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A Fluorescent Silver(I) Carbene Complex with Anticancer Properties: Synthesis, Characterization, and Biological Studies
ChemMedChem ( IF 3.6 ) Pub Date : 2018-12-14 , DOI: 10.1002/cmdc.201800672 Maria Giulia Fabbrini 1 , Damiano Cirri 2 , Alessandro Pratesi 2 , Lorenzo Ciofi 2 , Tiziano Marzo 3 , Annalisa Guerri 1 , Silvia Nistri 4 , Alfonso Dell'Accio 4 , Tania Gamberi 5 , Mirko Severi 5 , Andrea Bencini 1 , Luigi Messori 2
ChemMedChem ( IF 3.6 ) Pub Date : 2018-12-14 , DOI: 10.1002/cmdc.201800672 Maria Giulia Fabbrini 1 , Damiano Cirri 2 , Alessandro Pratesi 2 , Lorenzo Ciofi 2 , Tiziano Marzo 3 , Annalisa Guerri 1 , Silvia Nistri 4 , Alfonso Dell'Accio 4 , Tania Gamberi 5 , Mirko Severi 5 , Andrea Bencini 1 , Luigi Messori 2
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The silver(I) N‐heterocyclic carbene (NHC) complex bis(1‐(anthracen‐9‐ylmethyl)‐3‐ethylimidazol‐2‐ylidene) silver chloride ([Ag(EIA)2]Cl), bearing two anthracenyl fluorescent probes, has been synthesized and characterized. [Ag(EIA)2]Cl is stable in organic solvents and under physiological conditions, and shows potent cytotoxic effects in vitro toward human SH‐SY5Y neuroblastoma cells. The interactions of [Ag(EIA)2]Cl with a few model biological targets have been studied as well as its ability to be internalized in cells. The in vitro anticancer activity is apparently related to the level of drug internalization. Notably, [Ag(EIA)2]Cl does not react with a few model proteins, but is capable of binding the C‐terminal dodecapeptide of thioredoxin reductase hTrxR(488–499) and to strongly inhibit the activity of this enzyme. Binding occurs through an unconventional process leading to covalent binding of one or two carbene ligands to the C‐terminal dodecapeptide with concomitant release of the silver cation. To the best of our knowledge, this mode of interaction is reported here for the first time for Ag(NHC)2 complexes.
中文翻译：
具有抗癌性能的荧光银（I）卡宾配合物：合成，表征和生物学研究。
银（I）ñ -杂环卡宾（NHC）络合物双（1-（蒽-9-基甲基）-3-乙基咪唑烷-2-亚基）氯化银（将[Ag（EIA）2 ] Cl）的，带有两个蒽荧光探针，已经合成和表征。[Ag（EIA）2 ] Cl在有机溶剂中和生理条件下均稳定，并且在体外对人SH‐SY5Y神经母细胞瘤细胞显示出有效的细胞毒性作用。研究了[Ag（EIA）2 ] Cl与一些模型生物靶标的相互作用及其在细胞中内在化的能力。体外抗癌活性显然与药物内在化水平有关。值得注意的是，[Ag（EIA）2] Cl不会与一些模型蛋白发生反应，但能够与硫氧还蛋白还原酶hTrxR（488–499）的C端十二肽结合并强烈抑制该酶的活性。结合是通过非常规过程发生的，该过程导致一或两个卡宾配体与C端十二肽共价结合，同时释放出银阳离子。据我们所知，此处首次报道了Ag（NHC）2配合物的这种相互作用方式。
更新日期：2018-12-14
中文翻译：
具有抗癌性能的荧光银（I）卡宾配合物：合成，表征和生物学研究。
银（I）ñ -杂环卡宾（NHC）络合物双（1-（蒽-9-基甲基）-3-乙基咪唑烷-2-亚基）氯化银（将[Ag（EIA）2 ] Cl）的，带有两个蒽荧光探针，已经合成和表征。[Ag（EIA）2 ] Cl在有机溶剂中和生理条件下均稳定，并且在体外对人SH‐SY5Y神经母细胞瘤细胞显示出有效的细胞毒性作用。研究了[Ag（EIA）2 ] Cl与一些模型生物靶标的相互作用及其在细胞中内在化的能力。体外抗癌活性显然与药物内在化水平有关。值得注意的是，[Ag（EIA）2] Cl不会与一些模型蛋白发生反应，但能够与硫氧还蛋白还原酶hTrxR（488–499）的C端十二肽结合并强烈抑制该酶的活性。结合是通过非常规过程发生的，该过程导致一或两个卡宾配体与C端十二肽共价结合，同时释放出银阳离子。据我们所知，此处首次报道了Ag（NHC）2配合物的这种相互作用方式。
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