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基于雌二醇的水杨醛（硫代）缩氨基脲及其铜配合物的抗癌、抗菌和抗氧化活性。

Estradiol-Based Salicylaldehyde (Thio)Semicarbazones and Their Copper Complexes with Anticancer, Antibacterial and Antioxidant Activities.

机构信息

Department of Inorganic and Analytical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.

MTA-SZTE Lendület Functional Metal Complexes Research Group, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary.

出版信息

Molecules. 2022 Dec 21;28(1):54. doi: 10.3390/molecules28010054.

DOI:10.3390/molecules28010054
PMID:36615247
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9822434/
Abstract

A series of novel estradiol-based salicylaldehyde (thio)semicarbazones ((T)SCs) bearing (O,N,S) and (O,N,O) donor sets and their Cu(II) complexes were developed and characterized in detail by H and ¹³C nuclear magnetic resonance spectroscopy, UV-visible and electron paramagnetic resonance spectroscopy, electrospray ionization mass spectrometry and elemental analysis. The structure of the Cu(II)-estradiol-semicarbazone complex was revealed by X-ray crystallography. Proton dissociation constants of the ligands and stability constants of the metal complexes were determined in 30% () DMSO/HO. Estradiol-(T)SCs form mono-ligand complexes with Cu(II) ions and exhibit high stability with the exception of estradiol-SC. The Cu(II) complexes of estradiol-TSC and its -dimethyl derivative displayed the highest cytotoxicity among the tested compounds in MCF-7, MCF-7 KCR, DU-145, and A549 cancer cells. The complexes do not damage DNA according to both in vitro cell-free and cellular assays. All the Cu(II)-TSC complexes revealed significant activity against the Gram-positive bacteria strain. Estradiol-TSCs showed efficient antioxidant activity, which was decreased by complexation with Cu(II) ions. The exchange of estrone moiety to estradiol did not result in significant changes to physico-chemical and biological properties.

摘要

一系列新型基于雌二醇的水杨醛（硫代）半缩氨（(T)SCs），具有（O,N,S）和（O,N,O）供体，并对其 Cu(II) 配合物进行了详细的开发和表征，通过 H 和 ¹³C 核磁共振光谱、紫外-可见和电子顺磁共振光谱、电喷雾电离质谱和元素分析。Cu(II)-雌二醇-半缩氨配合物的结构通过 X 射线晶体学揭示。配体的质子离解常数和金属配合物的稳定常数在 30%() DMSO/HO 中确定。雌二醇-(T)SCs 与 Cu(II) 离子形成单配体配合物，除了雌二醇-SC 外，具有很高的稳定性。在 MCF-7、MCF-7 KCR、DU-145 和 A549 癌细胞中，雌二醇-TSC 及其 -二甲衍生物的 Cu(II) 配合物在测试化合物中表现出最高的细胞毒性。根据体外无细胞和细胞测定，这些配合物不会损伤 DNA。所有的 Cu(II)-TSC 配合物对革兰氏阳性 细菌菌株都显示出显著的活性。雌二醇-TSCs 表现出有效的抗氧化活性，与 Cu(II) 离子配位后活性降低。雌酮部分被雌二醇取代并没有导致物理化学和生物学性质发生显著变化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/089272a7b2d1/molecules-28-00054-g011.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/089272a7b2d1/molecules-28-00054-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/c2553e23b869/molecules-28-00054-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/7bd948ca4688/molecules-28-00054-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/29d48bb5b4cf/molecules-28-00054-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/939934425b35/molecules-28-00054-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/b72a92fd2498/molecules-28-00054-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3553/9822434/089272a7b2d1/molecules-28-00054-g011.jpg

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