Ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) as effective catalyzer of ascorbate and epinephrine oxidation and damager of neuroblastoma cells

Biochemical Pharmacology

Volumn 55, Issue 1, 1998, Pages 85-91

  Roginsky, Vitaly A ^a   Bruchelt, Gernot ^b   Bartuli, Olga ^b  

^a SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Ascorbate; Ascorbyl radical; Cytotoxicity; Epinephrine; Quinones; Redox cycling

Indexed keywords

ADRENALIN; ASCORBIC ACID; UBIQUINONE;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; ELECTRON SPIN RESONANCE; HUMAN; HUMAN CELL; IN VITRO STUDY; NEUROBLASTOMA CELL; OXIDATION; OXYGEN CONSUMPTION; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

ANTINEOPLASTIC AGENTS; ASCORBIC ACID; BENZOQUINONES; EPINEPHRINE; HUMANS; KINETICS; NEUROBLASTOMA; OXIDATION-REDUCTION; TUMOR CELLS, CULTURED;

EID: 0031889256     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00434-6     Document Type: Article

References (21)

1. 1. O'Brien PJ, Molecular mechanism of quinone cytotoxicity. Chem Biol Interact 80: 1-41, 1991.
2. 2. Afanas'ev IB, Superoxide Ion: Chemistry and Biological Implications. Volume II. CRC Press, Boca Raton, 1991.
3. 3. Weiner LM, Oxygen radical generation and DNA scission by anticancer and synthetic quinones. Methods Enzymol 233: 92-105, 1994.
4. 4. Powis G, Free radical formation by antitumor quinones. Free Rad Biol Med 6: 63-101, 1989.
5. 5. Wardman P, Reductive activation of quinones: redox properties and thiol reactivity. Free Rad Res Comm 8: 219-229, 1990.
6. 6. Brunmark A and Cadenas E, Redox and addition chemistry of quinoid compounds and its biological implications. Free Rad Biol Med 7: 435-477, 1989.
7. 7. Workman P, Enzyme-directed bioreductive drug development revisited - A commentary on recent progress and future prospects with emphasis on quinone anticancer agents and quinone metabolizing enzymes, particularly DT-diaphorase. Oncology Res 6: 461-475, 1994.
8. 8. Roginsky VA, Mohr D and Stocker R, Reduction of ubiquinone-1 by ascorbic acid is a catalytic process controlled by the concentration of molecular oxygen. Redox Report 2: 55-62, 1995.
9. 9. Pethig R, Gasconyne RPC, McLaughlin JA and Szent-Györgyi A, Ascorbate-quinone interactions: electrochemical, free radical, and cytotoxic properties. Proc Nat Acad Sci USA 80: 129-132, 1983.
10. 10. Buettner GR, In the absence of catalytic metals ascorbate does not autoxidize at pH 7: ascorbate as a test for catalytic metals. J Biochem Biophys Meth 16: 27-40, 1988.
11. 11. Roginsky VA and Stegmann HB, Ascorbyl radical as a natural indicator of oxidative stress: quantitative regularities. Free Rad Biol Med 17: 93-103, 1994.
12. 12. Roginsky VA and Stegmann HB, Kinetics of the reaction between ascorbate and free radical from vitamin E as studied by ESR steady-state method. Chem Phys Lipids 65: 103-112, 1993.
13. 13. Mosmann T, Rapid assay for cellular growth and arrival: Application to proliferation and cytotoxicity assay. J Immunol Methods 65: 55-63, 1983.
14. 14. Cano MS and Sanchez JV, Reduction kinetics of 2,3-dimethoxy-5-methyl-1,4-benzoquinone by ascorbic acid in acid solutions. J Chem Soc Perkin Trans 2: 427-430, 1993.
15. 15. Roginsky VA, Barsukova TK, Bruchelt G and Stegmann HB, Interaction of catecholamines and 6-hydroxydopamine with ascorbate during autoxidation. Pharmacol Res 31 Suppl: 141, 1995.
16. 16. Graham DG, Oxidative pathways for catecholamines in the genesis of neuromelanin and cytotoxic quinones. Mol Pharmacol 14: 633-643, 1978.
17. 2 on iron-dependent DNA strand breaks and related processes in the neuroblastoma cell line SK-N-SH. Cancer Res 51: 6066-6072, 1991.
18. 18. Wardrnan P, Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Reference Data 18: 1637-1755, 1989.
19. 2 generation in reduction and oxidation cycle of ubiquinones in a model of mitochondrial electron transport systems. Biochim Biophys Acta 936: 377-385, 1988.
20. 20. Biaglow JE, Jacobson B and Varnes M, The oxidation of ascorbate by electron affinic drugs and carcinogens. Photochem Photobiol 28: 869-876, 1978.
21. 21. Beyer RE, The participation of coenzyme Q in free radical production and antioxidatton. Free Rad Biol Med 8: 545-565, 1990.