A new boronic acid fluorescent sensor based on fluorene for monosaccharides at physiological pH.
Fluorescent boronic acids are very useful fluorescent sensor for detection of biologically important saccharides. Herein we synthesized a new fluorene-based fluorescent boronic acid that shows significant fluorescence changes upon addition of saccharides at physiological pH. Upon addition of fructose, sorbitol, glucose, galactose, ribose, and maltose at different concentration to the solution of 7-(dimethylamino)-9,9-dimethyl-9H-fluoren-2-yl-2-boronic acid (7-DMAFBA, 1), significant decreases in fluorescent intensity were observed. It was found that this boronic acid has high affinity (K(a)=3582.88 M(-1)) and selectivity for fructose over glucose at pH=7.4. The sensor 1 showed a linear response toward d-fructose in the concentrations ranging from 2.5×10(-5) to 4×10(-4) mol L(-1) with the detection limit of 1.3×10(-5) mol L(-1).
Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran. Electronic address: r.hosseinzadeh@umz.ac.ir.
Rahman
R
Hosseinzadeh
Department of Molecular and Cell Biology, Faculty of Basic Science, University of Mazandaran, Babolsar, Iran.
Maryam
M
Mohadjerani
Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran.
Mona
M
Pooryousef
Department of Inorganic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran.
Abbas
A
Eslami
Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
Saeed
S
Emami
D001897:Boronic Acids / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009005:Monosaccharides / Q000032:analysis*; D013050:Spectrometry, Fluorescence; D013997:Time Factors
D001897:Boronic Acids; D005449:Fluorenes; D005456:Fluorescent Dyes; D009005:Monosaccharides; C041509:fluorene
Boronic acid; Fluorene; Fluorescence; Monosaccharides; Sensor