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当手性起作用时:新型手性杂环卡宾-金和-银配合物的情况。

When Chirality Makes the Difference: The Case of Novel Enantiopure -Heterocyclic Carbene-Gold and -Silver Complexes.

机构信息

Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, Italy.

Department of Science, University of Basilicata, Viale dell'Ateneo Lucano 10, 85100 Potenza, Italy.

出版信息

Molecules. 2024 Nov 7;29(22):5262. doi: 10.3390/molecules29225262.

DOI:10.3390/molecules29225262
PMID:39598651
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11596155/
Abstract

-heterocyclic carbene (NHC)-gold and -silver complexes have attracted the interest of the scientific community because of their multiple applications and their versatility in being chemically modified in order to improve their biological properties. However, most of these complexes contain one or more chiral centers, and have been obtained and studied as racemic mixture. In particular, concerning the interesting biological and medicinal properties, many questions about how the chirality may influence these properties still remain unanswered. Aiming at a better understanding, herein a series of enantiopure NHC-gold and -silver complexes was synthesized, characterized and biologically evaluated in different in vitro systems. The individuated complexes exerted different properties based on the complexed metal and the specific configuration, with the ()-gold-NHC complexes being the most active, particularly as anti-inflammatory molecules. Docking simulations indicated a different binding mode for each enantiomer. Moreover, anticancer and antibacterial activities were also evaluated for the considered enantiomers. Overall, the reported data may contribute to a better understanding of the different biological properties exerted by the enantiopure gold and silver complexes.

摘要
  • 杂环卡宾(NHC)-金和 -银配合物因其多种应用和在化学修饰方面的多功能性而引起了科学界的兴趣,以便改善它们的生物特性。然而,这些配合物大多数都含有一个或多个手性中心,并且作为外消旋混合物获得和研究。特别是在涉及有趣的生物和药物特性时,关于手性如何影响这些特性的许多问题仍然没有答案。为了更好地理解,本文合成了一系列对映纯 NHC-金和 -银配合物,并在不同的体外系统中进行了生物评价。根据所结合的金属和特定的构型,所鉴定的配合物表现出不同的性质,其中()-金-NHC 配合物的活性最高,特别是作为抗炎分子。对接模拟表明,每个对映异构体的结合模式不同。此外,还评估了所考虑的对映异构体的抗癌和抗菌活性。总体而言,所报道的数据可能有助于更好地理解对映纯金和银配合物所表现出的不同生物学特性。
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/d2fe40a0c722/molecules-29-05262-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/efd28076c680/molecules-29-05262-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/c78e6138bd19/molecules-29-05262-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/7acf079eee72/molecules-29-05262-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/26950a30e279/molecules-29-05262-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/62c73f66c368/molecules-29-05262-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/d2fe40a0c722/molecules-29-05262-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/efd28076c680/molecules-29-05262-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/c78e6138bd19/molecules-29-05262-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/7acf079eee72/molecules-29-05262-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/26950a30e279/molecules-29-05262-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/62c73f66c368/molecules-29-05262-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7f6b/11596155/d2fe40a0c722/molecules-29-05262-g004.jpg

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