Beta-peptides with antifungal activity
AssigneeWisconsin Alumni Research Foundation
InventorsSean P. Palecek, Samuel H. Gellman, William C. Pomerantz
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Abstract
The present invention is directed to the design, synthesis and use of various β-peptides exhibiting antifungal activity. The β-peptides are relatively short in length, adopt globally amphiphilic conformations, and cause little lysis of human red blood cells at concentrations that kill Candida albicans, a common human fungal pathogen.
Claims23
A method of inhibiting fungal growth, comprising contacting a fungus to be inhibited with an inhibitory amount of a β-peptide.
An antifungal composition, comprising:
- (a) an inhibitory amount of a β-peptide having the structure:
- (R1—R2—R3)3
- wherein R1, R2, and R3 of each triad are independently selected from β-amino acid residues bearing hydrophobic and cationic side chains such that the R1—R2—R3 triads in the β-peptide consist of β-amino acid residues bearing hydrophobic and cationic side chains in the sequential pattern hydrophobic-hydrophobic-cationic, hydrophobic-cationic-hydrophobic, or cationic-hydrophobic-hydrophobic;
- and
- (b) a pharmaceutically-acceptable carrier.
A method of treating fungal growth in a subject, comprising administering to the subject a therapeutically effective amount of a β-peptide selected from the group consisting of (ACHC-β3Val-β3Lys)3, β3Tyr-(ACHC-β3Val-β3Lys)3, β3Tyr-(ACHC-β3Leu-β3Lys)3, β3Tyr-(ACHC-β3Phe-β3Lys)3, β3Tyr-(β3Val-β3Val-β3Lys)3, β3Tyr-(ACHC-ACHC-β3Lys)3, (ACHC-β3Val-β3Lys)3, β3Tyr-(ACHC-β3Val-β3 Arg)3, β3Tyr-(β3Leu-ACHC-β3Lys)3 and C9-β3Tyr-(ACHC-ACHC-β3Lys)3.
A β-peptide having the structure:
- (ACHC—R2—R3)3
- wherein R2 is β3Val, β3Leu or β3Phe;
- and R3 is β3Lys or β3Arg.
The β-peptide according to claim 21 wherein said ACHC, R2 and R3 residues are homo-chiral.
Dependencies are inferred from the claim text.