Amino acids and peptides. XXXI. Preparation of analogs of the laminin-related peptide YIGSR and their inhibitory effect on experimental metastasis.

Abstract

Analogs of a partial sequence peptide of laminin, i.e., Tyr-Ile-Gly-Ser-Arg (YIGSR) analogs and Cys-Asp-Pro-Gly-Tyr-Ile-Gly-Ser-Arg (CDPGYIGSR) analogs, were prepared by the solid-phase method and their inhibitory effects on experimental metastasis of B16-BL6 melanoma cells were examined. YIGSR analogs in which Ile was replaced by other hydrophobic amino acids (Met, Leu, Phe) were inhibitory. Cys-containing analogs of YIGSR were also prepared, but were less active than the parent peptide, YIGSR. Among them, CYIGSR was easily oxidized to form a disulfide bond. A Cys-containing YIGSR analog cyclized through a disulfide bond, cyclo(CYIGSRC)G, was prepared. The disulfide bond formation was performed on the resin by the silyl chloride-sulfoxide method and by the iodine oxidation method. The yield of the silyl chloride-sulfoxide method was much better than that of the iodine oxidation method.

• Authors: M Maeda, Y Izuno, K Kawasaki, Y Kaneda, Y Mu, Y Tsutsumi, S Nakagawa, T Mayumi
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 46 Issue 2 Pg. 347-50 (Feb 1998) ISSN: 0009-2363 [Print] Japan
• PMID: 9501469 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

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

Topics

• Animals
• Antineoplastic Agents (adverse effects, therapeutic use)
• Laminin (chemical synthesis, therapeutic use)
• Lung Neoplasms (prevention & control, secondary)
• Melanoma, Experimental (drug therapy, prevention & control, secondary)
• Mice
• Mice, Inbred C57BL
• Neoplasm Transplantation
• Oligopeptides (chemical synthesis, therapeutic use)