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Horm Metab Res 2008; 40(4): 233-238
DOI: 10.1055/s-2008-1058062
Original Basic

© Georg Thieme Verlag KG Stuttgart · New York

Evidence against Nitric Oxide-quenching Effects of Chemically Defined Maillard Reaction Products

T. Lauer 3 , T. Rassaf 3 , C. Planitz 4 , R. Preuss 2 , R. Krause 2 , T. Henle 2 , A. Deussen 1
  • 1Institute of Physiology, Medical Faculty, Technische Universität Dresden, Germany
  • 2Institute of Food Chemistry, Technische Universität Dresden, Germany
  • 3Department of Cardiology, Universitätsklinikum der RWTH Aachen, Germany
  • 4Clinic for Anesthesiology and Intensive Care Medicine, Technische Universität Dresden, Germany
Further Information

Publication History

received 16.07.2007

accepted 26.09.2007

Publication Date:
05 March 2008 (online)

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Abstract

Direct interaction between Maillard reaction products (MRPs) and nitric oxide (NO) has been suggested as a pathophysiological mechanism involved in enhanced diabetic arteriosclerosis. Only MRPs without structural characterization have been studied to date. Using chemically synthesized and analytically well defined individual MRPs, we investigated whether the native nitric oxide concentration is directly affected by the Amadori compound N-ε-fructosyllysine or the advanced glycation end product N-ε-carboxymethyllysine. MRPs were incubated with nitric oxide solution or NO donors (SNAP, spermine-NONOate). Changes in the nitrite (oxidative metabolite of NO) concentration served as indicator of NO availability. MRPs, either as free amino acids or covalently bound to bovine serum albumin (BSA), had no influence on nitrite concentration when using NO solution. In contrast, incubation of the respective NO donors with several covalently protein-bound MRPs as well as native BSA significantly reduced nitrite concentration. If SNAP was co-incubated with EDTA or with Fe2+ ions, nitrite concentration was decreased or increased, respectively, suggesting a metal ion-dependent alteration of the NO liberation rate. Native NO concentration was not affected by the MRPs tested. Substitution of native NO by NO-releasing substances may be inadequate as a model of NO-MRP interaction, as metal ions or chelators present in compound preparations may affect the NO-liberating mechanism of the donor.

Key words

AGEs - diabetes - nitric oxide - NO donors - endothelial dysfunction

References

  • 1 King H, Aubert RE, Herman WH. Global burden of diabetes, 1995-2025: prevalence, numerical estimates, and projections.  Diabetes Care. 1998;  21 1414-1431
    CrossrefPubMedSearch in Google Scholar
  • 2 Brownlee M. Biochemistry and molecular cell biology of diabetic complications.  Nature. 2001;  414 813-820
    CrossrefPubMedSearch in Google Scholar
  • 3 Marzion D Di, Mohn A, Molini ZH, Giannini C, Chiarelli F. Macroangiopathy in adults and children with diabetes: from molecular mechanisms to vascular damage.  Horm Metab Res. 2006;  38 591-705
    PubMedSearch in Google Scholar
  • 4 Jensen L, Ostergaard J, Flyvbjerg A. AGE-RAGE and AGE cross-link interaction: important players in the pathogenesis of diabetic kidney disease.  Horm Metab Res. 2004;  37 ((Suppl 1)) 26-34
    Thieme ConnectPubMedSearch in Google Scholar
  • 5 Degenhardt TP, Thorpe SR, Baynes JW. Chemical modification of proteins by methylglyoxal.  Cell Mol Biol. 1998;  44 1139-1145
    PubMedSearch in Google Scholar
  • 6 Wells-Knecht KJ, Zyzak DV, Lichtfield JE, Thorpe SR, Baynes JW. Mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose.  Biochemistry. 1995;  34 3702-3709
    CrossrefPubMedSearch in Google Scholar
  • 7 Thornalley PJ. The glyoxalase system: new developments towards functional characterization of a metabolic pathway fundamental to biological life.  Biochem J. 1990;  269 1-11
    CrossrefPubMedSearch in Google Scholar
  • 8 Henle T, Miyata T. Advanced glycation end products in uremia.  Adv Ren Replace Ther. 2003;  10 321-331
    CrossrefPubMedSearch in Google Scholar
  • 9 Verbeke P, Perichon M, Friguet B, Bakala H. Inhibition of nitric oxide synthase activity by early and advanced glycation end products in cultured rabbit proximal tubular epithelial cells.  Biochem Biophys Acta. 2000;  1502 481-494
    PubMedSearch in Google Scholar
  • 10 Bucala R, Tracey KJ, Cerami A. Advanced glycosylation products quench nitric oxide and mediate defective endothelium-dependent vasodilatation in experimental diabetes.  J Clin Invest. 1991;  87 432-438
    CrossrefPubMedSearch in Google Scholar
  • 11 Glorieux G, Helling R, Henle T, Brunet P, Deppisch R, Lameire N, Vanholder R. In vitro evidence for immune activating effect of specific AGE structures retained in uremia.  Kidney Int. 2004;  66 1873-1880
    CrossrefPubMedSearch in Google Scholar
  • 12 Seifert ST, Krause R, Gloe K, Henle T. Metal complexation by the peptide-bound maillard reaction products N(epsilon)-fructoselysine and N(epsilon)-carboxymethyllysine.  J Agric Food Chem. 2004;  52 2347-2350
    CrossrefPubMedSearch in Google Scholar
  • 13 Krause R, Knoll K, Henle T. Studies on the formation of furosine and pyridosine during acid hydrolysis of different Amadori products of lysine.  Eur Food Res Technol. 2003;  216 277-283
    PubMedSearch in Google Scholar
  • 14 Henle T, Klostermeyer H. Determination of protein-bound 2-amino-6-(2-formyl-1-pyrrolyl)-hexanoic acid („pyrraline”) by ion exchange chromatography and photodiode array detection.  Eur Food Res Technol. 1993;  196 1-4
    PubMedSearch in Google Scholar
  • 15 Foerster A, Henle T. Glycation in food and metaboloic transit of dietary AGEs (advanced glycation end-products): studies on the urinary excretion of pyrraline.  Biochem Soc Trans. 2003;  31 1383-1385
    PubMedSearch in Google Scholar
  • 16 Kelm M. Nitric oxide metabolism and breakdown.  Biochim Biophys Acta. 1999;  1411 273-289
    PubMedSearch in Google Scholar
  • 17 Lauer T, Kleinbongard P, Kelm M. Indexes of NO bioavailability in human blood.  News Physiol Sci. 2002;  17 251-255
    PubMedSearch in Google Scholar
  • 18 Lauer T, Kleinbongard P, Preik M, Rauch BH, Deussen A, Feelisch M, Strauer BE, Kelm M. Direct biochemical evidence for eNOS simulation by bradykinin in the human forearm vasculature.  Basic Res Cardiol. 2003;  98 84-89
    CrossrefPubMedSearch in Google Scholar
  • 19 Lauer T, Preik M, Rassaf T, Strauer BE, Deussen A, Feelisch M, Kelm M. Plasma nitrite rather than nitrate reflects regional endothelial nitric oxide synthase activity but lacks intrinsic vasodilator action.  Proc Natl Acad Sci USA. 2001;  98 12814-12819
    CrossrefPubMedSearch in Google Scholar
  • 20 Rassaf T, Preik M, Kleinbongaard P, Lauer T, Heiss C, Strauer BE, Feelisch M, Kelm M. Evidence for in vivo transport of bioactive nitric oxide in human plasma.  J Clin Invest. 2002;  109 1241-1248
    CrossrefPubMedSearch in Google Scholar
  • 21 Deussen A, Lloyd HG, Schrader J. Contribution of S-adenosylhomocysteine to cardiac adenosine formation.  J Mol Cell Cardiol. 1989;  21 773-782
    CrossrefPubMedSearch in Google Scholar
  • 22 Singh RJ, Hogg N, Joseph J, Kalyanaraman B. Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane. Possible use for site-directed nitric oxide production.  FEBS Lett. 1995;  360 47-51
    CrossrefPubMedSearch in Google Scholar
  • 23 Sexton DJ, Muruganandam A, MacKenney DJ, Mutus B. Visible light photochemical release of nitric oxide from S-nitrosoglutathione: potential photochemotherapeutic applications.  Photochem Photobiol. 1994;  59 ((4)) 463-467
    CrossrefPubMedSearch in Google Scholar
  • 24 Feelisch M. The biochemical pathways of nitric oxide formation from nitrovasodilators: Appropriate choice of exogenous NO donors and aspects of preparation and handling of aqueous NO solutions.  J Cardiovasc Pharmacol. 1991;  17 ((Suppl 3)) 25-33
    PubMedSearch in Google Scholar
  • 25 Singh RJ, Hogg N, Joseph J, Kalyanaraman B. Mechanism of nitric oxide release from S-nitrosothiols.  J Biol Chem. 1996;  271 18596-18603
    CrossrefPubMedSearch in Google Scholar
  • 26 Tannenbaum SR. Nitrate and nitrite: origin in humans.  Science. 1979;  205 1333-1337
    PubMedSearch in Google Scholar

Correspondence

T. LauerMD 

Med. Klinik I

Abteilung für Kardiologie

Pneumologie und Angiologie

Universitätsklinikum der RWTH Aachen

Pauwelsstraße 30

52074 Aachen

Germany

Phone: +49/241/803 63 04

Fax: +49/241/808 95 45

Email: tlauer@ukaachen.de