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

对映体药物 卡宾 手性(物理) 化学 立体化学 组合化学 有机化学 对映选择合成 催化作用 物理 粒子物理学 夸克 Nambu–Jona Lasinio模型 手征对称破缺
作者
Maria Marra,Annaluisa Mariconda,Domenico Iacopetta,Jessica Ceramella,Assunta D’Amato,Camillo Rosano,Kateryna Tkachenko,Michele Pellegrino,Stefano Aquaro,Maria Stefania Sinicropi,Pasquale Longo
出处
期刊:Molecules [Multidisciplinary Digital Publishing Institute]
卷期号:29 (22): 5262-5262 被引量:7
标识
DOI:10.3390/molecules29225262
摘要

N-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 (R)-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.
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