Synthesis, evaluation, and computational studies of naphthalimide-based long-wavelength fluorescent boronic Acid reporters.
Boronic acids that change fluorescence properties upon sugar binding are very useful for the synthesis of carbohydrate sensors. Along this line, boronic acids that fluoresce beyond 500 nm are especially useful. A series of boronic acid fluorescent reporter compounds based on the 4-amino-1,8-naphthalimide structure have been synthesized (1a-d) and evaluated under near physiological conditions. These compounds showed good water solubility and significant changes in fluorescence properties after binding with sugars, with the emission wavelength being at around 570 nm. Analogues in this series with different substitutions showed similar properties. We have also examined the mechanism of the observed fluorescence changes for these compounds.
Jin
Shan
S
Department of Chemistry and Center for Biotechnology and Drug Design, Gerogia State University, Atlanta, GA 30302-4089, USA.
Wang
Junfeng
J
Li
Minyong
M
Wang
Binghe
B
D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D003198:Computer Simulation; D005453:Fluorescence; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D053644:Naphthalimides / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
D001897:Boronic Acids; D002241:Carbohydrates; D053644:Naphthalimides