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Volumn 28, Issue 1, 2015, Pages 51-58

Auto-Oxidation of Isoniazid Leads to Isonicotinic-Lysine Adducts on Human Serum Albumin

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HUMAN SERUM ALBUMIN; ISONIAZID; ISONICOTINIC ACID; ISONICOTINIC N ACETYLLYSINE; LYSINE; LYSINE DERIVATIVE; N ACETYLLYSINE; OXIDOREDUCTASE; UNCLASSIFIED DRUG; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; PROTEIN BINDING; SERUM ALBUMIN;

EID: 84922422561     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500285k     Document Type: Article
Times cited : (32)

References (36)
  • 1
    • 84906237311 scopus 로고    scopus 로고
    • N-acetyltransferase 2 (NAT2) genotype as a risk factor for development of drug-induced liver injury relating to antituberculosis drug treatment in a mixed-ethnicity patient group
    • Ng, C. S., Hasnat, A., Al Maruf, A., Ahmed, M. U., Pirmohamed, M., Day, C. P., Aithal, G. P., and Daly, A. K. (2014) N-acetyltransferase 2 (NAT2) genotype as a risk factor for development of drug-induced liver injury relating to antituberculosis drug treatment in a mixed-ethnicity patient group Eur. J. Clin. Pharmacol. 70, 1079-1086
    • (2014) Eur. J. Clin. Pharmacol. , vol.70 , pp. 1079-1086
    • Ng, C.S.1    Hasnat, A.2    Al Maruf, A.3    Ahmed, M.U.4    Pirmohamed, M.5    Day, C.P.6    Aithal, G.P.7    Daly, A.K.8
  • 5
    • 84896690558 scopus 로고    scopus 로고
    • Detection of anti-isoniazid and anti-cytochrome P450 antibodies in patients with isoniazid-induced liver failure
    • Metushi, I. G., Sanders, C., The Acute Liver Study, G., Lee, W. M., and Uetrecht, J. (2014) Detection of anti-isoniazid and anti-cytochrome P450 antibodies in patients with isoniazid-induced liver failure Hepatology 59, 1084-1093
    • (2014) Hepatology , vol.59 , pp. 1084-1093
    • Metushi, I.G.1    Sanders, C.2    The Acute Liver Study, G.3    Lee, W.M.4    Uetrecht, J.5
  • 8
    • 0018597490 scopus 로고
    • The role of metabolism in the hepatotoxicity of isoniazid and iproniazid
    • Timbrell, J. A. (1979) The role of metabolism in the hepatotoxicity of isoniazid and iproniazid Drug. Metab. Rev. 10, 125-147
    • (1979) Drug. Metab. Rev. , vol.10 , pp. 125-147
    • Timbrell, J.A.1
  • 9
    • 84870539162 scopus 로고    scopus 로고
    • Mechanistic investigation of the oxidation of hydrazides: Implications for the activation of the TB drug isoniazid
    • Amos, R. I., Gourlay, B. S., Yates, B. F., Schiesser, C. H., Lewis, T. W., and Smith, J. A. (2013) Mechanistic investigation of the oxidation of hydrazides: implications for the activation of the TB drug isoniazid Org. Biomol. Chem. 11, 170-176
    • (2013) Org. Biomol. Chem. , vol.11 , pp. 170-176
    • Amos, R.I.1    Gourlay, B.S.2    Yates, B.F.3    Schiesser, C.H.4    Lewis, T.W.5    Smith, J.A.6
  • 10
    • 84869479030 scopus 로고    scopus 로고
    • Direct oxidation and covalent binding of isoniazid to rodent liver and human hepatic microsomes: Humans are more like mice than rats
    • Metushi, I. G., Nakagawa, T., and Uetrecht, J. (2012) Direct oxidation and covalent binding of isoniazid to rodent liver and human hepatic microsomes: humans are more like mice than rats Chem. Res. Toxicol. 25, 2567-2576
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 2567-2576
    • Metushi, I.G.1    Nakagawa, T.2    Uetrecht, J.3
  • 20
    • 0028990850 scopus 로고
    • Isoniazid overdose: Four case reports and review of the literature
    • Alvarez, F. G. and Guntupalli, K. K. (1995) Isoniazid overdose: four case reports and review of the literature Intensive Care Med. 21, 641-644
    • (1995) Intensive Care Med. , vol.21 , pp. 641-644
    • Alvarez, F.G.1    Guntupalli, K.K.2
  • 21
    • 0018909078 scopus 로고
    • Isoniazid hepatoxicity: The relationship between covalent binding and metabolism in vivo
    • Timbrell, J. A., Mitchell, J. R., Snodgrass, W. R., and Nelson, S. D. (1980) Isoniazid hepatoxicity: the relationship between covalent binding and metabolism in vivo J. Pharmacol. Exp. Ther. 213, 364-369
    • (1980) J. Pharmacol. Exp. Ther. , vol.213 , pp. 364-369
    • Timbrell, J.A.1    Mitchell, J.R.2    Snodgrass, W.R.3    Nelson, S.D.4
  • 22
    • 0017176137 scopus 로고
    • Isoniazid and iproniazid: Activation of metabolites to toxic intermediates in man and rat
    • Nelson, S. D., Mitchell, J. R., Timbrell, J. A., Snodgrass, W. R., and Corcoran, G. B., III (1976) Isoniazid and iproniazid: activation of metabolites to toxic intermediates in man and rat Science 193, 901-903
    • (1976) Science , vol.193 , pp. 901-903
    • Nelson, S.D.1    Mitchell, J.R.2    Timbrell, J.A.3    Snodgrass, W.R.4    Corcoran, G.B.5
  • 23
    • 84900870276 scopus 로고    scopus 로고
    • Real-time imaging of oxidative and nitrosative stress in the liver of live animals for drug-toxicity testing
    • Shuhendler, A. J., Pu, K., Cui, L., Uetrecht, J. P., and Rao, J. (2014) Real-time imaging of oxidative and nitrosative stress in the liver of live animals for drug-toxicity testing Nat. Biotechnol. 32, 373-380
    • (2014) Nat. Biotechnol. , vol.32 , pp. 373-380
    • Shuhendler, A.J.1    Pu, K.2    Cui, L.3    Uetrecht, J.P.4    Rao, J.5
  • 24
    • 0035979346 scopus 로고    scopus 로고
    • Evidence for isoniazid-dependent free radical generation catalyzed by Mycobacterium tuberculosis KatG and the isoniazid-resistant mutant KatG(S315T)
    • Wengenack, N. L. and Rusnak, F. (2001) Evidence for isoniazid-dependent free radical generation catalyzed by Mycobacterium tuberculosis KatG and the isoniazid-resistant mutant KatG(S315T) Biochemistry 40, 8990-8996
    • (2001) Biochemistry , vol.40 , pp. 8990-8996
    • Wengenack, N.L.1    Rusnak, F.2
  • 25
    • 0028100760 scopus 로고
    • Different oxidative pathways of isonicotinic-acid hydrazide and its meta-isomer, nicotinic-acid hydrazide
    • Vanderwalt, B. J., Vanzyl, J. M., and Kriegler, A. (1994) Different oxidative pathways of isonicotinic-acid hydrazide and its meta-isomer, nicotinic-acid hydrazide Int. J. Biochem. 26, 1081-1093
    • (1994) Int. J. Biochem. , vol.26 , pp. 1081-1093
    • Vanderwalt, B.J.1    Vanzyl, J.M.2    Kriegler, A.3
  • 26
  • 27
    • 0022347991 scopus 로고
    • Ionization constants of two active-site lysyl ε-amino groups of ribulosebisphosphate carboxylase/oxygenase
    • Hartman, F. C., Milanez, S., and Lee, E. H. (1985) Ionization constants of two active-site lysyl ε-amino groups of ribulosebisphosphate carboxylase/oxygenase J. Biol. Chem. 260, 13968-13975
    • (1985) J. Biol. Chem. , vol.260 , pp. 13968-13975
    • Hartman, F.C.1    Milanez, S.2    Lee, E.H.3
  • 28
    • 0003541946 scopus 로고
    • Metal-catalysed auto-oxidation of isoniazid
    • Winder, F. G. and Denneny, J. M. (1959) Metal-catalysed auto-oxidation of isoniazid Biochem. J. 73, 500-507
    • (1959) Biochem. J. , vol.73 , pp. 500-507
    • Winder, F.G.1    Denneny, J.M.2
  • 29
    • 0022938999 scopus 로고
    • Ascorbate autoxidation in the presence of iron and copper chelates
    • Buettner, G. R. (1986) Ascorbate autoxidation in the presence of iron and copper chelates Free Radical Res. Commun. 1, 349-353
    • (1986) Free Radical Res. Commun. , vol.1 , pp. 349-353
    • Buettner, G.R.1
  • 30
    • 0034823218 scopus 로고    scopus 로고
    • Oxidation of isoniazid by manganese and Mycobacterium tuberculosis catalase-peroxidase yields a new mechanism of activation
    • Bodiguel, J., Nagy, J. M., Brown, K. A., and Jamart-Gregoire, B. (2001) Oxidation of isoniazid by manganese and Mycobacterium tuberculosis catalase-peroxidase yields a new mechanism of activation J. Am. Chem. Soc. 123, 3832-3833
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3832-3833
    • Bodiguel, J.1    Nagy, J.M.2    Brown, K.A.3    Jamart-Gregoire, B.4
  • 31
    • 0030803588 scopus 로고    scopus 로고
    • Reference values for the trace elements copper, manganese, selenium, and zinc in the serum/plasma of children, adolescents, and adults
    • Rukgauer, M., Klein, J., and Kruse-Jarres, J. D. (1997) Reference values for the trace elements copper, manganese, selenium, and zinc in the serum/plasma of children, adolescents, and adults J. Trace Elem. Med. Biol. 11, 92-98
    • (1997) J. Trace Elem. Med. Biol. , vol.11 , pp. 92-98
    • Rukgauer, M.1    Klein, J.2    Kruse-Jarres, J.D.3
  • 32
    • 0345133299 scopus 로고    scopus 로고
    • The isoniazid-NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: Adduct affinity and drug resistance
    • Rawat, R., Whitty, A., and Tonge, P. J. (2003) The isoniazid-NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: adduct affinity and drug resistance Proc. Natl. Acad. Sci. U.S.A. 100, 13881-13886
    • (2003) Proc. Natl. Acad. Sci. U.S.A. , vol.100 , pp. 13881-13886
    • Rawat, R.1    Whitty, A.2    Tonge, P.J.3
  • 33
    • 0032472224 scopus 로고    scopus 로고
    • Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis
    • Rozwarski, D. A., Grant, G. A., Barton, D. H. R., Jacobs, W. R., and Sacchettini, J. C. (1998) Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis Science 279, 98-102
    • (1998) Science , vol.279 , pp. 98-102
    • Rozwarski, D.A.1    Grant, G.A.2    Barton, D.H.R.3    Jacobs, W.R.4    Sacchettini, J.C.5
  • 35
    • 34250361507 scopus 로고    scopus 로고
    • Improved pharmacokinetics of recombinant bispecific antibody molecules by fusion to human serum albumin
    • Muller, D., Karle, A., Meissburger, B., Hofig, I., Stork, R., and Kontermann, R. E. (2007) Improved pharmacokinetics of recombinant bispecific antibody molecules by fusion to human serum albumin J. Biol. Chem. 282, 12650-12660
    • (2007) J. Biol. Chem. , vol.282 , pp. 12650-12660
    • Muller, D.1    Karle, A.2    Meissburger, B.3    Hofig, I.4    Stork, R.5    Kontermann, R.E.6
  • 36
    • 0020664093 scopus 로고
    • A method to prevent the loss of isoniazid and acetylisoniazid in human plasma
    • Hutchings, A., Monie, R. D., Spragg, B., and Routledge, P. A. (1983) A method to prevent the loss of isoniazid and acetylisoniazid in human plasma Br. J. Clin. Pharmacol. 15, 263-266
    • (1983) Br. J. Clin. Pharmacol. , vol.15 , pp. 263-266
    • Hutchings, A.1    Monie, R.D.2    Spragg, B.3    Routledge, P.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.