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Peptide, a method for its preparation and a pharmaceutical composition containing the peptide
| Details |
Inventors: Deigin, Vladislav I.; Korotkov, Andrei Marxovich;
Assignee:
Primary Examiner: Tsang; Cecilia J.
Assistant Examiner: Harle; Jennifer
Attorney, Agent or Firm: Merchant, Gould, Smith, Edell, Welter & Schmidt, P.A.
A peptide of the formula I X-A-D-Trp-Y wherein X is hydrogen, glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophan, .alpha.-aminobutyric acid or .xi.-aminocaproic acid; A is D-glutamic acid or iD-glutamic acid; and Y is glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophn, .alpha.-aminobutyric acid, .xi.-aminocaproic acid, hydroxyl, or C.sub.1 -C.sub.3 substituted amide. |
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DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT The following standard abbreviations for the amino acid residues are used throughout the specification: Ala--alanine; Glu--glutamic acid; Phe--phenylalanine; Gly--glycine; Ile--isoleucine; Leu--leucine; Pro--proline; Val--valine; NVal--N-valine; Trp--tryptophan; and Tyr--tyrosine.
As mentioned previously, the present invention relates to a peptide of the formula I X-A-D-Trp-Y (I) wherein X is hydrogen, glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophan, .
alpha.
-aminobutyric acid, .
xi.
-aminocaproic acid; A is D-glutamic acid or iD-glutamic acid; and Y is glycine, alanine, leucine, isoleucine, valine, N-valine, proline, tyrosine, phenylalanine, tryptophan, D-alanine, D-leucine, D-isoleucine, D-valine, D-N-valine, D-proline, D-tyrosine, D-phenylalanine, D-tryptophan, .
alpha.
-aminobutyric acid, .
xi.
-aminocaproic acid, hydroxyl or C.
sub.
1 -C.
sub.
3 substituted amide.
In an embodiment of the invention, in the peptide of the formula I, X is hydrogen, A is D-glutamic acid or iD-glutamic acid, and Y is OH or a C.
sub.
1 -C.
sub.
3 substituted amide.
Preferred peptides of the invention have the sequence H-D-Glu-D-Trp-OH and H-iD-Glu-D-Trp-OH.
The peptides of the invention may additionally be characterized by the following physical and chemical properties: a yellowish-white or grey powder, soluble in water, moderately soluble in alcohol, and insoluble in chloroform.
The UV spectrum in the range of 250-300 nm has a maximum at 280.
+-.
2 nm, and a shoulder at 287.
+-.
2 nm.
The peptides of the invention may also include analogues of the peptide of the Formula I which may include, but are not limited to the peptide of the Formula I containing one or more amino acid insertions.
Amino acid insertions may consist of a single amino acid residue or sequential amino acids.
Analogues of the peptide of the invention exhibit the activity of the peptide and may further possess advantageous features such as increased bioavailability, stability, or reduced host immune recognition
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