메뉴 건너뛰기




Volumn 59, Issue 7, 2016, Pages 3163-3182

FimH Antagonists: Phosphate Prodrugs Improve Oral Bioavailability

Author keywords

[No Author keywords available]

Indexed keywords

FIMBRIA PROTEIN; MANNOSIDE; PHOSPHATE; PRODRUG;

EID: 84966378417     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01923     Document Type: Article
Times cited : (37)

References (56)
  • 1
    • 0038825532 scopus 로고    scopus 로고
    • Clinical practice. Acute uncomplicated urinary tract infection in women
    • Fihn, S. D. Clinical practice. Acute uncomplicated urinary tract infection in women N. Engl. J. Med. 2003, 349, 259-266 10.1056/NEJMcp030027
    • (2003) N. Engl. J. Med. , vol.349 , pp. 259-266
    • Fihn, S.D.1
  • 2
    • 46749131414 scopus 로고    scopus 로고
    • Origins and virulence mechanisms of uropathogenic Escherichia coli
    • Wiles, T. J.; Kulesus, R. R.; Mulvey, M. A. Origins and virulence mechanisms of uropathogenic Escherichia coli Exp. Mol. Pathol. 2008, 85, 11-19 10.1016/j.yexmp.2008.03.007
    • (2008) Exp. Mol. Pathol. , vol.85 , pp. 11-19
    • Wiles, T.J.1    Kulesus, R.R.2    Mulvey, M.A.3
  • 3
    • 84858650295 scopus 로고    scopus 로고
    • In vitro antimicrobial resistance of urinary Escherichia coli isolates among U.S. outpatients from 2000 to 2010
    • Sanchez, G. V.; Master, R. N.; Karlowsky, J. A.; Bordon, J. M. In vitro antimicrobial resistance of urinary Escherichia coli isolates among U.S. outpatients from 2000 to 2010 Antimicrob. Agents Chemother. 2012, 56, 2181-2183 10.1128/AAC.06060-11
    • (2012) Antimicrob. Agents Chemother. , vol.56 , pp. 2181-2183
    • Sanchez, G.V.1    Master, R.N.2    Karlowsky, J.A.3    Bordon, J.M.4
  • 4
    • 0030813508 scopus 로고    scopus 로고
    • Diagnosis and treatment of uncomplicated urinary tract infection
    • Hooton, T. M.; Stamm, W. E. Diagnosis and treatment of uncomplicated urinary tract infection Infect. Dis. Clin. North Am. 1997, 11, 551-581 10.1016/S0891-5520(05)70373-1
    • (1997) Infect. Dis. Clin. North Am. , vol.11 , pp. 551-581
    • Hooton, T.M.1    Stamm, W.E.2
  • 5
    • 0030879648 scopus 로고    scopus 로고
    • Bacterial virulence in urinary tract infection
    • Svanborg, C.; Godaly, G. Bacterial virulence in urinary tract infection Infect. Dis. Clin. North Am. 1997, 11, 513-529 10.1016/S0891-5520(05)70371-8
    • (1997) Infect. Dis. Clin. North Am. , vol.11 , pp. 513-529
    • Svanborg, C.1    Godaly, G.2
  • 6
    • 0035283006 scopus 로고    scopus 로고
    • Structure and function of Escherichia coli type 1 pili: New insight into the pathogenesis of urinary tract infections
    • Schilling, J. D.; Mulvey, M. A.; Hultgren, S. J. Structure and function of Escherichia coli type 1 pili: new insight into the pathogenesis of urinary tract infections J. Infect. Dis. 2001, 183, S36-S40 10.1086/318855
    • (2001) J. Infect. Dis. , vol.183 , pp. S36-S40
    • Schilling, J.D.1    Mulvey, M.A.2    Hultgren, S.J.3
  • 7
    • 33748145105 scopus 로고    scopus 로고
    • Structural and functional insights into the assembly of type 1 pili from Escherichia coli
    • Capitani, G.; Eidam, O.; Glockshuber, R.; Grütter, M. G. Structural and functional insights into the assembly of type 1 pili from Escherichia coli Microbes Infect. 2006, 8, 2284-2290 10.1016/j.micinf.2006.03.013
    • (2006) Microbes Infect. , vol.8 , pp. 2284-2290
    • Capitani, G.1    Eidam, O.2    Glockshuber, R.3    Grütter, M.G.4
  • 8
    • 33646103431 scopus 로고    scopus 로고
    • Carbohydrates as future anti-adhesion drugs for infectious diseases
    • Sharon, N. Carbohydrates as future anti-adhesion drugs for infectious diseases Biochim. Biophys. Acta, Gen. Subj. 2006, 1760, 527-537 10.1016/j.bbagen.2005.12.008
    • (2006) Biochim. Biophys. Acta, Gen. Subj. , vol.1760 , pp. 527-537
    • Sharon, N.1
  • 9
    • 0020336272 scopus 로고
    • Interaction of mannose-containing oligosaccharides with the fimbrial lectin of Escherichia coli
    • Firon, N.; Ofek, I.; Sharon, N. Interaction of mannose-containing oligosaccharides with the fimbrial lectin of Escherichia coli Biochem. Biophys. Res. Commun. 1982, 105, 1426-1432 10.1016/0006-291X(82)90947-0
    • (1982) Biochem. Biophys. Res. Commun. , vol.105 , pp. 1426-1432
    • Firon, N.1    Ofek, I.2    Sharon, N.3
  • 10
    • 0021106296 scopus 로고
    • Carbohydrate specificity of the surface lectins of Escherichia coli, Klebsiella pneumoniae, and Salmonella typhimurium
    • Firon, N.; Ofek, I.; Sharon, N. Carbohydrate specificity of the surface lectins of Escherichia coli, Klebsiella pneumoniae, and Salmonella typhimurium Carbohydr. Res. 1983, 120, 235-249 10.1016/0008-6215(83)88019-7
    • (1983) Carbohydr. Res. , vol.120 , pp. 235-249
    • Firon, N.1    Ofek, I.2    Sharon, N.3
  • 12
    • 0023095282 scopus 로고
    • Aromatic alpha-glycosides of mannose are powerful inhibitors of the adherence of type 1 fimbriated Escherichia coli to yeast and intestinal epithelial cells
    • Firon, N.; Ashkenazi, S.; Mirelman, D.; Ofek, I.; Sharon, N. Aromatic alpha-glycosides of mannose are powerful inhibitors of the adherence of type 1 fimbriated Escherichia coli to yeast and intestinal epithelial cells Infect. Immun. 1987, 55, 472-476
    • (1987) Infect. Immun. , vol.55 , pp. 472-476
    • Firon, N.1    Ashkenazi, S.2    Mirelman, D.3    Ofek, I.4    Sharon, N.5
  • 13
    • 33750197673 scopus 로고    scopus 로고
    • Evaluation of the carbohydrate recognition domain of the bacterial adhesin FimH. Design, synthesis and binding properties of mannoside ligands
    • Sperling, O.; Fuchs, A.; Lindhorst, T. K. Evaluation of the carbohydrate recognition domain of the bacterial adhesin FimH. Design, synthesis and binding properties of mannoside ligands Org. Biomol. Chem. 2006, 4, 3913-3922 10.1039/b610745a
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 3913-3922
    • Sperling, O.1    Fuchs, A.2    Lindhorst, T.K.3
  • 18
    • 84864409295 scopus 로고    scopus 로고
    • FimH antagonists: Structure-activity and structure-property relationships for biphenyl α- D -mannopyranosides
    • Pang, L.; Kleeb, S.; Lemme, K.; Rabbani, S.; Scharenberg, M.; Zalewski, A.; Schädler, F.; Schwardt, O.; Ernst, B. FimH antagonists: structure-activity and structure-property relationships for biphenyl α- d -mannopyranosides ChemMedChem 2012, 7, 1404-1422 10.1002/cmdc.201200125
    • (2012) ChemMedChem , vol.7 , pp. 1404-1422
    • Pang, L.1    Kleeb, S.2    Lemme, K.3    Rabbani, S.4    Scharenberg, M.5    Zalewski, A.6    Schädler, F.7    Schwardt, O.8    Ernst, B.9
  • 23
    • 0031824605 scopus 로고    scopus 로고
    • Inhibition of the type 1 fimbriae-mediated adhesion of Escherichia coli to erythrocytes by multiantennary d -mannosyl clusters: The effect of multivalency
    • Lindhorst, T. K.; Kieburg, C.; Krallmann-Wenzel, U. Inhibition of the type 1 fimbriae-mediated adhesion of Escherichia coli to erythrocytes by multiantennary d -mannosyl clusters: The effect of multivalency Glycoconjugate J. 1998, 15, 605-613 10.1023/A:1006920027641
    • (1998) Glycoconjugate J. , vol.15 , pp. 605-613
    • Lindhorst, T.K.1    Kieburg, C.2    Krallmann-Wenzel, U.3
  • 24
    • 12244292949 scopus 로고    scopus 로고
    • Inhibition of adhesion of type 1 fimbriated Escherichia coli to highly mannosylated ligands
    • Nagahori, N.; Lee, R. T.; Nishimura, S.-L.; Pagé, S.; Roy, R.; Lee, Y. C. Inhibition of adhesion of type 1 fimbriated Escherichia coli to highly mannosylated ligands ChemBioChem 2002, 3, 836-844 10.1002/1439-7633(20020902)3:9<836::AID-CBIC836>3.0.CO;2-2
    • (2002) ChemBioChem , vol.3 , pp. 836-844
    • Nagahori, N.1    Lee, R.T.2    Nishimura, S.-L.3    Pagé, S.4    Roy, R.5    Lee, Y.C.6
  • 26
    • 33646919890 scopus 로고    scopus 로고
    • A modular approach for the synthesis of oligosaccharide mimetics
    • Patel, A.; Lindhorst, T. K. A modular approach for the synthesis of oligosaccharide mimetics Carbohydr. Res. 2006, 341, 1657-1668 10.1016/j.carres.2006.01.024
    • (2006) Carbohydr. Res. , vol.341 , pp. 1657-1668
    • Patel, A.1    Lindhorst, T.K.2
  • 27
    • 37549038807 scopus 로고    scopus 로고
    • Mannosylated M(0) dendrimers with nanomolar affinities to Escherichia coli FimH
    • Touaibia, M.; Wellens, A.; Shiao, T. C.; Wang, Q.; Sirois, S.; Bouckaert, J.; Roy, R. Mannosylated M(0) dendrimers with nanomolar affinities to Escherichia coli FimH ChemMedChem 2007, 2, 1190-1201 10.1002/cmdc.200700063
    • (2007) ChemMedChem , vol.2 , pp. 1190-1201
    • Touaibia, M.1    Wellens, A.2    Shiao, T.C.3    Wang, Q.4    Sirois, S.5    Bouckaert, J.6    Roy, R.7
  • 28
    • 78651268228 scopus 로고    scopus 로고
    • The functional valency of dodecamannosylated fullerenes with Escherichia coli FimH - Towards novel bacterial antiadhesives
    • Durka, M.; Buffet, K.; Iehl, J.; Holler, M.; Nierengarten, J.-F.; Taganna, J.; Bouckaert, J.; Vincent, S. P. The functional valency of dodecamannosylated fullerenes with Escherichia coli FimH-towards novel bacterial antiadhesives Chem. Commun. 2011, 47, 1321-1323 10.1039/C0CC04468G
    • (2011) Chem. Commun. , vol.47 , pp. 1321-1323
    • Durka, M.1    Buffet, K.2    Iehl, J.3    Holler, M.4    Nierengarten, J.-F.5    Taganna, J.6    Bouckaert, J.7    Vincent, S.P.8
  • 29
    • 84878590386 scopus 로고    scopus 로고
    • Heptyl α- D -mannosides grafted on a β-cyclodextrin core to interfere with Escherichia coli adhesion: An in vivo multivalent effect
    • Bouckaert, J.; Li, Z.; Xavier, C.; Almant, M.; Caveliers, V.; Lahoutte, T.; Weeks, S. D.; Kovensky, J.; Gouin, S. G. Heptyl α- d -mannosides grafted on a β-cyclodextrin core to interfere with Escherichia coli adhesion: An in vivo multivalent effect Chem.-Eur. J. 2013, 19, 7847-7855 10.1002/chem.201204015
    • (2013) Chem. - Eur. J. , vol.19 , pp. 7847-7855
    • Bouckaert, J.1    Li, Z.2    Xavier, C.3    Almant, M.4    Caveliers, V.5    Lahoutte, T.6    Weeks, S.D.7    Kovensky, J.8    Gouin, S.G.9
  • 31
    • 0035953319 scopus 로고    scopus 로고
    • Property-based design: Optimization of drug absorption and pharmacokinetics
    • Van de Waterbeemd, H.; Smith, D. A.; Beaumont, K.; Walker, D. K. Property-based design: Optimization of drug absorption and pharmacokinetics J. Med. Chem. 2001, 44, 1313-1333 10.1021/jm000407e
    • (2001) J. Med. Chem. , vol.44 , pp. 1313-1333
    • Van De Waterbeemd, H.1    Smith, D.A.2    Beaumont, K.3    Walker, D.K.4
  • 32
    • 0028948839 scopus 로고
    • A theoretical basis for a biopharmaceutic drug classification: The correlation of in vitro drug product dissolution and in vivo bioavailability
    • Amidon, G. L.; Lennernäs, H.; Shah, V. P.; Crison, J. R. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 1995, 12, 413-420 10.1023/A:1016212804288
    • (1995) Pharm. Res. , vol.12 , pp. 413-420
    • Amidon, G.L.1    Lennernäs, H.2    Shah, V.P.3    Crison, J.R.4
  • 34
    • 34548024418 scopus 로고    scopus 로고
    • Prodrug strategies to overcome poor water solubility
    • Stella, V. J.; Nti-Addae, K. W. Prodrug strategies to overcome poor water solubility Adv. Drug Delivery Rev. 2007, 59, 677-694 10.1016/j.addr.2007.05.013
    • (2007) Adv. Drug Delivery Rev. , vol.59 , pp. 677-694
    • Stella, V.J.1    Nti-Addae, K.W.2
  • 35
    • 0022973596 scopus 로고
    • Uptake of prodrugs by rat intestinal mucosal cells: Mechanism and pharmaceutical implications
    • Stewart, B. H.; Amidon, G. L.; Brabec, R. K. Uptake of prodrugs by rat intestinal mucosal cells: mechanism and pharmaceutical implications J. Pharm. Sci. 1986, 75, 940-945 10.1002/jps.2600751005
    • (1986) J. Pharm. Sci. , vol.75 , pp. 940-945
    • Stewart, B.H.1    Amidon, G.L.2    Brabec, R.K.3
  • 36
    • 33344460707 scopus 로고    scopus 로고
    • Fosamprenavir: Clinical pharmacokinetics and drug interactions of the amprenavir prodrug
    • Wire, M. B.; Shelton, M. J.; Studenberg, S. Fosamprenavir: clinical pharmacokinetics and drug interactions of the amprenavir prodrug Clin. Pharmacokinet. 2006, 45, 137-168 10.2165/00003088-200645020-00002
    • (2006) Clin. Pharmacokinet. , vol.45 , pp. 137-168
    • Wire, M.B.1    Shelton, M.J.2    Studenberg, S.3
  • 38
    • 77957238759 scopus 로고    scopus 로고
    • Expression of the carbohydrate recognition domain of FimH and development of a competitive binding assay
    • Rabbani, S.; Jiang, X. H.; Schwardt, O.; Ernst, B. Expression of the carbohydrate recognition domain of FimH and development of a competitive binding assay Anal. Biochem. 2010, 407, 188-195 10.1016/j.ab.2010.08.007
    • (2010) Anal. Biochem. , vol.407 , pp. 188-195
    • Rabbani, S.1    Jiang, X.H.2    Schwardt, O.3    Ernst, B.4
  • 39
    • 34548040152 scopus 로고    scopus 로고
    • High throughput solubility measurement in drug discovery and development
    • Alsenz, J.; Kansy, M. High throughput solubility measurement in drug discovery and development Adv. Drug Delivery Rev. 2007, 59, 546-567 10.1016/j.addr.2007.05.007
    • (2007) Adv. Drug Delivery Rev. , vol.59 , pp. 546-567
    • Alsenz, J.1    Kansy, M.2
  • 40
    • 77749315417 scopus 로고    scopus 로고
    • Lipophilicity in drug discovery
    • Waring, M. J. Lipophilicity in drug discovery Expert Opin. Drug Discovery 2010, 5, 235-248 10.1517/17460441003605098
    • (2010) Expert Opin. Drug Discovery , vol.5 , pp. 235-248
    • Waring, M.J.1
  • 41
    • 0032568397 scopus 로고    scopus 로고
    • Physicochemical high throughput screening: Parallel artificial membrane permeation assay in the description of passive absorption processes
    • Kansy, M.; Senner, F.; Gubernator, K. Physicochemical high throughput screening: Parallel artificial membrane permeation assay in the description of passive absorption processes J. Med. Chem. 1998, 41, 1007-1010 10.1021/jm970530e
    • (1998) J. Med. Chem. , vol.41 , pp. 1007-1010
    • Kansy, M.1    Senner, F.2    Gubernator, K.3
  • 43
    • 0025804183 scopus 로고
    • Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells
    • Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells Biochem. Biophys. Res. Commun. 1991, 175, 880-885 10.1016/0006-291X(91)91647-U
    • (1991) Biochem. Biophys. Res. Commun. , vol.175 , pp. 880-885
    • Artursson, P.1    Karlsson, J.2
  • 44
    • 38449084547 scopus 로고    scopus 로고
    • Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers
    • Hubatsch, I.; Ragnarsson, E. G. E.; Artursson, P. Determination of drug permeability and prediction of drug absorption in Caco-2 monolayers Nat. Protoc. 2007, 2, 2111-2119 10.1038/nprot.2007.303
    • (2007) Nat. Protoc. , vol.2 , pp. 2111-2119
    • Hubatsch, I.1    Ragnarsson, E.G.E.2    Artursson, P.3
  • 46
    • 3042517866 scopus 로고    scopus 로고
    • Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi
    • Ma, Z.; Zhang, J.; Kong, F. Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi Carbohydr. Res. 2004, 339, 1761-1771 10.1016/j.carres.2004.04.012
    • (2004) Carbohydr. Res. , vol.339 , pp. 1761-1771
    • Ma, Z.1    Zhang, J.2    Kong, F.3
  • 47
    • 33846986010 scopus 로고    scopus 로고
    • Reagent-Dependent Regioselective Control in Multiple Carbohydrate Esterifications
    • Dong, H.; Pei, Z.; Byström, S.; Ramström, O. Reagent-Dependent Regioselective Control in Multiple Carbohydrate Esterifications J. Org. Chem. 2007, 72, 1499-1502 10.1021/jo0620821
    • (2007) J. Org. Chem. , vol.72 , pp. 1499-1502
    • Dong, H.1    Pei, Z.2    Byström, S.3    Ramström, O.4
  • 48
    • 67649398906 scopus 로고    scopus 로고
    • Evaluation of in vitro models for screening phosphatase-mediated bioconversion of phosphate ester prodrugs
    • Yuan, H.; Li, N.; Lai, Y. Evaluation of in vitro models for screening phosphatase-mediated bioconversion of phosphate ester prodrugs Drug Metab. Dispos. 2009, 37, 1443-1447 10.1124/dmd.108.026245
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1443-1447
    • Yuan, H.1    Li, N.2    Lai, Y.3
  • 49
    • 0026514715 scopus 로고
    • The in vitro enzymic labilities of chemically distinct phosphomonoester prodrugs
    • Kearny, A. S.; Stella, V. J. The in vitro enzymic labilities of chemically distinct phosphomonoester prodrugs Pharm. Res. 1992, 9, 497-503 10.1023/A:1015840329786
    • (1992) Pharm. Res. , vol.9 , pp. 497-503
    • Kearny, A.S.1    Stella, V.J.2
  • 50
    • 77951526971 scopus 로고    scopus 로고
    • A novel prodrug strategy for beta-dicarbonyl carbon acids: Syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives
    • Dhareshwar, S. S.; Stella, V. J. A novel prodrug strategy for beta-dicarbonyl carbon acids: syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives J. Pharm. Sci. 2010, 99, 2711-2723 10.1002/jps.22021
    • (2010) J. Pharm. Sci. , vol.99 , pp. 2711-2723
    • Dhareshwar, S.S.1    Stella, V.J.2
  • 51
    • 84966310347 scopus 로고    scopus 로고
    • The United States Pharmacopeia (USP 28); U. S. Pharmacopeia: Rockville, MD, 2004
    • The United States Pharmacopeia (USP 28); U. S. Pharmacopeia: Rockville, MD, 2004.
  • 52
    • 51649104303 scopus 로고    scopus 로고
    • Towards quantitative prediction of oral drug absorption
    • Dressman, J. B.; Thelen, K.; Jantratid, E. Towards quantitative prediction of oral drug absorption Clin. Pharmacokinet. 2008, 47, 655-667 10.2165/00003088-200847100-00003
    • (2008) Clin. Pharmacokinet. , vol.47 , pp. 655-667
    • Dressman, J.B.1    Thelen, K.2    Jantratid, E.3
  • 54
    • 77955519181 scopus 로고    scopus 로고
    • PKSolver: An add-in program for pharmacokinetic and pharmacodynamic data analysis in Microsoft Excel
    • Zhang, Y.; Huo, M.; Zhou, J.; Xie, S. PKSolver: An add-in program for pharmacokinetic and pharmacodynamic data analysis in Microsoft Excel Comput. Methods Programs Biomed. 2010, 99, 306-314 10.1016/j.cmpb.2010.01.007
    • (2010) Comput. Methods Programs Biomed. , vol.99 , pp. 306-314
    • Zhang, Y.1    Huo, M.2    Zhou, J.3    Xie, S.4
  • 55
    • 44749087279 scopus 로고    scopus 로고
    • Dissolution media simulating conditions in the proximal human gastrointestinal tract: An update
    • Jantratid, E.; Janssen, N.; Reppas, C.; Dressman, J. B. Dissolution media simulating conditions in the proximal human gastrointestinal tract: an update Pharm. Res. 2008, 25, 1663-1676 10.1007/s11095-008-9569-4
    • (2008) Pharm. Res. , vol.25 , pp. 1663-1676
    • Jantratid, E.1    Janssen, N.2    Reppas, C.3    Dressman, J.B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.