Transport of antimicrobial agents using peptide carrier systems: anticandidal activity of m-fluorophenylalanine-peptide conjugates

A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C. albicans with minimum in...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1983-12, Vol.26 (12), p.1725-1729
Main Authors: Kingsbury, William D, Boehm, Jeffrey C, Mehta, Rajanikant J, Grappel, Sarah F
Format: Article
Language:English
Subjects:
Biological Transport
Candida - drug effects
Candida albicans
Chemistry
Exact sciences and technology
m-fluorophenylalanine
Oligopeptides - metabolism
Oligopeptides - pharmacology
Organic chemistry
peptide synthesis
Peptides
Phenylalanine - analogs & derivatives
Phenylalanine - metabolism
Phenylalanine - pharmacology
Preparations and properties
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Summary:A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C. albicans with minimum inhibitory concentrations (MIC's) ranging from 0.5 to 63 micrograms/mL. The parent L-m-fluorophenylalanine and peptides containing D-m-fluorophenylalanine were inactive (MIC greater than 250 micrograms/mL) in these tests. The results of competitive antagonism studies support peptide transport mediated entry of the inhibitory peptides, followed by release of L-m-fluorophenylalanine inside the cell.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00366a013