Synthesis, Antioxidant and Anticancer Activities of 1,2,5-Selenadiazole Pyrimidine Heterocyclic Derivative ASPO

doi:10.3969/j.issn.0251-0790.2012.05.020

Abstract

Abstract: The trace element selenium(Se) is an essential nutrient of fundamental importance to human and animal. Epidemiological, preclinical and clinical studies have supported the role of Se as potent cancer chemopreventive agents. Se-containing heterocyclic compounds have attracted more and more attention due to their anticancer potential and interesting chemical properties. In the present study, a selenadiazole pyrimidine heterocyclic derivative 5-amino-[1,2,5]selenadiazolo-[3,4-d]pyrimidin-7-ol(ASPO) was synthesized and characterized by ESI-MS, ¹H NMR, elemental analysis, IR, UV-Vis absorption spectroscopy and fluorescence spectroscopy. Its antioxidant and anticancer activities were evaluated. The results show that ASPO can effectively scavenge the 2,2'-azinobis-3-ethylbenzothiazolin-6-sulfonic acid(ABTS) and 1,1-diphenyl-2-picryhydrazyl(DPPH) free radicals in a dose-dependent manner, demonstrating its strong antioxidant activity. The in vitro anticancer activities of ASPO were screened by MTT assay against various cancer cell lines and it was found that ASPO could effectively inhibit cancer cell growth, especially A-375 human melanoma cells. Further investigation on the action mode show that ASPO induces Sub-G1 peak accumulation, chromatin condensation and the formation of apoptotic bodies in a dose-dependent manner in A-375 cells, indicating that apoptosis is the main mechanism accounting for the anticancer action of ASPO. Moreover, it was showed that ASPO could bind to CT-DNA by minor groove. The results support that ASPO induces cancer cell apoptosis through its interaction with DNA.

Key words: Selenadiazole derivative, Antioxidant activity, Anticancer activity, Apoptosis, DNA Interaction

CLC Number:

O627

TrendMD:

HUANG Xiao-Chun, ZHENG Jun-Sheng, CHEN Tian-Feng, ZHANG Yi-Bo, LUO Yi, ZHENG Wen-Jie. Synthesis, Antioxidant and Anticancer Activities of 1,2,5-Selenadiazole Pyrimidine Heterocyclic Derivative ASPO[J]. Chem. J. Chinese Universities, 2012, 33(05): 976.

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Synthesis, Antioxidant and Anticancer Activities of 1,2,5-Selenadiazole Pyrimidine Heterocyclic Derivative ASPO

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