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

Org Biomol Chem. 2008 Feb 21;6(4):682-92. doi: 10.1039/b716978g. Epub 2008 Jan 4.

Abstract

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.

MeSH terms

  • 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

Substances

  • Chromogenic Compounds
  • Oxazines
  • 3-aminophenoxazone
  • Agar
  • Aminopeptidases
  • Alanine