메뉴 건너뛰기




Volumn 57, Issue 23, 2014, Pages 10072-10079

Chemical and computational methods for the characterization of covalent reactive groups for the prospective design of irreversible inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; BETA AMINOMETHYL SUBSTITUTED ACRYLAMIDE DERIVATIVE; ELECTROPHILE; ENZYME INHIBITOR; GLUTATHIONE; INDOPROFEN; IRREVERSIBLE INHIBITOR; NUCLEOPHILE; PHOSPHOTRANSFERASE INHIBITOR; SULFONAMIDE; THIOL REACTIVE COVALENT INHIBITOR; UNCLASSIFIED DRUG; DRUG;

EID: 84918547663     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501412a     Document Type: Article
Times cited : (247)

References (40)
  • 2
    • 84866772206 scopus 로고    scopus 로고
    • Targeted covalent enzyme inhibitors
    • In; Manoj, C. D. Academic Press: New York, Vol. Chapt. 27
    • Noe, M. C.; Gilbert, A. M. Targeted covalent enzyme inhibitors. In Annual Reports in Medicinal Chemistry; Manoj, C. D., Ed.; Academic Press: New York, 2012; Vol. 47, Chapt. 27, pp 413-439.
    • (2012) Annual Reports in Medicinal Chemistry , vol.47 , pp. 413-439
    • Noe, M.C.1    Gilbert, A.M.2
  • 3
    • 84862877720 scopus 로고    scopus 로고
    • Drug discovery for a new generation of covalent drugs
    • Kalgutkar, A. S.; Dalvie, D. K. Drug discovery for a new generation of covalent drugs Expert Opin. Drug Discovery 2012, 7, 561-581
    • (2012) Expert Opin. Drug Discovery , vol.7 , pp. 561-581
    • Kalgutkar, A.S.1    Dalvie, D.K.2
  • 4
    • 64349093749 scopus 로고    scopus 로고
    • Covalent modifiers: An orthogonal approach to drug design
    • Potashman, M. H.; Duggan, M. E. Covalent modifiers: An orthogonal approach to drug design J. Med. Chem. 2009, 52, 1231-1246
    • (2009) J. Med. Chem. , vol.52 , pp. 1231-1246
    • Potashman, M.H.1    Duggan, M.E.2
  • 5
    • 77953631133 scopus 로고    scopus 로고
    • Strategies for discovering and derisking covalent, irreversible enzyme inhibitors
    • Johnson, D. S.; Weerapana, E.; Cravatt, B. F. Strategies for discovering and derisking covalent, irreversible enzyme inhibitors Future Med. Chem. 2010, 2, 949-964
    • (2010) Future Med. Chem. , vol.2 , pp. 949-964
    • Johnson, D.S.1    Weerapana, E.2    Cravatt, B.F.3
  • 6
    • 61849182463 scopus 로고    scopus 로고
    • Immune-mediated adverse drug reactions
    • Uetrecht, J. Immune-mediated adverse drug reactions Chem. Res. Toxicol. 2009, 22, 24-34
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 24-34
    • Uetrecht, J.1
  • 9
    • 84907482057 scopus 로고    scopus 로고
    • Design of reversible, cysteine-targeted Michael acceptors guided by kinetic and computational analysis
    • Krishnan, S.; Miller, R. M.; Tian, B.; Mullins, R. D.; Jacobson, M. P.; Taunton, J. Design of reversible, cysteine-targeted Michael acceptors guided by kinetic and computational analysis J. Am. Chem. Soc. 2014, 136, 12624-12630
    • (2014) J. Am. Chem. Soc. , vol.136 , pp. 12624-12630
    • Krishnan, S.1    Miller, R.M.2    Tian, B.3    Mullins, R.D.4    Jacobson, M.P.5    Taunton, J.6
  • 10
    • 84907478550 scopus 로고    scopus 로고
    • Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments
    • Jost, C.; Nitsche, C.; Scholz, T.; Roux, L.; Klein, C. D. Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments J. Med. Chem. 2014, 57, 7590-7599
    • (2014) J. Med. Chem. , vol.57 , pp. 7590-7599
    • Jost, C.1    Nitsche, C.2    Scholz, T.3    Roux, L.4    Klein, C.D.5
  • 11
    • 84888040808 scopus 로고    scopus 로고
    • Benchmarking in vitro covalent binding burden as a tool to assess potential toxicity caused by nonspecific covalent binding of covalent drugs
    • Dahal, U. P.; Obach, R. S.; Gilbert, A. M. Benchmarking in vitro covalent binding burden as a tool to assess potential toxicity caused by nonspecific covalent binding of covalent drugs Chem. Res. Toxicol. 2013, 26, 1739-1745
    • (2013) Chem. Res. Toxicol. , vol.26 , pp. 1739-1745
    • Dahal, U.P.1    Obach, R.S.2    Gilbert, A.M.3
  • 12
    • 62249155473 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from nonhepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction
    • Bauman, J. N.; Kelly, J. M.; Tripathy, S.; Zhao, S. X.; Lam, W. W.; Kalgutkar, A. S.; Obach, R. S. Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from nonhepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction Chem. Res. Toxicol. 2009, 22, 332-340
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 332-340
    • Bauman, J.N.1    Kelly, J.M.2    Tripathy, S.3    Zhao, S.X.4    Lam, W.W.5    Kalgutkar, A.S.6    Obach, R.S.7
  • 13
    • 70349103856 scopus 로고    scopus 로고
    • A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding
    • Nakayama, S.; Atsumi, R.; Takakusa, H.; Kobayashi, Y.; Kurihara, A.; Nagai, Y.; Nakai, D.; Okazaki, O. A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding Drug Metab. Dispos. 2009, 37, 1970-1977
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1970-1977
    • Nakayama, S.1    Atsumi, R.2    Takakusa, H.3    Kobayashi, Y.4    Kurihara, A.5    Nagai, Y.6    Nakai, D.7    Okazaki, O.8
  • 14
    • 79952269716 scopus 로고    scopus 로고
    • Cysteine mapping in conformationally distinct kinase nucleotide binding sites: Application to the design of selective covalent inhibitors
    • Leproult, E.; Barluenga, S.; Moras, D.; Wurtz, J.-M.; Winssinger, N. Cysteine mapping in conformationally distinct kinase nucleotide binding sites: Application to the design of selective covalent inhibitors J. Med. Chem. 2011, 54, 1347-1355
    • (2011) J. Med. Chem. , vol.54 , pp. 1347-1355
    • Leproult, E.1    Barluenga, S.2    Moras, D.3    Wurtz, J.-M.4    Winssinger, N.5
  • 17
    • 0026490208 scopus 로고
    • Rates of ethyl acrylate binding to glutathione and protein
    • Potter, D. W.; Tran, T.-B. Rates of ethyl acrylate binding to glutathione and protein Toxicol. Lett. 1992, 62, 275-285
    • (1992) Toxicol. Lett. , vol.62 , pp. 275-285
    • Potter, D.W.1    Tran, T.-B.2
  • 18
    • 66049102623 scopus 로고    scopus 로고
    • Kinetic glutathione chemoassay to quantify thiol reactivity of organic electrophiles: Application to α,β-unsaturated ketones, acrylates, and propiolates
    • Böhme, A.; Thaens, D.; Paschke, A.; Schüürmann, G. Kinetic glutathione chemoassay to quantify thiol reactivity of organic electrophiles: Application to α,β-unsaturated ketones, acrylates, and propiolates Chem. Res. Toxicol. 2009, 22, 742-750
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 742-750
    • Böhme, A.1    Thaens, D.2    Paschke, A.3    Schüürmann, G.4
  • 20
    • 84864246491 scopus 로고    scopus 로고
    • Irreversible protein kinase inhibitors: Balancing the benefits and risks
    • Barf, T.; Kaptein, A. Irreversible protein kinase inhibitors: Balancing the benefits and risks J. Med. Chem. 2012, 55, 6243-6262
    • (2012) J. Med. Chem. , vol.55 , pp. 6243-6262
    • Barf, T.1    Kaptein, A.2
  • 22
    • 0000189906 scopus 로고
    • Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,β-unsaturated compounds
    • Friedman, M.; Cavins, J. F.; Wall, J. S. Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,β-unsaturated compounds J. Am. Chem. Soc. 1965, 87, 3672-3682
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 3672-3682
    • Friedman, M.1    Cavins, J.F.2    Wall, J.S.3
  • 23
    • 0035210936 scopus 로고    scopus 로고
    • Systematic modulation of Michael-type reactivity of thiols through the use of charged amino acids
    • Lutolf, M. P.; Tirelli, N.; Cerritelli, S.; Cavalli, L.; Hubbell, J. A. Systematic modulation of Michael-type reactivity of thiols through the use of charged amino acids Bioconjugate Chem. 2001, 12, 1051-1056
    • (2001) Bioconjugate Chem. , vol.12 , pp. 1051-1056
    • Lutolf, M.P.1    Tirelli, N.2    Cerritelli, S.3    Cavalli, L.4    Hubbell, J.A.5
  • 25
    • 84856834259 scopus 로고    scopus 로고
    • Analysis and functional prediction of reactive cysteine residues
    • Marino, S. M.; Gladyshev, V. N. Analysis and functional prediction of reactive cysteine residues J. Biol. Chem. 2012, 287, 4419-4425
    • (2012) J. Biol. Chem. , vol.287 , pp. 4419-4425
    • Marino, S.M.1    Gladyshev, V.N.2
  • 26
    • 79958862780 scopus 로고    scopus 로고
    • Transition states and energetics of nucleophilic additions of thiols to substituted α,β-unsaturated ketones: Substituent effects involve enone stabilization, product branching, and solvation
    • Krenske, E. H.; Petter, R. C.; Zhu, Z.; Houk, K. N. Transition states and energetics of nucleophilic additions of thiols to substituted α,β-unsaturated ketones: Substituent effects involve enone stabilization, product branching, and solvation J. Org. Chem. 2011, 76, 5074-5081
    • (2011) J. Org. Chem. , vol.76 , pp. 5074-5081
    • Krenske, E.H.1    Petter, R.C.2    Zhu, Z.3    Houk, K.N.4
  • 27
    • 84855823066 scopus 로고    scopus 로고
    • Predicting Michael-acceptor reactivity and toxicity through quantum chemical transition-state calculations
    • Mulliner, D.; Wondrousch, D.; Schueuermann, G. Predicting Michael-acceptor reactivity and toxicity through quantum chemical transition-state calculations Org. Biomol. Chem. 2011, 9, 8400-8412
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 8400-8412
    • Mulliner, D.1    Wondrousch, D.2    Schueuermann, G.3
  • 28
    • 80053101719 scopus 로고    scopus 로고
    • Progress in the research of GSH in cells
    • Zhao, H.-M.; Ruan, H.-H.; Li, H.-T. Progress in the research of GSH in cells Chin. Sci. Bull. 2011, 56, 3057-3063
    • (2011) Chin. Sci. Bull. , vol.56 , pp. 3057-3063
    • Zhao, H.-M.1    Ruan, H.-H.2    Li, H.-T.3
  • 30
    • 85067778852 scopus 로고    scopus 로고
    • Presented at the 235th ACS National Meeting, New Orleans, LA, Apr 6-10, ORGN 242.
    • Taunton, J. Defining the druggable cysteinome. Presented at the 235th ACS National Meeting, New Orleans, LA, Apr 6-10, 2008, ORGN 242.
    • (2008) Defining the Druggable Cysteinome.
    • Taunton, J.1
  • 32
    • 24544443240 scopus 로고
    • Intermolecular N-H···O hydrogen bonds assisted by resonance. Heteroconjugated systems as hydrogen-bond-strengthening functional groups
    • Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. Intermolecular N-H···O hydrogen bonds assisted by resonance. Heteroconjugated systems as hydrogen-bond-strengthening functional groups Acta Crystallogr., Sect. B: Struct. Sci. 1995, B51, 1004-1015
    • (1995) Acta Crystallogr., Sect. B: Struct. Sci. , vol.51 , pp. 1004-1015
    • Bertolasi, V.1    Gilli, P.2    Ferretti, V.3    Gilli, G.4
  • 33
    • 0000375053 scopus 로고
    • Concerning the relationship between the strength of acids and their capacity to preserve neutrality
    • Henderson, L. J. Concerning the relationship between the strength of acids and their capacity to preserve neutrality Am. J. Physiol. 1908, 21, 173-179
    • (1908) Am. J. Physiol. , vol.21 , pp. 173-179
    • Henderson, L.J.1
  • 35
    • 85067748312 scopus 로고    scopus 로고
    • MacroModel, version 9.9, Schrödinger, LLC, New York, NY.
    • MacroModel, version 9.9, Schrödinger, LLC, New York, NY, 2012.
    • (2012)
  • 37
    • 0344778061 scopus 로고
    • Semianalytical treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical treatment of solvation for molecular mechanics and dynamics J. Am. Chem. Soc. 1990, 112, 6127-6129
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 39
    • 17244367197 scopus 로고    scopus 로고
    • New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-zeta basis set 6-311+G(d,p)
    • Andersson, M. P.; Uvdal, P. New scale factors for harmonic vibrational frequencies using the B3LYP density functional method with the triple-zeta basis set 6-311+G(d,p) J. Phys. Chem. A 2005, 109 (12) 2937-2941
    • (2005) J. Phys. Chem. A , vol.109 , Issue.12 , pp. 2937-2941
    • Andersson, M.P.1    Uvdal, P.2
  • 40
    • 66349120487 scopus 로고    scopus 로고
    • Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions
    • Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 2009, 113 (18) 6378-6396
    • (2009) J. Phys. Chem. B , vol.113 , Issue.18 , pp. 6378-6396
    • Marenich, A.V.1    Cramer, C.J.2    Truhlar, D.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.