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: Y Nishiyama, T Yoshikawa, K Kurita, K Hojo, H Kamada, Y Tsutsumi, T Mayumi, K Kawasaki
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 47 Issue 3 Pg. 451-3 (Mar 1999) ISSN: 0009-2363 [Print] Japan
• PMID: 10212395 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents
• Laminin
• Oligopeptides
• tyrosyl-isoleucyl-glycyl-seryl-arginine
• Chitin
• Chitosan

Topics

• Animals
• Antineoplastic Agents (chemical synthesis, pharmacology)
• Chitin (analogs & derivatives, chemistry)
• Chitosan
• Laminin (chemistry)
• Lung Neoplasms (drug therapy, secondary)
• Melanoma, Experimental (pathology)
• Mice
• Oligopeptides (chemistry)