diglycinate show attractive secondary electrostatic interactions, and a DD/AA hydrogen bonding pattern is formed. The noncovalent interactions of the cationic complex and the solvated N,N′-(1,4-phenylenedicarbonyl)diglycinate counter anion were explored with a Hirshfeld surface analysis, and related contributions to crystal cohesion were determined. The results of the N,N′-(1,4-phenylenedicarbonyl)diglycinate counter anion were compared to those of a solvated N,N′-(1,4-phenylenedicarbonyl)diglycine molecule of a previously described copper(II) complex.

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Platinum coordination compounds with potent anticancer activity

Cited by 157 publications

References 193 publications

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Cytotoxic Activity of Organotin(IV) Derivatives with Triazolopyrimidine Containing Exocyclic Oxygen Atoms

Supramolecular Architecture in a Ni(II) Complex with a Weakly Bonded N,N′-(1,4-phenylenedi- carbonyl)Diglycinate Counter-Anion: Crystal Structure Investigation and Hirshfeld Surface Analysis

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