title: Design and synthesis of a bis(cycloisodityrosine) analogue of RA-VII, an antitumor bicyclic hexapeptide.
abstract: An analogue of an antitumor bicyclic hexapeptide RA-VII was prepared, in which the Ala-2 and Tyr-3 residues of RA-VII were replaced by a cycloisodityrosine unit. In the crystalline state, the peptide backbone structures and the side-chain conformations at Tyr-3, Tyr-5, and Tyr-6 of this analogue and of RA-II were very similar. This analogue, however, showed much weaker cytotoxicity against P-388 leukemia cells than parent RA-VII.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
authors.forename: Ji-Ean
authors.initials: JE
authors.lastname: Lee
authors.forename: Yukio
authors.initials: Y
authors.lastname: Hitotsuyanagi
authors.forename: Yoshie
authors.initials: Y
authors.lastname: Nakagawa
authors.forename: Saori
authors.initials: S
authors.lastname: Kato
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fukaya
authors.forename: Koichi
authors.initials: K
authors.lastname: Takeya
mesh_terms: D002626:Chemistry, Pharmaceutical / Q000379:methods; D018360:Crystallography, X-Ray / Q000379:methods; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000378:metabolism; D045470:Rubia / Q000378:metabolism; D014443:Tyrosine / Q000737:chemistry
chemical_list: D010455:Peptides; D010456:Peptides, Cyclic; D010936:Plant Extracts; C018234:bouvardin; D014443:Tyrosine; C043548:RA VII