Polypeptide and anti-hiv agent prepared therefrom

Details Polypeptide and anti-hiv agent prepared therefrom Polypeptide and anti-hiv agent prepared therefrom

C - Chemistry, Metallurgy

07

K

C07K 7/08 (2006.01) A61K 38/10 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2151283

A polypeptide represented by formula (I), [in which: A1 is an amino acid or a peptide having one or at least two basic amino acids selected from lysine, arginine and ornithine, said amino acid or peptide in which amino terminal N- .alpha. may be replaced with an acyl group or a substituted thiocarbamoyl group; A2 is a tyrosine or phenylalanine; A3 is a lysine or arginine; A4 is an -OH or an -NH2; and X is a peptide such as D-ornithyl-proline, prolyl-D- ornithine, D-lysyl-proline, prolyl-D-lysine, D-arginyl-proline, prolyl-D- arginine, glycyl-ornithine, ornithyl-glycine, glycyl-lysine, lysyl-glycine, glycyl-arginine and arginyl-glycine, in which the hydrogen atom of the .omega.- amino group of D-lysine, L-lysine, D-ornithine and L-ornithine may be replaced by an .omega.-amino acyl group, and said peptide is connected to the amino acid residues at the 6th and the 8th positions via peptide bond per se; Trp is a tryptophan; and Cys is a cysteine], and one example of such polypeptide be represented as formula (1) is presented. The above presented polypeptide may be useful in a pharmaceutical composition as an antimicrobial or antiviral agent, specifically as an anti-HIV agent and as a component of the DNA- transfecting systems for gene therapy.

Polypeptide représenté par la formule (I) [dans laquelle A¿1? est un acide aminé ou un peptide comportant un ou au moins deux acides aminés sélectionnés parmi la lysine, l'arginine et l'ornithine, la terminaison amino N-.alpha. de l'acide aminé ou du peptide pouvant être remplacée par un groupe acyle ou un groupe thiocarbamoyle substitué; A¿2? est une tyrosine ou une phénylalanine; A¿3? est une lysine ou une arginine; A¿4? est un groupe -OH ou -NH¿2?; et X est un peptide tel que D-ornithyl-proline, prolyl-D-ornithine, D-lysyl-proline, prolyl-D-lysine, D-arginyl-proline, prolyl-D-arginine, glycyl-ornithine, ornithyl-glycine, glycyl-lysine, lysyl-glycine, glycyl-arginine et arginyl-glycine, où l'atome d'hydrogène du groupe .omega.-amino de D-lysine, L-lysine, D-ornithine et L-ornithine peut être remplacé par un groupe acyle .omega.-amino, et ledit peptide est relié aux restes d'acides aminés en positions 6 et 8 par l'intermédiaire de liaisons peptides en soi; Trp est un tryptophane; et Cys est une cystéine]. On présente également unexemple de ce polypeptide représenté par la formule (1). Ce polypeptide peut être utilisé dans une composition pharmaceutique comme agent antimicrobien ou antiviral, notamment comme agent anti-VIH et comme composant de systèmes de transfection d'ADN pour la thérapie génique.

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