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Creatine plays a direct role as a protein modifier in the formation of a novel advanced glycation end product.

Abstract

Pentosidine, a cross-link structure between lysine and arginine residues, is one of the major advanced glycation end products (AGE). It is formed by the reaction of ribose with lysine and arginine. The pentosidine concentration produced by in vitro incubation of plasma obtained from uremic patients was reported to be higher than in normal plasma, indicating that uremic plasma contains an enhancer(s) for pentosidine formation [Miyata, T., Ueda, Y., Yamada, Y., Izuhara, Y., Wada, T., Jadoul, M., Saito, A., Kurokawa, K., and Strihou, C.Y. (1998) J. Am. Soc. Nephrol. 9, 2349-2356]. Since our preliminary study using a monoclonal anti-pentosidine antibody identified creatine as the most effective enhancer, the purpose of the present study was to clarify the mechanism by which creatine contributes to pentosidine formation. Lysine was incubated with ribose in the presence of creatine and analyzed by reverse phase high performance liquid chromatography. A novel fluorescent peak (lambda(ex/em) = 335/385 nm) was detected at 8 min, under conditions at which the authentic pentosidine (lysine was incubated with ribose in the presence of arginine under identical conditions) eluted at 12 min. Structural analyses of this compound revealed a pentosidine-like structure in which the arginine residue was replaced by creatine. This novel AGE-structure, named here creatine-derived pentosidine (C-pentosidine), was detected in the plasma of patients on hemodialysis. These results indicate that creatine increases the formation of C-pentosidine but not authentic pentosidine. This study indicates that creatine plays a direct role as a protein modifier in C-pentosidine formation, although the clinical significance of C-pentosidine is still unknown.

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  • Authors+Show Affiliations

    ,

    Department of Biochemistry, Kumamoto University School of Medicine, Honjo, Kumamoto 860-0811, Japan.

    ,

    Source

    Journal of biochemistry 132:4 2002 Oct pg 543-50

    MeSH

    Antibodies, Monoclonal
    Arginine
    Chromatography, High Pressure Liquid
    Creatine
    Creatinine
    Enzyme-Linked Immunosorbent Assay
    Fluorescence
    Glycation End Products, Advanced
    Humans
    Lysine
    Nuclear Magnetic Resonance, Biomolecular
    Ribose
    Serum Albumin, Bovine
    Spectrometry, Mass, Fast Atom Bombardment
    Urea

    Pub Type(s)

    Journal Article

    Language

    eng

    PubMed ID

    12359068

    Citation

    Miyazaki, Kiminori, et al. "Creatine Plays a Direct Role as a Protein Modifier in the Formation of a Novel Advanced Glycation End Product." Journal of Biochemistry, vol. 132, no. 4, 2002, pp. 543-50.
    Miyazaki K, Nagai R, Horiuchi S. Creatine plays a direct role as a protein modifier in the formation of a novel advanced glycation end product. J Biochem. 2002;132(4):543-50.
    Miyazaki, K., Nagai, R., & Horiuchi, S. (2002). Creatine plays a direct role as a protein modifier in the formation of a novel advanced glycation end product. Journal of Biochemistry, 132(4), pp. 543-50.
    Miyazaki K, Nagai R, Horiuchi S. Creatine Plays a Direct Role as a Protein Modifier in the Formation of a Novel Advanced Glycation End Product. J Biochem. 2002;132(4):543-50. PubMed PMID: 12359068.
    * Article titles in AMA citation format should be in sentence-case
    TY - JOUR T1 - Creatine plays a direct role as a protein modifier in the formation of a novel advanced glycation end product. AU - Miyazaki,Kiminori, AU - Nagai,Ryoji, AU - Horiuchi,Seikoh, PY - 2002/10/3/pubmed PY - 2003/6/5/medline PY - 2002/10/3/entrez SP - 543 EP - 50 JF - Journal of biochemistry JO - J. Biochem. VL - 132 IS - 4 N2 - Pentosidine, a cross-link structure between lysine and arginine residues, is one of the major advanced glycation end products (AGE). It is formed by the reaction of ribose with lysine and arginine. The pentosidine concentration produced by in vitro incubation of plasma obtained from uremic patients was reported to be higher than in normal plasma, indicating that uremic plasma contains an enhancer(s) for pentosidine formation [Miyata, T., Ueda, Y., Yamada, Y., Izuhara, Y., Wada, T., Jadoul, M., Saito, A., Kurokawa, K., and Strihou, C.Y. (1998) J. Am. Soc. Nephrol. 9, 2349-2356]. Since our preliminary study using a monoclonal anti-pentosidine antibody identified creatine as the most effective enhancer, the purpose of the present study was to clarify the mechanism by which creatine contributes to pentosidine formation. Lysine was incubated with ribose in the presence of creatine and analyzed by reverse phase high performance liquid chromatography. A novel fluorescent peak (lambda(ex/em) = 335/385 nm) was detected at 8 min, under conditions at which the authentic pentosidine (lysine was incubated with ribose in the presence of arginine under identical conditions) eluted at 12 min. Structural analyses of this compound revealed a pentosidine-like structure in which the arginine residue was replaced by creatine. This novel AGE-structure, named here creatine-derived pentosidine (C-pentosidine), was detected in the plasma of patients on hemodialysis. These results indicate that creatine increases the formation of C-pentosidine but not authentic pentosidine. This study indicates that creatine plays a direct role as a protein modifier in C-pentosidine formation, although the clinical significance of C-pentosidine is still unknown. SN - 0021-924X UR - https://www.unboundmedicine.com/medline/citation/12359068/Creatine_plays_a_direct_role_as_a_protein_modifier_in_the_formation_of_a_novel_advanced_glycation_end_product_ L2 - https://joi.jlc.jst.go.jp/JST.Journalarchive/biochemistry1922/132.543?lang=en&from=PubMed DB - PRIME DP - Unbound Medicine ER -