Benzophenone-sensitized photooxidation of sarcoplasmic reticulum membranes: Site-specific modification of the Ca2+-ATPase

Free Radical Biology and Medicine

Volumn 23, Issue 7, 1997, Pages 1009-1020

  Krainev, Arkadi G ^a   Viner, Rosa I ^a   Bigelow, Diana J ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

Benzophenone; Ca2+ ATPase; Phospholipid membrane; Photooxidation; Protein modification; Sarcoplasmic reticulum

Indexed keywords

ADENOSINE TRIPHOSPHATASE (CALCIUM); BENZOPHENONE; LINOLEIC ACID; STEARIC ACID;

AMINO ACID COMPOSITION; ANIMAL TISSUE; ARTICLE; BILAYER MEMBRANE; BINDING SITE; CALCIUM TRANSPORT; ENZYME ACTIVITY; HYDROPHOBICITY; LIPID PEROXIDATION; LIPID VESICLE; NONHUMAN; OXIDATIVE STRESS; PHOSPHOLIPID MEMBRANE; PHOTOOXIDATION; PRIORITY JOURNAL; PROTEIN LOCALIZATION; PROTEIN MODIFICATION; RABBIT; SARCOPLASMIC RETICULUM;

AMINO ACIDS; ANIMALS; BENZOPHENONES; CALCIUM-TRANSPORTING ATPASES; INTRACELLULAR MEMBRANES; LIPID PEROXIDATION; LIPOSOMES; OXIDATION-REDUCTION; PHOTOSENSITIZING AGENTS; RABBITS; SARCOPLASMIC RETICULUM;

EID: 0030822655     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(97)00131-7     Document Type: Article

References (54)

1. Emerit I., Chance B. Free radicals and aging. 1992;Birkḧauser, Berlin.
2. Kukreja R. C., Hess M. L. Free radicals, cardiovascular dysfunction and protection strategies. 1994;R. G. Landes Co, Austin.
3. Kagan V. E. Lipid peroxidation in membranes. 1984;CRC Press, Boca Raton.
4. Gubskii Yu. I., Zadorina O. V., Fedorov A. N., Bogdanova L. A. Peroxide modification of the sarcoplasmic reticulum of the skeletal muscles in antioxidant deficiency and ionol action: I. Calcium transport in sarcoplasmic reticulum membranes. Ukr. Biokhim. Zh. 63:1991;81-87.
5. Dinis T. C. P., Almeida L. M., Madeira V. M. C. Lipid peroxidation in sarcoplasmic reticulum membranes: Effect on functional and biophysical properties. Arch. Biochem. Biophys. 301:1993;256-264.
6. Custodio J. B. A., Dinis T. C. P., Almeida L. M., Madeira V. M. C. Tamoxifen and hydroxytamoxyfen as intramembraneous inhibitors of lipid peroxidation: Evidence for peroxyl radical scavenging activity. Biochem. Pharmacol. 47:1994;1989-1998.
7. 2+-ATPase via thiol oxidation by its phenoxyl radical. Arch. Biochem. Biophys. 321:1995;140-152.
8. Palozza P., Moualla S., Krinsky N. I. Effects of beta-carotene and alpha-tocopherol on radical-initiated peroxidation of microsomes. Free Radic. Biol. Med. 13:1992;127-136.
9. 2+-ATPase by peroxynitrite. Free Radic. Res. 24:1996;243-259.
10. Fleming S. A. Chemical reagents in photoaffinity labeling. Tetrahedron. 51:1995;12479-12520.
11. Dorḿan G., Prestwitch G. D. Benzophenone photophores in biochemistry. Biochemistry. 33:1994;5661-5673.
12. Marcovic D. Z., Patterson L. K. Benzophenone-sensitized lipid peroxidation in linoleate micelles. Photochem. Photobiol. 58:1993;329-334.
13. Scaiano J. C., Abuin E. B., Stewart L. C. Photochemistry of benzophenone in micelles. Formation and decay of radical pairs. J. Am. Chem. Soc. 104:1982;5673-5679.
14. Encinas M. V., Scaiano J. C. Reaction of benzophenone triplets with allylic hydrogens. A laser flash photolysis study. J. Am. Chem. Soc. 103:1981;6393-6397.
15. Inbar S., Linschitz H., Cohen S. G. Primary quantum yields of ketyl radicals in photoreduction by amines. Abstraction of H from N. J. Am. Chem. Soc. 102:1980;1419-1421.
16. Finch S. A. E., Stier A. Rotational diffusion of homo- and heterooligomers of cytochrome P450, the functional significance of cooperativity and the membrane structure. Ruckpaul K., Rein H. Membrane organization and phospholipid interaction of cytochrome P450. 5:1991;34-71 Akademie Verlag, Berlin.
17. MacLennan D. H. Molecular tools to elucidate problems in exitation-contraction coupling. Biophys. J. 58:1990;1355-1365.
18. Toyoshima C., Sasabe H., Stokes D. L. Three-dimensional cryo-electron microscopy of the calcium ion pump in the sarcoplasmic reticulum membrane. Nature. 362:1993;469-471.
19. Stadtman E. R. Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu. Rev. Biochem. 62:1993;797-821.
20. Krainev A. G., Ferrington D. A., Williams T. D., Squier T. C., Bigelow D. J. Adaptive changes in lipid composition of skeletal sarcoplasmic reticulum membranes associated with aging. Biochim. Biophys. Acta. 1235:1995;406-418.
21. McKenna R., Ḱezdy F. J., Epps D. E. Kinetic analysis of the free-radical-induced lipid peroxidation in human erythrocyte membranes: Evaluation of potential antioxidants using cis-parinaric acid to monitor peroxidation. Anal. Biochem. 196:1991;443-450.
22. Lanzetta P. A., Alvarez L. J., Reinach P. S., Candia O. A. An important assay for nanomole amounts of inorganic phosphate. Anal. Biochem. 100:1979;95-97.
23. Voss J., Jones L. R., Thomas D. D. The physical mechanism of calcium pump regulation in the heart. Biophys. J. 67:1994;190-196.
24. Cordis G. A., Maulik N., Bagchi D., Engelman R. M., Das D. K. Estimation of the extent of lipid peroxidation in the ischemic and reperfused heart by monitoring lipid metabolic products with the aid of high-performance liquid chromatography. J. Chromatogr. 632:1993;97-103.
25. Esterbauer H., Striegl G., Puhl H., Rotheneder M. Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Radic. Res. Commun. 6:1989;67-75.
26. Krainev A. G., Bigelow D. J. Comparison of 2,2′-azobis(2-amidinopropane) hydrochloride (AAPH) and 2,2′-azobis(2,4-dimethylvaleronitrile) (AMVN) as free radical initiators: A spin trapping study. J. Chem. Soc. Perkin 2. 4:1996;747-754.
27. Lakowicz J. R. Principles of fluorescence spectroscopy. 1:1983;Plenum, New York.
28. Ellman G. L. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82:1959;70-77.
29. Murphy A. J. Sulfhydryl group modification of sarcoplasmic reticulum membranes. Biochemistry. 15:1976;4492-4496.
30. Scḧagger H., von Jacow G. Tricine-sodium dodecul sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa. Anal. Biochem. 166:1987;368-379.
31. 3. Anal. Biochem. 181:1989;33-39.
32. Scholze H. Determination of phenylthiocarbamyl amino acids by reversed phase high-performance liquid chromatography. J. Chromatogr. 350:1985;453-460.
33. Brandl C. J., Green N. M., Korzak B., MacLennan D. H. Two Ca-ATPase genes: Homologies and mechanistic implications of deduced amino acid sequences. Cell. 44:1986;597-607.
34. Wolff S. P., Dean R. T. Fragmentation of proteins by free radicals and its effect on their susceptibility to enzymic hydrolysis. Biochem. J. 234:1986;399-403.
35. Gratton E., Limkeman M. A continuously variable frequency cross-correlation phase fluorometer with picosecond resolution. Biophys. J. 44:1983;315-324.
36. Yao Y., Scḧoneich C., Squier T. C. Resolution of structural changes associated with calcium activation of calmodulin using frequency domain fluorescence spectroscopy. Biochemistry. 33:1994;7797-7810.
37. Cox B. G. Modern liquid phase kinetics. 1994;Oxford University Press, Oxford.
38. Inesi G. Teaching active transport at the turn of the twenty-first century: Recent discoveries and conceptual changes. Biophys. J. 66:1994;554-560.
39. Gryczynski I., Wiczk W., Inesi G., Squier T., Lakowicz J. R. Characterization of the tryptophan fluorescence from sarcoplasmic reticulum adenosinetriphosphatase by frequency-domain fluorescence spectroscopy. Biochemistry. 28:1989;3490-3498.
40. Bachowski G. J., Pintar T. J., Girotti A. W. Photosensitized lipid peroxidation and enzyme inactivation by membrane-bound merocyanine 540: Reaction mechanisms in the absence and presence of ascorbate. Photochem. Photobiol. 53:1991;481-491.
41. Zang L.-Y., Misra B. R., Misra H. P. Generation of free radicals during photosensitization of hypocrellin A and their effects on cardiac membranes. Photochem. Photobiol. 56:1992;453-462.
42. Okereke C. S., Barat S. A., Abdel-Rahman M. S. Safety evaluation of benzophenone-3 after dermal administration in rats. Toxicol. Lett. 80:1995;61-67.
43. Wolf P., Cox P., Yarosh D. B., Kripke M. L. Sunscreens and T4N5 liposomes differ in their ability to protect against ultraviolet-induced sunburn cell formation, alterations of dendritic epidermal cells, and local suppression of contact hypersensitivity. J. Invest. Dermatol. 104:1995;278-292.
44. Kadry A. M., Okereke C. S., Abdel-Rahman M. S., Friedman M. A., Davis R. A. Pharmacokinetics of benzophenone-3 after oral exposure in male rats. J. Appl. Toxicol. 15:1995;97-102.
45. Robinson S. H., Odio M. R., Thompson E. D., Aardema M. J., Kraus A. L. Assessment of the in vivo genotoxicity of 2-hydroxy 4-methoxybenzophenone. Environ. Mol. Mutagen. 23:1994;312-317.
46. Madubunyi I. I. Antimicrobial activities of the constituents of Garcinia kola seeds. Int. J. Pharmacog. 33:1995;232-237.
47. Iinuma M., Tosa H., Tanaka T., Kanamaru S., Asai F., Kobayashi Y., Miyauchi K. I., Shimano R. Antibacterial activity of some Garcinia benzophenone derivatives against methicillin-resistant Staphylococcus aureus. Biol. Pharmacol. Bull. 19:1996;311-314.
48. Beckett A., Porter G. Primary photochemical processes in aromatic molecules, part 9. Photochemistry of benzophenone in solution. Trans. Faraday Soc. 59:1963;2038-2050.
49. von Sonntag C., Schuchmann H.-P. The elucidation of peroxyl radical reactions in aqueous solution with the help of radiation-chemical methods. Angew. Chem. Int. Ed. Engl. 30:1991;1229-1253.
50. van Sickle D. E., Mayo F. R., Arluck R. M. Liquid-phase oxidations of cyclic alkenes. J. Am. Chem. Soc. 87:1965;4824-4832.
51. ̇OH and electron acceptors. J. Chem. Soc. Perkin. II:1980;1708-1713.
52. Lu C. R., Wong A. Glutamic acid-88 is close to SH-1 in the tertiary structure of myosin subfragment. Biochemistry. 28:1989;4826-4829.
53. Amici A., Levine R. L., Tsai L., Stadtman E. R. Conversion of amino acid residues in proteins and amino acid homopolymers to carbonyl derivatives by metal-catalyzed oxidation reactions. J. Biol. Chem. 264:1989;3341-3346.
54. 2+-ATPase. Biochemistry. 36:1997;7706-7716.