Photoinduced Reactivity of Doxorubicin: Catalysis and Degradation

Doxorubicin exhibits unusual photoreactivity in aqueous solutions. Our data show that there are two distinct photoreactive pathways for doxorubicin. One is a two-step process that leads to the formation of 3-methoxysalicylic acid, a stable degradation product. The other pathway is a photoreduction o...

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Bibliographic Details
Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2012-05, Vol.116 (17), p.4330-4337
Main Authors: Nawara, Krzysztof, Krysinski, Pawel, Blanchard, G. J
Format: Article
Language:English
Subjects:
Catalysis
Degradation
Dihydroquinone
Doxorubicin
Doxorubicin - chemistry
Fluorescence
Formations
Hydrogen peroxide
Hydrogen Peroxide - chemistry
Molecular Structure
Pathways
Photochemical Processes
Physical chemistry
Reactive Oxygen Species - chemistry
Salicylates - chemical synthesis
Salicylates - chemistry
Ultraviolet Rays
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Summary:Doxorubicin exhibits unusual photoreactivity in aqueous solutions. Our data show that there are two distinct photoreactive pathways for doxorubicin. One is a two-step process that leads to the formation of 3-methoxysalicylic acid, a stable degradation product. The other pathway is a photoreduction of doxorubicin to form the corresponding dihydroquinone, which undergoes spontaneous oxidation mediated by dissolved oxygen to recover doxorubicin with the formation of hydrogen peroxide. Our data account for the known nonlinear dependence of doxorubicin fluorescence intensity on concentration.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp303218r