Photosensitized Oxidation of Oxopurines by Rose Bengal † | Zendy

Murgida Daniel H. | Zendy; Aramendía Pedro F. | Zendy; Balsells Rosa Erra | Zendy

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Photosensitized Oxidation of Oxopurines by Rose Bengal †

Author(s) -

Murgida Daniel H.,

Aramendía Pedro F.,

Balsells Rosa Erra

Publication year - 1998

Publication title -

photochemistry and photobiology

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.818

H-Index - 131

eISSN - 1751-1097

pISSN - 0031-8655

DOI - 10.1111/j.1751-1097.1998.tb02501.x

Subject(s) - rose bengal , chemistry , theobromine , reaction rate constant , theophylline , photochemistry , quenching (fluorescence) , solvent , reaction mechanism , medicinal chemistry , organic chemistry , kinetics , catalysis , fluorescence , medicine , physics , quantum mechanics , endocrinology

Photosensitized oxidations of oxopurines (OP) as caffeine, theophylline, theobromine and 1,3,7‐trimethyluric acid (TMU) by Rose Bengal were investigated. In all cases photooxidations occur by a type II mechanism. Reactive and nonreactive 1 O 2 quenching rate constants by OP were determined in different solvents. Based on the correlations of the rate constants with different solvent parameters (α, β, E T [30], AN, DN, *,), the initial formation of an exciplex between 1 O 2 and OP is proposed that evolves to a zwitterionic transition state. Some reaction products were characterized, among them 3‐mefh‐yl‐5‐(methylamine)‐1,5‐dehydrohydantoin was obtained as the main photooxidation product of TMU. A reaction mechanism is proposed for the formation of this and other reaction products.

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