@article{wang_echekki_2011, title={Investigation of lifted jet flames stabilization mechanism using RANS simulations}, volume={46}, ISSN={["1873-7226"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-79956106844&partnerID=MN8TOARS}, DOI={10.1016/j.firesaf.2011.02.007}, abstractNote={The mean structure, stability and the lift-off heights of lifted methane-air flames in a turbulent round jet are computed using the Reynolds-averaged Navier-Stokes (RANS) approach coupled with the Eddy-Dissipation Model (EDM) for combustion. The computations are based on a 5-step methane-air reduced mechanism. The simulation results show that the EDM model reproduces a mean partially-premixed flame structure at the leading edge of the lifted flame. The fine-tuning of the main EDM parameter for experimental lifted flames with co-flow also results in very good predictions of the lift-off height for lifted flames without co-flow. Implications of the use of the EDM concept for partially premixed flames are discussed.}, number={5}, journal={FIRE SAFETY JOURNAL}, author={Wang, Wei and Echekki, Tarek}, year={2011}, month={Jul}, pages={254–261} }
 @misc{wang_gao_wang_2002, title={Boronic acid-based sensors}, volume={6}, ISSN={["1875-5348"]}, DOI={10.2174/1385272023373446}, abstractNote={There has been a great deal of interest in recent years in using boronic acid as the recognition motif for the development of sensors. Because boronic acids can form tight and reversible complexes with diol compounds such as carbohydrates, the majority of the efforts, led by the Shinkai group, have been on the development of sensors for carbohydrates. Boronic acids are also known to selectively recognize fluoride among halides and other anions. Therefore, there have also been efforts in using boronic acid compounds for the development fluoride sensors. This paper reviews the progress in this field during the last five years. Keywords: Boronic, Acid-Based Sensors}, number={14}, journal={CURRENT ORGANIC CHEMISTRY}, author={Wang, W and Gao, XM and Wang, BH}, year={2002}, month={Dec}, pages={1285–1317} }
 @article{gao_wang_wang_2001, title={A new OsO4-mediated carbon-carbon bond cleavage reaction leading to the formation of anthraquinone}, number={1}, journal={Chemistry Letters}, author={Gao, S. H. and Wang, W. and Wang, B. H.}, year={2001}, pages={48–49} }
 @article{gao_wang_wang_2001, title={Building fluorescent sensors for carbohydrates using template-directed polymerizations}, volume={29}, ISSN={["0045-2068"]}, DOI={10.1006/bioo.2001.1219}, abstractNote={The ability to custom-make fluorescent sensors for different analytes could have a tremendous impact in a variety of areas. Template-directed polymerization or molecular imprinting seems to be a promising approach for the preparation of high-affinity and specific binding sites for different template molecules. However, the application of molecular imprinting in the preparation of fluorescent sensors has been hampered by the lack of suitable fluorescent tags, which would respond to the binding event with significant fluorescence intensity changes. We have designed and synthesized a fluorescent monomer (1) that allows for the preparation of fluorescent sensors of cis diols using molecular imprinting methods. This monomer has been used for the preparation of imprinted polymers as sensitive fluorescent sensors for D-fructose. The imprinted polymers prepared showed significant fluorescence intensity enhancement upon binding with the template carbohydrate.}, number={5}, journal={BIOORGANIC CHEMISTRY}, author={Gao, SH and Wang, W and Wang, BH}, year={2001}, month={Oct}, pages={308–320} }
 @article{springsteen_ballard_gao_wang_wang_2001, title={The development of photometric sensors for boronic acids}, volume={29}, ISSN={["0045-2068"]}, DOI={10.1006/bioo.2001.1217}, abstractNote={Boronic acids bind certain 1,2- and 1,3-diols with high affinity through reversible formation of boronate esters. They have been utilized as the recognition moiety for artificial receptors, particularly receptors for carbohydrates that have cis-diol moieties. Therefore, sensors for boronic acids could serve as universal reporters for monitoring boronate formation. This paper reports the design and synthesis of a series of photometric chemosensors for phenylboronic acid using diethanolamine as the recognition moiety. Diethanolamine, which binds strongly to boronic acids, has been linked to three different types of optical reporters. A photoinduced electron transfer system based on the anthracene fluorophore has been used to create sensors that show up to a fivefold increase in fluorescent intensity in the presence of millimolar concentrations of phenylboronic acid. Sensor designs based on the restriction of free rotation of extended pi systems and on the perturbed electronic properties of azo dyes are also included. This work demonstrates that sensors based on several different designs can be used for the detection of boronic acids.}, number={5}, journal={BIOORGANIC CHEMISTRY}, author={Springsteen, G and Ballard, CE and Gao, S and Wang, W and Wang, BH}, year={2001}, month={Oct}, pages={259–270} }
 @article{wang_camenisch_sane_zhang_hugger_wheeler_borchardt_wang_2000, title={A coumarin-based prodrug strategy to improve the oral absorption of RGD peptidomimetics}, volume={65}, ISSN={["0168-3659"]}, DOI={10.1016/S0168-3659(99)00241-2}, abstractNote={In recent years, major progress has been made in the design and synthesis of fibrinogen antagonists, which are peptidomimetic Arg-Gly-Asp (RGD) analogs. These RGD analogs are very promising antiplatelet agents. However, the clinical development of orally active RGD analogs has been hindered by the low oral bioavailability of many such RGD analogs. Aimed at enhancing their oral bioavailability, we have synthesized several coumarin-based cyclic prodrugs of RGD analogs, which have the two most polar functional groups, a carboxyl and an amino group, masked as an ester and an amide, respectively. As expected, these cyclic prodrugs have higher membrane interaction potentials as estimated by determining their partitioning between aqueous buffer and an immobilized artificial membrane than the corresponding RGD analogs. Consequently, these cyclic prodrugs are 5-6-fold more able to permeate monolayers of Caco-2 cells, an in vitro cell culture model of the intestinal mucosa barrier. Preliminary studies using dog also indicate the promising potential of using this coumarin-based prodrug strategy to improve the oral bioavailability of such RGD analogs.}, number={1-2}, journal={JOURNAL OF CONTROLLED RELEASE}, author={Wang, W and Camenisch, G and Sane, DC and Zhang, HJ and Hugger, E and Wheeler, GL and Borchardt, RT and Wang, BH}, year={2000}, month={Mar}, pages={245–251} }
 @article{shan_zheng_ballard_wang_borchardt_wang_2000, title={A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis}, volume={48}, number={2}, journal={Chemical & Pharmaceutical Bulletin}, author={Shan, D. X. and Zheng, A. L. and Ballard, C. E. and Wang, W. and Borchardt, R. T. and Wang, B. H.}, year={2000}, pages={238–244} }
 @article{wang_borchardt_wang_2000, title={Orally active peptidomimetic RGD analogs that are glycoprotein IIb/IIIa antagonists}, volume={7}, number={4}, journal={Current Medicinal Chemistry}, author={Wang, W. and Borchardt, R. T. and Wang, B.}, year={2000}, pages={437–453} }
 @article{wang_springsteen_gao_wang_2000, title={The first fluorescent sensor for boronic and boric acids with sensitivity at sub-micromolar concentrations}, number={14}, journal={Chemical Communications (Cambridge, England)}, author={Wang, W. and Springsteen, G. and Gao, S. H. and Wang, B. H.}, year={2000}, pages={1283–1284} }
 @article{wang_gao_wang_1999, title={Building fluorescent sensors by template polymerization: The preparation of a fluorescent sensor for D-Fructose}, volume={1}, ISSN={["1523-7060"]}, DOI={10.1021/ol9908732}, abstractNote={[formula: see text] The application of molecular imprinting in making fluorescent sensors has been hampered by the lack of suitable fluorescent tags, which would respond to the binding event with significant fluorescence intensity changes. We have designed and synthesized a fluorescent monomer which allows for the preparation of fluorescent sensors of cis diols using molecular imprinting methods. This monomer was used for the preparation of sensitive fluorescent sensors for D-fructose.}, number={8}, journal={ORGANIC LETTERS}, author={Wang, W and Gao, SH and Wang, BH}, year={1999}, month={Oct}, pages={1209–1212} }
 @article{liao_wang_wang_1999, title={Building fluorescent sensors by template polymerization: The preparation of a fluorescent sensor for L-tryptophan}, volume={27}, ISSN={["0045-2068"]}, DOI={10.1006/bioo.1999.1151}, abstractNote={Abstract The development of fluorescent sensors for organic molecules is of great practical importance in chemical, biological, and pharmaceutical sciences. Using l -tryptophan as an example, we have studied a new way of making polymeric fluorescent sensors using template polymerization or molecular imprinting techniques. The fluorescent polymers were prepared using functional monomers with a fluorescent probe attached to it. The fluorescence of this polymer could be quenched by 4-nitrobenzaldehyde. Addition of the template molecules, l -tryptophan, increased the fluorescence intensity of the imprinted polymer/quencher mixture in a concentration-dependent fashion, presumably through the displacement of the quencher from the binding sites by l -tryptophan. This fluorescence intensity change upon mixing with l -tryptophan allows the binding event to be detected easily. The sensor also exhibited enantioselectivity for the template molecules. For example, the effect of d -tryptophan on the fluorescence intensity of the polymer is about 70% that of its l -enantiomer. Furthermore, the effect of l -phenylalanine and l -alanine on the fluorescence intensity change is much smaller than that of l -tryptophan. Because the approach used does not require the de novo design of the complementary binding site and does not rely on any specific structural features of the template molecule or prior knowledge of its three-dimensional structure, the same principle could potentially be useful for the future construction of practical fluorescent sensors for many other compounds.}, number={6}, journal={BIOORGANIC CHEMISTRY}, author={Liao, Y and Wang, W and Wang, BH}, year={1999}, month={Dec}, pages={463–476} }
 @article{gudmundsson_pauletti_wang_shan_zhang_wang_borchardt_1999, title={Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability}, volume={16}, ISSN={["0724-8741"]}, DOI={10.1023/A:1018828207920}, abstractNote={{"Label"=>"UNLABELLED"} To evaluate the cellular permeation characteristics and the chemical and enzymatic stability of coumarinic acid-based cyclic prodrugs 1 and 2 of the opioid peptides [Leu5]-enkephalin (H-Tyr-Gly-Gly-Phe-Leu-OH) and DADLE (H-Tyr-D-Ala-Gly-Phe-D-Leu-OH), respectively. {"Label"=>"METHODS", "NlmCategory"=>"METHODS"} The rates of conversion of the cyclic prodrugs 1 and 2 to [Leu5]-enkephalin and DADLE, respectively, in HBSS, pH 7.4 (Caco-2 cell transport buffer) and in various biological media having measurable esterase activity were determined by HPLC. The cell permeation characteristics of [Leu5]-enkephalin, DADLE and cyclic prodrugs 1 and 2 were measured using Caco-2 cell monolayers grown onto microporus membranes and monitored by HPLC. {"Label"=>"RESULTS", "NlmCategory"=>"RESULTS"} In HBSS, pH 7.4, cyclic prodrugs 1 and 2 degraded chemically to intermediates that further degraded to [Leu5]-enkephalin and DADLE, respectively, in stoichiometric amounts. In 90% human plasma and rat liver homogenate, the disappearance of cyclic prodrugs 1 and 2 was significantly faster than in HBSS, pH 7.4. The half-lives in 90% human plasma and in rat liver homogenate were substantially longer after pretreatment with paraoxon, a known inhibitor of serine-dependent esterases. When applied to the AP side of a Caco-2 cell monolayer, cyclic prodrug 1 exhibited significantly greater stability against peptidase metabolism than did [Leu5]-enkephalin. Cyclic prodrug 2 and DADLE exhibited similar stability when applied to the AP side of the Caco-2 cell monolayer. Prodrug 1 was 665-fold more able to permeate the Caco-2 cell monolayers than was [Leu5]-enkephalin, in part because of its increased enzymatic stability. Prodrug 2 was shown to be approximately 31 fold more able to permeate a Caco-2 cell monolayer than was DADLE. {"Label"=>"CONCLUSIONS", "NlmCategory"=>"CONCLUSIONS"} Cyclic prodrugs 1 and 2, prepared with the coumarinic acid promoiety, were substantially more able to permeate Caco-2 cell monolayers than were the corresponding opioid peptides. Prodrug 1 exhibited increased stability to peptidase metabolism compared to [Leu5]-enkephalin. In various biological media, the opioid peptides were released from the prodrugs by an esterase-catalyzed reaction, which is sensitive to paraoxon inhibition.}, number={1}, journal={PHARMACEUTICAL RESEARCH}, author={Gudmundsson, OS and Pauletti, GM and Wang, W and Shan, DX and Zhang, HJ and Wang, BH and Borchardt, RT}, year={1999}, month={Jan}, pages={7–15} }
 @article{wang_jiang_ballard_wang_1999, title={Prodrug approaches to the improved delivery of peptide drugs}, volume={5}, number={4}, journal={Current Pharmaceutical Design}, author={Wang, W. and Jiang, J. and Ballard, C. E. and Wang, B.}, year={1999}, pages={265–287} }
 @article{wang_wang_camenisch_elmo_zhang_borchardt_1999, title={Synthesis and evaluation of novel coumarin-based esterase- sensitive cyclic prodrugs of peptidomimetic RGD analogs with improved membrane permeability}, volume={47}, number={1}, journal={Chemical & Pharmaceutical Bulletin}, author={Wang, B. H. and Wang, W. and Camenisch, G. P. and Elmo, J. and Zhang, H. J. and Borchardt, R. T.}, year={1999}, pages={90–95} }
 @article{wang_nimkar_wang_zhang_shan_gudmundsson_gangwar_siahaan_borchardt_1999, title={Synthesis and evaluation of the physicochemical properties of esterase-sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers}, volume={53}, ISSN={["1397-002X"]}, DOI={10.1034/j.1399-3011.1999.00071.x}, abstractNote={Abstract: In an attempt to improve the membrane permeabilities of opioid peptides, we have synthesized cyclic prodrugs of [Leu5]‐enkephalin and DADLE using a coumarinic acid or a phenylpropionic acid linker. The synthesis of the coumarinic acid‐ and phenylpropionic acid‐based cyclic prodrugs followed similar strategies. Key intermediates were the compounds with the C‐terminal amino acids of opioid peptides (L‐Leu, [Leu5]‐enkephalin; D‐Leu, DADLE) attached to the phenol hydroxyl group and the remaining amino acids of the peptide linked via the N‐terminal amino acid (L‐Tyr) attached to the carboxylic acid groups of the prodrug moieties (coumarinic acid or propionic acid). Cyclization of these linear precursors gave the cyclic prodrugs in 30–50% yields. These cyclic prodrugs exhibited excellent transcellular permeation characteristics across Caco‐2 cell monolayers, an in vitro model of the intestinal mucosa. To correlate the cellular permeabilities of these cyclic prodrugs with their physicochemical properties, we calculated their Stokes–Einstein molecular radii from their diffusion coefficients which were determined by NMR and we determined their membrane interaction potentials using immobilized artificial membrane (IAM) column chromatography. The cyclic prodrugs exhibited molecular radii similar to those of the parent compounds, [Leu5]‐enkephalin and DADLE. However, these cyclic prodrugs were shown to have much higher membrane interaction potentials than their corresponding opioid peptides. Therefore, the enhanced cellular permeation of the cyclic prodrugs is apparently due to the alteration of their lipophilicity and hydrogen bonding potential, but not their molecular sizes.}, number={4}, journal={JOURNAL OF PEPTIDE RESEARCH}, author={Wang, B and Nimkar, K and Wang, W and Zhang, H and Shan, D and Gudmundsson, O and Gangwar, S and Siahaan, T and Borchardt, RT}, year={1999}, month={Apr}, pages={370–382} }
 @article{zheng_wang_zhang_wang_1999, title={Two new improved approaches to the synthesis of coumarin-based prodrugs}, volume={55}, ISSN={["0040-4020"]}, DOI={10.1016/S0040-4020(99)00121-0}, abstractNote={Abstract Our laboratory has recently reported the development of a coumarin-based, esterase-sensitive prodrug system for the preparation of prodrugs of amines, peptides, and peptidomimetics. Biological evaluations including animal studies have demonstrated the clinical potential of this prodrug system. However, the original synthetic method used required a long sequence of reactions with a relatively low overall yield. In this report, we describe two new approaches to the synthesis of these coumarin-based prodrugs. The first approach is a photochemical approach taking advantage of the photoisomerization of cinnamic acid and its derivatives. The second approach is through the catalytic hydrogenation of a triple bond for the generation of the cis double bond in the coumarinic acid moiety. Both approaches allow for the synthesis of these prodrugs in fewer steps with much improved overall yield.}, number={14}, journal={TETRAHEDRON}, author={Zheng, AL and Wang, W and Zhang, HJ and Wang, B}, year={1999}, month={Apr}, pages={4237–4254} }
 @article{camenisch_wang_wang_borchardt_1998, title={A comparison of the bioconversion rates and the Caco-2 cell permeation characteristics of coumarin-based cyclic prodrugs and methylester-based linear prodrugs of RGD peptidomimetics}, volume={15}, ISSN={["0724-8741"]}, DOI={10.1023/A:1011975404789}, abstractNote={{"Label"=>"PURPOSE", "NlmCategory"=>"OBJECTIVE"} To compare the bioconversion rates in various biological media and the Caco-2 cell permeation characteristics of coumarin based cyclic prodrugs (3a, 3b) and methylester-based linear prodrugs (1b, 2b) of two RGD peptidomimetics (1a, 2a). {"Label"=>"METHODS", "NlmCategory"=>"METHODS"} Bioconversion rates of the prodrugs to the RGD peptidomimetics were determined in Hank balances salt solution (HBSS), pH 7,4, at 37 degrees C and in various biological media (human blood plasma, rat liver homogenate, Caco-2 cell homogenate) known to have esterase activity. Transport rates of the prodrugs and the RGD peptidomimetics were determined using Caco-2 cell monolayers, an in vitro cell culture model of the intestinal mucosa. RESULTS. In HBSS, pH 7,4, the coumarin-based cyclic prodrugs 3a and 3b degraded slowly and quantitatively to the RGD peptidomimetics 1a and 2a, respectively (3a, t1/2 = 630+2-14 min; 3b, t1/2 = 301 +/-12 min). The methylester-based linear prodrugs 1b and 2b were more stable to chemical hydrolysis (1b and 2b, t1/2 > 2000 min). Both the coumarin-based cyclic prodrugs and the methylester-based linear prodrugs degraded more rapidly in biological media containing esterase activity (e.g., 90% human blood plasma: 1b, t1/2 < 5 min; 2b, t1/2 < 5 min; 3a, t1/2 < 91+/-1 min; 3b, 1/2 < 57+/-2 min). When the apical (AP)-to-basolateral (BL) permeation characteristics were determined using Caco-2 cell monolayers, it was found that the methylester prodrugs 1b and 2b underwent esterase bioconversion (>80%) to the RGD peptidomimetics 1a and 2a, respectively, In contrast, the cyclic prodrugs 3a and 3b permeated the cell monolayers intact. Considering the appearance of both the prodrug and the RGD peptidomimetic on the BL side, the methylester prodrugs 1b and 2b were approximately 12-fold more able to permeate than were the RGD peptidomimetics 1a and 2a. When similar analysis of the transport data for the coumarin prodrugs 3a and 3b was performed, they were shown to be approximately 6-fold and 5-fold more able to permeate than were the RGD peptidomimetics 1a and 12a, respectively. {"Label"=>"CONCLUSION", "NlmCategory"=>"CONCLUSIONS"} The coumarin-based cyclic prodrugs 3a and 3b were chemically less stable, but metabolically more stable, then the methylester based linear prodrugs. The esterase stability of the cyclic prodrugs 3a and 3b means that they are transported intact across the Caco-2 cell monolayer in contrast to the methylester prodrugs 1b and 2b, which undergo facile bioconversion during their transport to the RGD peptidomimetics. However, both prodrug systems successfully delivered more (5-12-fold) of the RGD peptidomimetic and/or the precursor (prodrug) than did the RGD peptidomimetics themselves.}, number={8}, journal={PHARMACEUTICAL RESEARCH}, author={Camenisch, GP and Wang, W and Wang, BH and Borchardt, RT}, year={1998}, month={Aug}, pages={1174–1181} }
 @article{wang_zhang_zheng_wang_1998, title={Coumarin-based prodrugs. Part 3: Structural effects on the release kinetics of esterase-sensitive prodrugs of amines}, volume={6}, ISSN={["0968-0896"]}, DOI={10.1016/S0968-0896(98)00014-5}, abstractNote={To study the structural effects on the release kinetics of a coumarin-based esterase-sensitive prodrug system, two series of compounds with varying structural features of the ester 'trigger' part and the amine 'drug' part were synthesized. The half-lives of the nine model prodrugs in the presence of porcine liver esterase ranged from about 2 min to 190 min. The steric bulkiness of the acyl group seems to have only a very minor effect on the half-lives of the esterase-triggered release of amines from the model prodrugs. The rate of the lactonization depends on the steric and electronic properties of the amine moiety.}, number={4}, journal={BIOORGANIC & MEDICINAL CHEMISTRY}, author={Wang, BH and Zhang, HJ and Zheng, AL and Wang, W}, year={1998}, month={Apr}, pages={417–426} }
 @article{wang_lupke_di ventra_pantelides_gilligan_tolk_kizilyalli_roy_margaritondo_lucovsky_1998, title={Coupled electron-hole dynamics at the Si/SiO2 interface}, volume={81}, ISSN={["0031-9007"]}, DOI={10.1103/PhysRevLett.81.4224}, abstractNote={We report a new and surprising enhancement of the electric field at the Si/SiO2 interface following the cessation of intense pulsed near-infrared radiation. The phenomenon, measured by optical second-harmonic generation, occurs only for photon energies and oxide film thickness that exceed respective thresholds. We attribute the new effect to multiphoton hole injection into the oxide and to an asymmetry in electron and hole dynamics, in particular to distinctly different trapping and detrapping processes.}, number={19}, journal={PHYSICAL REVIEW LETTERS}, author={Wang, W and Lupke, G and Di Ventra, M and Pantelides, ST and Gilligan, JM and Tolk, NH and Kizilyalli, IC and Roy, PK and Margaritondo, G and Lucovsky, G}, year={1998}, month={Nov}, pages={4224–4227} }
 @article{liao_wang_wang_1998, title={Enantioselective polymeric transporters for tryptophan, phenylalanine, and histidine prepared using molecular imprinting techniques}, volume={26}, ISSN={["0045-2068"]}, DOI={10.1006/bioo.1998.1116}, abstractNote={Abstract Developing new methods for the separation of enantiomers is of great current interest because of the importance, challenge, and high cost associated with such separations. This is particularly true in the pharmaceutical industry because of the requirement for the high purity, including enantiopurity, of the final drug products. In this study, polymeric molecular transporters were prepared using molecular imprinting techniques with D -tryptophan, D -phenylalanine, and D -histidine as the templates, respectively. It was found that the transporters thus prepared were able to transport the template amino acids across a hydrophobic chloroform layer in a U-tube at rates that were 1.34- to 3.8-fold higher than the transport of their L -enantiomers. The magnitude of discrimination depends on the conditions of polymerization and the templates used. Molecular “receptors” prepared using molecular imprinting techniques could potentially be used for the separation of enantiomers through serial enantioselective transports.}, number={6}, journal={BIOORGANIC CHEMISTRY}, author={Liao, Y and Wang, W and Wang, BH}, year={1998}, month={Dec}, pages={309–322} }