D-carnosine octylester attenuates atherosclerosis and renal disease in ApoE null mice fed a Western diet through reduction of carbonyl stress and inflammation

British Journal of Pharmacology

Volumn 166, Issue 4, 2012, Pages 1344-1356

  Menini, Stefano ^a   Iacobini, Carla ^a   Ricci, Carlo ^a   Scipioni, Angela ^a   Fantauzzi, Claudia Blasetti ^a   Giaccari, Andrea ^b   Salomone, Enrica ^b   Canevotti, Renato ^c   Lapolla, Annunziata ^d   Orioli, Marica ^e   Aldini, Giancarlo ^e   Pugliese, Giuseppe ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CATHOLIC UNIVERSITY   (Italy)

^c Flamma SpA   (Italy)

^d UNIVERSITY OF PADOVA   (Italy)

^e UNIVERSITY OF MILAN   (Italy)

Author keywords

4 hydroxy 2 nonenal; advanced lipoxidation end products; atherosclerosis; carnosine; reactive carbonyl species; renal disease

Indexed keywords

4 HYDROXYNONENAL; DEXTRO CARNOSINE OCTYLESTER; ELECTROPHILE; PRODRUG; REACTIVE CARBONYL SPECIES; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; ATHEROGENIC DIET; ATHEROSCLEROSIS; CARBONYLATION; CELL DAMAGE; CELL PROLIFERATION; CELL VIABILITY; CELLULAR DISTRIBUTION; CHEMICAL STRESS; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG URINE LEVEL; FEMALE; FIBROSIS; HEMODYNAMIC PARAMETERS; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; KIDNEY DISEASE; METABOLIC PARAMETERS; MOUSE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN CARBONYLATION; PROTEIN EXPRESSION; TREATMENT DURATION; VASCULAR SMOOTH MUSCLE;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AORTA; APOLIPOPROTEINS E; ATHEROSCLEROSIS; CARNOSINE; CELL LINE; CELLS, CULTURED; DIET, ATHEROGENIC; FEMALE; FREE RADICAL SCAVENGERS; KIDNEY; MACROPHAGES; MESANGIAL CELLS; MICE; MICE, INBRED C57BL; MICE, KNOCKOUT; MUSCLE, SMOOTH, VASCULAR; OXIDATIVE STRESS; PRODRUGS; RENAL INSUFFICIENCY; STEREOISOMERISM;

EID: 84861313241     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2012.01834.x     Document Type: Article

References (42)

1. Aldini G, Maffei Facino R, Beretta G, Carini M, (2005). Carnosine and related dipeptides as quenchers of reactive carbonyl species: from structural studies to therapeutic perspectives. Biofactors 24: 77-87.
2. Aldini G, Dalle-Donne I, Colombo R, Maffei Facino R, Milzani A, Carini M, (2006). Lipoxidation-derived reactive carbonyl species as potential drug targets in preventing protein carbonylation and related cellular dysfunction. ChemMedChem 1: 1045-1058.
3. Aldini G, Orioli M, Rossoni G, Savi F, Braidotti P, Vistoli G, et al,. (2011). The carbonyl scavenger carnosine ameliorates dyslipidaemia and renal function in Zucker obese rats. J Cell Mol Med 15: 1339-1354.
4. Babizhayev MA, Deyev AI, Yermakova VN, Brikman IV, Bours J, (2004). Lipid peroxidation and cataracts: N-acetylcarnosine as a therapeutic tool to manage age-related cataracts in human and in canine eyes. Drugs R D 5: 125-139.
5. Canevotti R, Negrisoli G, Previtali M, (2008). Dipeptide compounds containing D-histidine. WO2008001175(A2).
6. Cheng J, Wang F, Yu DF, Wu PF, Chen JG, (2010). The cytotoxic mechanism of malondialdehyde and protective effect of carnosine via protein cross-linking/mitochondrial dysfunction/reactive oxygen species/MAPK pathway in neurons. Eur J Pharmacol 650: 184-194.
7. Cuzzocrea S, Genovese T, Failla M, Vecchio G, Fruciano M, Mazzon E, et al,. (2007). Protective effect of orally administered carnosine on bleomycin-induced lung injury. Am J Physiol 292: L1095-L1104.
8. Decker EA, Livisay SA, Zhou S, (2000). A re-evaluation of the antioxidant activity of purified carnosine. Biochemistry (Mosc) 65: 766-770.
9. Ellis EM, (2007). Reactive carbonyls and oxidative stress: potential for therapeutic intervention. Pharmacol Ther 115: 13-24.
10. Freedman BI, Hicks PJ, Sale MM, Pierson ED, Langefeld CD, Rich SS, et al,. (2007). A leucine repeat in the carnosinase gene CNDP1 is associated with diabetic end-stage renal disease in European Americans. Nephrol Dial Transplant 22: 1131-1135.
11. Go S-Y, Cooper ME, (2008). The role of advanced glycation end products in progression and complications of diabetes. J Clin Endocrinol Metab 93: 1143-1152.
12. Heeringa P, Cohen Tervaert JW, (2000). Role of oxidized low-density lipoprotein in renal disease. Curr Opin Nephrol Hypertens 11: 287-293.
13. Iacobini C, Oddi G, Menini S, Amadio L, Ricci C, Di Pippo C, et al,. (2005). Development of age-dependent glomerular lesions in galectin-3/AGE- receptor- 3 knockout mice. Am J Physiol 289: F611-F621.
14. Iacobini C, Menini S, Ricci C, Scipioni A, Sansoni V, Cordone S, et al,. (2009a). Accelerated lipid-induced atherogenesis in galectin-3 deficient mice: role of lipoxidation via receptor-mediated mechanisms. Arterioscler Thromb Vasc Biol 29: 831-836.
15. Iacobini C, Menini S, Ricci C, Scipioni A, Sansoni V, Mazzitelli G, et al,. (2009b). Advanced lipoxidation end-products mediate lipid-induced glomerular injury: role of receptor-mediated mechanisms. J Pathol 218: 360-369.
16. Jackson CL, Bennett MR, Biessen EA, Johnson JL, Krams R, (2007). Assessment of unstable atherosclerosis in mice. Arterioscler Thromb Vasc Biol 27: 714-720.
17. Janssen B, Hohenadel D, Brinkkoetter P, Peters V, Rind N, Fischer C, et al,. (2005). Carnosine as a protective factor in diabetic nephropathy: association with a leucine repeat of the carnosinase gene CNDP1. Diabetes 54: 2320-2327.
18. Kohen R, Yamamoto Y, Cundy KC, Ames BN, (1988). Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain. Proc Natl Acad Sci USA 85: 3175-3179.
19. Kubota C, Torii S, Hou N, Saito N, Yoshimoto Y, Imai H, et al,. (2010). Constitutive reactive oxygen species generation from autophagosome/lysosome in neuronal oxidative toxicity. J Biol Chem 285: 667-674.
20. Kurata H, Fujii T, Tsutsui H, Katayama T, Ohkita M, Takaoka M, et al,. (2006). Renoprotective effects of l-carnosine on ischemia/reperfusion-induced renal injury in rats. J Pharmacol Exp Ther 319: 640-647.
21. Leonarduzzi G, Chiarpotto E, Biasi F, Poli G, (2005). 4-Hydroxynonenal and cholesterol oxidation products in atherosclerosis. Mol Nutr Food Res 49: 1044-1049.
22. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, et al,. (2005). Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 70: 1673-1684.
23. Lusis AJ, (2000). Atherosclerosis. Nature 407: 233-241.
24. Mozdzan M, Szemraj J, Rysz J, Nowak D, (2005). Antioxidant properties of carnosine re-evaluated with oxidizing systems involving iron and copper ions. Basic Clin Pharmacol Toxicol 96: 352-360.
25. Negre-Salvayre A, Coatrieux C, Ingueneau C, Salvayre R, (2008). Advanced lipid peroxidation end products in oxidative damage to proteins. Potential role in diseases and therapeutic prospects for the inhibitors. Br J Pharmacol 153: 6-20.
26. Odetti P, Fogarthy J, Sell D, Monnier VM, (1992). Chromatographic quantitation of plasma and erythrocyte pentosidine in diabetic and uremic subjects. Diabetes 41: 153-159.
27. Oh YM, Jang EH, Ko JH, Kang JH, Park CS, Han SB, et al,. (2009). Inhibition of 6-hydroxydopamine-induced endoplasmic reticulum stress by L-carnosine in SH-SY5Y cells. Neurosci Lett 459: 7-10.
28. Orioli M, Vistoli G, Regazzoni L, Pedretti A, Lapolla A, Rossoni G, et al,. (2011). Design, synthesis, ADME Properties, and pharmacological activities of β-alanyl-D-histidine (D-Carnosine) prodrugs with improved bioavailability. ChemMedChem 6: 1269-1282.
29. Peters V, Schmitt CP, Zschocke J, Gross M-L, Brismar K, Forsberg E, (2011). Carnosine treatment largely prevents alterations of renal carnosine metabolism in diabetic mice. Amino Acids e-pub Aug 11.
30. Pfister F, Riedl E, Wang Q, vom Hagen F, Deinzer M, Harmsen MC, et al,. (2011). Oral carnosine supplementation prevents vascular damage in experimental diabetic retinopathy. Cell Physiol Biochem 28: 125-136.
31. Pläsier B, Lloyd DR, Paul GC, Thomas CR, Al-Rubeai M, (1999). Automatic image analysis for quantification of apoptosis in animal cell culture by annexin-V affinity assay. J Immunol Methods 229: 81-95.
32. Plump AS, Smith JD, Hayek T, Aalto-Setala K, Walsh A, Verstuyft JG, et al,. (1992). Severe hypercholesterolemia and atherosclerosis in apolipoprotein E-deficient mice created by homologous recombination in ES cells. Cell 71: 343-353.
33. Price DL, Rhett PM, Thorpe SR, Baynes JW, (2001). Chelating activity of advanced glycation end-product inhibitors. J Biol Chem 276: 48967-48972.
34. Rajanikant GK, Zemke D, Senut MC, Frenkel MB, Chen AF, Gupta R, et al,. (2007). Carnosine is neuroprotective against permanent focal cerebral ischemia in mice. Stroke 38: 3023-3031.
35. Riedl E, Pfister F, Braunagel M, Brinkkötter P, Sternik P, Deinzer M, et al,. (2011). Carnosine prevents apoptosis of glomerular cells and podocyte loss in STZ diabetic rats. Cell Physiol Biochem 28: 279-288.
36. Tabas I, (2005). Consequences and therapeutic implications of macrophage apoptosis in atherosclerosis: the importance of lesion stage and phagocytic efficiency. Arterioscler Thromb Vasc Biol 25: 2255-2264.
37. Uchida K, (2000). Role of reactive aldehyde in cardiovascular diseases. Free Radic Biol Med 28: 1685-1696.
38. Velez S, Nair NG, Reddy VP, (2008). Transition metal ion binding studies of carnosine and histidine: biologically relevant antioxidants. Colloids Surf B Biointerfaces 66: 291-294.
39. Vistoli G, Orioli M, Pedretti A, Regazzoni L, Canevotti R, Negrisoli G, et al,. (2009). Design, synthesis, and evaluation of carnosine derivatives as selective and efficient sequestering agents of cytotoxic reactive carbonyl species. ChemMedChem 4: 967-975.
40. Wen M, Segerer S, Dantas M, Brown PA, Hudkins KL, Goodpaster T, et al,. (2002). Renal injury in apolipoprotein E-deficient mice. Lab Invest 82: 999-1006.
41. Williams H, Pease RJ, Newell LM, Cordell PA, Graham RM, Kearney MT, et al,. (2010). Effect of transglutaminase 2 (TG2) deficiency on atherosclerotic plaque stability in the apolipoprotein E deficient mouse. Atherosclerosis 210: 94-99.
42. Zschocke J, Nebel A, Wicks K, Peters V, El Mokhtari NE, Krawczak M, et al,. (2008). Allelic variation in the CNDP1 gene and its lack of association with longevity and coronary heart disease. Mech Ageing Dev 127: 817-820.