Antiviral peptides
AssigneeHoughten Pharmaceuticals, Inc.
InventorsRichard A. Houghten, Patricia A. Weber
Life of this patent
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Abstract
The present invention provides antiviral peptides having the general structure, Arg-Arg-Trp-Trp-Cys-Arg-X, where X is an amino acid or an amino acid analog, the stereochemistry of the amino acids or amino acid analogs can be (D)- or (L)-amino acids and the amino and carboxy termini of the peptide can be modified. The invention also provides a pharmaceutical composition comprising an antiviral peptide and methods of using an antiviral peptide in vitro or in vivo to reduce or inhibit a herpes simplex virus infection.
Claims18
An antiviral peptide, comprising:
- ##STR3## wherein X is ##STR4## wherein R.sub.1 is H, COCH.sub.2, CH.sub.2 Ph, CH.sub.2 CH.sub.2 Ph, COPh, COO-t-butyl, COOCH.sub.2 Ph or a linear or branched alkyl having 2 to 6 carbons;
- R.sub.2 is H, C.sub.2 H.sub.5 or CH.sub.2 Ph;
- R.sub.3 is H, CH.sub.3, CH.sub.2 -Ph, CH.sub.2 -pyridyl, CH.sub.2 -imidazole, CH.sub.2 -indole, CH.sub.2 --(CH.sub.2).sub.2 COOH, CH.sub.2 --(CH.sub.2).sub.2 CONHR.sub.5, CH.sub.2 --(CH.sub.2).sub.n NHR.sub.5, CH.sub.2 --(CH.sub.2).sub.n SR.sub.5, CH.sub.2 --(CH.sub.2).sub.n NC(NH)NH.sub.2 ;
- or CH.sub.2 --(CH.sub.2).sub.n OH;
- R.sub.4 is OH, NH.sub.2, SH, NHCH.sub.3, N(CH.sub.3).sub.2, NHCH.sub.2 Ph, or OR.sub.5 ;
- and
- R.sub.5 is H, CH.sub.3, or a linear or branched alkyl having 2 to 6 carbons;
- and
- wherein Ph is C.sub.6 H.sub.5, Y is O or Ha, n is 0, 1, 2 or 3 and "*" denotes a chiral center, which can be R or S.
An antiviral peptide, comprising:
- Ac-Arg-Arg-Trp-Trp-Cys-Arg-Cys-NH.sub.2, wherein said amino acids are D-amino acids.
A composition of matter comprising a pharmaceutically acceptable carrier and an antiviral peptide, said peptide comprising:
- ##STR5## wherein X is ##STR6## wherein R.sub.1 is H, COCH.sub.3, CH.sub.2 Ph, CH.sub.2 CH.sub.2 Ph, COPh, COO-t-butyl, COOCH.sub.2 Ph or a linear or branched alkyl having 2 to 6 carbons;
- R.sub.2 is H, C.sub.2 H.sub.5 or CH.sub.2 Ph;
- R.sub.3 is H, CH.sub.2, CH.sub.2 --Ph, CH.sub.2 -pyridyl, CH.sub.2 -imidazole, CH.sub.2 -indole, CH.sub.2 -(CH.sub.2).sub.n COOH, CH.sub.2 --(CH.sub.2).sub.n CONHR.sub.5, CH.sub.2 --(CH.sub.2).sub.n NHR.sub.5, CH.sub.2 --(CH.sub.2).sub.n SR.sub.5, CH.sub.2 --(CH.sub.2).sub.n NC(NH)NH.sub.2 or CH.sub.2 --(CH.sub.2).sub.n OH;
- R.sub.4 is OH, NH.sub.a, SH, NHCH.sub.3, N(CH.sub.3).sub.2, NHCH.sub.2 Ph, or OR.sub.5 ;
- and R.sub.5 is H, CH.sub.3, or a linear or branched alkyl having 2 to 6 carbons;
- and
- wherein Ph is C.sub.6 H.sub.5, Y is O or H.sub.s, n is 0, 1, 2 or 3 and wherein "*" denotes a chiral center, which can be R or S.
Dependencies are inferred from the claim text.