@article{ni_kaur_springsteen_wang_franzen_2004, title={Regulating the fluorescence intensity of an anthracene boronic acid system: a B-N bond or a hydrolysis mechanism?}, volume={32}, ISSN={["1090-2120"]}, DOI={10.1016/j.bioorg.2004.06.004}, abstractNote={An anthracene-based fluorescent boronic acid system developed by the Shinkai group has been widely used for the preparation of fluorescent sensors for carbohydrates. Such application is based on the significant fluorescence intensity increase of this system upon binding with a carbohydrate. The mechanism through which this fluorescence intensity change happens was originally proposed to go through a B–N bond formation mechanism, which masks the nitrogen lone pair electrons. However, our own fluorescence studies suggest a possible alternative mechanism for the fluorescence change upon the formation of a boronic acid (1a) complex with diols. In this new proposed mechanism, complex formation induces solvolysis, which results in the protonation of the amine nitrogen if the reactions are carried out in a protic solvent such as water. This protonation prevents the photoinduced electron transfer, resulting in reduced quenching of the anthracene fluorescence. Such a solvolysis mechanism is supported by evidence from various types of experiments and theoretical calculations.}, number={6}, journal={BIOORGANIC CHEMISTRY}, author={Ni, WJ and Kaur, G and Springsteen, G and Wang, BH and Franzen, S}, year={2004}, month={Dec}, pages={571–581} } @article{ni_fang_springsteen_wang_2004, title={The design of boronic acid spectroscopic reporter compounds by taking advantage of the pK(a)-lowering effect of diol binding: Nitrophenol-based color reporters for diols}, volume={69}, ISSN={["1520-6904"]}, DOI={10.1021/jo0350357}, abstractNote={The complex that forms between a boronic acid and a diol is often much more acidic than the starting boronic acid. In conditions where the solution pH is between the two pK(a) values, the boron atom will convert from a neutral trigonal form to an anionic tetrahedral form upon complexation. Such a change is likely to dramatically alter the electron density of neighboring groups. Utilizing this effect, we have designed and synthesized two nitrophenol-based boronic acid reporter compounds that change ionization states and therefore spectroscopic properties upon diol binding. Both compounds show significant UV changes upon addition of saccharides. For example, a blue shift of the absorption max from 373 to 332 nm was observed with the addition of D-fructose to 2-hydroxy-5-nitrophenylboronic acid at neutral pH. Such a reporter compound can be used as a recognition and signaling unit for the construction of polyboronic acid sensors for the selective and specific recognitions of saccharides of biological significance.}, number={6}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Ni, WJ and Fang, H and Springsteen, G and Wang, BH}, year={2004}, month={Mar}, pages={1999–2007} } @article{franzen_ni_wang_2003, title={Study of the mechanism of electron-transfer quenching by boron-nitrogen adducts in fluorescent sensors}, volume={107}, ISSN={["1520-5207"]}, DOI={10.1021/jp027457a}, abstractNote={The mechanism of the change in fluorescence quenching by the amine in boronic acid-based carbohydrate sensor molecules has been explored using density functional theory (DFT). The geometric constra...}, number={47}, journal={JOURNAL OF PHYSICAL CHEMISTRY B}, author={Franzen, S and Ni, WJ and Wang, BH}, year={2003}, month={Nov}, pages={12942–12948} } @article{karnati_gao_gao_yang_ni_sankar_wang_2002, title={A glucose-selective fluorescence sensor based on boronic acid-diol recognition}, volume={12}, ISSN={["0960-894X"]}, DOI={10.1016/S0960-894X(02)00767-9}, abstractNote={A glucose selective diphenylboronic acid fluorescent sensor (10a) with a K(a) of 1472M(-1) has been synthesized and evaluated. This sensor shows a 43- and 49-fold selectivity for glucose over fructose and galactose, respectively. The binding affinity improvement is about 300-fold and the selectivity improvement for glucose over fructose is about 1400-fold compared with the monoboronic acid compound, phenylboronic acid. 1H NMR studies indicate that sensor 10a binds with alpha-D-glucofuranose in a bidentate manner (1:1 ratio).}, number={23}, journal={BIOORGANIC & MEDICINAL CHEMISTRY LETTERS}, author={Karnati, VV and Gao, XM and Gao, SH and Yang, WQ and Ni, WJ and Sankar, S and Wang, BH}, year={2002}, month={Dec}, pages={3373–3377} } @article{yang_gao_gao_karnati_ni_wang_hooks_carson_weston_2002, title={Diboronic acids as fluorescent probes for cells expressing sialyl Lewis X}, volume={12}, ISSN={["0960-894X"]}, DOI={10.1016/S0960-894X(02)00339-6}, abstractNote={A series of fluorescent diboronic acids was synthesized in nine steps as potential sensors for sialyl Lewis X (sLex). The fluorescent binding studies of these sensors with sLex were carried out in a mixed aqueous solution. Compound 7e was found to show the strongest fluorescence enhancement upon binding with sLex. Using cell cultures, 7e was shown to label sLex-expressing HEPG2 cells at 1 microM, while non-sLex-expressing cells were not labeled.}, number={16}, journal={BIOORGANIC & MEDICINAL CHEMISTRY LETTERS}, author={Yang, WQ and Gao, SH and Gao, XM and Karnati, VVR and Ni, WJ and Wang, BH and Hooks, WB and Carson, J and Weston, B}, year={2002}, month={Aug}, pages={2175–2177} }