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Singlet oxygen production and in vitro phototoxicity studies on fenofibrate, mycophenolate mofetil, trifusal, and their active metabolites
Author(s) -
MolinsMolina Oscar,
BresolíObach Roger,
GarciaLainez Guillermo,
Andreu Inmaculada,
ll Santi,
Miranda Miguel A.,
Jiménez M. Consuelo
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3722
Subject(s) - phototoxicity , chemistry , singlet oxygen , mycophenolate , metabolite , mycophenolic acid , active metabolite , prodrug , fenofibrate , in vivo , cinnamaldehyde , stereochemistry , pharmacology , photochemistry , in vitro , organic chemistry , oxygen , biochemistry , transplantation , catalysis , medicine , surgery , microbiology and biotechnology , biology
Singlet oxygen photosensitization (studied by time‐resolved near‐infrared emission spectroscopy) and in vitro phototoxicity (by means of the 3T3 neutral red uptake assay) have been investigated for the prodrugs fenofibrate ( FFB ), mycophenolate mofetil ( MMP ), and trifusal ( TFS ) as well as for their active metabolites fenofibric acid ( FFA ), mycophenolic acid ( MPA ), and 2‐hydroxy‐4‐(trifluoromethyl)benzoic acid ( HTB ). The results show that FFB and its active metabolite FFA generate 1 O 2 with a quantum yield in the range 0.30 to 0.40 and show a photo‐irritation factor (PIF) higher than 40. By contrast, MMP / MPA and TFS / HTB are not photoactive in the used assays. These results correlate well with the previously reported in vivo phototoxicity in treated patients.