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Modification of Amino Acid Residues in Carious Dentin Matrix
G.A. Kleter
Department of Cariology-Endodontology-Pedodontology, Academic Center for Dentistry Amsterdam (ACTA), Louwesweg 1, NL-1066 EA Amsterdam, Netherlands
J.J.M. Damen
Department of Cariology-Endodontology-Pedodontology, Academic Center for Dentistry Amsterdam (ACTA), Louwesweg 1, NL-1066 EA Amsterdam, Netherlands
M.J. Buijs
Department of Cariology-Endodontology-Pedodontology, Academic Center for Dentistry Amsterdam (ACTA), Louwesweg 1, NL-1066 EA Amsterdam, Netherlands
J.M. Ten Cate
Department of Cariology-Endodontology-Pedodontology, Academic Center for Dentistry Amsterdam (ACTA), Louwesweg 1, NL-1066 EA Amsterdam, Netherlands
The Maillard reaction between sugar and protein has been postulated as the cause for the browning and arrestment of caries lesions. This reaction has been implicated as the cause for decreased degradability of collagen in vivo. The aim of the present study was to verify the occurrence of the reaction in vivo. Carious and sound dentin samples were taken from extracted human teeth and analyzed for the fluorescence characteristic of the Maillard reaction and oxidation and, by HPLC, for Maillard products. In addition, physiological cross-links were analyzed by HPLC. Oxidation- and Maillard reaction-related fluore-scence increased in collagenase digests from carious dentin. Advanced Maillard products (carboxymethyllysine and pentosidine) increased, whereas furosine, a marker for the initial reaction, was not observed consistently. This implies no direct addition of sugars to protein, but rather the addi-tion of smaller metabolites and glycoxidation products. In addition, the physiological crosslinks hydroxylysinonorleucine and dihydroxylysinonorleucine decreased in carious dentin. Also for hydroxylysylpyridinoline, a decrease was observed, but not consistently. In conclusion, the caries process modifies amino acids in dentin collagen, which can lead to increased resistance against proteolysis and ulti-mately to caries arrestment.
Key Words: Maillard reaction physiological cross-links dentin caries.
REFERENCES
- Acharya AS, Manning JM (1983). Reaction of glycolaldehyde with proteins: latent crosslinking potential of a-hydroxyaldehydes. Proc Natl Acad Sci USA 80:3590-3594.[Abstract/Free Full Text]
- Ahmed MU, Thorpe SR, Baynes JW (1986). Identification of N
carboxymethyllysine as a degradation product of fructose-lysine in glycated protein. J Biol Chem 261:4889-4894.[Abstract/Free Full Text] - Al-Abed Y., Bucala R. (1995). N
-carboxymethyllysine formation by direct addition of glyoxal to lysine during the Maillard reaction. Bioorg Med Chem Lett 5:2161-2162. - Armstrong WG (1964). Modification of the properties and composition of the dentin matrix caused by dental caries. Adv Oral Biol 1:309-332.[Medline]
[Order article via Infotrieve]
- Boonstra W., de Vries J., ten Bosch J., Ogaard B., Arends J. (1993). Inhibition of bovine dentin demineralization by a glutardialdehyde pretreatment: an in vitro caries study. Scand J Dent Res 101:72-77.[Medline]
[Order article via Infotrieve]
- Carmichael DJ, Dodd CM, Veis A. ( 1977). The solubilization of bone and dentin collagens by pepsin. Effect of cross-linkages and non-collagen components. Biochim Biophys Acta 491:177-192.[Medline]
[Order article via Infotrieve]
- Cioni M., Pinzauti G., Vanni P. (1981). Comparative biochemistry of the glyoxalate cycle. Comp Biochem Physiol 70(B):1-26.
- Clarkson BH, Hall DL, Heilman JR, Wefel JS (1986). Effect of proteolytic enzymes on caries lesion formation in vitro. J Oral Pathol 15:423-429.[Medline]
[Order article via Infotrieve]
- Davis NR (1973). A method for the determination of lysine-derived collagen crosslinks. Biochem Biophys Res Commun 52:877-883.[Medline]
[Order article via Infotrieve]
- Dunn JA, Ahmed MU, Murtiashaw MH, Richardson JM, Walla MD, Thorpe SR, et al. (1990). Reaction of ascorbate with lysine and protein under autoxidizing conditions: formation of N
-(carboxymethyl)lysine by reaction between lysine and products of autoxidation of ascorbate. Biochemistry 29:10964-10970.[CrossRef][Medline]
[Order article via Infotrieve] - Dyer DG, Blackledge JA, Katz BM, Hull CJ, Adkisson HD, Thorpe SR, et al. (1991a). The Maillard reaction in vivo. Z Ernährungswiss 30:29-45.[CrossRef][Medline]
[Order article via Infotrieve]
- Dyer DG, Blackledge JA, Thorpe SR, Baynes JW (1991b). Formation of pentosidine during nonenzymatic browning of proteins by glucose; identification of glucose and other carbohydrates as possible precursors of pentosidine in vivo. J Biol Chem 266:11654-11660.[Abstract/Free Full Text]
- Eyre DR ( 1981). Crosslink maturation in bone collagen. Dev Biochem 22:51-55.
- Frank MM, Joiner K., Hammer C. (1987). The function of antibody and complement in the lysis of bacteria. Rev Infect Dis 9(Suppl 5):S537-S545.[Medline]
[Order article via Infotrieve]
- Glomb MA, Monnier VM (1995). Mechanism of protein modification by glyoxal and glycolaldehyde, reactive intermediates of the Maillard reaction. J Biol Chem 270:10017-10026.[Abstract/Free Full Text]
- Heyns K., Heukeshoven J., Brose KH (1968). Degradation of fructose amino acids to N-(2-furoylmethyl)amino acids. Intermediates in browning reactions. Angew Chem Int Ed 7:628-629.
- Hidalgo FJ, Zamora R. (1993). Fluorescent pyrrole products from carbonyl-amine reactions. J Biol Chem 268:16190-16197.[Abstract/Free Full Text]
- Higashi C. (1979). Calcium binding and calcification induction of organic matrices of the two layers of carious dentin. Kokubyo Gakkai Zasshi 46:245-255 (Jpn).[Medline]
[Order article via Infotrieve]
- Huggins TG, Wells-Knecht MC, Detorie NA, Baynes JW, Thorpe SR (1993). Formation of o-tyrosine and dityrosine in proteins during radiolytic and metal-catalyzed oxidation. J Biol Chem 268:12341-12347.[Abstract/Free Full Text]
- Jamall IS, Finelli VN, Que Hee SS (1981). A simple method to determine nanogram levels of 4-hydroxyproline in biological tissues. Anal Biochem 112:70-75.[CrossRef][Medline]
[Order article via Infotrieve]
- Katz S., Park KK, Palenik CJ (1987) In-vitro root surface caries studies. J Oral Med 42:40-48.[Medline]
[Order article via Infotrieve]
- King TP, Kochoumian L., Lichtenstein LM (1977). Preparation and immunochemical properties of methoxypolyethylene glycol-coupled and N-carboxymethylated derivatives of ragweed pollen allergen, antigen E. Arch Biochem Biophys 178:442-450.[Medline]
[Order article via Infotrieve]
- Kleter GA, Damen JJ, Everts V., Niehof J., ten Cate JM (1994). The influence of the organic matrix on demineralization of bovine root dentin in vitro. J Dent Res 73:1523-1529.
- Kleter GA, Damen Jjm, Buijs MJ, Ten Cate JM (1997). The Maillard reaction in demineralized dentin in vitro. Eur J Oral Sci 105:278-284.[Medline]
[Order article via Infotrieve]
- Kronick P., Maleeff B. (1990). Uneven natural cross-linking in hide fibrils. J Am Leather Chem Assoc 85:122-127.
- Kuboki Y., Ohgushi K., Fusayama T. (1977). Collagen biochemistry of the two layers of carious dentin. J Dent Res 56:1233-1237.
- LaBella F., Waykole P., Queen G. (1968). Formation of insoluble gels and dityrosine by the action of peroxidase on soluble collagens. Biochem Biophys Res Commun 30:333-338.[CrossRef][Medline]
[Order article via Infotrieve]
- Levine RS (1972). The distribution of hydroxyproline in the dentin of carious human teeth. Arch Oral Biol 17:127-135.[Medline]
[Order article via Infotrieve]
- Liardon R., De Weck-Gaudard D., Philippossian G., Finot P-A. (1987). Identification of N
-carboxymethyllysine: a new Maillard reaction product, in rat urine. J Agr Food Chem 35:427-431.[CrossRef] - Milch RA (1963). Studies of collagen tissue aging: interaction of certain intermediary metabolites with collagen. Gerontologia 7:129-152.
- Moore S. (1968). Amino acid analysis: aqueous dimethyl sulfoxide as solvent for the ninhydrin reaction. J Biol Chem 243:6281-6283.[Abstract/Free Full Text]
- Moore S., Stein WH (1954). A modified ninhydrin reagent for the photometric determination of amino acids and related compounds. J Biol Chem 211:907-913.[Free Full Text]
- Nkhumeleni FS, Raubenheimer EJ, Dauth J., Van Heerden WF, Smith PD, Pitout MJ (1992). Amino acid composition of dentin in permanent human teeth. Arch Oral Biol 37:157-158.[Medline]
[Order article via Infotrieve]
- Odetti P., Pronzato MA, Noberasco G., Cosso L., Traverso N., Cottalasso D., et al. (1994). Relationships between glycation and oxidation related fluorescences in rat collagen during aging. Lab Invest 70:61-67.[Medline]
[Order article via Infotrieve]
- Pollock JJ, Lotardo S., Gavai R., Grossbard BL (1987). Lysozymeprotease-inorganic monovalent anion lysis of oral bacterial strains in buffers and whole stimulated saliva. J Dent Res 66:467-474.
- Rivera EM, Yamauchi M. (1993). Site comparisons of dentin collagen cross-links from extracted human teeth. Arch Oral Biol 38:541-546.[Medline]
[Order article via Infotrieve]
- Sell DR, Monnier VM (1989). Structure elucidation of a senescence cross-link from human extracellular matrix; implication of pentoses in the aging process. J Biol Chem 264:21597-21602.[Abstract/Free Full Text]
- Slight SH, Prabhakaram M., Shin DB, Feather MS, Ortwerth BJ (1992). The extent of N
-(carboxymethyl)lysine formation in lens proteins and polylysine by the autoxidation products of ascorbic acid. Biochim Biophys Acta 1117:199-206.[Medline]
[Order article via Infotrieve] - Uchiyama A., Inoue T., Fujimoto D. (1981). Synthesis of pyridinoline during in vitro aging of bone collagen. J Biochem 90:1795-1798.[Abstract/Free Full Text]
- Walters C., Eyre DR ( 1983). Collagen crosslinks in human dentin: increasing content of hydroxypyridinium residues with age. Calcif Tissue Int 35:401-405.[CrossRef][Medline]
[Order article via Infotrieve]
- Wells-Knecht KJ, Zyzak DV, Litchfield JE, Thorpe SR, Baynes JW (1995a). Mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose. Biochemistry 34:3702-3709.[CrossRef][Medline]
[Order article via Infotrieve]
- Wells-Knecht MC, Thorpe SR, Baynes JW (1995b). Pathways of formation of glycoxidation products during glycation of collagen. Biochemistry 34:15134-15141.[CrossRef][Medline]
[Order article via Infotrieve]
Journal of Dental Research, Vol. 77, No. 3,
488-495 (1998)
DOI: 10.1177/00220345980770030801

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