Synthesis and cell imaging applications of fluorescent mono/di/tri-heterocyclyl-2,6-dicyanoanilines

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• 作者：Mahesh M. Pisal^a ; Ritesh A. Annadate^a ; Meghana C. Athalye^b ; Deepak Kumar^c ; Subhash P. Chavan^a ; Dhiman Sarkar^b ; Hanumant B. Borate^a ; ^{hb.borate@ncl.res.in}
• 关键词：Dicyanoanilines ; Cell imaging ; Fluorescence ; Heterocyclic
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2017
• 出版时间：15 February 2017
• 年：2017
• 卷：27
• 期：4
• 页码：979-988
• 全文大小：4604 K
• 卷排序：27

文摘

Synthesis of 3,4,5-triheterocyclyl-2,6-dicyanoanilines, starting from heterocyclic aldehydes and 1,2-diheterocycle-substituted ethanones, is described. 2,6-Dicyanoanilines with one or two heterocyclic substituents have also been synthesized. It was found that some of these molecules have selective cell-staining properties useful for cell imaging applications. The compounds 1g, 10f and 11 were found to stain cytoplasm of the cells in contact but not the nucleus while the compound 12 showed affinity to apoptotic cells resulting in blue fluorescence. The cell imaging results with compound 12 were similar to Annexin V-FITC, a known reagent containing recombinant Annexin V conjugated to green-fluorescent FITC dye, used for detection of apoptotic cells. These compounds were found to be non-cytotoxic and have potential application as cell imaging agents.