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Protegrins
| Details |
Inventors: Lehrer, Robert I.; Harwig, Sylvia S. L.; Kokryakov, Vladimir N.;
Assignee: University of California (Los Angeles, CA)
Primary Examiner: Wax; Robert A.
Assistant Examiner: Moore; William W.
Attorney, Agent or Firm: Pennie & Edmonds LLP
Peptide-based compounds containing four invariant cycteine residues which have been optionally oxidized to contain two intramolecular disulfide bonds, or modified forms where the cysteines are replaced are useful as preservatives and in preventing, treating, or ameliorating viral or microbial infection in animals and plants, and in inactivating endotoxin. These compounds, in one embodiment, are of the formula: ##STR1## and the N-terminal acylated and/or C-terminal amidated or esterified forms thereof, which is either in the optionally -SH stabilized linear or in a cystine-bridged form wherein each of A.sub.1 and A.sub.9 is independently a basic amino acid; each of A.sub.2 and A.sub.3 is independently a small amino acid; each of A.sub.5, A.sub.7, A.sub.12, A.sub.14 and A.sub.16 is independently a hydrophobic amino acid; A.sub.4 is a basic or a small amino acid; A.sub.10 is a basic or a small amino acid or is proline; A.sub.11 is a basic or a hydrophobic amino acid; A.sub.17 is not present or, if present, is a small amino acid; A.sub.18, is not present or, if present, is a basic amino acid; or a modified form of formula (1) and the N-terminal acylated and/or C-terminal amidated or esterified forms thereof wherein each of 1-4 cysteines is independently replaced by a hydrophobic amino acid or a small amino gacid. |
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DETAILED DESCRIPTION We claim: 1.
A purified and isolated or recombinantly produced compound having the formula: ##STR9## or a pharmaceutically acceptable salt or an N-terminal acylated or C-terminal amidated or esterified form thereof, which is either in a linear form or in a cystine-bridged form, wherein: each of A.
sub.
1 and A.
sub.
9 is independently a basic amino acid; each of A.
sub.
2 and A.
sub.
3 is independently a small amino acid; each of A.
sub.
5, A.
sub.
7, A.
sub.
12, A.
sub.
14 and A.
sub.
16 is independently a hydrophobic amino acid; A.
sub.
4 is a basic or a small amino acid; A.
sub.
10 is a basic or a small amino acid or is proline; A.
sub.
11 is a basic or a hydrophobic amino acid; A.
sub.
17 is not present or, if present, is a small amino acid; A.
sub.
18 is not present or, if present, is a basic amino acid; and each of C.
sub.
6, C.
sub.
8, C.
sub.
13 and C.
sub.
15 is independently selected from the group consisting of cysteine, a hydrophobic amino acid, a large polar amino acid and a small amino acid.
2.
The compound of claim 1 which has one or more characteristics selected from the grou p consisting of: the C-terminal carboxyl is of the formula selected from the group consisting of COOH or salts thereof; COOR, CONH.
sub.
2, CONHR and CONR.
sub.
2 wherein each R is independently a hydrocarbyl (1-6C); the amino group at the N-terminus is of the formula NH.
sub.
2 or NHCOR wherein R is a hydrocarbyl (1-6C) each of A.
sub.
1 and A.
sub.
9 is independently selected from the group consisting of R, K and Har; each of A.
sub.
2 and A.
sub.
3 is independently selected from the group consisting of G, A, S and T; A.
sub.
4 is R or G; each of A.
sub.
5, A.
sub.
14, and A.
sub.
16 is independently selected from the group consisting of I, V, NLe, L and F; each of A.
sub.
7 and A.
sub.
12 is independently selected from the group consisting of I, V, L, W, Y an d F; A.
sub.
10 is R, G or P; and A.
sub.
1 is R or W.
3.
The compound of claim 2, wherein said compound comprises two cystine bridges.
4.
The compound of claim 2, wherein said compound comprises one cystine bridges
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Drugs 
