Photo-induced synthesis of Axinastatin 3 analogs, the secondary structures and their in vitro antitumor activities.
Cyclic peptides combine several favorable properties such as good binding affinity, target selectivity and low toxicity that make them an attractive modality for drug development. In an effort to identify what conformation could be accounting for the bioactive disparity of natural and synthetic cyclic peptides, some structurally-constrained analogs of cyclopeptide Axinastatin 3 were prepared by photo-induced single electron transfer (SET) reaction. Detailed stereochemistry study was performed by experimental electronic circular dichroism combined with theoretical calculations. Our study suggested that the cyclopeptide 1 with βI-turn presented stronger antitumor activity comparing with those without such secondary structures. Moreover, a rare 'π helix unit' (compound 3) was realized because of the constrained cyclic structure, which could be considered an important research object for future study of unique helix secondary structures.
['Bao|Yujun|Y|', 'Zhao|Lishuang|L|', 'Wu|Jingwan|J|', 'Jiang|Shitian|S|', 'Wang|Zhiqiang|Z|', 'Jin|Yingxue|Y|']
D000818:Animals D000970:Antineoplastic Agents D002460:Cell Line D049109:Cell Proliferation D000077318:Density Functional Theory D004305:Dose-Response Relationship, Drug D004354:Drug Screening Assays, Antitumor D004579:Electron Transport D005347:Fibroblasts D006801:Humans D051379:Mice D008958:Models, Molecular D008968:Molecular Conformation D010456:Peptides, Cyclic D055668:Photochemical Processes D013237:Stereoisomerism D013329:Structure-Activity Relationship
Photo-induced Synthesis Antitumor activity Cyclopeptide