title: Regioselective conjugation of chitosan with a laminin-related peptide, Tyr-Ile-Gly-Ser-Arg, and evaluation of its inhibitory effect on experimental cancer metastasis.
abstract: A conjugate from the YIGSR peptide and chitosan has been prepared on the basis of a regioselective modification strategy of chitosan, and its antimetastatic activity has been assayed. Chitosan was converted to its organosoluble derivative, 6-O-trityl-chitosan, in 3 steps, and then coupled with the peptide portion containing a spacer amino acid, Ac-Tyr-Ile-Gly-Ser-Arg-beta Ala-OH [beta Ala; beta-alanine]. The product was treated with CHCl2CO2H to afford the desired conjugate, Ac-Tyr-Ile-Gly-Ser-Arg-beta Ala-chitosan, which proved to inhibit the experimental lung metastasis of B16BL6 melanoma cells in mice at lower doses than the parent peptide.
authors.affiliation: Department of Industrial Chemistry, Faculty of Engineering, Seikei University, Tokyo, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Nishiyama
authors.forename: T
authors.initials: T
authors.lastname: Yoshikawa
authors.forename: K
authors.initials: K
authors.lastname: Kurita
authors.forename: K
authors.initials: K
authors.lastname: Hojo
authors.forename: H
authors.initials: H
authors.lastname: Kamada
authors.forename: Y
authors.initials: Y
authors.lastname: Tsutsumi
authors.forename: T
authors.initials: T
authors.lastname: Mayumi
authors.forename: K
authors.initials: K
authors.lastname: Kawasaki
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002686:Chitin / Q000031:analogs & derivatives* / Q000737:chemistry; D048271:Chitosan; D007797:Laminin / Q000737:chemistry*; D008175:Lung Neoplasms / Q000188:drug therapy* / Q000556:secondary; D008546:Melanoma, Experimental / Q000473:pathology*; D051379:Mice; D009842:Oligopeptides / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D007797:Laminin; D009842:Oligopeptides; C081571:tyrosyl-isoleucyl-glycyl-seryl-arginine; D002686:Chitin; D048271:Chitosan