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源自海洋甜菜碱降海葵毒素的金（I）和金（III）卡宾配合物：对硫氧还蛋白还原酶的抑制作用、抗增殖和抗菌活性。

Gold(i) and gold(iii) carbene complexes from the marine betaine norzooanemonin: inhibition of thioredoxin reductase, antiproliferative and antimicrobial activity.

作者信息

Mahdavi Seyedeh Mahbobeh, Bockfeld Dirk, Esarev Igor V, Lippmann Petra, Frank René, Brönstrup Mark, Ott Ingo, Tamm Matthias

机构信息

Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig Hagenring30 38106 Braunschweig Germany

Institute of Medicinal and Pharmaceutical Chemistry, Technische Universität Braunschweig Beethovenstraße 55 38106 Braunschweig Germany.

出版信息

RSC Med Chem. 2024 Jul 31;15(9):3248-55. doi: 10.1039/d4md00358f.

DOI:10.1039/d4md00358f
PMID:39185451
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11342128/
Abstract

The natural marine betaine norzooanemonin (1,3-dimethylimidazolim-4-carboxylate) and its methyl and ethyl esters were used as ligand precursors to prepare a systematic series (12 members) of neutral monocarbene gold(i/iii) and cationic dicarbene gold(i/iii) complexes. The complexes were evaluated as inhibitors of bacterial thioredoxin reductase and for their antiproliferative and antimicrobial activities. While gold complexes with the parent norzooanemonin scaffold resulted in overall poor performance, the more lipophilic esters proved to be highly bioactive agents, related to their higher cellular uptake. The monocarbene gold(i/iii) complexes showed significant potency as inhibitors of bacterial thioredoxin reductase. In most assays, the efficacy of both gold(i) and gold(iii) analogues was found to be comparable. The cytotoxicity of dicarbene gold(i/iii) complexes against cancer cells was strong, in some cases exceeding that of the standard reference auranofin.

摘要

天然海洋甜菜碱去甲海葵素（1,3 - 二甲基咪唑 - 4 - 羧酸盐）及其甲酯和乙酯被用作配体前体，以制备一系列（12个成员）系统的中性单卡宾金（I/III）和阳离子双卡宾金（I/III）配合物。这些配合物被评估为细菌硫氧还蛋白还原酶的抑制剂，并测试了它们的抗增殖和抗菌活性。虽然具有母体去甲海葵素支架的金配合物总体表现不佳，但亲脂性更强的酯被证明是具有高生物活性的试剂，这与其更高的细胞摄取有关。单卡宾金（I/III）配合物作为细菌硫氧还蛋白还原酶的抑制剂表现出显著的效力。在大多数测定中，发现金（I）和金（III）类似物的功效相当。双卡宾金（I/III）配合物对癌细胞的细胞毒性很强，在某些情况下超过了标准参考药物金诺芬。

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本文引用的文献

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Cancer Chemother Pharmacol. 2023 Jul;92(1):57-69. doi: 10.1007/s00280-023-04548-1. Epub 2023 Jun 5.
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The gold complex auranofin: new perspectives for cancer therapy.金络合物金诺芬：癌症治疗的新视角。
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Gold(I) and Gold(III) N-Heterocyclic Carbene Complexes as Antibacterial Agents and Inhibitors of Bacterial Thioredoxin Reductase.金（I）和金（III）N-杂环卡宾配合物作为抗菌剂和细菌硫氧还蛋白还原酶抑制剂。
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