Antioxidant properties of carotenoids: QSAR prediction of their redox potentials

General Physiology and Biophysics

Volumn 26, Issue 2, 2007, Pages 97-103

  Kleinova M ^a,b   Hewitt, M ^b   Brezova V ^a   Madden, J C ^b   Cronin, M T D ^b   Valko, Marian ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

Antioxidant properties; Carotenoids; QSAR(s); Redox potential

Indexed keywords

15,15' (DIHEDRO) BETA CAROTENE; 4' APO BETA CAROTEN 4' NITRILE; 4' APO BETA CAROTENE 4' AL; 6' APO BETA CAROTEN 6' NITRILE; 6' APO BETA CAROTEN 6' OIC ACID ETHYL ESTER; 6' APO BETA CAROTENE 6' AL; 7' (4 CARBOXYPHENYL) 7' APO BETA CAROTENE; 7' (4 METHOXYCARBOXYPHENYL) 7' APO BETA CAROTENE; 7' (4 METHOXYPHENYL) 7' APO BETA CAROTENE; 7' (4 NITROPHENYL) 7' APO BETA CAROTENE; 7' (PENTAFLUOROPHENYL) 7' APO BETA CAROTENE; 7' (PHENYL) 7' APO BETA CAROTENE; 7' APO 7,7' DICYANO BETA CAROTENE; 8' APO BETA CAROTEN 8' NITRILE; 8' APO BETA CAROTEN 8' OIC ACID ETHYL ESTER; 8' APO BETA CAROTENE 8' AL; ASTAXANTHIN; BETA CAROTENE; CANTHAXANTHIN; CAROTENOID; CRYPTOXANTHIN; ECHINENONE; FUCOXANTHIN; ISOZEAXANTHIN; MERCUROUS CHLORIDE; RHODOXANTHIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIOLAXANTHIN; VITAMIN; ZEAXANTHIN;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DRUG STRUCTURE; ELECTROCHEMICAL ANALYSIS; ELECTRODE; OXIDATION REDUCTION POTENTIAL; POLARIZATION; POTENTIOMETRY; PREDICTION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; AUTOMATIC DATA PROCESSING; CAROTENOIDS; DATA COLLECTION; FREE RADICALS; MODELS, CHEMICAL; OXIDATION-REDUCTION; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REPRODUCIBILITY OF RESULTS;

EID: 34548812035     PISSN: 02315882     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Bauerová K., Bezek Š. (1999): Role of reactive oxygen and nitrogen species in etiopathogenesis of rheumatoid arthritis. Gen. Physiol. Biophys. 18, (Focus Issue)15-20
2. Bard A. J., Faulkner L. R. (1980): Electrochemical Methods, Fundamentals and Applications. Wiley, New York
3. Bors W., Michel C., Saran M. (1984): Inhibition of the bleaching of the carotenoid crocin - a rapid test for quantifying antioxidant activity. Biochim. Biophys. Acta 796, 312-319
4. Cadenas E., Packer L. (1996): Handbook of Antioxidants. Marcel Dekker Inc., New York
5. Chen X. (1991): Master Thesis, The University of Alabama, Tuscaloosa
6. Cronin M. T. D., Livingstone D. J. (2004): Modelling Environmental Fate and Toxicity. CRC Press, Boca Raton, FL, USA
7. Delasrivas J., Telfer A., Barber J. (1993): 2-coupled β-carotene molecules protect p680 from photodamage in isolated photosystem-ii reaction centers. Biochim. Biophys. Acta 1142, 155-164
8. Deng Y., Gao G., He Z., Kispert L. D. (2000): Effects of polyene chain length and acceptor substituents on the stability of carotenoid radical cations. J. Phys. Chem. B 104, 5651-5656
9. Grant J. L., Kramer V. J., Ding R., Kispert L. D. (1988): Carotenoid cation radicals - electrochemical, optical, and electronparamagnetic resonance study. J. Am. Chem. Soc. 110, 2151-2157
10. Gust D., Moore T. A., Moore A. L. (1993): Molecular mimicry of photosynthetic energy and electron-transfer. Acc. Chem. Res. 26, 198-205
11. Hapiot P. F., Kispert L. D., Konovalov V. V., Saveant J. M. (2001): Single two-electron transfers vs. successive one-electron transfers in polyconjugated systems illustrated by the electrochemical oxidation and reduction of carotenoids. J. Am. Chem. Soc. 123, 6669-6677
12. Hoischen D., Colmenares L. U., Koukhareva I., Ho M., Liu R. S. H. (1999): 9-CF3 and 13-CF3-β-carotene, canthaxanthin and related carotenoids. Synthesis, characterization and electrochemical data. J. Fluorine Chem. 97, 165-171
13. Jeevarajan A. S., Khaled M., Kispert L. D. (1994a): Simultaneous electrochemical and electron-paramagnetic-resonance studies of carotenoids - effect of electron-donating and accepting substituents. J. Phys. Chem. 98, 7777-7781
14. Jeevarajan A. S., Kispert L. D., Wu X. G. (1994b): Spectroelectrochemistry of carotenoids in solution. Chem. Phys. Lett. 219, 427-432
15. Juráinek I., Bezek Š. (2005): Controversy of free radical hypothesis: reactive oxygen species - cause or consequence of tissue injury? Gen. Physiol. Biophys. 24, 263-278
16. Khaled M. M. (1992): Ph.D. Dissertation, University of Alabama, Tuscaloosa
17. Khaled M., Hadjipetrou A., Kispert L. D. (1990): Electrochemical and electron-paramagnetic resonance studies of carotenoid cation radicals and dications - effect of deuteration. J. Phys. Chem. 94, 5164-5169
18. Khaled M., Hadjipetrou A., Kispert L. D. (1991): Simultaneous electrochemical and electron-paramagnetic resonance studies of carotenoid cation radicals and dications. J. Phys. Chem. 95, 2438-2442
19. Kispert L. D., Konovalova T., Gao Y. (2004): Carotenoid radical cations and dications: EPR, optical, and electrochemical studies. Arch. Biochem. Biophys. 430, 49-60
20. Lafferty J., Roach A. C., Sinclair R. S., Truscott T. G., Land E. J. (1977): Absorption-spectra of radical ions of polyenes of biological interest. J. Chem. Soc. Faraday Trans. I 73, 416-429
21. Lee S. W.-M. (1989): Ph.D. Thesis, University of Liverpool
22. Lien E. J., Ren S. J., Bui H. Y. H., Wang R. B. (1999): Quantitative structure-activity relationship analysis of phenolic antioxidants. Free Radic. Biol. Med. 26, 285-294
23. Liu D. Z., Gao Y. L., Kispert L. D. (2000): Electrochemical properties of natural carotenoids. J. Electroanal. Chem. 488, 140-150
24. Mairanovsky V. G., Engovatov A. A., Ioffe N. T., Samokhvalov G. I. (1975): Electron-donor and electron-acceptor properties of carotenoids - electrochemical study of carotenes. J. Electroanal. Chem. 66, 123-137
25. Mathis P., Vermeglio A. (1972): Transient forms of carotenoids - triplet-state and radical cation. Photochem. Photobiol. 15, 157
26. Niedzwiedzki D., Rusling J. F., Frank H. A. (2005): Voltammetric redox potentials of carotenoids associated with the xanthophyll cycle in photosynthesis. Chem. Phys. Lett. 415, 308-312
27. O'Neil M. P., Wasielevski, M. R., Khaled M. M., Kispert L. D. (1991): Solvent and temperature-dependence of the lowest excited singlet-state lifetime of all-trans-7′,7′-dicyano-7′-apo-β-carotene. J. Chem. Phys. 95, 7212-7218
28. Packer L. (1992): Carotenoids. Part A: Chemistry, Separation, Quantitation and Antioxidation. Academic, San Diego
29. Park S. M. (1978): Electrochemical studies of β-carotene, all-trans-retinal and all-trans-retinol in tetrahydrofuran. J. Electrochem. Soc. 125, 216-222
30. Polyakov N. E., Leshina T. V., Salakhutdinov N. F., Konovalova T. A., Kispert L. D. (2006): Antioxidant and redox properties of supramolecular complexes of carotenoids with β-glycyrrhizic acid. Free Radic. Biol. Med. 40, 1804-1809
31. Rice-Evans C. A., Diplock A. T. (1993): Current status of antioxidant therapy. Free Radic. Biol. Med. 15, 77-96
32. Rice-Evans C. A., Packer L. (1998): Flavonoids in Health and Disease. Marcel Dekker Inc., New York
33. van Breemen R. B., Huang C. R., Tan Y. C., Sander L. C., Schilling A. B. (1996): Liquid chromatography mass spectrometry of carotenoids using atmospheric pressure heroical ionization: J. Mass Spectrom. 31, 975-981
34. Verma R. P., Kurup A., Hansch C. (2005): On the role of polarizability in QSAR. Bioorg. Med. Chem. 13, 237-255