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混合天然芳基烯烃 - 喹啉铂(II)配合物:合成、结构表征及体外细胞毒性研究

Mixed natural arylolefin-quinoline platinum(II) complexes: synthesis, structural characterization and in vitro cytotoxicity studies.

作者信息

Chi Nguyen Thi Thanh, Thong Pham Van, Mai Truong Thi Cam, Van Meervelt Luc

机构信息

Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi, Vietnam.

Department of Chemistry, Quy Nhon University, 170 An Duong Vuong, Quy Nhon, Vietnam.

出版信息

Acta Crystallogr C Struct Chem. 2018 Dec 1;74(Pt 12):1732-1743. doi: 10.1107/S2053229618015978. Epub 2018 Nov 22.

Abstract

Five new platinum(II) complexes bearing a eugenol and a quinoline derivative, namely [η-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]-trans-dichlorido(quinoline-κN)platinum(II), [PtCl(CHO)(CHN)], (2), {η-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}-trans-dichlorido(quinoline-κN)platinum(II), [PtCl(CHO)(CHN)], (3), [η-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-8-olato-κN,O)platinum(II), [Pt(CHNO)Cl(CHO)], (4), {η-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}chlorido(quinolin-8-olato-κN,O)platinum(II), [Pt(CHNO)Cl(CHO)], (5), and [η-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-2-carboxylato-κN,O)platinum(II), [Pt(CHNO)Cl(CHO)], (6), have been synthesized and fully characterized spectroscopically. A single-crystal X-ray diffraction study was carried out for complexes (2) and (4)-(6). PrEug [or 4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene] in (2), (4) and (6), and PrEug (the propan-2-yloxy analogue of PrEug) in (3) and (5) coordinate with Pt at the ethylenic double bond of the allyl group. In (2)-(6), the donor N atom of the amine group occupies a trans position with respect to the double bond. A comparison of the IC values of 0.38-29.23 µM for (2)-(6) with cisplatin, as well as other platinum(II) complexes, indicates an excellent in vitro cytotoxicity against the KB, LU, Hep-G2 and MCF-7 cancer cell lines, with the highest cytotoxic effect (IC = 0.38-1.99 µM) being for complexes (4) and (5) bearing a quinolin-8-olate ligand.

摘要

合成了五种含有丁香酚和喹啉衍生物的新型铂(II)配合物,即[η-4-烯丙基-2-甲氧基-1-(丙氧基羰基甲氧基)苯]-反式二氯(喹啉-κN)铂(II),[PtCl(CHO)(CHN)],(2),{η-4-烯丙基-2-甲氧基-1-[(丙烷-2-基氧基)羰基甲氧基]苯}-反式二氯(喹啉-κN)铂(II),[PtCl(CHO)(CHN)],(3),[η-4-烯丙基-2-甲氧基-1-(丙氧基羰基甲氧基)苯]氯(喹啉-8-醇根-κN,O)铂(II),[Pt(CHNO)Cl(CHO)],(4),{η-4-烯丙基-2-甲氧基-1-[(丙烷-2-基氧基)羰基甲氧基]苯}氯(喹啉-8-醇根-κN,O)铂(II),[Pt(CHNO)Cl(CHO)],(5),以及[η-4-烯丙基-2-甲氧基-1-(丙氧基羰基甲氧基)苯]氯(喹啉-2-羧酸根-κN,O)铂(II),[Pt(CHNO)Cl(CHO)],(6),并通过光谱对其进行了全面表征。对配合物(2)和(4)-(6)进行了单晶X射线衍射研究。(2)、(4)和(6)中的PrEug [或4-烯丙基-2-甲氧基-1-(丙氧基羰基甲氧基)苯],以及(3)和(5)中的PrEug(PrEug的丙烷-2-基氧基类似物)在烯丙基的乙烯双键处与Pt配位。在(2)-(6)中,胺基的供体N原子相对于双键占据反式位置。(2)-(6)的IC值为0.38 - 29.23 μM,与顺铂以及其他铂(II)配合物相比,表明对KB、LU、Hep-G2和MCF-7癌细胞系具有优异的体外细胞毒性,细胞毒性最高(IC = 0.38 - 1.99 μM)的是带有喹啉-8-醇根配体的配合物(4)和(5)。

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