A Glutathione Conjugate of 2, 4-Dichloro-1-nitrobenzene: Its Detection as a Metabolic Intermediate and Further Metabolism in <i>Mucor javanicus</i>

Abstract

Formation of a 2, 4-dichloro-l-nitrobenzene glutathione conjugate [S-(5-chloro-2-nitrophenyl)glutathione, 2] was confirmed in the cell-free system of Mucor javanicus which metabolizes 2, 3-and 2, 4-dichloro-l-nitrobenzenes into the corresponding chloro-methylthio-nitrobenzenes or chloro-methylthiobenzenamines. Further metabolisms of 2, the corresponding cysteine conjugate (3) and 5-chloro-2-nitrobenzenethiol (4) were investigated. Oxidation products (S-oxides and S-dioxides) of the formerly identified methylthio-containing metabolites were isolated from the growing cultures of the fungus administered 2. S-(5-Chloro-2-nitrophenyl)cysteine (3) and N-acetyl-S-(5-chloro-2-nitrophenyl)cysteine (7) were newly identified as metabolites of 2 in the resting cell system of the fungus.

Glutathione Transferase fromMucor javamicus

“…Authentic· conjugates were prepared by reaction of each chloronitrobenzene (1.24 g) and glutathione (1.0 g) in 100 ml of water-methanol-acetone (43: 40 : 17) containing K 2 C0 3 (2.25 g). 3) Electrophoresis. Homogeneity of the enzyme preparation was tested by 7.5 % polyacrylamide gel electrophoresis (pH 8.0) by the method of Davis.…”

Metabolic Pathways of 2, 4-Dichloro-1-nitrobenzene in <i>Mucor javanicus</i>

“…(2), S-(5-chloro-2-nitrophenyl)cysteine (3), 5-chloro-2-nitrobenzenethiol (4), 4-chloro-2-methylthio-l-nitrobenzene (5), 4-chloro-2-methylthiobenzenamine (6), N -acetyl-S -(5-chloro -2-nitrophenyl)cysteine (7), 5-chloro-2-methylsulfinyl-l-nitrobenzene (8), 5-chloro-2-methylsulfonyl-l-nitrobenzene (9), 5-chloro-2-methylsulfinylbenzen-amine (10), 5-chloro-2-methylsulfonylbenzenamine (11) and 2, 4-dichlorobenzenamine (12) were obtained as described previously. [1][2][3] Bis(5 chloro-2-nitrophenyl) disulfide (13). Disulfide 13 was obtained as a by-product from the preparation of 5.…”