New results on the photochemistry of biopterin and neopterin in aqueous solution

Photochemistry and Photobiology

Volumn 85, Issue 1, 2009, Pages 365-373

  Vignoni, Mariana ^a   Cabrerizo, Franco M ^b   Lorente, Carolina ^a   Thomas, Andrés H ^a  

^a INSTITUTO DE INVESTIGACIONES FISICOQUÍMICAS TEÓRICAS Y APLICADAS INIFTA   (Argentina)

^b DEPARTAMENTO DE QUÍMICA ORGÁNICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

BIOPTERIN; CYTOCHROME C; NEOPTERIN; OXYGEN; SUPEROXIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; PHOTOCHEMISTRY; SOLUTION AND SOLUBILITY; SPECTROPHOTOMETRY;

BIOPTERIN; CYTOCHROMES C; MOLECULAR STRUCTURE; NEOPTERIN; OXYGEN; PHOTOCHEMISTRY; SOLUTIONS; SPECTROPHOTOMETRY; SUPEROXIDES;

EID: 58349084575     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2008.00450.x     Document Type: Article

References (33)

1. Nichol, C. A., G. K. Smith D. S. Duch (1985) Biosynthesis and metabolism of tetrahydrobiopterin and molybdopterin. Annu. Rev. Biochem. 54, 729 764.
2. Hevel, J. M. M. A. Marletta (1992) Macrophage nitric oxide synthase: Relationship between enzyme-bound tetrahydrobiopterin and synthase activity. Biochemistry 31, 7160 7165.
3. Huber, C., J. R. Batchelor, D. Fuchs, A. Hausen, A. Lang, D. Niederwieser, G. Reibnegger, P. Swetly, J. Troppmair H. Wachter (1984) Immune response-associated production of neopterin. Release from macrophages primarily under control of interferon-gamma. J. Exp. Med. 160, 310 316.
4. Fuchs, D., A. Hausen, G. Reibnegger, E. R. Werner, M. P. Dierich H. Wachter (1988) Neopterin as marker for activated cell-mediated immunity. Immunol. Today 9, 150 155.
5. Lorente, C. A. H. Thomas (2006) Photophysics and photochemistry of pterins in aqueous solution. Acc. Chem. Res. 39, 395 402.
6. Ito, K. S. Kawanishi (1997) Photoinduced hydroxylation of deoxyguanosine in DNA by pterins: Sequence specificity and mechanism. Biochemistry 36, 1774 1781.
7. Petroselli, G., R. Erra-Balsells, F. M. Cabrerizo, C. Lorente, A. L. Capparelli, A. M. Braun, E. Oliveros A. H. Thomas (2007) Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin. Org. Biomol. Chem. 5, 2792 2799.
8. Petroselli, G., M. L. Dántola, F. M. Cabrerizo, A. L. Capparelli, C. Lorente, E. Oliveros A. H. Thomas (2008) Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism. J. Am. Chem. Soc. 130, 3001 3011.
9. 2 accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: Identification of a general mechanism in regulation of all 6BH4-dependent processes? J. Invest. Dermatol. 116, 167 174.
10. 2 and pterin-6-carboxylic acid. Biochem. Biophys. Res. Commun. 292, 805 811.
11. Forrest, H. S. H. K. Mitchell (1955) Pteridines from Drosophila. III. Isolation and identification of three more pteridines. J. Am. Chem. Soc. 77, 4865 4869.
12. Viscontini, M. H. Raschig (1958) Fluoreszierende Stoffe aus Drosophila melanogaster. 7th Mitteilung. Helv. Chim. Acta 41, 108 113.
13. Mengel, R., W. Pfleiderer W. R. Knappe (1977) Norrish type II analogous photodegradation of neopterin and biopterin to 5,8-dihydropterin-6-aldehyde. Tetrahedron Lett. 32, 2817 2820.
14. Baur, R., M. Kappel, R. Mengel W. Pfleiderer (1979) Photochemistry of pteridines. In Chemistry and Biology of Pteridines (Edited by R. L. Kisliuk G. M. Brown pp. 13 18. Elsevier/North-Holland, New York.
15. Cabrerizo, F. M., A. H. Thomas, C. Lorente, M. L. Dántola, G. Petroselli, R. Erra-Balsells A. L. Capparelli (2004) Generation of reactive oxygen species during the photolysis of 6-hydroxymethylpterin in alkaline aqueous solutions. Helv. Chim. Acta 87, 349 365.
16. Thomas, A. H., R. Cabrerizo, M. Vignoni, R. Erra-Balsells, F. M. Cabrerizo A. L. Capparelli (2004) Photoinduced generation of reactive oxygen species by the acid form of 6-(hydroxymethyl)-pterin in aqueous solutions. Helv. Chim. Acta 89, 1090 1104.
17. Albert, A. (1953) Quantitative studies of the acidity of naturally occurring substances for trace metals. Biochem. J. 54, 646 654.
18. Lorente, C., A. L. Capparelli, A. H. Thomas, A. M. Braun E. Oliveros (2004) Quenching of the fluorescence of pterin derivatives by anions. Photochem. Photobiol. Sci. 3, 167 173.
19. Braun, A. M., M. T. Maurette E. Oliveros (1991) Photochemical Technology, Chapter 2 Edited by John Wiley & Sons pp. 85 88. John Wiley & Sons, Chichester.
20. Allain, C. C., L. S. Poon, C. S. G. Chan, W. Richmond P. C. Fu (1974) Enzymatic determination of total serum cholesterol. Clin. Chem. 20, 470 475.
21. Flegg, H. M. (1973) An investigation of the determination of serum chloresterol by an enzymatic method. Ann. Clin. Biochem. 10, 79 84.
22. McCord, J. M. J. Fridovich (1969) The utility of superoxide dismutase in studying free radical reactions. J. Biol. Chem. 244, 6049 6055.
23. Moore, D. E. J. Wang (1998) Electron-transfer mechanisms in photosensitization by the anti-inflammatory drug benzydamine. J. Photochem. Photobiol. B 43, 175 180.
24. •- by 6-formylpterin in aqueous solutions. Pteridines 17, 82 89.
25. g) production by pterin derivatives in aqueous solutions. Photochem. Photobiol. Sci. 2, 245 250.
26. g)): Physical quenching and chemical reaction. Photochem. Photobiol. 83, 526 534.
27. Pfleiderer, W. (1987) Chemistry and properties of dihydropterins. In Biochemical and Clinical Aspects of Pteridines, Vol. 5 (Edited by W. Pfleiderer, H. Wachter J. A. Blair pp. 3 21. Walter de Gruyter & Co., Berlin, New York.
28. Thomas, A. H., G. Suárez, F. M. Cabrerizo, R. Martino A. L. Capparelli (2000) Study of the photolysis of folic acid and 6-formylpterin in acid aqueous solutions. J. Photochem. Photobiol. A 135, 147 154.
29. Thomas, A. H., G. Suárez, F. M. Cabrerizo A. L. Capparelli (2001) Photochemistry of 6-formylpterin in alkaline medium. Helv. Chim. Acta 84, 3849 3860.
30. Kuciel, R. A. Mazurkiewicz (2004) Formation and detoxification of reactive oxygen species. Biochem. Mol. Biol. Educ. 32, 183 186.
31. Pauling, L. (1979) The discovery of superoxide radical. Trends Biochem. Sci. 4, N270 N271.
32. Chahidi, C., M. Aubailly, A. Momzikoff, M. Bazin R. Santus (1981) Photophysical and photosensitizing properties of 2-amino-4-pteridinone: A natural pigment. Photochem. Photobiol. 33, 641 649.
33. Ledbetter, J. W., W. Pfleiderer J. H. Freisheim (1995) Photosensitized reduction of L-biopterin in the active ternary complex of dihydrofolate reductase. Photochem. Photobiol. 62, 71 81.