New results on the photochemistry of biopterin and neopterin in aqueous solution
New photochemical studies of the reactivity of biopterin (BPT) and neopterin (NPT) in acidic (pH = 5.5) and alkaline (pH = 10.5) aqueous solutions at 350 nm and room temperature were performed. The photochemical properties of BPT are of particular interest because the photolysis of this compound tak...
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2009
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| LEADER | 11034caa a22010097a 4500 | ||
|---|---|---|---|
| 001 | PAPER-23262 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205455.0 | ||
| 008 | 190411s2009 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-58349084575 | |
| 024 | 7 | |2 cas |a biopterin, 22150-76-1; cytochrome c, 9007-43-6, 9064-84-0; neopterin, 670-65-5; oxygen, 7782-44-7; superoxide, 11062-77-4; Biopterin, 22150-76-1; Cytochromes c, 9007-43-6; Neopterin, 670-65-5; Oxygen, 7782-44-7; Solutions; Superoxides, 11062-77-4 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a PHCBA | ||
| 100 | 1 | |a Vignoni, M. | |
| 245 | 1 | 0 | |a New results on the photochemistry of biopterin and neopterin in aqueous solution |
| 260 | |c 2009 | ||
| 270 | 1 | 0 | |m Thomas, A. H.; Instituto de Investigaciones Fisicoquímicas Teóricas Y Aplicadas (INIFTA), CCT-La Plata-CONICET, Universidad Nacional de La Plata, La Plata, Argentina; email: athomas@inifta.unlp.edu.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Fuchs, D., Hausen, A., Reibnegger, G., Werner, E.R., Dierich, M.P., Wachter, H., Neopterin as marker for activated cell-mediated immunity (1988) Immunol. Today, 9, pp. 150-155 | ||
| 504 | |a Lorente, C., Thomas, A.H., Photophysics and photochemistry of pterins in aqueous solution (2006) Acc. Chem. Res., 39, pp. 395-402 | ||
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| 504 | |a Petroselli, G., Erra-Balsells, R., Cabrerizo, F.M., Lorente, C., Capparelli, A.L., Braun, A.M., Oliveros, E., Thomas, A.H., Photosensitization of 2′-deoxyadenosine-5′-monophosphate by pterin (2007) Org. Biomol. Chem., 5, pp. 2792-2799 | ||
| 504 | |a Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Capparelli, A.L., Lorente, C., Oliveros, E., Thomas, A.H., Oxidation of 2′-deoxyguanosine 5′-monophosphate photoinduced by pterin: Type I versus type II mechanism (2008) J. Am. Chem. Soc., 130, pp. 3001-3011 | ||
| 504 | |a Schallreuter, K.U., Moore, J., Wood, J.M., Beazley, W.D., Peters, E.M., Marles, L.K., Behrens-Williams, S.C., Thöny, B., Epidermal H2O2 accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: Identification of a general mechanism in regulation of all 6BH4-dependent processes? (2001) J. Invest. Dermatol., 116, pp. 167-174 | ||
| 504 | |a Rokos, H., Beazley, W.D., Schallreuter, K.U., Oxidative stress in vitiligo: Photo-oxidation of pterins produces H 2O2 and pterin-6-carboxylic acid (2002) Biochem. Biophys. Res. Commun., 292, pp. 805-811 | ||
| 504 | |a Forrest, H.S., Mitchell, H.K., Pteridines from Drosophila. III. Isolation and identification of three more pteridines (1955) J. Am. Chem. Soc., 77, pp. 4865-4869 | ||
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| 504 | |a Mengel, R., Pfleiderer, W., Knappe, W.R., Norrish type II analogous photodegradation of neopterin and biopterin to 5,8-dihydropterin-6-aldehyde (1977) Tetrahedron Lett., 32, pp. 2817-2820 | ||
| 504 | |a Baur, R., Kappel, M., Mengel, R., Pfleiderer, W., Photochemistry of pteridines (1979) Chemistry and Biology of Pteridines, pp. 13-18. , In. Edited by. R. L. Kisliuk. G. M. Brown. pp. Elsevier/North-Holland, New York | ||
| 504 | |a Cabrerizo, F.M., Thomas, A.H., Lorente, C., Dántola, M.L., Petroselli, G., Erra-Balsells, R., Capparelli, A.L., Generation of reactive oxygen species during the photolysis of 6-hydroxymethylpterin in alkaline aqueous solutions (2004) Helv. Chim. Acta, 87, pp. 349-365 | ||
| 504 | |a Thomas, A.H., Cabrerizo, R., Vignoni, M., Erra-Balsells, R., Cabrerizo, F.M., Capparelli, A.L., Photoinduced generation of reactive oxygen species by the acid form of 6-(hydroxymethyl)-pterin in aqueous solutions (2004) Helv. Chim. Acta, 89, pp. 1090-1104 | ||
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| 504 | |a Moore, D.E., Wang, J., Electron-transfer mechanisms in photosensitization by the anti-inflammatory drug benzydamine (1998) J. Photochem. Photobiol. B, 43, pp. 175-180 | ||
| 504 | |a Petroselli, G., Bartsch, J.M., Thomas, A.H., Photoinduced generation of H2O2 and O 2•- by 6-formylpterin in aqueous solutions (2006) Pteridines, 17, pp. 82-89 | ||
| 504 | |a Thomas, A.H., Lorente, C., Capparelli, A.L., Martínez, C.G., Braun, A.M., Oliveros, E., Singlet oxygen (1Δg) production by pterin derivatives in aqueous solutions (2003) Photochem. Photobiol. Sci., 2, pp. 245-250 | ||
| 504 | |a Cabrerizo, F.M., Dántola, M.L., Petroselli, G., Capparelli, A.L., Thomas, A.H., Braun, A.M., Lorente, C., Oliveros, E., Reactivity of conjugated and unconjugated pterins with singlet oxygen (O2(1Δg)): Physical quenching and chemical reaction (2007) Photochem. Photobiol., 83, pp. 526-534 | ||
| 504 | |a Pfleiderer, W., Chemistry and properties of dihydropterins (1987) Biochemical and Clinical Aspects of Pteridines, pp. 3-21. , In. Vol. 5 (Edited by. W. Pfleiderer, H. Wachter. J. A. Blair. pp. Walter de Gruyter & Co., Berlin, New York | ||
| 504 | |a Thomas, A.H., Suárez, G., Cabrerizo, F.M., Martino, R., Capparelli, A.L., Study of the photolysis of folic acid and 6-formylpterin in acid aqueous solutions (2000) J. Photochem. Photobiol. a, 135, pp. 147-154 | ||
| 504 | |a Thomas, A.H., Suárez, G., Cabrerizo, F.M., Capparelli, A.L., Photochemistry of 6-formylpterin in alkaline medium (2001) Helv. Chim. Acta, 84, pp. 3849-3860 | ||
| 504 | |a Kuciel, R., Mazurkiewicz, A., Formation and detoxification of reactive oxygen species (2004) Biochem. Mol. Biol. Educ., 32, pp. 183-186 | ||
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| 504 | |a Chahidi, C., Aubailly, M., Momzikoff, A., Bazin, M., Santus, R., Photophysical and photosensitizing properties of 2-amino-4-pteridinone: A natural pigment (1981) Photochem. Photobiol., 33, pp. 641-649 | ||
| 504 | |a Ledbetter, J.W., Pfleiderer, W., Freisheim, J.H., Photosensitized reduction of L-biopterin in the active ternary complex of dihydrofolate reductase (1995) Photochem. Photobiol., 62, pp. 71-81 | ||
| 520 | 3 | |a New photochemical studies of the reactivity of biopterin (BPT) and neopterin (NPT) in acidic (pH = 5.5) and alkaline (pH = 10.5) aqueous solutions at 350 nm and room temperature were performed. The photochemical properties of BPT are of particular interest because the photolysis of this compound takes place in the white skin patches of patients affected by vitiligo. The photochemical reactions were followed by UV/VIS spectrophotometry, HPLC, electrochemical measurement of dissolved O2 and enzymatic methods for hydrogen peroxide (H2O2) and superoxide anion (O 2•-) determinations. When BPT or NPT are exposed to UVA radiation, a red intermediate, very likely 6-formyl-5,8-dihydropterin, is generated in an O2-independent process. That product is rapidly oxidized on admission of O2 to yield 6-formylpterin and H 2O2. When the photolysis takes place in aerobic conditions, no additional pathways exist. On the other hand, in the absence of O2, the intermediate generated is not stable and leads to the formation of many products. O2•- is also generated during photo-oxidation of BPT and NPT. The quantum yields of reactant consumption depends on the O2 concentration: the higher the O 2 concentration, the lower the quantum yields. This behavior is discussed in connection with the excited state of the pterins. © 2008 The Authors. |l eng | |
| 593 | |a Instituto de Investigaciones Fisicoquímicas Teóricas Y Aplicadas (INIFTA), CCT-La Plata-CONICET, Universidad Nacional de La Plata, La Plata, Argentina | ||
| 593 | |a Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Departamento de Química Orgánica, Ciudad Universitaria, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a BIOPTERIN |
| 690 | 1 | 0 | |a CYTOCHROME C |
| 690 | 1 | 0 | |a NEOPTERIN |
| 690 | 1 | 0 | |a OXYGEN |
| 690 | 1 | 0 | |a SUPEROXIDE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a METABOLISM |
| 690 | 1 | 0 | |a PHOTOCHEMISTRY |
| 690 | 1 | 0 | |a SOLUTION AND SOLUBILITY |
| 690 | 1 | 0 | |a SPECTROPHOTOMETRY |
| 690 | 1 | 0 | |a BIOPTERIN |
| 690 | 1 | 0 | |a CYTOCHROMES C |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a NEOPTERIN |
| 690 | 1 | 0 | |a OXYGEN |
| 690 | 1 | 0 | |a PHOTOCHEMISTRY |
| 690 | 1 | 0 | |a SOLUTIONS |
| 690 | 1 | 0 | |a SPECTROPHOTOMETRY |
| 690 | 1 | 0 | |a SUPEROXIDES |
| 700 | 1 | |a Cabrerizo, F.M. | |
| 700 | 1 | |a Lorente, C. | |
| 700 | 1 | |a Thomas, A.H. | |
| 773 | 0 | |d 2009 |g v. 85 |h pp. 365-373 |k n. 1 |p Photochem. Photobiol. |x 00318655 |w (AR-BaUEN)CENRE-43 |t Photochemistry and Photobiology | |
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