Synthesis and fluorescence properties of intramolecularly quenched fluorogenic p-nitroanilides containing coumarin or quinolinone derivatives as fluorophores.
Nine model intramolecularly quenched fluorogenic substrates (IQFS) of the general structure F-Phe-NH-Np, containing coumarin or quinolinone derivatives as fluorophores (F) and the p-nitroanilide group (Np) as quencher, were synthesized. The study of the fluorescence properties of the substrates synthesized and the corresponding fluorophores showed that efficient quenching of fluorescence (>89%) was observed in all cases. The combination of 7-glutarylamido-4-methyl-coumarin (Mec-NH-Glt-OH) or 7-methoxy-4-coumaryl-acetic acid (Mca) with the p-nitroanilide group gave the best results (97.2 and 98.8% quenching, respectively). These fluorophores can be used to convert peptide p-nitroanilides into IQFS, which, retaining their chromogenic properties, may be applied in both fluorometric and colorimetric assays.
Charitos
C
C
Department of Chemistry, University of Athens, Greece.
Tzougraki
C
C
Kokotos
G
G
D000814:Aniline Compounds / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D008956:Models, Chemical; D010452:Peptide Biosynthesis; D015363:Quinolones / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D000814:Aniline Compounds; D003374:Coumarins; D005456:Fluorescent Dyes; D015363:Quinolones; C030123:coumarin; C023650:aniline