Photochemistry of dihydrobiopterin in aqueous solution

Organic & Biomolecular Chemistry
Mariana VignoniAndrés H Thomas

Abstract

Dihydrobiopterin (H(2)Bip) and its oxidized analogue, biopterin (Bip), accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder in which the protection against UV radiation fails. The photochemistry of H(2)Bip was studied in neutral aqueous solutions upon UV-A irradiation (320-400 nm) at room temperature. The photochemical reactions were followed by UV/vis spectrophotometry, HPLC and enzymatic methods for hydrogen peroxide (H(2)O(2)) determination. Photoproducts were analyzed by means of electrospray ionization mass spectrometry. Under anaerobic conditions, excitation of H(2)Bip leads to the formation of at least two isomeric dimers with molecular masses equal to exactly twice the molecular mass of the reactant. This reaction takes place from the singlet excited state of the reactant. To the best of our knowledge, this is the first time that the photodimerization of a dihydropterin is reported. In the presence of air, the dimers are again the main photoproducts at the beginning of the reaction, but a small proportion of the reactant is converted into Bip. As the reaction proceeds and enough Bip accumulates in the solution, a photosensitized process starts, where Bip photoinduces the oxidatio...Continue Reading

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Citations

Nov 16, 2010·Photochemistry and Photobiology·Mariana VignoniAndrés H Thomas
Dec 25, 2010·Photochemistry and Photobiology·Helmut GörnerLászló Biczók
Oct 6, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·M Laura DántolaAndrés H Thomas
Feb 1, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Mariana VignoniAndrés H Thomas
Mar 17, 2011·Physical Chemistry Chemical Physics : PCCP·Mariana P SerranoAndrés H Thomas
Jul 25, 2012·Physical Chemistry Chemical Physics : PCCP·Mariana P SerranoAndrés H Thomas
Sep 19, 2014·Journal of the American Chemical Society·Ek Raj ThapaliyaFrançisco M Raymo
May 21, 2013·Photochemistry and Photobiology·Carolina CastañoCarolina Lorente
Jul 11, 2013·Photochemistry and Photobiology·Mariana P SerranoAndrés H Thomas
Apr 30, 2014·Photochemistry and Photobiology·Andrey A BuglakMikhail S Kritsky
May 10, 2017·Physical Chemistry Chemical Physics : PCCP·R M DiScipioC E Crespo-Hernández

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