Ethyl pyruvate and ethyl lactate down-regulate the production of pro-inflammatory cytokines and modulate expression of immune receptors

Biochemical Pharmacology

Volumn 76, Issue 5, 2008, Pages 631-644

  Hollenbach, Marcus ^a   Hintersdorf, Anja ^a   Huse, Klaus ^b   Sack, Ulrich ^c,d   Bigl, Marina ^a   Groth, Marco ^a,b   Santel, Thore ^a   Buchold, Martin ^a   Lindner, Inge ^a   Otto, Andreas ^a   Sicker, Dieter ^e   Schellenberger, Wolfgang ^a   Almendinger, Johannes ^f   Pustowoit, Barbara ^f   Birkemeyer, Claudia ^g   Platzer, Mathias ^b   Oerlecke, Ilka ^a   Hemdan, Nasr ^c,d,h   Birkenmeier, Gerd ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b FRITZ LIPMANN INSTITUTE   (Germany)

^c Institute of Clinical Immunology and Transfusion Medicine   (Germany)

^d FRAUNHOFER INSTITUTE FOR CELL THERAPY AND IMMUNOLOGY   (Germany)

^e Institut for Organic Chemistry   (Germany)

^f Institute of Virology   (Germany)

^g Institute of Physiological Chemistry   (Germany)

^h Alexandria University Faculty Of Science   (Egypt)

Author keywords

Ethyl lactate; Ethyl pyruvate; Glyoxalase; Immune receptors; Methylglyoxal; Pro inflammatory cytokines

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA OXO CARBONIC ACID ESTER; CARBONIC ACID DERIVATIVE; CD14 ANTIGEN; CYTOKINE; GLUTATHIONE; GLYOXALASE; HLA DR ANTIGEN; INTERLEUKIN 1BETA; INTERLEUKIN 6; INTERLEUKIN 8; LACTIC ACID ETHYL ESTER; LIPOPOLYSACCHARIDE; LOW DENSITY LIPOPROTEIN RECEPTOR RELATED PROTEIN; METHYLGLYOXAL; PYRUVIC ACID; PYRUVIC ACID ETHYL ESTER; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DOWN REGULATION; ENZYME INHIBITION; HUMAN; HUMAN CELL; IMMUNE RESPONSE; IMMUNOCOMPETENT CELL; INFLAMMATION; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CYTOKINES; DOWN-REGULATION; ENZYME-LINKED IMMUNOSORBENT ASSAY; FLOW CYTOMETRY; HUMANS; LACTATES; LACTOYLGLUTATHIONE LYASE; MACROPHAGES; MICE; MONOCYTES; PYRUVALDEHYDE; PYRUVATES; RECEPTORS, IMMUNOLOGIC; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION;

EID: 49349099815     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.06.006     Document Type: Article

References (40)

1. Fink M.P. Reactive oxygen species as mediators of organ dysfunction caused by sepsis, acute respiratory distress syndrome, or hemorrhagic shock: potential benefits of resuscitation with Ringer's ethyl pyruvate solution. Curr Opin Clin Nutr Metab Care 5 (2002) 167-174
2. Ulloa L., Ochani M., Yang H., Tanovic M., Halperin D., Yang R., et al. Ethyl pyruvate prevents lethality in mice with established lethal sepsis and systemic inflammation. Proc Natl Acad Sci USA 99 (2002) 12351-12356
3. Han Y., Englert J.A., Yang R., Delude R.L., and Fink M.P. Ethyl pyruvate inhibits nuclear factor-{kappa}B-dependent signaling by directly targeting p65. J Pharmacol Exp Ther 312 (2005) 1097-1105
4. Thornalley P.J. Glutathione-dependent detoxification of alpha-oxoaldehydes by the glyoxalase system: involvement in disease mechanisms and antiproliferative activity of glyoxalase I inhibitors. Chem Biol Interact 111-112 (1998) 137-151
5. Lo T.W., Westwood M.E., McLellan A.C., Selwood T., and 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 269 (1994) 32299-32305
6. Lo T.W., Selwood T., and Thornalley P.J. The reaction of methylglyoxal with aminoguanidine under physiological conditions and prevention of methylglyoxal binding to plasma proteins. Biochem Pharmacol 48 (1994) 1865-1870
7. Mannervik B., Aronsson A.C., and Tibbelin G. Glyoxalase I from human erythrocytes. Methods Enzymol 90 Pt E (1982) 535-541
8. Allen R.E., Lo T.W., and Thornalley P.J. Purification and characterisation of glyoxalase II from human red blood cells. Eur J Biochem 213 (1993) 1261-1267
9. Averbeck M., Gebhardt C., Anderegg U., Termeer C., Sleeman J.P., and Simon J.C. Switch in syndecan-1 and syndecan-4 expression controls maturation associated dendritic cell motility. Exp Dermatol 16 (2007) 580-589
10. Kuhla B., Luth H.J., Haferburg D., Weick M., Reichenbach A., Arendt T., et al. Pathological effects of glyoxalase I inhibition in SH-SY5Y neuroblastoma cells. J Neurosci Res 83 (2006) 1591-1600
11. Pustowoit B., Grangeot-Keros L., Hobman T.C., and Hofmann J. Evaluation of recombinant rubella-like particles in a commercial immunoassay for the detection of anti-rubella IgG. Clin Diagn Virol 5 (1996) 13-20
12. Shangari N., and O'Brien P.J. The cytotoxic mechanism of glyoxal involves oxidative stress. Biochem Pharmacol 68 (2004) 1433-1442
13. Fink M.P. Ringer's ethyl pyruvate solution: a novel resuscitation fluid. Minerva Anestesiol 67 (2001) 190-192
14. Das U.N. Pyruvate is an endogenous anti-inflammatory and anti-oxidant molecule. Med Sci Monit 12 (2006) RA79-RA84
15. Song M., Kellum J.A., Kaldas H., and Fink M.P. Evidence that glutathione depletion is a mechanism responsible for the anti-inflammatory effects of ethyl pyruvate in cultured lipopolysaccharide-stimulated RAW 264.7 cells. J Pharmacol Exp Ther 308 (2004) 307-316
16. Lluis C., and Bozal J. LDH and structural analogues of pyruvate (author's transl). Rev Esp Fisiol 32 (1976) 9-13
17. Miller A.G., Smith D.G., Bhat M., and Nagaraj R.H. Glyoxalase I is critical for human retinal capillary pericyte survival under hyperglycemic conditions. J Biol Chem 281 (2006) 11864-11871
18. Thornalley P.J., Edwards L.G., Kang Y., Wyatt C., Davies N., Ladan M.J., et al. Antitumour activity of S-p-bromobenzylglutathione cyclopentyl diester in vitro and in vivo. Inhibition of glyoxalase I and induction of apoptosis. Biochem Pharmacol 51 (1996) 1365-1372
19. Maeta K., Izawa S., and Inoue Y. Methylglyoxal, a metabolite derived from glycolysis, functions as a signal initiator of the high osmolarity glycerol-mitogen-activated protein kinase cascade and calcineurin/Crz1-mediated pathway in Saccharomyces cerevisiae. J Biol Chem 280 (2005) 253-260
20. de Arriba S.G., Stuchbury G., Yarin J., Burnell J., Loske C., and Munch G. Methylglyoxal impairs glucose metabolism and leads to energy depletion in neuronal cells-protection by carbonyl scavengers. Neurobiol Aging 28 (2007) 1044-1050
21. Ghosh M., Talukdar D., Ghosh S., Bhattacharyya N., Ray M., and Ray S. In vivo assessment of toxicity and pharmacokinetics of methylglyoxal. Augmentation of the curative effect of methylglyoxal on cancer-bearing mice by ascorbic acid and creatine. Toxicol Appl Pharmacol 212 (2006) 45-58
22. Speer O., Morkunaite-Haimi S., Liobikas J., Franck M., Hensbo L., Linder M.D., et al. Rapid suppression of mitochondrial permeability transition by methylglyoxal. Role of reversible arginine modification. J Biol Chem 278 (2003) 34757-34763
23. Zuin A., Vivancos A.P., Sanso M., Takatsume Y., Ayte J., Inoue Y., et al. The glycolytic metabolite methylglyoxal activates Pap1 and Sty1 stress responses in Schizosaccharomyces pombe. J Biol Chem 280 (2005) 36708-36713
24. Sakamoto H., Mashima T., Yamamoto K., and Tsuruo T. Modulation of heat-shock protein 27 (Hsp27) anti-apoptotic activity by methylglyoxal modification. J Biol Chem 277 (2002) 45770-45775
25. Lee H.J., Howell S.K., Sanford R.J., and Beisswenger P.J. Methylglyoxal can modify GAPDH activity and structure. Ann N Y Acad Sci 1043 (2005) 135-145
26. Ramasamy R., Yan S.F., and Schmidt A.M. Methylglyoxal comes of AGE. Cell 124 (2006) 258-260
27. Galter D., Mihm S., and Droge W. Distinct effects of glutathione disulphide on the nuclear transcription factor kappa B and the activator protein-1. Eur J Biochem 221 (1994) 639-648
28. Fink M.P. Ethyl pyruvate: a novel anti-inflammatory agent. J Int Med 261 (2007) 349-362
29. Laga M., Cottyn A., Van Herreweghe F., Berghe W.V., Haegeman G., Van Oostveldt P., et al. Methylglyoxal suppresses TNF-[alpha]-induced NF-[kappa]B activation by inhibiting NF-[kappa]B DNA-binding. Biochem Pharmacol 74 (2007) 579-589
30. Gao Y., and Wang Y. Site-selective modifications of arginine residues in human hemoglobin induced by methylglyoxal. Biochemistry 45 (2006) 15654-15660
31. Jia X., Olson D.J., Ross A.R., and Wu L. Structural and functional changes in human insulin induced by methylglyoxal. FASEB J 20 (2006) 1555-1557
32. Fukuzumi M., Shinomiya H., Shimizu Y., Ohishi K., and Utsumi S. Endotoxin-induced enhancement of glucose influx into murine peritoneal macrophages via GLUT1. Infect Immun 64 (1996) 108-112
33. Krauss S., Brand M.D., and Buttgereit F. Signaling takes a breath-new quantitative perspectives on bioenergetics and signal transduction. Immunity 15 (2001) 497-502
34. Warburg O. On respiratory impairment in cancer cells. Science 124 (1956) 269-270
35. Vander Jagt D.L., Hassebrook R.K., Hunsaker L.A., Brown W.M., and Royer R.E. Metabolism of the 2-oxoaldehyde methylglyoxal by aldose reductase and by glyoxalase-I: roles for glutathione in both enzymes and implications for diabetic complications. Chem Biol Interact 130-132 (2001) 549-562
36. Ramana K.V., Fadl A.A., Tammali R., Reddy A.B., Chopra A.K., and Srivastava S.K. Aldose reductase mediates the lipopolysaccharide-induced release of inflammatory mediators in RAW264.7 murine macrophages. J Biol Chem 281 (2006) 33019-33029
37. Gottfried E., Kunz-Schughart L.A., Ebner S., Mueller-Klieser W., Hoves S., Andreesen R., et al. Tumor-derived lactic acid modulates dendritic cell activation and antigen expression. Blood 107 (2006) 2013-2021
38. Cianciolo G.J., Enghild J.J., and Pizzo S.V. Covalent complexes of antigen and alpha(2)-macroglobulin: evidence for dramatically-increased immunogenicity. Vaccine 20 (2001) 554-562
39. Binder R.J., and Srivastava P.K. Essential role of CD91 in re-presentation of gp96-chaperoned peptides. Proc Natl Acad Sci USA 101 (2004) 6128-6133
40. Sato S., Kwon Y., Kamisuki S., Srivastava N., Mao Q., Kawazoe Y., et al. Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin. J Am Chem Soc 129 (2007) 873-880