Drug – bio-affecting and body treating compositions – Immunoglobulin – antiserum – antibody – or antibody fragment,... – Reduced antigenicity – reduced ability to bind complement – or...
Patent
1981-06-01
1983-08-16
Phillips, Delbert R.
Drug, bio-affecting and body treating compositions
Immunoglobulin, antiserum, antibody, or antibody fragment,...
Reduced antigenicity, reduced ability to bind complement, or...
2601125R, A61K 3700, C07C10352
Patent
active
043991246
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel peptides having biological properties, notably immunostimulating. It relates more particularly by way of novel industrial products, to peptides of samll size comprising--if one disregards the possible optical isomerism of their various aminoacyl residues--a peptide sequence (below called "common peptide sequence") in common with bradykinin and at least one aminoacyl residue separate from that to which the N-terminal end of said "common peptide sequence" is attached in the bradykinin itself. In particular, a peptide according to the invention, which comprises at the most seven aminoacyl residues, is characterised in that it contains a sequence prolyl.fwdarw.prolyl.fwdarw.glycyl, the carboxylic group of the glycyl residue being, as necessary, engaged in the peptide bond with another aminoacyl residue and in that the amino group of the first prolyl residue is engaged in a peptide bond with a different aminoacyl residue from arginyl, preferably of the lysyl or histidyl type.
The formula of bradykinin can be represented as follows: w.seryl.fwdarw.prolyl.fwdarw.phenylalanyl.fwdarw.arginine the N-terminal end towards the C-terminal end). This nomenclature will be also adopted in the following as regards the representation of the formulae of the peptides according to the invention.
Smaller peptides (among which are the pentapeptide arginyl.fwdarw.prolyl.fwdarw.prolyl.fwdarw.glycyl.fwdarw.phenyl-alanine) corresponding to sequences of bradykinin have been described in the literature. For the state of the art, reference may be made to the following documents:
Journal of the American Chemical Society, 1974, 96(12), pages 3990-9, R. J. Beuhler et al.: "Proton transfer mass spectrometry of peptides. Rapid heating technique for underivatized peptides containing arginine",
Acta Phys. Chem. 1974, 20(4), pages 465-470 L. Balaspiri et al.: "Preparation of fragments of bradykinin analogs containing optically active pipecolic acid",
George R. Pettit: "Synthetic peptides", Van Nostrand Reinhold Company, New York (US) pages 262, 460,
NATURE, vol. 187, no. 4739, Aug. 27, 1960, Mc Millan Ltd., London (GB), E. D. Nicolaides et al.: "Synthesis and biological properties of L-Arginyl-L-Prolyl-L-Prolyl-Glycyl-L-Phenylalanyl-L-Seryl-L-Phenylalanyl-L -Arginine, an Octapeptide related to Bradykinin", pages 773-774,
Canadian Journal of Physiology and Pharmacology, 1977, vol. 55, pages 855-867, D. Regoli et al.
To the extent that certain of these articles make reference to biological tests on smaller peptides than bradykinin, there has been observed, especially as regards peptides comprising at the most 7 aminoacyl residues, that they were quite devoid of the previously known activities of bradykinin. The discovery that certain of them possess important immunostimulant properties has only been more surprising.
The invention relates therefore also to pharmaceutical compositions, applicable to the treatment of diseases involving an activation mechanism of the macrophages and containing, in association with a physiologically acceptable vehicle, a peptide comprising at the most seven aminoacyl residues and including the abovesaid "common peptide sequence" whose N-terminal end is connected either to arginyl (corresponding to the aminoacyl residue contained by bradykinin at the corresponding place of its peptide chain), or to a separate aminoacyl residue.
By way of novel industrial products, the invention relates more particularly therefore to the novel peptides comprising at the most seven aminoacids and characterized in that they contain a prolyl.fwdarw.prolyl.fwdarw.glycyl sequence, the carboxylic group of the glycyl residue being, possibly, engaged in a peptide link with another aminoacyl residue, and in that the amino group of the first prolyl residue of the abovesaid prolyl.fwdarw.prolyl.fwdarw.glycyl sequence is engaged in a peptide link with a lysyl or histidyl residue.
By way of active peptides entering within the preferred pharmaceutical compositions of the invention, will be mentioned those which include
REFERENCES:
Nature, vol. 187, (1960) 773-774.
Petit, Synthetic Peptides vol. 1 (1970) 262,263.
American Chemical Society, Journal 96, (1974) 3990-3999.
Institut Pasteur
Phillips Delbert R.
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