Emission properties of dihydropterins in aqueous solutions

被引:35
作者
Serrano, Mariana P. [1 ]
Vignoni, Mariana [1 ]
Laura Dantola, M. [1 ]
Oliveros, Esther [2 ]
Lorente, Carolina [1 ]
Thomas, Andres H. [1 ]
机构
[1] Univ Nacl La Plata, Fac Ciencias Exactas, CONICET, CCT La Plata,Dept Quim,INIFTA, RA-1900 La Plata, Buenos Aires, Argentina
[2] Univ Toulouse 3, CNRS, Lab Interact Mol Reactivite Chim & Photochim IMRC, UMR 5623,UPS, F-31062 Toulouse 9, France
关键词
PTERIN DERIVATIVES; FOLIC-ACID; FLUORESCENCE; 7,8-DIHYDROPTERINS; BIOSYNTHESIS; DNA;
D O I
10.1039/c0cp02912b
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Pterins belong to a class of heterocyclic compounds present in a wide range of living systems and accumulate in the skin of patients affected by vitiligo, a depigmentation disorder. The study of the emission of 7,8-dihydropterins is difficult because these compounds are more or less unstable in the presence of O-2 and their solutions are contaminated with oxidized pterins which have much higher fluorescence quantum yields (Phi(F)). In this work, the emission properties of six compounds of the dihydropterin family (6-formyl-7,8-dihydropterin (H(2)Fop), sepiapterin (Sep), 7,8-dihydrobiopterin (H(2)Bip), 7,8-dihydroneopterin (H(2)Nep), 6-hydroxymethyl-7,8-dihydropterin (H(2)Hmp), and 6-methyl-7,8-dihydropterin (H(2)Mep)) have been studied in aqueous solution. The fluorescence characteristics (spectra, Phi(F), lifetimes (tau(F))) of the neutral form of these compounds have been investigated using the single-photon-counting technique. Phi(F) and tau(F) values obtained lie in the ranges 3-9 x 10(-3) and 0.18-0.34 ns, respectively. The results are compared to those previously reported for oxidized pterins.
引用
收藏
页码:7419 / 7425
页数:7
相关论文
共 31 条
[1]  
BROWN DJ, 1988, CHEM HETEROCYCLIC 3, V24, P1
[2]   Substituent effects on the photophysical properties of pterin derivatives in acidic and alkaline aqueous solutions [J].
Cabrerizo, FM ;
Petroselli, G ;
Lorente, C ;
Capparelli, AL ;
Thomas, AH ;
Braun, AM ;
Oliveros, E .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2005, 81 (05) :1234-1240
[3]   Reaction between 7,8-dihydropterins and hydrogen peroxide under physiological conditions [J].
Dantola, M. Laura ;
Schuler, Tobias M. ;
Denofrio, M. Paula ;
Vignoni, Mariana ;
Capparelli, Alberto L. ;
Lorente, Carolina ;
Thomas, Andres H. .
TETRAHEDRON, 2008, 64 (37) :8692-8699
[4]   Stability of 7,8-dihydropterins in air-equilibrated aqueous solutions [J].
Dantola, M. Laura ;
Vignoni, Mariana ;
Capparelli, Alberto L. ;
Lorente, Carolina ;
Thomas, Andres H. .
HELVETICA CHIMICA ACTA, 2008, 91 (03) :411-425
[5]  
Eaton D. F., 1989, HDB ORGANIC PHOTOCHE, VI, P233
[6]   Synthesis and fluorescence characterization of pteridine adenosine nucleoside analogs for DNA incorporation [J].
Hawkins, ME ;
Pfleiderer, W ;
Jungmann, O ;
Balis, FM .
ANALYTICAL BIOCHEMISTRY, 2001, 298 (02) :231-240
[7]  
HUBER C, 1983, J IMMUNOL, V130, P1047
[8]   Photoinduced hydroxylation of deoxyguanosine in DNA by pterins: Sequence specificity and mechanism [J].
Ito, K ;
Kawanishi, S .
BIOCHEMISTRY, 1997, 36 (07) :1774-1781
[9]   Pterin-dependent amino acid hydroxylases [J].
Kappock, TJ ;
Caradonna, JP .
CHEMICAL REVIEWS, 1996, 96 (07) :2659-2756
[10]   Electron-transfer processes induced by the triplet state of pterins in aqueous solutions [J].
Laura Dantola, M. ;
Vignoni, Mariana ;
Gonzalez, Constanza ;
Lorente, Carolina ;
Vicendo, Patricia ;
Oliveros, Esther ;
Thomas, Andres H. .
FREE RADICAL BIOLOGY AND MEDICINE, 2010, 49 (06) :1014-1022