Nicotine-enhanced oxidation of low-density lipoprotein and its components by myeloperoxidase/H₂O₂/Cl- system.

In this study, the effect of nicotine on the LDL oxidation by the MPO/H2O2/Cl- system and the effect of HOCl on LDL and some of its components, such as methyl linoleate, vitamin E and the amino acid tryptophan were explored. Nicotine, in micromolar concentrations, enhanced the tryptophan oxidation, either present in LDL or free, in solution. Nicotine also decreased the formation of conjugated dienes and oxygen consumption in a methyl linoleate / HOCl system, and there was evidence to suggest an increase in chlorohydrin formation. Acceleration of the vitamin E oxidation by HOCl was also observed in the presence of nicotine. These data show that the interaction of nicotine and HOCl can promote significant biochemical modifications in LDL particle and some of its components involved in the pathogenesis of cardiovascular and other diseases.

[1]  K. Hirata,et al.  Serum myeloperoxidase/paraoxonase 1 ratio as potential indicator of dysfunctional high-density lipoprotein and risk stratification in coronary artery disease. , 2014, Atherosclerosis.

[2]  R. Snapka,et al.  Nicotine Mediates Hypochlorous Acid-Induced Nuclear Protein Damage in Mammalian Cells , 2014, Inflammation.

[3]  J. Ribalta,et al.  Trans‐vessel gradient of myeloperoxidase in coronary artery disease , 2013, European journal of clinical investigation.

[4]  K. Webster,et al.  Nicotine potentiates proatherogenic effects of oxLDL by stimulating and upregulating macrophage CD36 signaling. , 2013, American journal of physiology. Heart and circulatory physiology.

[5]  Kevin McAdam,et al.  Spectroscopic Studies on Nicotine and Nornicotine in the UV Region† , 2013, Chirality.

[6]  A. Kettle,et al.  Redox reactions and microbial killing in the neutrophil phagosome. , 2013, Antioxidants & redox signaling.

[7]  A. C. Gasparovic,et al.  Assays for the measurement of lipid peroxidation. , 2013, Methods in molecular biology.

[8]  A. Khosrowbeygi,et al.  Antioxidant properties and inhibitory effects of Satureja khozestanica essential oil on LDL oxidation induced-CuSO(4) in vitro. , 2013, Asian Pacific journal of tropical biomedicine.

[9]  M. Honma,et al.  Miscoding properties of 8-chloro-2'-deoxyguanosine, a hypochlorous acid-induced DNA adduct, catalysed by human DNA polymerases. , 2013, Mutagenesis.

[10]  K. Groundstroem,et al.  Serum myeloperoxidase is independent of the risk factors of atherosclerosis , 2012, Coronary Artery Disease.

[11]  A. Sokolov,et al.  The free amino acid tyrosine enhances the chlorinating activity of human myeloperoxidase. , 2012, Journal of inorganic biochemistry.

[12]  D. Teupser,et al.  Alpha-Tocopherol Distribution in Lipoproteins and Anti-Inflammatory Effects Differ between CHD-Patients and Healthy Subjects , 2006, Journal of the American College of Nutrition.

[13]  M. Davies,et al.  Modification of low-density lipoprotein by myeloperoxidase-derived oxidants and reagent hypochlorous acid. , 2006, Biochimica et biophysica acta.

[14]  R. Mecham,et al.  Specific sequence motifs direct the oxygenation and chlorination of tryptophan by myeloperoxidase. , 2006, Biochemistry.

[15]  A. Kettle,et al.  A sensitive and selective assay for chloramine production by myeloperoxidase. , 2005, Free radical biology & medicine.

[16]  G. Spiteller Is Atherosclerosis a Multifactorial Disease or Is It Induced by a Sequence of Lipid Peroxidation Reactions? , 2005, Annals of the New York Academy of Sciences.

[17]  M. Davies,et al.  Hypochlorous acid-mediated oxidation of lipid components and antioxidants present in low-density lipoproteins: absolute rate constants, product analysis, and computational modeling. , 2003, Chemical research in toxicology.

[18]  F. Mattivi,et al.  Synergistic antioxidant effect of catechin and malvidin 3-glucoside on free radical-initiated peroxidation of linoleic acid in micelles. , 2002, Archives of biochemistry and biophysics.

[19]  P. Bickford,et al.  Nicotine's oxidative and antioxidant properties in CNS. , 2002, Life sciences.

[20]  Toshinori Suzuki,et al.  Nicotine‐modulated formation of spiroiminodihydantoin nucleoside via 8‐oxo‐7,8‐dihydro‐2′‐deoxyguanosine in 2′‐deoxyguanosine–hypochlorous acid reaction , 2002, FEBS letters.

[21]  E. Niki,et al.  Formation of active oxygen species and lipid peroxidation induced by hypochlorite. , 2002, Archives of biochemistry and biophysics.

[22]  増田 光治 Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils : Catalysis by nicotine and trimethylamine , 2002 .

[23]  E J Topol,et al.  Association between myeloperoxidase levels and risk of coronary artery disease. , 2001, JAMA.

[24]  J. Cadet,et al.  Chlorination of Guanosine and Other Nucleosides by Hypochlorous Acid and Myeloperoxidase of Activated Human Neutrophils , 2001, The Journal of Biological Chemistry.

[25]  M. Hammel,et al.  Comparison of HOCl traps with myeloperoxidase inhibitors in prevention of low density lipoprotein oxidation. , 2000, Biochimica et biophysica acta.

[26]  A. Pitt,et al.  Pathways of phospholipid oxidation by HOCl in human LDL detected by LC-MS. , 2000, Free radical biology & medicine.

[27]  J. Hook,et al.  Oxidation of 2,2,7,8-tetramethyl-6-chromanol, the model compound of γ-tocopherol, by hypochlorous acid , 2000, Redox report : communications in free radical research.

[28]  R. Stocker,et al.  Redox reactions related to indoleamine 2,3-dioxygenase and tryptophan metabolism along the kynurenine pathway. , 1999, Redox report : communications in free radical research.

[29]  W. Prütz Reactions of hypochlorous acid with biological substrates are activated catalytically by tertiary amines. , 1998, Archives of biochemistry and biophysics.

[30]  M. Hayn,et al.  Human low density lipoprotein as a target of hypochlorite generated by myeloperoxidase. , 1998, Free radical biology & medicine.

[31]  K. Arnold,et al.  The action of hypochlorous acid on phosphatidylcholine liposomes in dependence on the content of double bonds. Stoichiometry and NMR analysis. , 1995, Chemistry and physics of lipids.

[32]  T. Melø,et al.  UV-initiated autoxidation of methyl linoleate in micelles studied by optical absorption. , 1995, Chemistry and physics of lipids.

[33]  Wei Li,et al.  Cholesterol chlorohydrin synthesis by the myeloperoxidase-hydrogen peroxide-chloride system: potential markers for lipoproteins oxidatively damaged by phagocytes. , 1994, Biochemistry.

[34]  A. Stern,et al.  Membrane changes associated with lysis of red blood cells by hypochlorous acid. , 1994, Free radical biology & medicine.

[35]  E. Roitman,et al.  Chlorohydrin formation from unsaturated fatty acids reacted with hypochlorous acid. , 1992, Archives of biochemistry and biophysics.

[36]  E. P. Brestel Co-oxidation of luminol by hypochlorite and hydrogen peroxide implications for neutrophil chemiluminescence. , 1985, Biochemical and biophysical research communications.

[37]  W. Ostrowski,et al.  Chloramines as intermediates of oxidation reaction of amino acids by myeloperoxidase. , 1971, Biochimica et biophysica acta.

[38]  O. H. Lowry,et al.  Protein measurement with the Folin phenol reagent. , 1951, The Journal of biological chemistry.

[39]  Fraps Gs The premature death of white rats fed low levels of carotenes from different sources. , 1947 .