메뉴 건너뛰기




Volumn 42, Issue 12, 2012, Pages 1170-1177

Glutathione conjugation of busulfan produces a hydroxyl radical-trapping dehydroalanine metabolite

Author keywords

Busulfan; Carbon centered radical; Dehydroalanine; EPR; Glutathione; Hydroxyl radical; Metabolite

Indexed keywords

ANTIOXIDANT; BUSULFAN; CARBON; DEHYDROALANINE; FREE RADICAL; GAMMA GLUTAMYLDEHYDROALANYLGLYCINE; GLUTATHIONE; GLYCINE DERIVATIVE; HYDROXYL RADICAL; SCAVENGER; THIOL; TRIPEPTIDE; UNCLASSIFIED DRUG;

EID: 84868616918     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2012.696740     Document Type: Article
Times cited : (7)

References (49)
  • 2
    • 0023268413 scopus 로고
    • Potentiation of the therapeutic activity of cyclophosphamide by an original N-acyldehydroalanine
    • Allemon AM, Buc Calderon P, Roberfroid M. (1987). Potentiation of the therapeutic activity of cyclophosphamide by an original N-acyldehydroalanine. Drugs Exp Clin Res 13:359-365.
    • (1987) Drugs Exp Clin Res , vol.13 , pp. 359-365
    • Allemon, A.M.1    Buc Calderon, P.2    Roberfroid, M.3
  • 3
    • 0023505008 scopus 로고
    • Spin trapping: ESR parameters of spin adducts
    • Buettner GR. (1987). Spin trapping: ESR parameters of spin adducts. Free Radic Biol Med 3:259-303.
    • (1987) Free Radic Biol Med , vol.3 , pp. 259-303
    • Buettner, G.R.1
  • 4
    • 0023605020 scopus 로고
    • Free radical modulation by N-substituted dehydroalanines, a new way to improve therapeutic activity of anticancer drugs
    • Buc-Calderon P, Praet M, Ruysschaert JM, Roberfroid M. (1987). Free radical modulation by N-substituted dehydroalanines, a new way to improve therapeutic activity of anticancer drugs. Cancer Treat Rev 14:379-382.
    • (1987) Cancer Treat Rev , vol.14 , pp. 379-382
    • Buc-Calderon, P.1    Praet, M.2    Ruysschaert, J.M.3    Roberfroid, M.4
  • 5
    • 0024430687 scopus 로고
    • N-acyl dehydroalanines protect from radiation toxicity and inhibit radiation carcinogenesis in mice
    • Buc-Calderon P, Defresne MP, Barvais C, Roberfroid M. (1989). N-acyl dehydroalanines protect from radiation toxicity and inhibit radiation carcinogenesis in mice. Carcinogenesis 10:1641-1644.
    • (1989) Carcinogenesis , vol.10 , pp. 1641-1644
    • Buc-Calderon, P.1    Defresne, M.P.2    Barvais, C.3    Roberfroid, M.4
  • 6
    • 0025181578 scopus 로고
    • AD 5, a dehydroalanine derivative, decreases the amount of reactive oxygen species formed during nitrofurantion microsomal metabolism
    • Buc-Calderon P, Roberfroid M. (1990). AD 5, a dehydroalanine derivative, decreases the amount of reactive oxygen species formed during nitrofurantion microsomal metabolism. Life Sci 46:207-215.
    • (1990) Life Sci , vol.46 , pp. 207-215
    • Buc-Calderon, P.1    Roberfroid, M.2
  • 7
    • 0025139778 scopus 로고
    • N-acyl dehydroalanines scavenge oxygen radicals and inhibit in vitro free radical mediated processes
    • Buc-Calderon P, Sipe HJ Jr, Flitter W, Mason RP, Roberfroid M. (1990). N-acyl dehydroalanines scavenge oxygen radicals and inhibit in vitro free radical mediated processes. Chem Biol Interact 73:77-88.
    • (1990) Chem Biol Interact , vol.73 , pp. 77-88
    • Buc-Calderon, P.1    Sipe Jr., H.J.2    Flitter, W.3    Mason, R.P.4    Roberfroid, M.5
  • 9
    • 14844316005 scopus 로고    scopus 로고
    • A high-throughput liquid chromatography/tandem mass spectrometry method for screening glutathione conjugates using exact mass neutral loss acquisition
    • Castro-Perez J, Plumb R, Liang L, Yang E. (2005). A high-throughput liquid chromatography/tandem mass spectrometry method for screening glutathione conjugates using exact mass neutral loss acquisition. Rapid Commun Mass Spectrom 19:798-804.
    • (2005) Rapid Commun Mass Spectrom , vol.19 , pp. 798-804
    • Castro-Perez, J.1    Plumb, R.2    Liang, L.3    Yang, E.4
  • 10
    • 78649869142 scopus 로고    scopus 로고
    • Chemical mutagenesis: Selective postexpression interconversion of protein amino acid residues
    • Chalker JM, Davis BG. (2010). Chemical mutagenesis: Selective postexpression interconversion of protein amino acid residues. Curr Opin Chem Biol 14:781-789.
    • (2010) Curr Opin Chem Biol , vol.14 , pp. 781-789
    • Chalker, J.M.1    Davis, B.G.2
  • 11
    • 79959221560 scopus 로고    scopus 로고
    • Reversible and irreversible protein glutathionylation: Biological and clinical aspects
    • Cooper AJ, Pinto JT, Callery PS. (2011). Reversible and irreversible protein glutathionylation: biological and clinical aspects. Expert Opin Drug Metab Toxicol 7:891-910.
    • (2011) Expert Opin Drug Metab Toxicol , vol.7 , pp. 891-910
    • Cooper, A.J.1    Pinto, J.T.2    Callery, P.S.3
  • 12
    • 0026703191 scopus 로고
    • Antiarrhythmic agents. Scavengers of hydroxyl radicals and inhibitors of NADPH-dependent lipid peroxidation in bovine lung microsomes
    • Das KC, Misra HP. (1992). Antiarrhythmic agents. Scavengers of hydroxyl radicals and inhibitors of NADPH-dependent lipid peroxidation in bovine lung microsomes. J Biol Chem 267:19172-19178.
    • (1992) J Biol Chem , vol.267 , pp. 19172-19178
    • Das, K.C.1    Misra, H.P.2
  • 13
    • 76249112419 scopus 로고    scopus 로고
    • Comparative effect of N-substituted dehydroamino acids and α-tocopherol on rat liver lipid peroxidation activities
    • Ferreira PM, Monteiro LS, Coban T, Suzen S. (2009). Comparative effect of N-substituted dehydroamino acids and α-tocopherol on rat liver lipid peroxidation activities. J Enzyme Inhib Med Chem 24:967-971.
    • (2009) J Enzyme Inhib Med Chem , vol.24 , pp. 967-971
    • Ferreira, P.M.1    Monteiro, L.S.2    Coban, T.3    Suzen, S.4
  • 14
    • 0032965144 scopus 로고    scopus 로고
    • Chemistry, biochemistry, nutrition, and microbiology of lysinoalanine, lanthionine, and histidinoalanine in food and other proteins
    • Friedman M. (1999). Chemistry, biochemistry, nutrition, and microbiology of lysinoalanine, lanthionine, and histidinoalanine in food and other proteins. J Agric Food Chem 47:1295-1319.
    • (1999) J Agric Food Chem , vol.47 , pp. 1295-1319
    • Friedman, M.1
  • 15
    • 77956114547 scopus 로고    scopus 로고
    • Emerging biological importance of central nervous system lanthionines
    • Hensley K, Venkova K, Christov A. (2010). Emerging biological importance of central nervous system lanthionines. Molecules 15:5581-5594.
    • (2010) Molecules , vol.15 , pp. 5581-5594
    • Hensley, K.1    Venkova, K.2    Christov, .A.3
  • 16
    • 69149104334 scopus 로고    scopus 로고
    • Radical cations of amino acids and peptides: Structures and stabilities
    • Hopkinson AC. (2009). Radical cations of amino acids and peptides: Structures and stabilities. Mass Spectrom Rev 28:655-671.
    • (2009) Mass Spectrom Rev , vol.28 , pp. 655-671
    • Hopkinson, A.C.1
  • 18
    • 83055196762 scopus 로고    scopus 로고
    • Antioxidant activity and free radical scavenging reactions of gentisic acid: In-vitro and pulse radiolysis studies
    • Joshi R, Gangabhagirathi R, Venu S, Adhikari S, Mukherjee T. (2012). Antioxidant activity and free radical scavenging reactions of gentisic acid: in-vitro and pulse radiolysis studies. Free Radic Res 46:11-20.
    • (2012) Free Radic Res , vol.46 , pp. 11-20
    • Joshi, R.1    Gangabhagirathi, R.2    Venu, S.3    Adhikari, S.4    Mukherjee, .T.5
  • 19
    • 0029947061 scopus 로고    scopus 로고
    • Effect of superoxide dismutase mimics on radical adduct formation during the reaction between peroxynitrite and thiols-an ESR-spin trapping study
    • Karoui H, Hogg N, Joseph J, Kalyanaraman B. (1996). Effect of superoxide dismutase mimics on radical adduct formation during the reaction between peroxynitrite and thiols-an ESR-spin trapping study. Arch Biochem Biophys 330:115-124.
    • (1996) Arch Biochem Biophys , vol.330 , pp. 115-124
    • Karoui, H.1    Hogg, N.2    Joseph, J.3    Kalyanaraman, B.4
  • 20
    • 0035214437 scopus 로고    scopus 로고
    • Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric observation of a peptide triplet induced by thermal cleavage of cystine
    • Kim JS, Kim HJ. (2001). Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric observation of a peptide triplet induced by thermal cleavage of cystine. Rapid Commun Mass Spectrom 15:2296-2300.
    • (2001) Rapid Commun Mass Spectrom , vol.15 , pp. 2296-2300
    • Kim, J.S.1    Kim, H.J.2
  • 21
    • 0035206733 scopus 로고    scopus 로고
    • Scavenging of reactive oxygen species by chlorophyllin: An ESR study
    • Kumar SS, Devasagayam TP, Bhushan B, Verma NC. (2001). Scavenging of reactive oxygen species by chlorophyllin: An ESR study. Free Radic Res 35:563-574.
    • (2001) Free Radic Res , vol.35 , pp. 563-574
    • Kumar, S.S.1    Devasagayam, T.P.2    Bhushan, B.3    Verma, N.C.4
  • 23
    • 20944446301 scopus 로고    scopus 로고
    • Glutathionylation of lens proteins through the formation of thioether bond
    • Linetsky M, LeGrand RD. (2005). Glutathionylation of lens proteins through the formation of thioether bond. Mol Cell Biochem 272:133-144.
    • (2005) Mol Cell Biochem , vol.272 , pp. 133-144
    • Linetsky, M.1    LeGrand, R.D.2
  • 24
    • 0033525599 scopus 로고    scopus 로고
    • A glycyl radical site in the crystal structure of a class III ribonucleotide reductase
    • Logan DT, Andersson J, Sjoberg BM, Nordlund P. (1999). A glycyl radical site in the crystal structure of a class III ribonucleotide reductase. Science 283:1499-1504.
    • (1999) Science , vol.283 , pp. 1499-1504
    • Logan, D.T.1    Andersson, J.2    Sjoberg, B.M.3    Nordlund, P.4
  • 26
    • 0001505683 scopus 로고
    • Spin trapping of hydroxyl in water: A kinetic evaluation of two popular traps
    • Mariott PR, Perkins MJ, Griller D. (1980). Spin trapping of hydroxyl in water: A kinetic evaluation of two popular traps. Canadian J Chem, 58, 803-807.
    • (1980) Canadian J Chem , vol.58 , pp. 803-807
    • Mariott, P.R.1    Perkins, M.J.2    Griller, D.3
  • 27
    • 0034004098 scopus 로고    scopus 로고
    • Pirfenidone inhibits NADPH-dependent microsomal lipid peroxidation and scavenges hydroxyl radicals
    • Misra HP, Rabideau C. (2000). Pirfenidone inhibits NADPH-dependent microsomal lipid peroxidation and scavenges hydroxyl radicals. Mol Cell Biochem 204:119-126.
    • (2000) Mol Cell Biochem , vol.204 , pp. 119-126
    • Misra, H.P.1    Rabideau, C.2
  • 29
    • 0346992397 scopus 로고    scopus 로고
    • Michael addition of amines and thiols to dehydroalanine amides: A remarkable rate acceleration in water
    • Naidu BN, Sorenson ME, Connolly TP, Ueda Y. (2003). Michael addition of amines and thiols to dehydroalanine amides: A remarkable rate acceleration in water. J Org Chem 68:10098-10102.
    • (2003) J Org Chem , vol.68 , pp. 10098-10102
    • Naidu, B.N.1    Sorenson, M.E.2    Connolly, T.P.3    Ueda, Y.4
  • 31
    • 29644439202 scopus 로고    scopus 로고
    • The kinetics of oxidation of GSH by protein radicals
    • Nauser T, Koppenol WH, Gebicki JM. (2005). The kinetics of oxidation of GSH by protein radicals. Biochem J 392:693-701.
    • (2005) Biochem J , vol.392 , pp. 693-701
    • Nauser, T.1    Koppenol, W.H.2    Gebicki, J.M.3
  • 32
    • 0036287677 scopus 로고    scopus 로고
    • Hydroxyl radical scavenging action of capsaicin
    • Okada Y, Okajima H, Shima Y, Ohta H. (2002). Hydroxyl radical scavenging action of capsaicin. Redox Rep 7:153-157.
    • (2002) Redox Rep , vol.7 , pp. 153-157
    • Okada, Y.1    Okajima, H.2    Shima, Y.3    Ohta, H.4
  • 36
    • 2442432688 scopus 로고    scopus 로고
    • Mechanism of hydroxyl radical scavenging by rebamipide: Identification of monohydroxylated rebamipide as a major reaction product
    • Sakurai K, Sasabe H, Koga T, Konishi T. (2004). Mechanism of hydroxyl radical scavenging by rebamipide: identification of monohydroxylated rebamipide as a major reaction product. Free Radic Res 38:487-494.
    • (2004) Free Radic Res , vol.38 , pp. 487-494
    • Sakurai, K.1    Sasabe, H.2    Koga, T.3    Konishi, T.4
  • 37
    • 0018454939 scopus 로고
    • Methods of reactivity umpolung
    • Seebach D. (1979). Methods of reactivity umpolung. Angewandte Chemie, 18, 239-258.
    • (1979) Angewandte Chemie , vol.18 , pp. 239-258
    • Seebach, D.1
  • 38
    • 0029555458 scopus 로고
    • Scavenging effects of baicalin on free radicals and its protection on erythrocyte membrane from free radical injury
    • Shi H, Zhao B, Xin W. (1995). Scavenging effects of baicalin on free radicals and its protection on erythrocyte membrane from free radical injury. Biochem Mol Biol Int 35:981-994.
    • (1995) Biochem Mol Biol Int , vol.35 , pp. 981-994
    • Shi, H.1    Zhao, B.2    Xin, W.3
  • 39
    • 0034100482 scopus 로고    scopus 로고
    • Antioxidant properties of (-)-epicatechin-3-gallate and its inhibition of Cr(VI)-induced DNA damage and Cr(IV)- or TPA-stimulated NF-κB activation
    • Shi X, Ye J, Leonard SS, Ding M, Vallyathan V, Castranova V, Rojanasakul Y, Dong Z. (2000). Antioxidant properties of (-)-epicatechin-3-gallate and its inhibition of Cr(VI)-induced DNA damage and Cr(IV)- or TPA-stimulated NF-κB activation. Mol Cell Biochem 206:125-132.
    • (2000) Mol Cell Biochem , vol.206 , pp. 125-132
    • Shi, X.1    Ye, J.2    Leonard, S.S.3    Ding, M.4    Vallyathan, V.5    Castranova, V.6    Rojanasakul, Y.7    Dong, Z.8
  • 40
    • 0027407663 scopus 로고
    • Identification of the free radical formed by addition of hydroxyl radical to dehydroalanine compounds
    • Sipe HJ, Buc-Calderon P, Roberfroid M, Mason RP. (1993). Identification of the free radical formed by addition of hydroxyl radical to dehydroalanine compounds. Chem Biol Interact 86:93-102.
    • (1993) Chem Biol Interact , vol.86 , pp. 93-102
    • Sipe, H.J.1    Buc-Calderon, P.2    Roberfroid, M.3    Mason, R.P.4
  • 41
    • 79955054158 scopus 로고    scopus 로고
    • Biosynthesis of aminovinylcysteine- containing peptides and its application in the production of potential drug candidates
    • Sit CS, Yoganathan S, Vederas JC. (2011). Biosynthesis of aminovinylcysteine- containing peptides and its application in the production of potential drug candidates. Acc Chem Res 44:261-268.
    • (2011) Acc Chem Res , vol.44 , pp. 261-268
    • Sit, C.S.1    Yoganathan, S.2    Vederas, J.C.3
  • 43
    • 0001185733 scopus 로고
    • Capto-dative substituent effects in synthesis with radicals and radicophiles
    • Viehe HG, Merenyi R, Stella L, Janousek Z. (1979). Capto-dative substituent effects in synthesis with radicals and radicophiles. Agnew Chem, 18:917-932.
    • (1979) Agnew Chem , vol.18 , pp. 917-932
    • Viehe, H.G.1    Merenyi, R.2    Stella, L.3    Janousek, Z.4
  • 44
    • 0026051802 scopus 로고
    • Effects of N-acyl dehydroalanines on phorbol ester-elicited tumor development and other events in mouse skin
    • Vo TK, Fischer SM, Slaga TJ. (1991). Effects of N-acyl dehydroalanines on phorbol ester-elicited tumor development and other events in mouse skin. Cancer Lett 60:25-32.
    • (1991) Cancer Lett , vol.60 , pp. 25-32
    • Vo, T.K.1    Fischer, S.M.2    Slaga, T.J.3
  • 45
    • 74249088148 scopus 로고    scopus 로고
    • Desulfurization of cysteine-containing peptides resulting from sample preparation for protein characterization by mass spectrometry
    • Wang Z, Rejtar T, Zhou ZS, Karger BL. (2010). Desulfurization of cysteine-containing peptides resulting from sample preparation for protein characterization by mass spectrometry. Rapid Commun Mass Spectrom 24:267-275.
    • (2010) Rapid Commun Mass Spectrom , vol.24 , pp. 267-275
    • Wang, Z.1    Rejtar, T.2    Zhou, Z.S.3    Karger, B.L.4
  • 46
    • 0033960220 scopus 로고    scopus 로고
    • On the role of hydroxyl radical and the effect of tetrandrine on nuclear factor-κB activation by phorbol 12-myristate 13-acetate
    • Ye J, Ding M, Zhang X, Rojanasakul Y, Shi X. (2000). On the role of hydroxyl radical and the effect of tetrandrine on nuclear factor-κB activation by phorbol 12-myristate 13-acetate. Ann Clin Lab Sci 30:65-71.
    • (2000) Ann Clin Lab Sci , vol.30 , pp. 65-71
    • Ye, J.1    Ding, M.2    Zhang, X.3    Rojanasakul, Y.4    Shi, X.5
  • 49
    • 35848937158 scopus 로고    scopus 로고
    • Detection and structural characterization of glutathione-trapped reactive metabolites using liquid chromatography-high-resolution mass spectrometry and mass defect filtering
    • Zhu M, Ma L, Zhang H, Humphreys WG. (2007). Detection and structural characterization of glutathione-trapped reactive metabolites using liquid chromatography-high-resolution mass spectrometry and mass defect filtering. Anal Chem 79:8333-8341.
    • (2007) Anal Chem , vol.79 , pp. 8333-8341
    • Zhu, M.1    Ma, L.2    Zhang, H.3    Humphreys, W.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.