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手性双膦钌(II)配合物对癌细胞的对映选择性细胞毒性。

Enantioselective Cytotoxicity of Chiral Diphosphine Ruthenium(II) Complexes Against Cancer Cells.

机构信息

Dipartimento di Scienze Agroalimentari, Ambientali e Animali, Università di Udine, Via Cotonificio 108, 33100, Udine, Italy.

Dipartimento di Area Medica - Istituto di Genetica Medica, Università di Udine, Via Chiusaforte, F3, 33100, Udine, Italy.

出版信息

Chemistry. 2022 Jun 10;28(33):e202200200. doi: 10.1002/chem.202200200. Epub 2022 May 5.

DOI:10.1002/chem.202200200
PMID:35394095
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9322675/
Abstract

The chiral cationic complex [Ru(η -OAc)(CO)((R,R)-Skewphos)(phen)]OAc (2 ), isolated from reaction of [Ru(η -OAc)(η -OAc)(R,R)-Skewphos)(CO)] (1 ) with phen, reacts with NaOPiv and KSAc affording [RuX(CO)((R,R)-Skewphos)(phen)]Y (X=Y=OPiv 3 ; X=SAc, Y=OAc 4 ). The corresponding enantiomers 2 -4 have been obtained from 1 containing (S,S)-Skewphos. Reaction of 2 and 2 with (S)-cysteine and NaPF at pH=9 gives the diastereoisomers [Ru((S)-Cys)(CO)(PP)(phen)]PF (PP=(R,R)-Skewphos 2 -Cys; (S,S)-Skewphos 2 -Cys). The DFT energetic profile for 2 with (S)-cysteine in H O indicates that aquo and hydroxo species are involved in formation of 2 -Cys. The stability of the ruthenium complexes in 0.9 % w/v NaCl solution, PBS and complete DMEM medium, as well as their n-octanol/water partition coefficient (logP), have been evaluated. The chiral complexes show high cytotoxic activity against SW1736, 8505 C, HCT-116 and A549 cell lines with EC values of 2.8-0.04 μM. The (R,R)-Skewphos derivatives show higher cytotoxicity compared to their enantiomers, 4 (EC =0.04 μM) being 14 times more cytotoxic than 4 against the anaplastic thyroid cancer 8505 C cell line.

摘要

手性阳离子配合物[Ru(η-OAc)(CO)((R,R)-Skewphos)(phen)]OAc(2)，由[Ru(η-OAc)(η-OAc)(R,R)-Skewphos)(CO)] (1)与phen 反应得到，与 NaOPiv 和 KSAc 反应得到[RuX(CO)((R,R)-Skewphos)(phen)]Y(X=Y=OPiv 3；X=SAc，Y=OAc 4)。相应的对映异构体 2-4 是由含有(S,S)-Skewphos 的 1 得到的。2 和 2 与(S)-半胱氨酸和 NaPF 在 pH=9 下反应，得到非对映异构体[Ru((S)-Cys)(CO)(PP)(phen)]PF(PP=(R,R)-Skewphos 2-Cys；(S,S)-Skewphos 2-Cys)。DFT 能量曲线表明，在 H2O 中，2 与(S)-半胱氨酸的反应涉及水合和羟物种的形成。在 0.9%w/v NaCl 溶液、PBS 和完全 DMEM 培养基中的稳定性，以及它们的正辛醇/水分配系数(logP)都进行了评估。手性配合物对 SW1736、8505 C、HCT-116 和 A549 细胞系表现出高的细胞毒性，EC 值为 2.8-0.04 μM。(R,R)-Skewphos 衍生物比它们的对映异构体显示出更高的细胞毒性，4(EC=0.04 μM)对甲状腺癌细胞系 8505 C 的细胞毒性比 4 高 14 倍。

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