Synthesis and testing of chromogenic phenoxazinone substrates for beta-alanyl aminopeptidase

Novel 7-N-(beta-alanyl)aminophenoxazin-3-one salts 27a-d have been synthesized and tested as chromogenic substrates for beta-alanyl aminopeptidase, which is present in Pseudomonas aeruginosa, the most common respiratory pathogen in patients with cystic fibrosis. The biological results show that 7-N-...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2008-01, Vol.6 (4), p.682-692
Main Authors: Zaytsev, Andrey V, Anderson, Rosaleen J, Bedernjak, Alexandre, Groundwater, Paul W, Huang, Yongxue, Perry, John D, Orenga, Sylvain, Roger-Dalbert, Celine, James, Arthur
Format: Article
Language:English
Subjects:
Agar - chemistry
Alanine - analogs & derivatives
Alanine - chemical synthesis
Alanine - chemistry
Alanine - metabolism
Alanine - pharmacology
Aminopeptidases - metabolism
Chromogenic Compounds - chemical synthesis
Chromogenic Compounds - metabolism
Chromogenic Compounds - pharmacology
Color
Oxazines - chemical synthesis
Oxazines - chemistry
Oxazines - metabolism
Oxazines - pharmacology
Pseudomonas aeruginosa - drug effects
Pseudomonas aeruginosa - enzymology
Pseudomonas aeruginosa - growth & development
Pseudomonas aeruginosa - metabolism
Substrate Specificity
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Summary:Novel 7-N-(beta-alanyl)aminophenoxazin-3-one salts 27a-d have been synthesized and tested as chromogenic substrates for beta-alanyl aminopeptidase, which is present in Pseudomonas aeruginosa, the most common respiratory pathogen in patients with cystic fibrosis. The biological results show that 7-N-(beta-alanyl)amino-1-pentylphenoxazin-3-one trifluoroacetate salt 27a is a chromogenic substrate for this bacterium, with a low degree of diffusion in nutrient media for growing bacterial cultures and a bright red colour, making it easily distinguishable from the agar background.
ISSN:1477-0520
1477-0539
DOI:10.1039/b716978g