Novel acenaphtho[1,2-b]pyrrole-carboxylic acid family: Synthesis, cytotoxicity, DNA-binding and cell cycle evaluation |
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Authors: | Lijuan Xie Yi Xiao Fang Wang Yufang Xu Xuhong Qian Rong Zhang Jingnan Cui Jianwen Liu |
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Institution: | aState Key Laboratory of Fine Chemicals, Dalian University of Technology, PO Box 89, 158 Zhongshan Road, Dalian 116012, China;bShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, PO Box 544, 130 Meilong Road, Shanghai 200237, China |
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Abstract: | A family of 8-oxo-8H-acenaphtho1,2-b]pyrrole-9-carboxylic acid derivatives were synthesized as a result of our efforts to modify a series of acenaphthopyrrole aromatic-heterocycle compounds that proved to be potent anticancer drugs. Among the derivatives, 3d (3-(dimethylamino-propylamino)-8-oxo-8H-acenaphtho-1,2-b]pyrrole-9-carboxylic acid) and 3g (3-piperidine-8-oxo-8H-acenaphtho-1,2-b]pyrrole-9-carboxylic acid) showed potential anticancer activity and different action mechanism from our previously reported compounds. UV–vis absorption, circular dichroism and viscosity measurement indicated that effect of both compounds on the advanced DNA conformation was different, although they could bind to DNA in the same way. Cell cycle analysis showed that 3d could induce S-phase arrest followed by apoptosis, while 3g induced apoptosis. The results seem to imply that different action mechanism could contribute to the dissimilitude of biological activities toward 3d and 3g. |
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Keywords: | Acenaphtho[1 2-b]pyrrole Cell cycle Apoptosis DNA |
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