title: The bulky side chain of antillatoxin is important for potent toxicity: rational design of photoresponsive cytotoxins based on SAR studies.
abstract: Antillatoxin is a cyclic peptide with potent neurotoxic and neuritogenic activities. We designed and synthesized six analogues that have photocleavable protecting groups at the terminus of the side chain. Among these compounds, the bis-o-nitrobenzyl acetal derivative was found to exhibit high toxicity and was effectively deactivated by photochemical removal, proving that the biological activity of antillatoxin was modulated by altering the size of the terminal group.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Okura
authors.forename: Shigeru
authors.initials: S
authors.lastname: Matsuoka
authors.forename: Masayuki
authors.initials: M
authors.lastname: Inoue
mesh_terms: D000080:Acetals / Q000737:chemistry; D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D015195:Drug Design; D020128:Inhibitory Concentration 50; D008027:Light; D055666:Lipopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010777:Photochemistry; D013329:Structure-Activity Relationship
chemical_list: D000080:Acetals; D055666:Lipopeptides; D010456:Peptides, Cyclic; C121886:antillatoxin