Thiol chelation of Cu2+ by dihydrolipoic acid prevents human low density lipoprotein peroxidation

Free Radical Biology and Medicine

Volumn 25, Issue 3, 1998, Pages 287-297

  Lodge, John K ^a   Traber, Maret G ^a   Packer, Lester ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antioxidants; Binding; ESR; Free radical; Lipoic acid; Oxidation; Reduction

Indexed keywords

COPPER ION; DIHYDROLIPOATE; HYDROXYL RADICAL; LOW DENSITY LIPOPROTEIN; THIOCTIC ACID; CHELATING AGENT; COPPER; DRUG DERIVATIVE; FREE RADICAL; THIOL DERIVATIVE;

ARTICLE; CHELATION; COMPLEX FORMATION; ELECTRON SPIN RESONANCE; LIPID PEROXIDATION; PRIORITY JOURNAL; REDUCTION; CHEMISTRY; DRUG EFFECT; HUMAN; KINETICS; OXIDATION REDUCTION REACTION; PH;

CHELATING AGENTS; COPPER; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; OXIDATION-REDUCTION; SULFHYDRYL COMPOUNDS; THIOCTIC ACID;

EID: 0032129206     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00048-3     Document Type: Article

References (30)

1. Steinberg D., Parthasarathy S., Carew T. E., Khoo J. C., Witztum J. L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320:1989;915-924.
2. Wood J. L., Graham A. Structural requirements for oxidation of low-density lipoproteins by thiols. FEBS Lett. 366:1995;75-80.
3. Sparrow C. P., Olszewski J. Cellular oxidation of low density lipoprotein is caused by thiol production in media containing transition metal ions. J. Lipid Res. 34:1993;1219-1228.
4. Heinecke J. W., Rosen H., Suzuki L. A., Chait A. The role of sulfur-containing amino acids in superoxide production and modification of low density lipoprotein by arterial smooth muscle cells. J. Biol. Chem. 262:1987;10098-10103.
5. Heinecke J. W., Kawamura M., Suzuki L., Chait A. Oxidation of low density lipoprotein by thiols superoxide-dependent and -independent mechanisms . J. Lipid Res. 34:1993;2051-2061.
6. Berliner J. A., Heinecke J. W. The role of oxidized lipoproteins in atherogenesis. Free Radic. Biol. Med. 20:1996;707-727.
7. Lynch S. M., Frei B. Reduction of copper, but not iron, by human low density lipoprotein (LDL). Implications for metal ion-dependent oxidative modification of LDL. J. Biol. Chem. 270:1995;5158-5163.
8. 2+ in human lipoproteins. J. Biol. Chem. 271:1996;11106-11112.
9. Heinecke J. W., Baker L., Rosen H., Chait A. Superoxide-mediated modification of low density lipoprotein by arterial smooth muscle cells. J. Clin. Invest. 77:1986;757-761.
10. Santanam N., Parthasarathy S. Cellular cysteine generation does not contribute to the initiation of LDL oxidation. J. Lipid Res. 36:1995;2203-2211.
11. Lynch S. M., Frei B. Physiological thiol compounds exert pro- and anti-oxidant effects, respectively, on iron- and copper-dependent oxidation of human low-density lipoprotein. Biochim. Biophys. Acta. 1345:1997;215-221.
12. Handelman G. J., Han D., Tritschler H., Packer L. Alpha-lipoic acid reduction by mammalian cells to the dithiol form, and release into the culture medium. Biochem. Pharmacol. 47:1994;1725-1730.
13. Packer L., Witt E. H., Tritschler H. J. Alpha-lipoic acid as a biological antioxidant. Free Radic. Biol. Med. 19:1995;227-250.
14. Ou P., Tritschler H. J., Wolff S. P. Thioctic (lipoic) acid a therapeutic metal-chelating antioxidant? Biochem. Pharmacol. 50:1994;123-126.
15. 2+ in solution. Arch. Biochem. Biophys. 187:1978;208-214.
16. Kagan V. E., Serbinova E. A., Forte T., Scita G., Packer L. Recycling of vitamin E in human low density lipoproteins. J. Lipid Res. 33:1992;385-397.
17. Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
18. Esterbauer H., Dieber-Rotheneder M., Waeg G., Striegl G., Jurgens G. Biochemical, structural and functional properties of oxidized low-density lipoprotein. Chem. Res. Toxicol. 3:1990;77-92.
19. Sedlak J., Lindsay R. H. Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal. Biochem. 25:1968;192-205.
20. Han D., Handelman G. J., Packer L. Analysis of reduced and oxidized lipoic acid in biological samples by high-performance liquid chromatography. Methods Enzymol. 251:1995;315-325.
21. Buettner G. R. Spin trapping ESR parameters of spin adducts . Free Radic. Biol. Med. 3:1987;259-303.
22. Devasagayam T. P. A., Subramanian M., Pradhan D. S., Sies H. Prevention of singlet oxygen-induced DNA damage by lipoate. Chem. Biol. Interact. 86:1993;79-92.
23. Scott B. C., Aruoma O. I., Evans P. J., O'Neill C., Van der Vliet A., Cross C. E., Tritschler H., Halliwell B. Lipoic and dihydrolipoic acids as antioxidants. A critical evaluation. Free Radic. Res. Comm. 20:1994;119-133.
24. Kalyanaraman B., Karoui H., Singh R. J., Felix C. C. Detection of thiyl radical adducts formed during hydroxyl radical- and peroxynitrite-mediated oxidation of thiols - A high resolution ESR spin-trapping study at Q-band (35 GHz). Anal. Biochem. 241:1996;75-81.
25. Misik V., Tong Mak I., Stafford R. E., Weglicki W. B. Reactions of captopril and epicaptopril with transition metal ions and hydroxyl radicals an EPR spectroscopy study . Free Radic. Biol. Med. 15:1993;611-619.
26. Sigel H., McCormick D. B., Griesser R., Prijs B., Wright L. D. Metal ion complexes with biotin and biotin derivatives. Participation of sulfur in the orientation of divalent cations. Biochemistry. 8:1969;2687-2695.
27. Dill K., Adams E. R., O'Connor R. J., McGown E. L. Structure and dynamics of a lipoic acid-arsenical adduct. Chem. Res. Toxicol. 2:1989;181-185.
28. Bonomi F., Cerioli A., Pagani S. Molecular aspects of the removal of ferritin-bound iron by dl-dihydrolipoate. Biochim. Biophys. Acta. 994:1989;180-186.
29. Frausto da Silva, J. J. R.; Williams, R. J. P. The biological chemistry of the elements: the inorganic chemistry of life. Oxford: Oxford University Press; 1991.
30. Spear N., Aust S. D. Hydroxylation of deoxyguanosine in DNA by copper and thiols. Arch. Biochem. Biophys. 317:1995;142-148.