@article{smith_liu_wang_liu_chen_starkey_bai_2010, title={Aphid feeding activates expression of a transcriptome of oxylipin-based defense signals in wheat involved in resistance to herbivory}, volume={36}, number={3}, journal={Journal of Chemical Ecology}, author={Smith, C. M. and Liu, X. M. and Wang, L. J. and Liu, X. and Chen, M. S. and Starkey, S. and Bai, J. F.}, year={2010}, pages={260–276} }
 @article{lin_yan_huang_altier_li_carrasco_suyemoto_johnston_wang_wang_et al._2007, title={Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA}, volume={35}, DOI={10.1093/nar/gkl1091}, abstractNote={The boronic acid moiety is a versatile functional group useful in carbohydrate recognition, glycoprotein pull-down, inhibition of hydrolytic enzymes and boron neutron capture therapy. The incorporation of the boronic-acid group into DNA could lead to molecules of various biological functions. We have successfully synthesized a boronic acid-labeled thymidine triphosphate (B-TTP) linked through a 14-atom tether and effectively incorporated it into DNA by enzymatic polymerization. The synthesis was achieved using the Huisgen cycloaddition as the key reaction. We have demonstrated that DNA polymerase can effectively recognize the boronic acid-labeled DNA as the template for DNA polymerization, that allows PCR amplification of boronic acid-labeled DNA. DNA polymerase recognitions of the B-TTP as a substrate and the boronic acid-labeled DNA as a template are critical issues for the development of DNA-based lectin mimics via in vitro selection.}, number={4}, journal={Nucleic Acids Research}, author={Lin, N. and Yan, J. and Huang, Z. and Altier, C. and Li, M. Y. and Carrasco, N. and Suyemoto, M. and Johnston, L. and Wang, S. M. and Wang, Q. and et al.}, year={2007}, pages={1222–1229} }
 @article{yang_lin_wang_2005, title={A new type of boronic acid fluorescent reporter compound for sugar recognition}, volume={46}, ISSN={["0040-4039"]}, DOI={10.1016/j.tetlet.2005.09.074}, abstractNote={Fluorescent boronic acids that change fluorescent properties upon carbohydrate binding are very useful for the preparation of fluorescent sensors for sugars. Herein we report 5-quinolineboronic acid (5-QBA) that shows significant fluorescent property changes through a unique pKa-switching mechanism upon binding a diol in aqueous solution.}, number={46}, journal={TETRAHEDRON LETTERS}, author={Yang, WQ and Lin, L and Wang, BH}, year={2005}, month={Nov}, pages={7981–7984} }
 @misc{wang_weston_yang_2005, title={Fluorescent sensor compounds for detecting saccharides}, volume={6,916,660}, publisher={Washington, DC: U.S. Patent and Trademark Office}, author={Wang, B. and Weston, B. and Yang, W.}, year={2005} }
 @article{chen_yang_sivamani_bruneau_wang_qu_2005, title={Selective elimination of perennial ryegrass by activation of a pro-herbicide through engineering E-coli argE gene}, volume={15}, ISSN={["1572-9788"]}, DOI={10.1007/s11032-004-7243-z}, number={4}, journal={MOLECULAR BREEDING}, author={Chen, X and Yang, WQ and Sivamani, E and Bruneau, AH and Wang, BH and Qu, RD}, year={2005}, month={May}, pages={339–347} }
 @article{yang_li_wang_2004, title={A  new type of water-soluble fluorescent boronic acid suitable for construction of polyboronic acids for carbohydrate recognition}, volume={10}, number={6}, journal={Heterocyclic Communications}, author={Yang, W. Q. and Li, L. and Wang, B. H.}, year={2004}, pages={383–388} }
 @article{zych_yang_liao_griffin_wang_2004, title={The effect of substitution patterns on the release rates of opioid peptides DADLE and [Leu(5)]-enkephalin from coumarin prodrug moieties}, volume={32}, ISSN={["1090-2120"]}, DOI={10.1016/j.bioorg.2003.12.002}, abstractNote={A coumarin-based prodrug system has been developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. The effect of the phenyl ring substitutions on the release kinetics of such prodrugs of model amines was examined recently and it was found that appropriately positioned alkyl substituents on the phenyl ring could help to facilitate the release. Aimed at further understanding the structure-release rate relationship of the coumarin-based cyclic prodrugs, we synthesized and examined a series of substituted coumarinic acid derivatives of opioid peptides, DADLE, and [Leu(5)]-enkephalin.}, number={2}, journal={BIOORGANIC CHEMISTRY}, author={Zych, LA and Yang, WQ and Liao, Y and Griffin, KR and Wang, BH}, year={2004}, month={Apr}, pages={109–123} }
 @article{yang_yan_springsteen_deeter_wang_2003, title={A novel type of fluorescent boronic acid that shows large fluorescence intensity changes upon binding with a carbohydrate in aqueous solution at physiological pH}, volume={13}, ISSN={["1464-3405"]}, DOI={10.1016/S0960-894X(03)00086-6}, abstractNote={In this paper we report 8-quinolineboronic acid as a novel type of fluorescent probe for carbohydrates. This boronic acid responds to the binding of a carbohydrate with over 40-fold increases in fluorescence intensity and shows optimal fluorescence change at physiological pH in aqueous solution.}, number={6}, journal={BIOORGANIC & MEDICINAL CHEMISTRY LETTERS}, author={Yang, WQ and Yan, J and Springsteen, G and Deeter, S and Wang, BH}, year={2003}, month={Mar}, pages={1019–1022} }
 @misc{yang_gao_wang_2003, title={Boronic acid compounds as potential pharmaceutical agents}, volume={23}, ISSN={["1098-1128"]}, DOI={10.1002/med.10043}, abstractNote={Abstract}, number={3}, journal={MEDICINAL RESEARCH REVIEWS}, author={Yang, WQ and Gao, XM and Wang, BH}, year={2003}, month={May}, pages={346–368} }
 @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{yang_yan_fang_wang_2003, title={The first fluorescent sensor for D-glucarate based on the cooperative action of boronic acid and guanidinium groups}, ISSN={["1364-548X"]}, DOI={10.1039/b300098b}, abstractNote={A new fluorescent sensor (1) with a recognition unit consisting of a boronic acid moiety and a guanidinium unit shows selective binding of D-glucarate in aqueous solution.}, number={6}, journal={CHEMICAL COMMUNICATIONS}, author={Yang, WQ and Yan, J and Fang, H and Wang, BH}, year={2003}, pages={792–793} }
 @article{springsteen_wang_2002, title={A detailed examination of boronic acid-diol complexation}, volume={58}, ISSN={["0040-4020"]}, DOI={10.1016/S0040-4020(02)00489-1}, abstractNote={Boronic acids bind with compounds containing diol moieties with high affinity through reversible boronate formation. However, the conditions that foster tight binding between the diol and the boronic acid are not well understood. Also, due to the multiple ionic states of both the boronic acid and boronate ester, the equilibrium constants reported in the literature have not always been strictly defined, and therefore there is a lack of ‘comparability’ between the reported values. To address these issues, we have developed a method for examining boronate ester stability using the fluorescent reporter Alizarin Red S. We have used this system to determine the binding constants of a series of diols, and as a basis from which to derive a number of relationships that correlate the various equilibrium constants in the literature.}, number={26}, journal={TETRAHEDRON}, author={Springsteen, G and Wang, BH}, year={2002}, month={Jun}, pages={5291–5300} }
 @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{yu_ballard_boyle_wang_2002, title={An inexpensive carbohydrate derivative used as a chiral auxiliary in the synthesis of alpha-hydroxy carboxylic acids}, volume={58}, ISSN={["0040-4020"]}, DOI={10.1016/S0040-4020(02)00871-2}, abstractNote={Protected α-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate (α-hydroxy acetate) enolates using a d-fructose-derived chiral auxiliary. The new chiral center was assigned the R configuration based on comparisons of optical rotations and on one crystal structure analysis. This alkylation methodology is compatible with several hydroxyl protecting groups. The free hydroxy acids were obtained upon removal of the protecting group from the hydroxyl functionality followed by saponification.}, number={38}, journal={TETRAHEDRON}, author={Yu, HW and Ballard, CE and Boyle, PD and Wang, BH}, year={2002}, month={Sep}, pages={7663–7679} }
 @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{yang_gao_springsteen_wang_2002, title={Catechol pendant polystyrene for solid-phase synthesis}, volume={43}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(02)01370-9}, abstractNote={A catechol pendant polystyrene polymer was prepared from the Merrifield resin via a convenient procedure with high-density loading. Due to the high affinity binding between catechol and boronic acid, the polymer resin readily captures boronic acid compounds. The feasibility of using immobilized catechol to capture boronic acid products for purification and solid-phase transformation was demonstrated. Moreover, the immobilized catechol was also used for the preparation of resin-bound catecholborane, which can be used as a solid-phase amidation reagent.}, number={36}, journal={TETRAHEDRON LETTERS}, author={Yang, WQ and Gao, XM and Springsteen, G and Wang, BH}, year={2002}, month={Sep}, pages={6339–6342} }
 @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} }
 @misc{ballard_yu_wang_2002, title={Recent developments in depsipeptide research}, volume={9}, ISSN={["1875-533X"]}, DOI={10.2174/0929867023371049}, abstractNote={This review focuses on the major developments in depsipeptide research since 1995. Depsipeptides are bio-oligomers composed of hydroxy and amino acids linked by amide and ester bonds. Many depsipeptides show very promising biological activities, including anticancer, antibacterial, antiviral, antifungal, anti-inflammatory, and anti-clotting or anti-antherogenic properties. In this report depsipeptides exhibiting these properties are discussed. Their isolation, structural determination, and notable structural features are discussed, but their biological properties and therapeutic potentials are emphasized. Depsipeptides have shown the greatest therapeutic potential as anticancer agents. Four depsipeptides have entered clinical trials for cancer treatment. Among the antiviral compounds discovered, the callipeltins and the quinoxapeptins are particularly promising due to their inhibitory activities against HIV. These compounds have the potential to be developed as anti-AIDS drugs or to serve as lead compounds for the discovery of structurally related anti-AIDS compounds. Antifungal compounds, such as the jaspamides, may lead to therapies against many of the opportunistic infections that accompany AIDS. Anti-inflammatory compounds such as SCH217048 act as neurokinin antagonists and may lead to anti-inflammatory treatments. Some depsipeptides such as micropeptins and A90720A have been found to be effective plasmin inhibitors, which have implications as treatments for cardiovascular diseases. Compounds such as SCH58149 help control the levels of HDL and LDL.}, number={4}, journal={CURRENT MEDICINAL CHEMISTRY}, author={Ballard, CE and Yu, H and Wang, B}, year={2002}, month={Feb}, pages={471–498} }
 @article{yu_ballard_wang_2001, title={A highly stereoselective entry to alpha-hydroxy carboxylic acids using D-fructose diacetonide as a chiral auxiliary}, volume={42}, ISSN={["0040-4039"]}, DOI={10.1016/S0040-4039(01)00043-0}, abstractNote={Protected α-hydroxy carboxylic acids were synthesized in moderate yield and high diastereoselectivity by alkylation of glycolate ester enolates using a d-fructose-derived chiral auxiliary. The new chiral center was assigned the (R)-configuration based upon comparisons to the literature. Both enantiomers of the auxiliary are readily available.}, number={10}, journal={TETRAHEDRON LETTERS}, author={Yu, HW and Ballard, E and Wang, BH}, year={2001}, month={Mar}, pages={1835–1838} }
 @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{springsteen_wang_2001, title={Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates}, number={17}, journal={Chemical Communications (Cambridge, England)}, author={Springsteen, G. and Wang, B. H.}, year={2001}, pages={1608–1609} }
 @article{yu_wang_2001, title={Arylboronic acid-facilitated selective reduction of aldehydes by tributyltin hydride}, volume={31}, ISSN={["0039-7911"]}, DOI={10.1081/SCC-100105400}, abstractNote={Aldehydes were selectively reduced in the presence of a ketone with tributyltin hydride (n-Bu3SnH) and arylboronic acids. The double bond of an α,β-unsaturated system was not affected under the reaction conditions.}, number={17}, journal={SYNTHETIC COMMUNICATIONS}, author={Yu, HW and Wang, BH}, year={2001}, pages={2719–2725} }
 @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{latta_springsteen_wang_2001, title={Development and synthesis of an arylboronic acid-based solid-phase amidation catalyst}, number={11}, journal={Synthesis (Stuttgart)}, author={Latta, R. and Springsteen, G. and Wang, B. H.}, year={2001}, pages={1611–1613} }
 @article{wang_thakker_2001, title={Editorial announcement}, volume={21}, ISSN={["0198-6325"]}, DOI={10.1002/1098-1128(200103)21:2<103::AID-MED1001>3.0.CO;2-Z}, abstractNote={Medicinal Research ReviewsVolume 21, Issue 2 p. 103-104 Free Access Editorial announcement Binghe Wang, Corresponding Author Binghe Wang Editor Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695Search for more papers by this authorDhiren R. Thakker, Dhiren R. Thakker Editor School of Pharmacy, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599Search for more papers by this author Binghe Wang, Corresponding Author Binghe Wang Editor Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695Search for more papers by this authorDhiren R. Thakker, Dhiren R. Thakker Editor School of Pharmacy, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599Search for more papers by this author First published: 14 February 2001 https://doi.org/10.1002/1098-1128(200103)21:2<103::AID-MED1001>3.0.CO;2-ZAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume21, Issue2March 2001Pages 103-104 RelatedInformation}, number={2}, journal={MEDICINAL RESEARCH REVIEWS}, author={Wang, BH and Thakker, DR}, year={2001}, month={Mar}, pages={103–104} }
 @article{gao_herzig_wang_2001, title={OsO4-mediated conversion of primary amines to nitriles}, number={4}, journal={Synthesis (Stuttgart)}, author={Gao, S. H. and Herzig, D. and Wang, B. H.}, year={2001}, pages={544–546} }
 @article{jiang_wang_sane_wang_2001, title={Synthesis of RGD analogs as potential vectors for targeted drug delivery}, volume={29}, ISSN={["0045-2068"]}, DOI={10.1006/bioo.2001.1227}, abstractNote={RGD analogs bind to integrin receptors with high affinity and therefore have the potential to be used as vectors for the targeted delivery of pharmaceutical agents to designated sites. Critical to this application is the ability to synthesize RGD analogs with different side chain functional groups that allow for the ready tethering of pharmaceutical agents without sacrificing their affinity for the target receptor significantly. A series of RGD analogs intended to be used as delivery vectors of pharmaceutical agents were prepared and evaluated for their ability to inhibit platelet aggregation by binding to glycoprotein IIb/IIIa. Among them, compound 11 showed the lowest IC50 against platelets activated by ADP. It was found that such RGD analogs could tolerate side chain modification fairly well with various functional groups attached such as amide, amine, ester, protected amine and poly(ethylene glycol). The fact that the compound with a side chain modification of poly(ethylene glycol) retained high affinity for glycoprotein IIb/IIIa (IC50 150 nM) suggests the feasibility of tethering fairly large pharmaceutical agents to such RGD analogs without significant sacrifice of their affinity to the intended receptor.}, number={6}, journal={BIOORGANIC CHEMISTRY}, author={Jiang, J and Wang, W and Sane, DC and Wang, BH}, year={2001}, month={Dec}, pages={357–379} }
 @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{liao_hendrata_bae_wang_2000, title={The effect of phenyl substituents on the release rates of esterase-sensitive coumarin-based prodrugs}, volume={48}, number={8}, journal={Chemical & Pharmaceutical Bulletin}, author={Liao, Y. and Hendrata, S. and Bae, S. Y. and Wang, B. H.}, year={2000}, pages={1138–1147} }
 @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{zheng_shan_shi_wang_1999, title={A novel resin linker for solid-phase peptide synthesis which call be cleaved using two sequential mild reactions}, volume={64}, ISSN={["0022-3263"]}, DOI={10.1021/jo990770x}, abstractNote={The interest in developing new linkers for solid-phase peptide and organic synthesis has increased tremendously as a result of the rapid development of combinatorial chemistry. Herein, we report the development of a new redox-sensitive linker for solid-phase peptide synthesis. This linker can be readily cleaved under mild conditions by using two sequential mild reactions, a reduction followed by a base (Bu4N+F-)-catalyzed cyclic ether formation. By using this new linker, two short peptides, a tetrapeptide [Boc-Trp-Ala-Gly-Gly-OH] and a pentapeptide [Boc-Asn-Ala-Ser(OBn)-Gly-Glu(OBn)-OH)], were synthesized. Because the cleavage does not use acidic conditions, this resin linker provides an alternative when acidic conditions are not desirable. Furthermore, the cleavage conditions do not affect most of the side chain protecting group. Therefore, the peptides synthesized can be used for the segment synthesis of larger peptides without the need to reprotect the side chain functional groups.}, number={20}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Zheng, AL and Shan, DX and Shi, XL and Wang, BH}, year={1999}, month={Oct}, pages={7459–7466} }
 @article{zheng_shan_wang_1999, title={A redox-sensitive resin linker for the solid phase synthesis of C-terminal modified peptides}, volume={64}, ISSN={["0022-3263"]}, DOI={10.1021/jo981528d}, abstractNote={With the rapid development of combinatorial chemistry using solid phase synthesis, there is a great deal of interest in developing new solid phase linkers, which are stable during the solid phase synthesis process and yet readily cleavable under mild conditions. By taking advantage of a "trimethyl lock"-facilitated lactonization reaction, we have developed a redox-sensitive resin linker for the synthesis of C-terminal-modified peptides. The cleavage only requires mild reducing agents such as sodium hydrosulfite, which is not expected to cause any problem with the commonly seen organic functional groups. Using this new linker, three short peptides were synthesized with high isolated yields (70-90%). Such a linker could potentially be used for the synthesis of modified peptide libraries, which allows for the ready cleavage of the linker under mild conditions.}, number={1}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Zheng, A and Shan, D and Wang, B}, year={1999}, month={Jan}, pages={156–161} }
 @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_vanzile_schlueter_geiser_kini_sche_koo_whangbo_nixon_winter_et al._1999, title={In-plane ESR microwave conductivity measurements and electronic band structure studies of the organic superconductor beta ''-(BEDT-TTF)(2)SF5CH2CF2SO3}, volume={103}, ISSN={["1089-5647"]}, DOI={10.1021/jp991268j}, abstractNote={The electronic structure of the organic superconductor {beta}''-(BEDT-TTF){sub 2}SF{sub 5}CH{sub 2}CF{sub 2}SO{sub 3} (BEDT-TTF is bis(ethylenedithio)tetrathiafulvalene) was characterized with the use of electron spin resonance (ESR) spectroscopy and electronic band structure calculations. The room-temperature ESR line width is 24-27 G in the plane of a donor molecule layer (i.e., in the ab-plane) and {approx}32 G along the normal to this plane (i.e., along the c*-direction). The ab-plane anisotropy of the microwave conductivity was extracted for the first time from the ESR Dysonian line shape analysis. The in-plane conductivity varies sinusoidally, is maximal along the interstack direction (b-axis), and is minimal along the donor stack direction (a-axis). The Fermi surfaces of the title compound consist of a 2D hole pocket and a pair of 1D wavy lines. The directions for the in-plane conductivity maximum and minimum are in excellent agreement with the electronic band structure calculated for {beta}''-(BEDT-TTF){sub 2}SF{sub 5}CH{sub 2}CF{sub 2}SO{sub 3}, and the origin of the in-plane conductivity anisotropy lies in the one-dimensional part of the Fermi surface. This is the first time that an organic conductor shows Dysonian ESR line shape due to its 2D and strongly metallic nature, yet the 1D character is revealed simultaneously through themore » in-plane conductivity anisotropy.« less}, number={26}, journal={JOURNAL OF PHYSICAL CHEMISTRY B}, author={Wang, HH and VanZile, ML and Schlueter, JA and Geiser, U and Kini, AM and Sche, PP and Koo, HJ and Whangbo, MH and Nixon, PG and Winter, RW and et al.}, year={1999}, month={Jul}, pages={5493–5499} }
 @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{liao_wang_1999, title={Substituted coumarins as esterase-sensitive prodrug moieties with improved release rates}, volume={9}, number={13}, journal={Bioorganic & Medicinal Chemistry Letters}, author={Liao, Y. and Wang, B. H.}, year={1999}, pages={1795–1800} }
 @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{gudmundsson_jois_vander velde_siahaan_wang_borchardt_1999, title={The effect of conformation on the membrane permeation of coumarinic acid- and phenylpropionic acid-based cyclic prodrugs of opioid peptides}, volume={53}, ISSN={["1397-002X"]}, DOI={10.1034/j.1399-3011.1999.00076.x}, abstractNote={Abstract: In an earlier study using Caco‐2 cells, an in vitro cell culture model of the intestinal mucosa, we have shown that the coumarinic‐based (3 and 4) and the phenylpropionic acid‐based (5 and 6) cyclic prodrugs were more able to permeate the cell monolayers than were the corresponding opioid peptides, [Leu5]‐enkephalin (1, H‐Tyr‐Gly‐Gly‐Phe‐Leu‐OH) and DADLE (2, H‐Tyr‐D‐Ala‐Gly‐Phe‐D‐Leu‐OH). In an attempt to explain the increased permeation of the cyclic prodrugs, we have determined the possible conformations of these cyclic prodrugs in solution, using spectroscopic techniques (2D‐NMR, CD) and molecular dynamics simulations. Spectroscopic as well as molecular dynamic studies indicate that cyclic prodrug 4 exhibits two major conformers (A and B) in solution. Conformer A exhibited a type I β‐turn at Tyr1‐D‐Ala2‐Gly3‐Phe4. The presence of a turn was supported by ROE cross‐peaks between the NH of D‐Ala2 and the NH of Gly3 and between the NH of Gly3 and the NH of Phe4. Conformer B of cyclic prodrug 4 consisted of type II β‐turns at the same positions. The type II turn was stabilized by hydrogen bonding, thus forming a more compact structure, whereas the type I turn did not exhibit similar intramolecular hydrogen bonding. Spectroscopic data for compounds 3, 5 and 6 are consistent with the conclusion that these cyclic prodrugs have solution structures similar to those observed with cyclic prodrug 4. The increased lipophilicity and well‐defined secondary structures in cyclic prodrugs 3–6, but not in the linear peptides 1 and 2, could both contribute to the enhanced ability of these prodrugs to permeate membranes.}, number={4}, journal={JOURNAL OF PEPTIDE RESEARCH}, author={Gudmundsson, OS and Jois, SDS and Vander Velde, DG and Siahaan, TJ and Wang, B and Borchardt, RT}, year={1999}, month={Apr}, pages={383–392} }
 @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{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} }
 @article{wang_zheng_1997, title={A photo-sensitive protecting group for amines based on coumarin chemistry}, volume={45}, number={4}, journal={Chemical & Pharmaceutical Bulletin}, author={Wang, B.-H and Zheng, A. L}, year={1997}, pages={715–718} }
 @misc{shan_nicolaou_borchardt_wang_1997, title={Prodrug strategies based on intramolecular cyclization reactions}, volume={86}, ISSN={["0022-3549"]}, DOI={10.1021/js970069d}, abstractNote={Several new prodrug systems for amines, alcohols, and peptides are reviewed. The design of these new prodrug systems takes advantage of several facile intramolecular cyclization reactions, that permit separate manipulation of the release kinetics independent of the structural features of the drug moiety. Such systems can be used for the preparation of esterase-, phosphatase-, and redox-sensitive prodrugs of amines and alcohols and esterase-sensitive cyclic prodrugs of peptides and peptide mimetics.}, number={7}, journal={JOURNAL OF PHARMACEUTICAL SCIENCES}, author={Shan, DX and Nicolaou, MG and Borchardt, RT and Wang, BH}, year={1997}, month={Jul}, pages={765–767} }
 @misc{gangwar_pauletti_wang_siahaan_stella_borchardt_1997, title={Prodrug strategies to enhance the intestinal absorption of peptides}, volume={2}, ISSN={["1359-6446"]}, DOI={10.1016/S1359-6446(97)01011-8}, abstractNote={Clinical development of orally active peptide drugs has been restricted by the unfavorable physicochemical properties of these molecules limiting intestinal mucosal permeation and the lack of stability of peptides against enzymatic degradation. Successful oral delivery of peptides will depend, therefore, on strategies designed to alter the physicochemical characteristics of these potential drugs, without changing their biological activity, in order to increase the permeation across intestinal cells. This manuscript will focus on the biological barrier properties that limit oral peptide bioavailability and on prodrug strategies designed to overcome these barriers.}, number={4}, journal={DRUG DISCOVERY TODAY}, author={Gangwar, S and Pauletti, GM and Wang, BH and Siahaan, TJ and Stella, VJ and Borchardt, RT}, year={1997}, month={Apr}, pages={148–155} }