Design of unsymmetrical azo initiators to increase radical generation efficiency in low-density lipoproteins

References

• (a)Nicholson, A.C., Hajjar, D.P. Atherosclerosis. The American Scientist 1995; 83: 460–467, (b) N. Noguchi, N. Gotoh, and E. Niki (1993) Dynamics of the oxidation of low-density lipoprotein induced by free radicals. Biochimica Biophysica Acta 1168, 348–357.
   Web of Science ®Google Scholar
• Burton G.W., Joyce A., Ingold K.U. Is vitamin E the only lipid-soluble, chain-breaking antioxidant in human blood plasma and erythrocyte membranes?. Archives of Biochemistry and Biphysics 1983; 221: 281–290
   PubMed Web of Science ®Google Scholar
• Bowry V.W., Ingold K.U. The unexpected role of vitamin E (α-tocopherol) in the peroxidation of human low-density lipoprotein. Accounts of Chemical Research 1999; 32: 27–34
   Web of Science ®Google Scholar
• Noguchi N., Yamashita H., Gotoh N., Yamamoto R., Niki E. 2,2′-Azobis (4-methoxy-2,4-dimethylvaleronitrile), a new lipid-soluble azo initiator: application to oxidations of lipids and low-density lipoprotein in solution and in aqueous dispersions. Free Radicals in Biology and Medicine 1998; 24: 259–268
   PubMed Web of Science ®Google Scholar
• Goss S.P.A., Singh R.J., Hogg N., Kalyanaraman B. Reactions of ·NO, ·NO2 and peroxynitrite in membranes: physiological implications. Free Radical Research 1999; 31: 597–606
   PubMed Web of Science ®Google Scholar
• Abuja P.M., Albertini R., Esterbauer H. Simulation of the induction of oxidation of low-density lipoprotein by high copper concentrations: evidence for a nonconstant rate of initiation. Chemical Research in Toxicology 1997; 10: 644–651
   PubMed Web of Science ®Google Scholar
• Neuzil J., Thomas S.R., Stocker R. Requirement for, promotion, or inhibition by α-tocopherol of radical-induced initiation of plasma lipoprotein lipid peroxidation. Free Radicals in Biology and Medicine 1997; 22: 57–71
   PubMed Web of Science ®Google Scholar
• Bowry V.W., Stocker R. Tocopherol-mediated peroxidation. The prooxidant effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. The Journal of the American Chemical Society 1993; 115: 6029–6044
   Web of Science ®Google Scholar
• Synthesis and efficiency studies reported in more detail for the initiators C-16, C-12, and C-8.Culbertson, S.M., Porter, N.A. Unsymmetrical azo initiators increase efficiency of radical generation in aqueous dispersions, liposomal membranes, and lipoproteins. The Journal of the American Chemical Society 2000; 122: 4032–4038
   Web of Science ®Google Scholar
• (a)Hammond, G.S., Neuman, R.C., Jr. The mechanism of decomposition of azo compounds. Ill. Cage effects with positively charged geminate radical pairs. The Journal of the American Chemical Society 1963; 85: 1501–1508, (b) T. J. Dougherty (1961) Chemistry of 2,2′-azobisisobutryamidine hydrochloride in aqueous solution: a water-soluble azo initiator. The Journal of the American Chemical Society, 83, 4849–4853.
   Web of Science ®Google Scholar
• Reynaud P., Brion J., Menard G. Èchange d'ammoniac dans les amidines par réaction avec les amines: Mécanisme et application à la préparation d'amidines mono et N,N'-disubstituées. Bulletin. Societe Chimie France 1978; 9–10: II–449
   Google Scholar
• Fujie H., Shiraki K., Miyagawa T., Mnamii N. Preparation and thermal decomposition of cyclic azoamidinium salts as water-soluble radical initiators for polymerization over a wide temperature range. Pure and Applied Chemistry 1992; A29: 741–751
   Google Scholar
• Schumaker V.N., Puppione D.L. Sequential Flotation Ultracentrifugation. Methods in Enzymology 1986; 128: 155–181
   PubMed Web of Science ®Google Scholar
• Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the folin phenol reagent. The Journal of Biological Chemistry 1951; 193: 265–275
   PubMed Web of Science ®Google Scholar
• Sattler W., Mohr D., Stocker R. Rapid isolation of lipoproteins and assessment of their peroxidation by high-performance liquid chromatography postcolumn chemiluminescence. Methods in Enzymology 1994; 233: 469–489
   PubMed Web of Science ®Google Scholar
• Woodburn K., Kessel D., Sykes E. Separation of plasma lipoproteins with the TLN-120 near vertical tube rotor. Technical Information Bulletin T-1734. Beckman Instruments, Inc. 1993
   Google Scholar
• Kenar J.A., Havrilla C.M., Porter N.A., Guyton J.R., Brown S.A., Klemp K.F., Selinger E. Identification and quantification of the regioisomeric cholesteryl linoleate hydroperoxides in oxidized human low-density lipoprotein and high density lipoprotein. Chemical Research in Toxicology 1996; 9: 737–744
   PubMed Web of Science ®Google Scholar
• Lang J.K., Gohil K., Packer L. Simultaneous determination of tocopherols, ubiquinols, and ubiquinones in blood, plasma, tissue homogenates, and subcellular fractions. Analytical Biochemistry 1986; 157: 106–116
   PubMed Web of Science ®Google Scholar
• Motchnik P.A., Frei B., Ames B.N. Measurement of antioxidants in human blood plasma. Methods in Enzymology 1994; 234: 269–279
   PubMed Web of Science ®Google Scholar
• Komuro E.K., Takahashi M., Morita T., Tsuchiya J., Yoshitaka A., Yamamoto Y., Niki E. Inhibition of peroxidations of lipids and membranes by estrogens. The Journal of Physical Organic Chemistry 1990; 3: 309–315
   Web of Science ®Google Scholar
• (a)Niki, E., Saito, M., Yoshikawa, Y., Yamamoto, Y., Kamiya, Y., Y. Oxidation of lipids. XII. Inhibition of oxidation of soybean phosphatidylcholine and methyl linoleate in aqueous dispersions by uric acid. The Bulletin of the Chemical Society of Japan 1986; 59: 471–477, (b) E. Niki, T. Saito, A. Kawakami, and Y. Kamiya, Y. (1984) Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. The Journal of Biological Chemistry, 259, 4177–4182.
   Web of Science ®Google Scholar
• Simic M.G., Javanovic S.V. Antioxidation mechanisms of uric acid. The Journal of the American Chemical Society 1989; 111: 5778–5782
   Web of Science ®Google Scholar
• Cadenas E. Mechanisms of antioxidant action. Free Radicals, Oxidative Stress, and Antioxidants: Pathological and Physiological Significance, T. Ozben. Plenum Press, New York 1998; 237–251, In
   Google Scholar