Tetra and penta-peptides useful in regulating the immune system
AssigneeImmunobiology Research Institute, Inc.
InventorsGeorge Heavner, Gideon Goldstein, Tapan Audhya
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Abstract
Tetrapeptides and pentapeptides are disclosed which are capable of regulating the function of cells of the mammalian immune system. Also provided are pharmaceutical compositions containing the peptides and methods of use thereof.
Claims30
A tetrapeptide having the formula
- R--Arg--X--Y--Z--R.sup.1
- or a pharmaceutically acceptable acid or base addition salt thereof, wherein
- R is H, lower alkyl, acetyl, formyl, lower alkanoyl;
- X is Pro, dehydro-Pro, hydroxyl-Pro, D-Lys, Aib or Lys;
- Y is a D or L form of an amino acid selected from Ala, Asp, Glu, Gln, Asn, beta-Asp, Val or Ile;
- Z is Gly or a D or L form of an amino acid selected from Val, Ala, Leu or Ile;
- R.sup.1 is NR.sup.2 R.sup.3, wherein R.sup.2 or R.sup.3 are H or a straight chain or branched alkyl or alkenyl having 1 to 6 carbon atoms, optionally substituted with an aryl group or aryl substituted with either a halogen or a straight chain or branched alkyl or alkenyl having 1 to 6 carbon atoms or wherein R.sup.2 or R.sup.3 together comprise a cyclic methylene group of 3 to 7 carbon atoms, provided that when X is Lys, and Z is Val, Y is other than Asp, Asn, Ala or Glu, and when X is Lys, Y is other than Asp.
A tetrapeptide selected from the group consisting of
- Arg-Pro-Asp-Val
- Arg-Pro-Asp-Val-NH.sub.2
- Formyl-Arg-Pro-Asp-Val
- Acetyl-Arg-Pro-Asp-Val
- Acetyl-Arg-Pro-Asp-Val-NH.sub.2
- Acetyl-Arg-Pro-Asp-Val-NH(CH.sub.3)
- Acetyl-Arg-Pro-Ala-Val-NH.sub.2
- Acetyl-Arg-Pro-D-beta Asp-Val-NH.sub.2
- Acetyl-Arg-Pro-Glu-Val-NH.sub.2
- Acetyl-Arg-Pro-Glu-Val
- Acetyl-Arg-Aib-Glu-Val-NH.sub.2
- Acetyl-Arg-Aib-Ala-Val-NH.sub.2 or
- Acetyl-Arg-Pro-beta-Asp-Gly-NH.sub.2.
A peptide Acetyl-Arg-Pro-Val-Ala-NH.sub.2.
A peptide Acetyl-Arg-Pro-Val-Ala-NH(CH.sub.3).
A peptide Acetyl-Arg-Pro-Glu-Val-NH.sub.2.
A peptide Acetyl-Arg-Pro-Glu-Val-NH(CH.sub.3).
A peptide Acetyl-Arg-Pro-Asp-Val-NH(CH.sub.3).
A pentapeptide having the formula
- R.sup.4 -Arg-X'-Ala-Y'-Z'-R.sup.5
- or a pharmaceutically acceptable acid or base addition salt thereof, wherein
- R.sup.4 is H, lower alkyl, acetyl, formyl, lower alkanoyl or des-amino;
- X' is Pro, dehydro-Pro, hydroxy-Pro, D-Lys, Aib, or Lys;
- Y' is a D or L form of an amino acid selected from Val, Ile, Leu, Ala, Asp, Glu, Gln, Lys;
- Z' is a D or L form of an amino acid selected from Tyr, Val, Leu, His, Ala, Phe or Trp;
- R.sup.5 is OH or NR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 are H or a straight chain or branched alkyl or alkenyl having 1 to 6 carbon atoms, optionally substituted with an aryl group or aryl substituted with either a halogen or a straight chain or branched alkyl or alkenyl having 1 to 6 carbon atoms or wherein R.sup.4 and R.sup.5 together comprise a cyclic methylene group of 3 to 7 carbon atoms.
A peptide Arg-Pro-Ala-Val-Tyr.
A peptide Arg-Pro-Ala-Val-Tyr-NH.sub.2.
A peptide Acetyl-Arg-Lys-Ala-Val-Tyr-NH.sub.2.
Dependencies are inferred from the claim text.