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KuQuinones Equilibria Assessment for Biomedical Applications
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-18 00:00:00 , DOI: 10.1021/acs.joc.7b01602
Federica Sabuzi 1 , Sara Lentini 1 , Fabio Sforza 2 , Silvia Pezzola 1 , Silvia Fratelli 1 , Olga Bortolini 2 , Barbara Floris 1 , Valeria Conte 1 , Pierluca Galloni 1
Affiliation  

A small library of pentacyclic quinoid compounds, called KuQuinones (KuQs), has been prepared through a one-pot reaction. KuQuinones complex structure is made up by two naphthoquinone units connected by a five-membered ring. Due to KuQs structural features, keto–enol tautomerization in solution likely occurs, leading to the generation of four different species, i.e., the enol, the enolate, the external enol and the diquinoid species. The interchange among KuQ tautomers leads to substantial spectral variations of the dye depending on the experimental conditions used. The comprehension of tautomeric equilibria of this new class of quinoid compounds is strongly required in order to explain their behavior in solution and in biological environment. UV–vis, 1H NMR spectroscopies, and DFT calculations resulted appropriate tools to understand the nature of the prevalent KuQuinone species in solution. Moreover, due to the structural similarity of KuQuinones with camptothecin (CPT), a largely used anticancer agent, KuQs have been tested against Cisplatin-resistant SKOV3 and SW480 cancer cell lines. Results highlighted that KuQs are highly active toward the analyzed cell lines and almost nontoxic for healthy cell, indicating a high specific activity.

中文翻译:

KuQuinones生物医学应用平衡评估

通过一锅反应制备了一个小的五环醌化合物库,称为KuQuinones(KuQs)。KuQuinones复杂结构是由两个萘醌单元通过一个五元环连接而成。由于KuQs的结构特征,在溶液中可能发生酮-烯醇互变异构,导致生成四种不同的物质,即烯醇,烯醇化物,外部烯醇和二喹啉物质。KuQ互变异构体之间的互换导致染料的光谱变化很大,具体取决于所使用的实验条件。为了解释它们在溶液和生物环境中的行为,强烈需要理解这类新的醌类化合物的互变异构平衡。紫外线–可见11 H NMR光谱学和DFT计算产生了适当的工具,以了解溶液中普遍存在的KuQuinone物质的性质。此外,由于KuQuinones与喜树碱(CPT)(喜树碱)(一种广为使用的抗癌药)的结构相似性,已对KuQs进行了耐顺铂性SKOV3和SW480癌细胞系的测试。结果强调,KuQ对分析的细胞系具有很高的活性,对健康细胞几乎无毒,表明具有较高的比活性。
更新日期:2017-09-18
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