Rietjens, Ivonne M. C. M. published the artcileDifferent metabolic pathways of 2,5-difluoronitrobenzene and 2,5-difluoroaminobenzene compared to molecular orbital substrate characteristics, SDS of cas: 120103-18-6, the publication is Chemico-Biological Interactions (1995), 94(1), 49-72, database is CAplus and MEDLINE.
The in vivo metabolite patterns of 2,5-difluoroaminobenzene and of its nitrobenzene analog, 2,5-difluoronitrobenzene, were determined using 19F NMR anal. of urine samples. Results obtained demonstrate significant differences between the biotransformation patterns of these two analogs. For the aminobenzene, cytochrome P 450 catalyzed aromatic hydroxylation presents the main metabolic pathway. 2,5-Difluoronitrobenzene was predominantly metabolized through glutathione conjugation leading to excretion of 5-fluoro-2-(N-acetylcysteinyl)-nitrobenzene and fluoride anions, and, to a minor extent, through cytochrome P 450 catalyzed hydroxylation and nitro reduction Pretreatment of the rats with various inducers of cytochrome P 450 enzymes, known also to influence glutathione S-transferase enzyme patterns, followed by exposure to the 2,5-difluoroamino- or 2,5-difluoronitrobenzene, generally resulted in metabolite patterns that varied only to a small (≤12%) extent. Based on these results it was concluded that the biotransformation enzyme pattern is not the predominant factor in determining the metabolic route of these two model compounds Addnl. in vitro microsomal and cytosolic incubations with 2,5-difluoroaminobenzene and 2,5-difluoronitrobenzene qual. confirmed the in vivo results. NADPH/oxygen supported microsomal cytochrome P 450 catalyzed hydroxylation was observed only for 2,5-difluoroaminobenzene whereas cytosolic GSH conjugation occurred only in incubations with 2,5-difluoronitrobenzene as the substrate. Outcomes from MO calculations provided a working hypothesis that can explain the difference in metabolic pathways of the nitro- and aminobenzene derivative on the basis of their chem. characteristics. This hypothesis states that the chances for a nitro- or aminobenzene derivative to enter either a cytochrome P 450 or a glutathione conjugation pathway are determined by the relative energy levels of the frontier orbitals of the compounds The aminobenzene derivative has relatively high energy MOs leading to an efficient reaction of its HOMO (HOMO) with the singly occupied MO of the cytochrome P 450 (FeO)3+ intermediate, but a low reactivity of its LUMO with the HOMO of glutathione. The nitrobenzene, on the other hand, has MOs of relatively low energy, explaining the efficient interaction, and, thus, reaction between its LUMO and the HOMO electrons of glutathione, but resulting in low reactivity with the SOMO electron of the cytochrome P 450 (FeO)3+ reaction intermediate.
Chemico-Biological Interactions published new progress about 120103-18-6. 120103-18-6 belongs to alcohols-buliding-blocks, auxiliary class Fluoride,Nitro Compound,Benzene,Phenol, name is 2,5-Difluoro-4-nitrophenol, and the molecular formula is C6H3F2NO3, SDS of cas: 120103-18-6.
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