abstract
The oxidation of drugs using metalloporphyrins has been the subject of several studies in recent years. Diclofenac, one of the most frequently used anti-inflammatory drugs, is metabolized in humans by cytochrome P450 (CYP) enzymes to hydroxy-derivatives and to some metabolites resulting from oxidative decarboxylation. In this paper, the in vitro formation of several new diclofenac derivatives, initially resulting from oxidative decarboxylation, similar to what happens in vivo, is revealed. Chloro [5,10,15,20-tetrakis(2,6-dichlorophenyl) porphyrinato] manganese(III), [Mn(TDCPP) Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl) porphyrinato] manganese(III), [Mn(TPFPP) Cl], are tested in the presence of hydrogen peroxide at room temperature. The new products obtained are fully characterized, three of them being characterized in the solid state using X-ray diffraction studies.
keywords
AOT REVERSE MICELLES; HYDROGEN-PEROXIDE; CARBOXYLIC-ACIDS; DRUG-METABOLISM; METALLOPORPHYRIN CATALYSTS; EPOXIDATION REACTIONS; BIOMIMETIC OXIDATION; MN(III) PORPHYRINS; MASS-SPECTROMETRY; SODIUM PERIODATE
subject category
Chemistry
authors
Neves, CMB; Simoes, MMQ; Domingues, MRM; Santos, ICMS; Neves, MGPMS; Paz, FAA; Silva, AMS; Cavaleiro, JAS
our authors
Filipe Alexandre Almeida Paz
Principal Researcher
Isabel Cristina Maia da Silva Santos Vieira
Junior Researcheracknowledgements
Thanks are due to Fundacao para a Ciencia e a Tecnologia (FCT/FEDER) for funding QOPNA (Project PEst-C/QUI/UI0062/2011) and CICECO (Project PEst-C/CTM/LA0011/2011) and for specific funding towards the purchase of the single-crystal X-ray diffractometer. Authors also acknowledge the Portuguese National NMR Network supported with funds from FCT.