Reactive oxygen species generation through NADH oxidation by 6-formylpterin derivatives in the dark

Biochemical and Biophysical Research Communications

Volumn 353, Issue 4, 2007, Pages 1105-1110

  Nonogawa, Mitsuru ^a   Pack, Seung Pil ^a   Arai, Toshiyuki ^b   Endo, Nobuyuki ^c   Sommani, Piyanart ^a   Kodaki, Tsutomu ^a   Makino, Keisuke ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY HOSPITAL   (Japan)

^c WAKASA WAN ENERGY RESEARCH CENTER   (Japan)

Author keywords

6 Formylpterin; 6 Formylpterin derivatives; Generation of reactive oxygen species in the dark; H2O2 formation from O2; Oxidation of NADH to NAD+

Indexed keywords

2 (N,N DIMETHYLAMINOMETHYLENEAMINO) 6 FORMYL 3 METHYLPTERIDIN 4 ONE; 2 (N,N DIMETHYLAMINOMETHYLENEAMINO) 6 FORMYL 3 PIVALOYLPTERIDIN 4 ONE; 2 (N,N DIMETHYLAMINOMETHYLENEAMINO) 6 FORMYLPTERIDIN 4 ONE; 2 AMINO 6 FORMYL 3 METHYLPTERIDIN 4 ONE; DIMETHYLAMINE; HYDROGEN PEROXIDE; METHYL GROUP; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXYGEN; OXYGEN RADICAL; PTERIN 6 ALDEHYDE; PTERIN DERIVATIVE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONFORMATION; CONTROLLED STUDY; DARKNESS; LIGHT EXPOSURE; OXIDATION KINETICS; PRIORITY JOURNAL; SYNTHESIS;

DARKNESS; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN PEROXIDE; MOLECULAR STRUCTURE; NAD; OXIDATION-REDUCTION; OXYGEN; PTERINS; REACTIVE OXYGEN SPECIES; TIME FACTORS;

EID: 33846130011     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2006.12.171     Document Type: Article

References (18)

1. 3-folate complexes of Escherichia coli methylenetetrahydrofolate reductase reveal a spartan strategy for a ping-pong reaction. Biochemistry 44 (2005) 11447-11457
2. Wei C., Wang Z., Wang Q., Meade A.L., Hemann C., Hille R., and Stuehr D.J. Rapid kinetic studies link tetrahydrobiopterin radical formation to heme-dioxy reduction and arginine hydroxylation in inducible nitric-oxide synthase. J. Biol. Chem. 276 (2001) 315-319
3. Kwon N.S., Nathan C.F., and Stuehr D.J. Reduced biopterin as a cofactor in the generation of nitrogen oxides by murine macrophages. J. Biol. Chem. 264 (1989) 20496-20501
4. Kaufman S. Studies on the Mechanism of the enzymatic conversion of phenylalanine to tyrosine. J. Biol. Chem. 234 (1959) 2677-2682
5. Thomas A.H., Suárez G., Cabrerizo F.M., Martino R., and Capparelli A.L. Study of the photolysis of folic acid and 6-formylpterin in acid aqueous solutions. J. Photochem. Photobiol. A 135 (2000) 147-154
6. Halpern R., Halpern B.C., Stea B., Dunplap A., Conklin K., Clark B., Ashe H., Sperling L., Halpern J.A., Hardy D., and Smith R.A. Pterin-6-aldehyde, a cancer cell catabolite: identification and application in diagnosis and treatment of human cancer. Proc. Natl. Acad. Sci. USA 74 (1977) 587-591
7. Lorente C., and Thomas A.H. Photophysics and photochemistry of pterines in aqueous solution. Acc. Chem. Res. 39 (2006) 395-402
8. Cabrerizo F.M., Thomas A.H., Lorente C., Dántola M.L., Petroselli G., Erra-Balsells R., and Capparelli A.L. Generation of reactive oxygen species during the photolysis of 6-(Hydroxymethyl)pterin in alkaline aqueous solutions. Helv. Chim. Acta 87 (2004) 349-365
9. Mori H., Arai T., Ishii H., Adachi T., Endo N., Makino K., and Mori K. Neuroprotective effects of pterin-6-aldehyde in gerbil global brain ischemia: comparison with those of α-phenyl-N-tert-butyl nitrone. Neurosci. Lett. 241 (1998) 99-102
10. Funakoshi T., Miyata H., Imoto T., Arai T., Endo N., Makino K., Yang C.H., and Ohama E. 6-Formylpterin protects retinal neurons from transient ischemia-reperfusion injury in rats: a morphological and immunohistochemical study. Neuropathology 23 (2003) 161-168
11. Arai T., Yamada H., Namba T., Mori H., Ishii H., Yamashita K., Sasada M., Makino K., and Fukuda K. Effects of intracellular reactive oxygen species generated by 6-formylpterin on T cell functions. Biochem. Pharmacol. 67 (2004) 1185-1193
12. Arai T., Endo N., Yamashita K., Sasada M., Mori H., Ishii H., Hirota K., Makino K., and Fukuda K. 6-Formylpterin, a xanthine oxidase inhibitor, intercellularly generates reactive oxygen species involved in apoptosis and cell proliferation. Free Radic. Biol. Med. 30 (2001) 248-259
13. Suzuki Y.J., Forman H.J., and Sevanian A. Oxidants as stimulators of signal transduction. Free. Radic. Biol. Med. 22 (1997) 269-285
14. 2 to ROS conversion activities. Org. Biomol. Chem. 4 (2006) 1811-1816
15. Alberts B., Bray D., Lewis J., Raff M., Roberts K., and Watson J.D. Molecular Biology of the Cell. third ed. (1994), Garland Publishing Inc., New York
16. 5-cyclopentadienyl)-1-[2-(N,N-dimethylaminomethyleneamino)-3- methyl-4-oxopteridine-6-yl]ethane-1,2-dithiolatocobalt (III). J. Chem. Soc. Perkin Trans. 1 (1997) 801-807
17. Yamada H., Arai T., Endo N., Yamashita K., Nonogawa M., Makino K., Fukuda K., Sasada M., and Uchiyama T. Photodynamic effects of a novel pterin derivatives on a pancreatic cancer cell line. Biochem. Biophys. Res. Commun. 333 (2005) 763-767
18. + analogues. J. Am. Chem. Soc. 112 (1990) 3579-3583