title: Structure-activity relationship of a novel pentapeptide with cancer cell growth-inhibitory activity.
abstract: We previously reported that yamamarin, a pentapeptide with an amidated C-terminus (DILRG-NH(2)) isolated from larvae of the silkmoth, and its palmitoylated analog (C16-DILRG-NH(2)) suppressed proliferation of rat hepatoma (liver cancer) cells. In this study, we investigated the structure-activity relationship of yamamarin by in vitro assay and spectroscopic methods (CD and NMR) for various analogs. The in vitro assay results demonstrated that the chemical structure of the C-terminal part (-RG-NH(2)) of yamamarin is essential for its activity. The CD and NMR results indicated that yamamarin and its analog adopt predominantly a random coil conformation. Moreover, a comparison of NMR spectra of DILRG-NH(2) and C16-DILRG-NH(2) revealed that the N-terminal palmitoyl group of C16-DILRG-NH(2) did not affect the conformation of the C-terminal part, which is essential for activity. Together, these results should assist in the design of more sophisticated anticancer drugs.
authors.affiliation: Graduate School of Life Science, Hokkaido University, Sapporo 060-0810, Japan.
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Kamiya
authors.forename: Keisuke
authors.initials: K
authors.lastname: Oyauchi
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Sato
authors.forename: Takuya
authors.initials: T
authors.lastname: Yokoyama
authors.forename: Mofei
authors.initials: M
authors.lastname: Wang
authors.forename: Tomoyasu
authors.initials: T
authors.lastname: Aizawa
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Kumaki
authors.forename: Mineyuki
authors.initials: M
authors.lastname: Mizuguchi
authors.forename: Kunio
authors.initials: K
authors.lastname: Imai
authors.forename: Makoto
authors.initials: M
authors.lastname: Demura
authors.forename: Koichi
authors.initials: K
authors.lastname: Suzuki
authors.forename: Keiichi
authors.initials: K
authors.lastname: Kawano
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D009842:Oligopeptides