Synthesis of pseudopeptides based L-tryptophan as a potential antimicrobial agent.
Four compounds named L-BTrpPA, L-Trp-o-PA, L-Trp-m-PA and L-Trp-p-PA, pseudopeptides constructed from pyridine and tryptophan units, were synthesized and tested against the Gram-positive, Gram-negative strains of bacteria and human pathogenic fungi. L-Trp-o-PA proved to be a broad-spectrum antimicrobial agent, showing a significant inhibition of the growth of Gram-positive bacteria (Staphylococcus aureus, methicillin-resistant S. aureus, Bacillus subtilis, Micrococcus luteus), and pathogenic fungi (Candida spp., Cryptococcus neoformans, Rhodotorula glutinis, Saccharomyces cerevisiae, Aspergillus spp., Rhizopus nigricans) tested and activity against Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa and Proteus vulgaris, Enterobacter aerogenes) tested. The in vitro cell cytotoxicity of L-Trp-o-PA was evaluated using haemolytic assay, in which the compound was found to have low lytic property, even up to the concentration of 4000 microg/mL, it only lysed 6-7% of erythrocytes, which was 100-fold greater than the MICs (minimum inhibitory concentration).
Lv
Jian
J
Department of Chemistry, The Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Yin
Liang
L
Liu
Tingting
T
Wang
Yongmei
Y
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010455:Peptides / Q000138:chemical synthesis* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D014364:Tryptophan / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D010455:Peptides; D014364:Tryptophan