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Volumn 188, Issue 1, 2010, Pages 21-30

Influence of the microenvironment of thiol groups in low molecular mass thiols and serum albumin on the reaction with methylglyoxal

Author keywords

HSA; Low molecular mass thiols; Methylglyoxal; Protein glycation; Thiol group reactivity and microenvironment

Indexed keywords

ACETYLCYSTEINE; CARBOCISTEINE; CYSTEINE; GLUTATHIONE; HUMAN SERUM ALBUMIN; METHYLGLYOXAL; SCAVENGER; THIOL GROUP; SERUM ALBUMIN; THIOL DERIVATIVE;

EID: 77956169770     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.07.013     Document Type: Article
Times cited : (19)

References (49)
  • 1
    • 0027396022 scopus 로고
    • The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal
    • Phillips S.A., Thornalley P.J. The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal. Eur. J. Biochem. 1993, 212:101-105.
    • (1993) Eur. J. Biochem. , vol.212 , pp. 101-105
    • Phillips, S.A.1    Thornalley, P.J.2
  • 3
    • 0028292698 scopus 로고
    • Glyoxalase system in clinical diabetes mellitus and correlation with diabetic complications
    • McLellan A.C., Thornalley P.J., Benn J., Sonksen P.H. Glyoxalase system in clinical diabetes mellitus and correlation with diabetic complications. Clin. Sci. (Lond.) 1994, 87:21-29.
    • (1994) Clin. Sci. (Lond.) , vol.87 , pp. 21-29
    • McLellan, A.C.1    Thornalley, P.J.2    Benn, J.3    Sonksen, P.H.4
  • 4
    • 0033525849 scopus 로고    scopus 로고
    • Increase in three alpha,beta-dicarbonyl compound levels in human uremic plasma: specific in vivo determination of intermediates in advanced Maillard reaction
    • Odani H., Shinzato T., Matsumoto Y., Usami J., Maeda K. Increase in three alpha,beta-dicarbonyl compound levels in human uremic plasma: specific in vivo determination of intermediates in advanced Maillard reaction. Biochem. Biophys. Res. Commun. 1999, 256:89-93.
    • (1999) Biochem. Biophys. Res. Commun. , vol.256 , pp. 89-93
    • Odani, H.1    Shinzato, T.2    Matsumoto, Y.3    Usami, J.4    Maeda, K.5
  • 5
    • 23744447530 scopus 로고    scopus 로고
    • Dicarbonyl intermediates in the maillard reaction
    • Thornalley P.J. Dicarbonyl intermediates in the maillard reaction. Ann. N. Y. Acad. Sci. 2005, 1043:111-117.
    • (2005) Ann. N. Y. Acad. Sci. , vol.1043 , pp. 111-117
    • Thornalley, P.J.1
  • 6
    • 0028605299 scopus 로고
    • Binding and modification of proteins by methylglyoxal under physiological conditions. A kinetic and mechanistic study with N alpha-acetylarginine, N alpha-acetylcysteine, and N alpha-acetyllysine, and bovine serum albumin
    • Lo T.W., Westwood M.E., McLellan A.C., Selwood T., Thornalley P.J. Binding and modification of proteins by methylglyoxal under physiological conditions. A kinetic and mechanistic study with N alpha-acetylarginine, N alpha-acetylcysteine, and N alpha-acetyllysine, and bovine serum albumin. J. Biol. Chem. 1994, 269:32299-32305.
    • (1994) J. Biol. Chem. , vol.269 , pp. 32299-32305
    • Lo, T.W.1    Westwood, M.E.2    McLellan, A.C.3    Selwood, T.4    Thornalley, P.J.5
  • 7
    • 76649085190 scopus 로고    scopus 로고
    • Effect of reactive-aldehydes on the modification and dysfunction of human serum albumin
    • Mera K., Takeo K., Izumi M., Maruyama T., Nagai R., Otagiri M. Effect of reactive-aldehydes on the modification and dysfunction of human serum albumin. J. Pharm. Sci. 2010, 99:1614-1625.
    • (2010) J. Pharm. Sci. , vol.99 , pp. 1614-1625
    • Mera, K.1    Takeo, K.2    Izumi, M.3    Maruyama, T.4    Nagai, R.5    Otagiri, M.6
  • 8
    • 0348136791 scopus 로고    scopus 로고
    • Protecting the genome: defence against nucleotide glycation and emerging role of glyoxalase I overexpression in multidrug resistance in cancer chemotherapy
    • Thornalley P.J. Protecting the genome: defence against nucleotide glycation and emerging role of glyoxalase I overexpression in multidrug resistance in cancer chemotherapy. Biochem. Soc. Trans. 2003, 31:1372-1377.
    • (2003) Biochem. Soc. Trans. , vol.31 , pp. 1372-1377
    • Thornalley, P.J.1
  • 9
    • 44949216859 scopus 로고    scopus 로고
    • Advanced glycation end-products (AGEs): involvement in aging and in neurodegenerative diseases
    • Grillo M.A., Colombatto S. Advanced glycation end-products (AGEs): involvement in aging and in neurodegenerative diseases. Amino Acids 2008, 35:29-36.
    • (2008) Amino Acids , vol.35 , pp. 29-36
    • Grillo, M.A.1    Colombatto, S.2
  • 11
    • 0034659178 scopus 로고    scopus 로고
    • Glycoxidation and lipoxidation in atherogenesis
    • Baynes J.W., Thorpe S.R. Glycoxidation and lipoxidation in atherogenesis. Free Radic. Biol. Med. 2000, 28:1708-1716.
    • (2000) Free Radic. Biol. Med. , vol.28 , pp. 1708-1716
    • Baynes, J.W.1    Thorpe, S.R.2
  • 12
    • 37049008850 scopus 로고    scopus 로고
    • The ligand activity of AGE-proteins to scavenger receptors is dependent on their rate of modification by AGEs
    • Nagai R., Mera K., Nakajou K., Fujiwara Y., Iwao Y., Imai H., Murata T., Otagiri M. The ligand activity of AGE-proteins to scavenger receptors is dependent on their rate of modification by AGEs. Biochim. Biophys. Acta 2007, 1772:1192-1198.
    • (2007) Biochim. Biophys. Acta , vol.1772 , pp. 1192-1198
    • Nagai, R.1    Mera, K.2    Nakajou, K.3    Fujiwara, Y.4    Iwao, Y.5    Imai, H.6    Murata, T.7    Otagiri, M.8
  • 13
    • 38749130432 scopus 로고    scopus 로고
    • The tandem of free radicals and methylglyoxal
    • Kalapos M.P. The tandem of free radicals and methylglyoxal. Chem. Biol. Interact. 2008, 171:251-271.
    • (2008) Chem. Biol. Interact. , vol.171 , pp. 251-271
    • Kalapos, M.P.1
  • 14
    • 31044442243 scopus 로고    scopus 로고
    • Methylglyoxal comes of AGE
    • Ramasamy R., Yan S.F., Schmidt A.M. Methylglyoxal comes of AGE. Cell 2006, 124:258-260.
    • (2006) Cell , vol.124 , pp. 258-260
    • Ramasamy, R.1    Yan, S.F.2    Schmidt, A.M.3
  • 15
    • 0037099548 scopus 로고    scopus 로고
    • Inactivation of cellular enzymes by carbonyls and protein-bound glycation/glycoxidation products
    • Morgan P.E., Dean R.T., Davies M.J. Inactivation of cellular enzymes by carbonyls and protein-bound glycation/glycoxidation products. Arch. Biochem. Biophys. 2002, 403:259-269.
    • (2002) Arch. Biochem. Biophys. , vol.403 , pp. 259-269
    • Morgan, P.E.1    Dean, R.T.2    Davies, M.J.3
  • 16
    • 23844502010 scopus 로고    scopus 로고
    • Evidence for the formation of adducts and S-(carboxymethyl)cysteine on reaction of alpha-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins
    • Zeng J., Davies M.J. Evidence for the formation of adducts and S-(carboxymethyl)cysteine on reaction of alpha-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins. Chem. Res. Toxicol. 2005, 18:1232-1241.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1232-1241
    • Zeng, J.1    Davies, M.J.2
  • 18
    • 34547614831 scopus 로고    scopus 로고
    • Plasma protein advanced glycation end products, carboxymethyl cysteine, and carboxyethyl cysteine, are elevated and related to nephropathy in patients with diabetes
    • Mostafa A.A., Randell E.W., Vasdev S.C., Gill V.D., Han Y., Gadag V., Raouf A.A., El S.H. Plasma protein advanced glycation end products, carboxymethyl cysteine, and carboxyethyl cysteine, are elevated and related to nephropathy in patients with diabetes. Mol. Cell Biochem. 2007, 302:35-42.
    • (2007) Mol. Cell Biochem. , vol.302 , pp. 35-42
    • Mostafa, A.A.1    Randell, E.W.2    Vasdev, S.C.3    Gill, V.D.4    Han, Y.5    Gadag, V.6    Raouf, A.A.7    El, S.H.8
  • 19
    • 0346731073 scopus 로고    scopus 로고
    • Maillard reaction products in tissue proteins: new products and new perspectives
    • Thorpe S.R., Baynes J.W. Maillard reaction products in tissue proteins: new products and new perspectives. Amino Acids 2003, 25:275-281.
    • (2003) Amino Acids , vol.25 , pp. 275-281
    • Thorpe, S.R.1    Baynes, J.W.2
  • 21
    • 33845780096 scopus 로고    scopus 로고
    • Protein and low molecular mass thiols as targets and inhibitors of glycation reactions
    • Zeng J., Davies M.J. Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. Chem. Res. Toxicol. 2006, 19:1668-1676.
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 1668-1676
    • Zeng, J.1    Davies, M.J.2
  • 22
    • 0029165873 scopus 로고
    • Molecular characteristics of methylglyoxal-modified bovine and human serum albumins. Comparison with glucose-derived advanced glycation endproduct-modified serum albumins
    • Westwood M.E., Thornalley P.J. Molecular characteristics of methylglyoxal-modified bovine and human serum albumins. Comparison with glucose-derived advanced glycation endproduct-modified serum albumins. J. Protein Chem. 1995, 14:359-372.
    • (1995) J. Protein Chem. , vol.14 , pp. 359-372
    • Westwood, M.E.1    Thornalley, P.J.2
  • 23
    • 77349122592 scopus 로고    scopus 로고
    • The role of thiol group in protein modification with methylglyoxal
    • Acimovic J.M., Stanimirovic B.D., Mandic Lj.M. The role of thiol group in protein modification with methylglyoxal. J. Serb. Chem. Soc. 2009, 74:867-883.
    • (2009) J. Serb. Chem. Soc. , vol.74 , pp. 867-883
    • Acimovic, J.M.1    Stanimirovic, B.D.2    Mandic, L.3
  • 24
    • 0035009582 scopus 로고    scopus 로고
    • The importance of proteins in defense against oxidation
    • Bourdon E., Blache D. The importance of proteins in defense against oxidation. Antioxid. Redox Signal. 2001, 3:293-311.
    • (2001) Antioxid. Redox Signal. , vol.3 , pp. 293-311
    • Bourdon, E.1    Blache, D.2
  • 26
    • 38949158548 scopus 로고    scopus 로고
    • Impairment of the antioxidant properties of serum albumin in patients with diabetes: protective effects of metformin
    • Faure P., Wiernsperger N., Polge C., Favier A., Halimi S. Impairment of the antioxidant properties of serum albumin in patients with diabetes: protective effects of metformin. Clin. Sci. (Lond.) 2008, 114:51-256.
    • (2008) Clin. Sci. (Lond.) , vol.114 , pp. 51-256
    • Faure, P.1    Wiernsperger, N.2    Polge, C.3    Favier, A.4    Halimi, S.5
  • 27
    • 0026575313 scopus 로고
    • Mechanistic studies of advanced glycosylation end product inhibition by aminoguanidine
    • Edelstein D., Brownlee M. Mechanistic studies of advanced glycosylation end product inhibition by aminoguanidine. Diabetes 1992, 41:26-29.
    • (1992) Diabetes , vol.41 , pp. 26-29
    • Edelstein, D.1    Brownlee, M.2
  • 28
    • 0142029114 scopus 로고    scopus 로고
    • Novel inhibitors of advanced glycation endproducts
    • Rahbar S., Figarola J.L. Novel inhibitors of advanced glycation endproducts. Arch. Biochem. Biophys. 2003, 419:63-79.
    • (2003) Arch. Biochem. Biophys. , vol.419 , pp. 63-79
    • Rahbar, S.1    Figarola, J.L.2
  • 29
    • 0032702642 scopus 로고    scopus 로고
    • Reaction of metformin with dicarbonyl compounds. Possible implication in the inhibition of advanced glycation end product formation
    • Ruggiero-Lopez D., Lecomte M., Moinet G., Patereau G., Lagarde M., Wiernsperger N. Reaction of metformin with dicarbonyl compounds. Possible implication in the inhibition of advanced glycation end product formation. Biochem. Pharmacol. 1999, 58:1765-1773.
    • (1999) Biochem. Pharmacol. , vol.58 , pp. 1765-1773
    • Ruggiero-Lopez, D.1    Lecomte, M.2    Moinet, G.3    Patereau, G.4    Lagarde, M.5    Wiernsperger, N.6
  • 31
    • 0014978020 scopus 로고
    • Albumin standards and the measurement of serum albumin with bromcresol green
    • Doumas B.T., Watson W.A., Biggs H.G. Albumin standards and the measurement of serum albumin with bromcresol green. Clin. Chim. Acta 1971, 31:87-96.
    • (1971) Clin. Chim. Acta , vol.31 , pp. 87-96
    • Doumas, B.T.1    Watson, W.A.2    Biggs, H.G.3
  • 33
    • 0032560621 scopus 로고    scopus 로고
    • Ionization-reactivity relationships for cysteine thiols in polypeptides
    • Bulaj G., Kortemme T., Goldenberg D.P. Ionization-reactivity relationships for cysteine thiols in polypeptides. Biochemistry 1998, 37:8965-8972.
    • (1998) Biochemistry , vol.37 , pp. 8965-8972
    • Bulaj, G.1    Kortemme, T.2    Goldenberg, D.P.3
  • 34
    • 22144469136 scopus 로고    scopus 로고
    • Heterogeneity and oxidation status of commercial human albumin preparations in clinical use
    • Bar-Or D., Bar-Or R., Rael L.T., Gardner D.K., Slone D.S., Craun M.L. Heterogeneity and oxidation status of commercial human albumin preparations in clinical use. Crit. Care Med. 2005, 33:1638-1641.
    • (2005) Crit. Care Med. , vol.33 , pp. 1638-1641
    • Bar-Or, D.1    Bar-Or, R.2    Rael, L.T.3    Gardner, D.K.4    Slone, D.S.5    Craun, M.L.6
  • 35
    • 0027252911 scopus 로고
    • Spectrophotometric method for simultaneous determination of proteins and amino acids with p-benzoquinone
    • Zaia D.A.M., Barreto W.J. Spectrophotometric method for simultaneous determination of proteins and amino acids with p-benzoquinone. Anal. Chim. Acta 1993, 277:89-95.
    • (1993) Anal. Chim. Acta , vol.277 , pp. 89-95
    • Zaia, D.A.M.1    Barreto, W.J.2
  • 37
    • 0021715583 scopus 로고
    • Spectrophotometric determination of arginine in proteins
    • Sastry C.S.P., Tummuru M.K. Spectrophotometric determination of arginine in proteins. Food Chem. 1984, 15:257-260.
    • (1984) Food Chem. , vol.15 , pp. 257-260
    • Sastry, C.S.P.1    Tummuru, M.K.2
  • 38
    • 0001073978 scopus 로고
    • Resolution-sensitive procedure for comparing protein surfaces and its application to the comparison of antigen-combining sites
    • Gerstein M.A. Resolution-sensitive procedure for comparing protein surfaces and its application to the comparison of antigen-combining sites. Acta Crystallogr. 1992, A48:271-276.
    • (1992) Acta Crystallogr. , vol.48 A , pp. 271-276
    • Gerstein, M.A.1
  • 39
    • 8644279840 scopus 로고    scopus 로고
    • Spectroscopic studies of methylglyoxal in water and dimethylsulfoxide
    • Nemet I., Vikic-Topic D., Varga-Defterdarovic L. Spectroscopic studies of methylglyoxal in water and dimethylsulfoxide. Bioorg. Chem. 2004, 32:560-570.
    • (2004) Bioorg. Chem. , vol.32 , pp. 560-570
    • Nemet, I.1    Vikic-Topic, D.2    Varga-Defterdarovic, L.3
  • 40
    • 0028281741 scopus 로고
    • Stereospecificity of substrate usage by glyoxalase 1: nuclear magnetic resonance studies of kinetics and hemithioacetal substrate conformation
    • Rae C., O'Donoghue S.I., Bubb W.A., Kuchel P.W. Stereospecificity of substrate usage by glyoxalase 1: nuclear magnetic resonance studies of kinetics and hemithioacetal substrate conformation. Biochemistry 1994, 33:3548-3559.
    • (1994) Biochemistry , vol.33 , pp. 3548-3559
    • Rae, C.1    O'Donoghue, S.I.2    Bubb, W.A.3    Kuchel, P.W.4
  • 41
    • 0031900403 scopus 로고    scopus 로고
    • Incidence and potential implications of the toxic metabolite methylglyoxal in cell culture: a review
    • Chaplen W.R. Incidence and potential implications of the toxic metabolite methylglyoxal in cell culture: a review. Cytotechnology 1998, 26:173-183.
    • (1998) Cytotechnology , vol.26 , pp. 173-183
    • Chaplen, W.R.1
  • 42
    • 0030176306 scopus 로고    scopus 로고
    • Pharmacology of methylglyoxal: formation, modification of proteins and nucleic acids, and enzymatic detoxification-a role in pathogenesis and antiproliferative chemotherapy
    • Thornalley P.J. Pharmacology of methylglyoxal: formation, modification of proteins and nucleic acids, and enzymatic detoxification-a role in pathogenesis and antiproliferative chemotherapy. Gen. Pharmacol. 1996, 27:565-573.
    • (1996) Gen. Pharmacol. , vol.27 , pp. 565-573
    • Thornalley, P.J.1
  • 43
    • 0000328844 scopus 로고
    • A new vertex algorithm to calculate solvent acessible surface areas
    • Sridharan S., Nicholls A., Honig B. A new vertex algorithm to calculate solvent acessible surface areas. Biophys. J. 1992, 61:A174.
    • (1992) Biophys. J. , vol.61
    • Sridharan, S.1    Nicholls, A.2    Honig, B.3
  • 44
    • 84948882698 scopus 로고
    • Generation of Swiss cheese flavor components by the reaction of amino acids with carbonyl compounds
    • Griffith R., Hammond E.G. Generation of Swiss cheese flavor components by the reaction of amino acids with carbonyl compounds. J. Dairy Sci. 1989, 72:604-613.
    • (1989) J. Dairy Sci. , vol.72 , pp. 604-613
    • Griffith, R.1    Hammond, E.G.2
  • 45
    • 0037048767 scopus 로고    scopus 로고
    • Possible mechanism for involvement of cysteine in aroma production in wine
    • de S., Marchand R.G., Vercauteren J., Bertrand A. Possible mechanism for involvement of cysteine in aroma production in wine. J. Agric. Food Chem. 2002, 50:6160-6164.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 6160-6164
    • de, S.1    Marchand, R.G.2    Vercauteren, J.3    Bertrand, A.4
  • 47
    • 4444291143 scopus 로고    scopus 로고
    • Lipid peroxidation and resistance to oxidation in patients with type 2 diabetes mellitus
    • Pasaoglu H., Sancak B., Bukan N. Lipid peroxidation and resistance to oxidation in patients with type 2 diabetes mellitus. Tohoku J. Exp. Med. 2004, 203:211-218.
    • (2004) Tohoku J. Exp. Med. , vol.203 , pp. 211-218
    • Pasaoglu, H.1    Sancak, B.2    Bukan, N.3
  • 49
    • 33845280446 scopus 로고
    • Comparing the polarities of the amino-acids - side-chain distribution coefficients between the vapor-phase, cyclohexane, 1-octanol, and neutral aqueous-solution
    • Radzicka A., Wolfenden R. Comparing the polarities of the amino-acids - side-chain distribution coefficients between the vapor-phase, cyclohexane, 1-octanol, and neutral aqueous-solution. Biochemistry 1988, 27:1664-1670.
    • (1988) Biochemistry , vol.27 , pp. 1664-1670
    • Radzicka, A.1    Wolfenden, R.2


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