Synthesis and evaluation of fluorogenic 2-amino-1,8-naphthyridine derivatives for the detection of bacteria

Organic & Biomolecular Chemistry
Linda VáradiRosaleen J Anderson

Abstract

Several novel fluorogenic N-aminoacylnaphthyridine substrates were synthesized in good yield and tested for their ability to detect pathogenic bacteria in agar-based cell culture. Simple 2-N-(β-alanyl)amino-5,7-dialkylnaphthyridine substrates were selectively hydrolysed by β-alanylaminopeptidase expressing bacteria, but were subject to diffusion in the agar medium. Diffusion was reduced in the 2-N-(β-alanyl)amino-7-alkylnaphthyridine substrates with longer alkyl chains, but inhibition of growth was increased. 2-N-(β-Alanyl)amino-7-octylnaphthyridine inhibited the growth of all species tested, except for strains resistant to colistin/polymyxin, providing a rationale for the development of substrates for the selective detection of drug resistant species in clinical samples.

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Citations

Sep 24, 2015·ACS Medicinal Chemistry Letters·Huan WangYefeng Tang
Jan 10, 2013·Annals of Laboratory Medicine·Alex van BelkumWilliam Michael Dunne
Oct 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Linda VáradiPaul W Groundwater
Nov 10, 2013·Bioconjugate Chemistry·A BunschotenF W B van Leeuwen

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