Jiang Shitian, Zhao Lishuang, Wu Jingwan, Bao Yujun, Wang Zhiqiang, Jin Yingxue
Key Laboratory of Photochemistry Biomaterials and Energy Storage Materials of Heilongjiang Province, College of Chemistry & Chemical Engineering, Harbin Normal University Harbin 150025 China
Key Laboratory of Molecular Cytogenetics and Genetic Breeding of Heilongjiang Province, College of Life Science and Technology, Harbin Normal University Harbin 150025 China.
RSC Adv. 2019 Dec 24;10(1):210-214. doi: 10.1039/c9ra09163g. eCollection 2019 Dec 20.
A cyclic analog of natural peptide Yunnanin A was synthesized photoinduced single electron transfer reaction (SET) in the paper. The resulting compound exhibited potent bioactivity (with IC values 29.25 μg mL against HepG-2 cell lines and 65.01 μg mL against HeLa cell lines), but almost have no toxicity to normal cells (with IC values 203.25 μg mL against L929 cell lines), which may be served as a potential antitumor drug for medical treatment. The spatial structure was examined by experimental electronic circular dichroism (ECD) and quantum chemistry calculations. Moreover, the theoretical study suggested that special intramolecular hydrogen bonds and γ, β-turn secondary structures may be possible sources affecting cyclic peptide's bioactivity.
本文通过光诱导单电子转移反应(SET)合成了天然肽云南素A的环状类似物。所得化合物表现出强大的生物活性(对HepG-2细胞系的IC值为29.25μg/mL,对HeLa细胞系的IC值为65.01μg/mL),但对正常细胞几乎没有毒性(对L929细胞系的IC值为203.25μg/mL),这可能使其成为一种潜在的用于医学治疗的抗肿瘤药物。通过实验性电子圆二色光谱(ECD)和量子化学计算对其空间结构进行了研究。此外,理论研究表明,特殊的分子内氢键和γ,β-转角二级结构可能是影响环肽生物活性的潜在因素。