Hydrophobic peptide esters and amides

US5068223A · kind A · utility

Assignee

• The Board of Regents of the University of Texas System · US

Inventors

• Peter E. Lipsky · Dallas, US
• Dwain L. Thiele · Coppell, US

Key dates

• Filing date: Mar 15, 1989
• Grant date: Nov 26, 1991
• Expiry date: Mar 15, 2009

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K38/05
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Esters or amides of a peptide, preferebly a dipeptide, consisting essentially of natural or synthetic L-amino acids with hydrophobic side chains were found to have specific cellular toxicities. Preferable amino acids of the peptide are leucine, phenylalanine valine, isoleucine, alanine, proline, glycine or aspartic acid beta methyl ester. Preferable dipeptides are L leucyl L-leucine, L-leucyl L-phenylalanine, L-valyl L-phenylalanine, L-Leucyl L-isoleucine, L-henylalanyl L-phenylalanine, L-valyl L-leucine, L-leucyl L-alanine, L-valyl L-valine, L-phenylalanyl L leucine, L prolyl L-leucine, L-leucyl L-valine, L-phenylalanyl L-valine, L glycyl L-leucine, L-leucyl L-glycine, glycyl L-phenylalanine and L-aspartyl beta methyl ester L-phenylalanine. Most preferable dipeptides are L-leucyl L-leucine, L-leucyl L-phenylalanine, L-valyl L-phenylalanine, L-phenylalanyl L-leucine, L-leucyl L-isoleucine L-phenylalanyl L-phenylalanine and L-valyl L-leucine. The ester or amide of the dipeptide is most preferably alkyl, aralkyl or aryl a preferred alkylester is a methyl ester and may also be an ethyl ester or alkyl of up to about four carbon atoms such as propyl, isopropyl, butyl or isobutyl. Yet la…