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Hybrids of a fibronectin-related peptide[Arg-Gly-Asp (RGD)] with poly(ethylene glycol) (PEG) analogs were prepared by a simple and easy procedure. Two amino-PEG analogs were used as carriers for hybrid formation of the RGD. One was poly(oxyethylene)dipropylamine and the other was Jeffamine ED type, which has branched chains. RGD peptides were formed stepwise on PEG analogs by the diisopropylcarbodiimide method. The synthetic intermediates were easily purified by molecular-sieve gel chromatography and the final products were purified by molecular-sieve gel chromatography, followed by HPLC. This simple and easy preparation procedure using molecular-sieve gel chromatography for purification of synthetic intermediates is advantageous for the preparation of peptide-polymer hybrids. We found that PEG is stable to HF treatment at 0 degree C for 1 h. The inhibitory effect of the RGD hybrids on experimental metastasis of B16-BL6 was examined in mice. The Jeffamine type hybrid showed no inhibitory effect at the dose of 1 mg/mouse, but poly(oxyethylene)dipropylamine type hybrid was inhibitory at the same dose. The effect of the latter hybrid was about the same as that of 1 mg of RGD. One mg of the hybrid contains 0.18 mumol of RGD and 1 mg of RGD is 2.38 mumol. Thus it can be said that the inhibitory effect of RGD was potentiated by hybrid formation with poly(oxyethylene)diisopropylamine.

Amino Acids and Peptides. XXX. Preparation of Arg-Gly-Asp (RGD) Hybrids with Poly(Ethylene Glycol) Analogs and Their Antimetastatic Effect.