Synthesis, Evaluation, and Computational Studies of Naphthalimide‐Based Long‐Wavelength Fluorescent Boronic Acid Reporters

Abstract

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.

Density functional theory based quantitative structure-property relationship studies on coumarin-based prodrugs

“…All the geometries are fully optimized, and the character of the stationary points found is confirmed by a harmonic frequency calculation at the same theory level to ensure a minimum is located. Such a practice is also the same as we have done in past studies (39,40). The kinetic constants and all structure parameters related to enzyme hydrolysis interaction and intramolecular lactonization of each compound are listed in Table 2.…”

Covalent Interactions in Chemosensor Design

“…Several recent reviews and research papers comprehensively summarize the use of boronic acids in sensor designs for carbohydrates [9,[14][15][16]66], fluoride [47][48][49][50][51], and cyanides [45,46], and have in-depth discussions of factors [15,19,67] that should be considered in designing such sensors. In addition, there have also been quite a few reviews [8,15,66] and research papers [54,[68][69][70][71][72][73][74][75][76][77][78][79][80][81][82][83][84][85] on boronic acids that change their fluorescent properties upon binding to a nucleophilic analyte or pH changes. Obviously, it would not be possible to describe all these findings here; therefore, readers are referred to the above-referenced papers for details.…”

A new boronic acid fluorescent sensor based on fluorene for monosaccharides at physiological pH

“…Several interesting fluorescence probes functionalized with boronic acids have been developed over the past decade. The most popular fluorophores are anthracene [21], naphthalene [22,23], naphthalimide [24,25] and quinoline [26].…”