Structure and redox properties of radicals derived from one-electron oxidised methylxanthines

Redox Report

Volumn 13, Issue 3, 2008, Pages 123-133

  Santos, Pedro M P ^a   Telo, João P ^b   Vieira, Abel J S C ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

Author keywords

Free radicals; Redox properties; Structure; Xanthine derivatives

Indexed keywords

1 METHYLXANTHINE; 1,9 DIMETHYLXANTHINE; 3 METHYLXANTHINE; 3,9 DIMETHYLXANTHINE; 7 METHYLXANTHINE; 9 METHYLXANTHINE; METHYLXANTHINE DERIVATIVE; PARAXANTHINE; SULFATE; THEOBROMINE; THEOPHYLLINE; XANTHINE DERIVATIVE; XANTHOSINE;

ANTIOXIDANT ACTIVITY; ARTICLE; CALCULATION; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; EQUILIBRIUM CONSTANT; OXIDATION REDUCTION POTENTIAL; PH MEASUREMENT; POTENTIOMETRY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REDUCTION KINETICS; THEORETICAL STUDY;

ANIONS; ANTIOXIDANTS; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; FREE RADICALS; HYDROGEN-ION CONCENTRATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RIBONUCLEOSIDES; SULFATES; TIME FACTORS; XANTHINE; XANTHINES;

EID: 48749095441     PISSN: 13510002     EISSN: None     Source Type: Journal    
DOI: 10.1179/135100008X259231     Document Type: Article

References (19)

1. Sullivan GW, Patsclas TN, Redick JA, Mandell GL. Enhancement of chemotaxis and protection of mice from infection. Trans Assoc Am Phys 1984; 97: 337-45.
2. Pasquier C, Franzini E, Abedinzadeh Z, Kaouadji MN, Hakin JC. Gamma and pulse-radiolysis study of pentoxifylline, a methylxanthine. Int J Radiat Biol 1991; 60: 433-47.
3. Bhat VB, Madyastha KM. Antioxidant and radical scavenging properties of 8-oxo derivatives of xanthine drugs pentoxifilline and lisofylline. Biochem Biophys Res Commun 2001; 288: 1212-7.
4. Telo JP. Radicals derived from uric acid and its methyl derivatives in aqueous solution: An EPR spectroscopy and theoretical study. Org Biomol Chem 2003; 1: 588-92.
5. von Sonntag C. The Chemical Basis of Radiation Biology. London: Taylor and Francis, 1987.
6. Cadet J, Berger M. Radiation-induced decomposition of the purine-bases within DNA and related model compounds. Int J Radiat Biol 1985; 47: 127-43.
7. - and OH adducts. Chem Rev 1989; 89: 503-20.
8. Myers LS. In: Pryor WA. (ed) Free Radicals in Biology. New York: Academic Press, 1990.
9. Langman SR, Shohoji MCBL, Telo JP, Vieira AJSC, Novais HM. EPR spectroscopy study of the radical oxidation of hydroxypurines in aqueous solution: Acid-base properties of the derived radicals. J Chem Soc, Perkin Trans 2 1996; 1461-5.
10. Vieira AJSC, Telo JP, Pereira HF, Patrocinio PF, Dias RMB. Antioxidant effect of naturally occurring xanthines on the oxidative damage of DNA bases. J Chim Phys 1999; 96: 116-23.
11. Dias RMB, Vieira AJSC. Structure and redox properties of one-electron oxidized radicals from adenine and derivatives. Redox Rep 1996; 2: 279-83.
12. Frisch MJ et al. Gaussian 98, Revision A.7. Pittsburgh PA: Gaussian, Inc., 1998.
13. 1-substituted cytosines in aqueous solution. Calculation of isotropic hyperfine coupling constants by a density functional method. J Chem Soc, Perkin Trans 2 2001; 1648-53.
14. Reynisson J, Steenken S. DFT studies on the pairing abilities of the one-electron reduced or oxidized adenine-thymine base pair. Phys Chem Chem Phys 2002; 4: 5353-8.
15. Katrizky R, Physical Methods in the Heterocyclic Chemistry. New York: Academic Press, 1963.
16. Vinchurkar MS, Rao BSM, Mohan H, Mittal JP. Kinetics, spectral and redox behaviour of OH adducts of methylxanthines: A radiation chemical study. J Chem Soc Perkin Trans 2 1999; 609-17.
17. Spataru N, Sarada BV, Tryk DA, Fujishima A. Anodic voltammetry of xanthine, theophylline, theobromine and caffeine at conductive diamond electrodes and its analytical application. Electronalysis 2002; 14: 721-8.
18. Goyal RN, Srivastava AK, Bansal V. Oxidation of 3,9-dimethyl-9H-purine-2,6(1H,3H)-dione at stationary pyrolytic-graphite electrode. J Chem Soc Perkin Trans 2 1994: 1709-15.
19. Telo JP, Vieira AJSC. Mechanism of free radical oxidation of caffeine in aqueous solution. J Chem Soc. Perkin Trans 2 1997; 1755-7.