A conjugate from a laminin-related peptide, Tyr-Ile-Gly-Ser-Arg, and chitosan: efficient and regioselective conjugation and significant inhibitory activity against experimental cancer metastasis
- 23 March 2000
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1161-1165
- https://doi.org/10.1039/a908145c
Abstract
A laminin-related antimetastatic peptide was conjugated with chitosan, and antimetastatic activity of the peptide–chitosan conjugate was assayed. Chitosan was converted to its organosoluble derivative, 6-O-trityl-chitosan, in 3 steps, and then coupled with the peptide portion, Ac-Tyr-Ile-Gly-Ser-Arg-βAla-OH (βAla; β-alanine), which contains a spacer amino acid at the carboxy-terminus. The product was treated with CHCl2CO2H to afford the desired conjugate, Ac-Tyr-Ile-Gly-Ser-Arg-βAla–chitosan. The peptide was introduced to every 6.3 glucosamine residues. The conjugate proved to have higher inhibitory activity against experimental lung metastasis of B16BL6 melanoma cells in mice than did the parent peptide.Keywords
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