发现新型去氢枞酸衍生物作为 DNA/BSA 结合剂和抗癌剂。
Discovery of novel dehydroabietic acid derivatives as DNA/BSA binding and anticancer agents.
机构信息
Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China.
Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China; State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin 541004, China.
出版信息
Spectrochim Acta A Mol Biomol Spectrosc. 2021 Feb 5;246:118944. doi: 10.1016/j.saa.2020.118944. Epub 2020 Sep 15.
To explore the biological properties of rosin derivatives, two dehydroabietic acid derivatives N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2-carboxamide (DTPC) and di-N-(5-dehydroabietyl-1,3,4-thiadiazole)-yl-pyridine-2,6-carboxamide (DDTPC) with 1,3,4-thiadiazole, pyridine and amide moieties were designed and synthesized according to superposition principle of activity group. They interact with calf thymus DNA (CT DNA) via intercalation based on the results of circular dichroism (CD) and fluorescence spectroscopy, DNA denaturation and viscosity studies. Fluorescence and CD spectral experiments indicate that they might be transported and stored by protein like bovine serum albumin (BSA). MTT assay was further carried out to examine their cytotoxicity, they both showed selective cytotoxicity and DTPC exhibited better cytotoxicity. The antiproliferative effect of DTPC toward A431 cell line was stronger than that of clinically used cisplatin and oxaliplatin. In addition, the cytotoxicity of DTPC and DDTPC was closely related with their DNA binding ability.
为了探索松香衍生物的生物性质，根据活性基团叠加原理，设计并合成了两种具有 1,3,4-噻二唑、吡啶和酰胺部分的脱氢枞酸衍生物 N-(5-脱氢枞基-1,3,4-噻二唑)-吡啶-2-甲酰胺（DTPC）和二 N-(5-脱氢枞基-1,3,4-噻二唑)-吡啶-2,6-甲酰胺（DDTPC）。基于圆二色性（CD）和荧光光谱、DNA 变性和粘度研究的结果，它们通过嵌入与小牛胸腺 DNA（CT DNA）相互作用。荧光和 CD 光谱实验表明，它们可能像牛血清白蛋白（BSA）一样通过蛋白质运输和储存。进一步进行 MTT 测定以检查它们的细胞毒性，结果表明它们都具有选择性细胞毒性，并且 DTPC 表现出更好的细胞毒性。DTPC 对 A431 细胞系的增殖抑制作用强于临床使用的顺铂和奥沙利铂。此外，DTPC 和 DDTPC 的细胞毒性与其 DNA 结合能力密切相关。
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