Synthesis of Vitamin E-Carnosine (VECAR): New Antioxidant Molecule with Potential Application in Atherosclerosis

REFERENCES

• Halliwell , B. Oxidative stress and neurodegeneration: Where are we now? J. Neurochem. 2006 , 97 , 1634 – 1658 .
   PubMed Web of Science ®Google Scholar
• Cooke , J. P. Nutriceuticals for cardiovascular health . Am. J. Cardiol. 1998 , 82 , 43S – 46S .
   PubMed Web of Science ®Google Scholar
• Young , I. S. ; Woodside , J. V. Antioxidants in health and disease . J. Clin. Pathol. 2001 , 54 , 176 – 186 .
   PubMed Web of Science ®Google Scholar
• Sagin , F. G. ; Sozmen , E. Y. Anti-inflammatory effects of dietary antioxidants . Curr. Med. Chem. 2004 , 3 , 19 – 30 .
   Google Scholar
• Willcox , J. K. ; Ash , S. L. ; Catignani , G. L. Antioxidants and prevention of chronic disease . Crit. Rev. Food Sci. Nutr. 2004 , 44 , 275 – 295 .
   PubMed Web of Science ®Google Scholar
• Halliwell , B. Antioxidant defence Mechanisms: From the beginning to the end (of the beginning) . Free Radical Res. 1999 , 31 , 261 – 272 .
   PubMed Web of Science ®Google Scholar
• Visioli , F. ; Keaney , J. F. ; Halliwell , B. Antioxidants and cardiovascular disease: Panaceas or tonics for tired sheep? Cardiovasc. Res. 2000 , 47 , 409 .
   PubMed Web of Science ®Google Scholar
• Thom , T. ; Haase , N. ; Rosamond , W. ; Howard , V. J. ; Rumsfeld , J. ; Manolio , T. ; Zheng , Z. J. ; Flegal , K. ; O'donnell , C. ; et al. . Heart disease and stroke statistics, 2006 update: A report from the American Heart Association Statistics Committee and Stroke Statistics Subcommittee . Circulation 2006 , 113 , E85 – E151 .
   PubMed Web of Science ®Google Scholar
• Davies , K. J. Oxidative stress, antioxidant defenses, and damage removal, repair, and replacement systems . IUBMB Life 2000 , 50 , 279 – 289 .
   PubMed Web of Science ®Google Scholar
• Pryor , W. A. Measurement of oxidative stress status in humans . Cancer Epidemiol. Biomarkers Prev. 1993 , 2 , 289 – 292 .
   PubMed Web of Science ®Google Scholar
• Pryor , W. A. Vitamin E and heart disease: Basic science to clinical intervention trials . Free Radical Biol. Med. 2000 , 28 , 141 – 164 .
   PubMed Web of Science ®Google Scholar
• Morel , D. W. ; Dicorleto , P. E. ; Chisolm , G. M. Endothelial and smooth-muscle cells alter low-density lipoprotein invitro by free-radical oxidation . Arteriosclerosis 1984 , 4 , 357 – 364 .
   PubMedGoogle Scholar
• Steinberg , D. ; Berliner , J. A. ; Burton , G. W. ; Carew , T. E. ; Chait , A. ; Chisolm , G. M. ; Esterbauer , H. ; Fogelman , A. M. ; Fox , P. L. ; et al. . Antioxidants in the prevention of human atherosclerosis: Summary of the proceedings of a national Heart Lung and Blood Institute Workshop, September 5–6, 1991, Bethesda, Maryland . Circulation 1992 , 85 , 2338 – 2344 .
   Web of Science ®Google Scholar
• Chisolm , G. M. ; Steinberg , D. The oxidative modification hypothesis of atherogenesis: An overview . Free Radical Biol. Med. 2000 , 28 , 1815 – 1826 .
   PubMed Web of Science ®Google Scholar
• Traber , M. G. ; Burton , G. W. ; Ingold , K. U. ; Kayden , H. J. Rrr- and Srr-α-tocopherols are secreted without discrimination in human chylomicrons, but Rrr-α-tocopherol is preferentially secreted in very low density lipoproteins . J. Lipid Res. 1990 , 31 , 675 – 685 .
   PubMed Web of Science ®Google Scholar
• Traber , M. G. ; Rudel , L. L. ; Burton , G. W. ; Hughes , L. ; Ingold , K. U. ; Kayden , H. J. Nascent Vldl from liver perfusions of cynomolgus monkeys are preferentially enriched in Rrr- compared with Srr-α-tocopherol: Studies using deuterated tocopherols. J. Lipid Res. 1990, 31, 687–694.
   PubMed Web of Science ®Google Scholar
• Blatt , D. H. ; Leonard , S. W. ; Traber , M. G. Vitamin E kinetics and the function of tocopherol regulatory proteins . Nutrition 2001 , 17 , 799 – 805 .
   PubMed Web of Science ®Google Scholar
• Noguchi , N. ; Niki , E. Apolipoprotein-B protein oxidation in low-density lipoproteins . Method. Enzymol. 1994 , 233 , 490 – 494 .
   PubMed Web of Science ®Google Scholar
• Fuller , C. J. ; Agil , A. ; Lender , D. ; Jialal , I. Superoxide Production and Ldl oxidation by diabetic neutrophils . J. Diabetes Complicat. 1996 , 10 , 206 – 210 .
   PubMed Web of Science ®Google Scholar
• Jialal , I. ; Devaraj , S. Low density lipoprotein oxidation, antioxidants, and atherosclerosis: A clinical biochemistry perspective . Clin. Chem. 1996 , 42 , 498 – 506 .
   PubMed Web of Science ®Google Scholar
• Mashima , R. ; Yoshimura , S. ; Yamamoto , Y. Reduction of lipid hydroperoxides by apolipoprotein B-100 . Biochem. Biophys. Res. Commun. 1999 , 259 , 185 – 189 .
   PubMed Web of Science ®Google Scholar
• Theriault , A. ; Chao , J. T. ; Wang , Q. ; Gapor , A. ; Adeli , K. Tocotrienol: A review of its therapeutic potential . Clin. Biochem. 1999 , 32 , 309 – 319 .
   PubMed Web of Science ®Google Scholar
• Halliwell , B. ; Zhao , K. ; Whiteman , M. Nitric oxide and peroxynitrite: The ugly, the uglier and the not so good: A personal view of recent controversies . Free Radical Res. 1999 , 31 , 651 – 669 .
   PubMed Web of Science ®Google Scholar
• Shi , H. L. ; Noguchi , N. ; Niki , E. Dynamics of antioxidant action of ubiquinol: A reappraisal . BioFactors. 1999 , 9 , 141 – 148 .
   PubMed Web of Science ®Google Scholar
• Woodside , J. V. ; Denholm , E. E. ; Campbell , M. J. ; Young , I. S. ; Honour , J. ; Leathem , A. The effect of phyto-oestrogen supplementation on antioxidant status . Proc. Nutr. Soc. 2000 , 59 , 48a – 48a .
   Web of Science ®Google Scholar
• Choy , K. J. ; Deng , Y. M. ; Hou , J. Y. ; Wu , B. ; Lau , A. ; Witting , P. K. ; Stocker , R. Coenzyme Q(10) supplementation inhibits aortic lipid oxidation but fails to attenuate intimal thickening in balloon-injured New Zealand white rabbits . Free Radical Biol. Med. 2003 , 35 , 300 – 309 .
   PubMed Web of Science ®Google Scholar
• Niki , E. ; Yoshida , Y. ; Saito , Y. ; Piga , R. ; Noguchi , N. Antioxidant action of vitamin E isoforms . Free Radical Res. 2003 , 37 , 40 – 40 .
   Web of Science ®Google Scholar
• Stocker , R. Antioxidant activities of bile pigments . Antioxidants Redox Signaling 2004 , 6 , 841 – 849 .
   PubMed Web of Science ®Google Scholar
• Pryor , W. A. β-Carotene, vitamin E, and lung cancer . New Engl. J. Med. 1994 , 331 , 612 – 612 .
   PubMedGoogle Scholar
• Rehman , A. ; Collis , C. S. ; Yang , M. ; Kelly , M. ; Diplock , A. T. ; Halliwell , B. ; Rice-Evans , C. The effects of iron and vitamin C co-supplementation on oxidative damage to DNA in healthy volunteers . Biochem. Biophys. Res. Commun. 1998 , 246 , 293 – 298 .
   PubMed Web of Science ®Google Scholar
• Cooke , M. S. ; Evans , M. D. ; Mistry , N. ; Lunec , J. Role of dietary antioxidants in the prevention of in vivo oxidative DNA damage . Nutr. Res. Rev. 2002 , 15 , 19 – 41 .
   PubMed Web of Science ®Google Scholar
• Engler , M. M. ; Engler , M. B. ; Malloy , M. J. ; Chiu , E. Y. ; Schloetter , M. C. ; Paul , S. M. ; Stuehlinger , M. ; Lin , K. Y. ; Cooke , J. P. ; et al. . Antioxidant vitamins C and E improve endothelial function in children with hyperlipidemia: Endothelial assessment of risk from lipids in youth (early) trial . Circulation 2003 , 108 , 1059 – 1063 .
   PubMed Web of Science ®Google Scholar
• Hipkiss , A. R. ; Michaelis , J. ; Syrris , P. ; Kumar , S. ; Lam , Y. Carnosine protects proteins against in vitro glycation and cross linking . Biochem. Soc. Trans. 1994 , 22 , S399 – S399 .
   PubMed Web of Science ®Google Scholar
• Hipkiss , A. R. ; Brownson , C. ; Bertani , M. F. ; Ruiz , E. ; Ferro , A. Reaction of carnosine with aged proteins: Another protective process? Ann. N.Y. Acad. Sci. 2002 , 959 , 285 – 294 .
   PubMed Web of Science ®Google Scholar
• Hipkiss , A. R. On the mechanisms of ageing suppression by dietary restriction: Is persistent glycolysis the problem? Mech. Ageing Dev. 2006 , 127 , 8 – 15 .
   PubMed Web of Science ®Google Scholar
• Chasovnikova , L. V. ; Formazyuk , V. E. ; Sergienko , V. I. ; Boldyrev , A. A. ; Severin , S. E. The antioxidative properties of carnosine and other drugs . Biochem. Int. 1990 , 20 , 1097 – 1103 .
   PubMedGoogle Scholar
• Salim-Hanna , M. ; Lissi , E. ; Videla , L. A. Free radical scavenging activity of carnosine. Free. Radic. Res. Commun. 1991, 14, 263–270.
   PubMed Web of Science ®Google Scholar
• Boissonneault , G. A. ; Hardwick , T. A. ; Bogardus , S. L. ; Glauert , H. P. ; Chow , C. K. ; Decker , E. A. Interactions between carnosine and vitamin E in mammary-cancer risk . FASEB J . 1994 , 8 , A425 – A425 .
   Web of Science ®Google Scholar
• Decker , E. A. ; Ivanov , V. ; Zhu , B. Z. ; Frei , B. Inhibition of low-density lipoprotein oxidation by carnosine histidine . J. Agric. Food. Chem. 2001 , 49 , 511 – 516 .
   PubMed Web of Science ®Google Scholar
• Boldyrev , A. A. Protection of proteins from oxidative stress: A new illusion or a novel strategy? Ann. N. Y. Acad. Sci. 2005 , 1057 , 193 – 205 .
   PubMed Web of Science ®Google Scholar
• Guiotto , A. ; Calderan , A. ; Ruzza , P. ; Borin , G. Carnosine and carnosine-related antioxidants: A review . Curr. Med. Chem. 2005 , 12 , 2293 – 2315 .
   PubMed Web of Science ®Google Scholar
• Stvolinsky , S. ; Antipin , M. ; Meguro , K. ; Sato , T. ; Abe , H. ; Boldyrev , A. Effect of carnosine and its Trolox-modified derivatives on life span of Drosophila melanogaster . Rejuv. Res. 2010 , 13 , 453 – 457 .
   Google Scholar
• Rosenau , T. ; Habicher , W. D. Novel tocopherol derivatives, 5: The first organometallic derivative of vitamin E . Synlett 1996 , 427 .
   Google Scholar
• Rosenau , T. ; Habicher , W. D. ; Chen , C. L. Novel tocopherol compounds, 4: 5-Tocopherylacetic acid and its derivatives . Heterocycles 1996 , 43 , 787 – 798
   Web of Science ®Google Scholar
• Gille , L. ; Gregor , W. ; Rosenau , T. ; Nohl , H. Antioxidant properties of new vitamin E derivatives . Naunyn-Schmiedeberg's Arch. Pharmacol. 2004 , 369 , R137 – R137 .
   Google Scholar
• Campo , G. M. ; Ceccarelli , S. ; Squadrito , F. ; Altavilla , D. ; Dorigotti , L. ; Caputi , A. P. Raxofelast (Irfi 016): A new hydrophilic vitamin E–like antioxidant agent . Cardiovasc. Drug Rev. 1997 , 15 , 157 – 173 .
   Web of Science ®Google Scholar
• Watanabe , A. ; Noguchi , N. ; Fujisawa , A. ; Kodama , T. ; Tamura , K. ; Cynshi , O. ; Niki , E. Stability and reactivity of aryloxyl radicals derived from a novel antioxidant Bo-653 and related compounds: Effects of substituent and side chain in solution and membranes . J. Am. Chem. Soc. 2000 , 122 , 5438 – 5442 .
   Web of Science ®Google Scholar
• Noguchi , N. ; Sakai , H. ; Kato , Y. ; Tsuchiya , J. ; Yamamoto , Y. ; Niki , E. ; Horikoshi , H. ; Kodama , T. Inhibition of oxidation of low density lipoprotein by troglitazone . Atherosclerosis 1996 , 123 , 227 – 234 .
   PubMed Web of Science ®Google Scholar
• Rosenau , T. ; Habicher , W. D. “Vitamin Ce,” a novel prodrug form of vitamin E . Chem. Pharm. Bull. (Tokyo) 1997 , 45 , 1080 – 1084
   PubMed Web of Science ®Google Scholar
• Meier , R. ; Tomizaki , T. ; Schulze-Briese , C. ; Baumann , U. ; Stocker , A. The molecular basis of vitamin E retention: Structure of human α-tocopherol transfer protein . J. Mol. Biol. 2003 , 331 , 725 – 734 .
   PubMed Web of Science ®Google Scholar
• Hosomi , A. ; Arita , M. ; Sato , Y. ; Kiyose , C. ; Ueda , T. ; Igarashi , O. ; Arai , H. ; Inoue , K. Affinity for α-tocopherol transfer protein as a determinant of the biological activities of vitamin E analogs . FEBS Lett. 1997 , 409 , 105 – 108 .
   PubMed Web of Science ®Google Scholar
• Parks , E. ; Traber , M. G. Mechanisms of vitamin E regulation: Research over the past decade and focus on the future . Antioxid. Redox Signal. 2000 , 2 , 405 – 412 .
   PubMed Web of Science ®Google Scholar
• Burton , G. W. ; Traber , M. G. ; Acuff , R. V. ; Walters , D. N. ; Kayden , H. ; Hughes , L. ; Ingold , K. U. Human Plasma and Tissue α-tocopherol concentrations in response to supplementation with deuterated natural and synthetic vitamin E . Am. J. Clin. Nutr. 1998 , 67 , 669 – 684 .
   PubMed Web of Science ®Google Scholar
• Traber , M. G. Regulation of human plasma vitamin E . Adv. Pharmacol. 1997 , 38 , 49 – 63 .
   PubMedGoogle Scholar
• Lei , H. ; Marks , V. ; Pasquale , T. ; Atkinson , J. K. Synthesis of photoaffinity label analogues of α-tocopherol . Bioorg. Med. Chem. Lett. 1998 , 8 , 3453 – 3458 .
   PubMed Web of Science ®Google Scholar
• Lei , H. S. ; Atkinson , J. Synthesis of phytyl- and chroman-derivatized photoaffinity labels based on α-tocopherol . J. Org. Chem. 2000 , 65 , 2560 – 2567 .
   PubMed Web of Science ®Google Scholar
• Sudo , Y. ; Wada , T. Characteristics of octadecylsilylated silica gels end-capped by high-temperature silylation . J. Chromatogr. A 1998 , 813 , 239 – 246 .
   Web of Science ®Google Scholar
• Luo , X. D. ; Basile , M. J. ; Kennelly , E. J. Polyphenolic antioxidants from the fruits of chrysophyllum cainito L. (star apple). J. Agric. Food. Chem. 2002, 50, 1379–1382
   PubMed Web of Science ®Google Scholar
• Qian , J. ; Wilson , K. ; Nava , P. ; Morley , S. ; Atkinson , J. ; Manor , D. Intracellular localization of α-tocopherol transfer protein and α-tocopherol . Ann. N.Y. Acad. Sci. 2004 , 1031 , 330 – 331 .
   PubMed Web of Science ®Google Scholar
• Qian , J. H. ; Atkinson , J. ; Manor , D. Biochemical consequences of heritable mutations in the α-tocopherol transfer protein . Biochemistry 2006 , 45 , 8236 – 8242 .
   PubMed Web of Science ®Google Scholar
• Atkinson , J. K. ; Nava , P. ; Frahm , G. ; Curtis , V. ; Manor , D. Fluorescent tocopherols as probes of intervesicular transfer catalyzed by the α-tocopherol transfer protein . Ann. N.Y. Acad. Sci. 2004 , 1031 , 324 – 327 .
   PubMed Web of Science ®Google Scholar
• Bradford , A. ; Atkinson , J. ; Fuller , N. ; Rand , R. P. The effect of vitamin E on the structure of membrane lipid assemblies . J. Lipid Res. 2003 , 44 , 1940 – 1945 .
   PubMed Web of Science ®Google Scholar
• Galli , F. ; Lee , R. ; Atkinson , J. ; Floridi , A. ; Kelly , F. J. Γ-Tocopherol biokinetics and transformation in humans . Free Radical Res. 2003 , 37 , 1225 – 1233 .
   PubMed Web of Science ®Google Scholar
• Traber , M. G. ; Paterson , E. ; Atkinson , J. ; Ramakrishnan , R. ; Iacovoni , V. ; Cross , C. Studies in humans using deuterium-labeled α- and Γ-tocopherols demonstrate rapid plasma Γ-tocopherol disappearance . FASEB J . 2003 , 17 , A279 – A279 .
   Web of Science ®Google Scholar
• Lawson , K. A. ; Anderson , K. ; Menchaca , M. ; Atkinson , J. ; Sun , L. Z. ; Knight , V. ; Gilbert , B. E. ; Conti , C. ; Sanders , B. G. ; Kline , K. Novel vitamin E analogue decreases syngeneic mouse mammary tumor burden and reduces lung metastasis . Mol. Cancer Ther. 2003 , 2 , 437 – 444 .
   PubMed Web of Science ®Google Scholar
• Morley , S. ; Thakur , V. ; Danielpour , D. ; Parker , R. ; Arai , H. ; Atkinson , J. ; Barnholtz-Sloan , J. ; Klein , E. ; Manor , D. Tocopherol transfer protein sensitizes prostate cancer cells to vitamin E . J. Biol. Chem. 2010 , 285 , 35578 – 35589 .
   PubMed Web of Science ®Google Scholar
• Morley , S. ; Panagabko , C. ; Stocker , A. ; Atkinson , J. ; Manor , D. Structure–function relationship in the tocopherol transfer protein . Ann. N. Y. Acad. Sci. 2004 , 1031 , 332 – 333 .
   PubMed Web of Science ®Google Scholar
• Abdo , M. R. ; Joseph , P. ; Boigegrain , R. A. ; Liautard , J. P. ; Montero , J. L. ; Kohler , S. ; Winum , J. Y. Brucella suis histidinol dehydrogenase: Synthesis and inhibition studies of a series of substituted benzylic ketones derived from histidine . Biorg. Med. Chem. 2007 , 15 , 4427 – 4433 .
   PubMed Web of Science ®Google Scholar
• Zhao , M. ; Bi , L. R. ; Bi , W. ; Wang , C. ; Yang , Z. ; Ju , J. F. ; Peng , S. Q. Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity . Biorg. Med. Chem. 2006 , 14 , 4761 – 4774 .
   PubMed Web of Science ®Google Scholar
• Wu , G. ; Liu , J. ; Bi , L. ; Zhao , M. ; Wang , C. ; Baudy-Floc'h , M. ; Ju , J. ; Peng , S. Toward breast cancer resistance protein (Bcrp) inhibitors: Design, synthesis of a series of new simplified fumitremorgin C analogues . Tetrahedron 2007 , 63 , 5510 – 5528 .
   Web of Science ®Google Scholar
• Montalbetti , C. A. G. N. ; Falque , V. Amide bond formation and peptide coupling . Tetrahedron 2005 , 61 , 10827 – 10852 .
   Web of Science ®Google Scholar