Disease relevance of Reranil

• Resistance of Rhizobium strains to phygon, spergon, and thiram [1].
• Production of tetrachloro-1,4-benzoquinone (Cl4-1,4-BQ) adducts, on the other hand, was proportionally greater at high doses of PCP [greater than 60-230 mg/kg body weight] and was 2- to 11-fold greater in mice than in rats over the entire range of dosages [2].
• The present study was designed to assess the relevance of the oxidative metabolites in HCB-induced toxicity, with special attention to the role of the reactive tetrachlorobenzoquinone (TCBQ) [3].
• By the Oppenauer oxidation and/or by dehydration of 4 and 5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil), the corresponding D-lactones 6-12 were obtained [4].
• Special attention is directed to a very reactive metabolite, tetrachloro-1,4-benzoquinone, which has a high capacity to efficiently react with protein, thus possibly linking the oxidative biotransformation of hexachlorobenzene and the molecular mechanism of enzyme inactivation leading to hepatic porphyria [5].

Psychiatry related information on Reranil

• Carbonyl compounds are conveniently converted into their corresponding dimethyl acetals in good yields and short reaction times by means of a photochemical reaction in methanol with a catalytic amount of chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone, CA) as the sensitizer [6].

High impact information on Reranil

• The electron-transfer rate obeys pseudo-first-order kinetics and the pseudo-first-order rate constant increases linearly with increasing p-chloranil concentration [7].
• The ESR spectra of the fullerene radical cations were also detected in frozen PhCN at 193 K under photoirradiation of the fullerene/p-chloranil/Sc(3+) systems [7].
• These adducts did not correspond to those derived from calf thymus DNA treated with tetrachloro-1,4-benzoquinone [8].
• Chemical modification at subunit 1 of rat kidney Alpha class glutathione transferase with 2,3,5,6-tetrachloro-1,4-benzoquinone: Close structural connectivity between glutathione conjugation activity and non-substrate ligand binding [9].
• Treatment of PCP/dG with rat liver microsomes (RLM) failed to generate 4; instead, an adduct derived from the benzoquinone electrophile tetrachloro-1,4-benzoquinone (chloranil) was observed in the extracted ion chromatogram from the RLM/NADPH-treated PCP/dG sample [10].

Biological context of Reranil

• These results suggest that oxidative biotransformation, and thus the formation of the very reactive tetrachloro-1,4-benzoquinone, is directly related to the porphyrinogenic action of hexachlorobenzene [11].
• Studies on the active site of rat glutathione S-transferase isoenzyme 4-4. Chemical modification by tetrachloro-1,4-benzoquinone and its glutathione conjugate [12].
• As expected, the best selectivity towards sulfoxide is obtained with a conventional energy transfer sensitizer such as Rose Bengal (RB), but also with a quinone with a low-lying triplet state, 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil or CHLO) and with 9,10-dicyanoanthracene (DCA) [13].

Anatomical context of Reranil

• Chloranil (1.25 to 1.75 ppm) treated embryos showed abnormalities of the otolith, optic cup, and general pigmentation [14].

Associations of Reranil with other chemical compounds

• Oxidative damage and direct adducts in calf thymus DNA induced by the pentachlorophenol metabolites, tetrachlorohydroquinone and tetrachloro-1,4-benzoquinone [15].
• Thus, we proposed and verified experimentally that PcpD is a tetrachlorobenzoquinone reductase that catalyzes the NADPH-dependent reduction of tetrachlorobenzoquinone to tetrachlorohydroquinone [16].
• Finally, the binding of bilirubin, as measured by means of circular dichroism, was inhibited by preincubation of the enzyme with tetrachloro-1,4-benzoquinone in a manner which strongly correlated with the loss of enzymatic activity, the protection against inactivation by diethylpyrocarbonate, and the fluorescence quenching [12].
• Incubation of the pentachlorophenol (PCP) metabolites, tetrachloro-p-benzoquinone (chloranil, TCpBQ), tetrachloro-p-hydroquinone (TCpHQ) and tetrachloro-p-benzoquinone (TCoBQ) with V79 Chinese hamster cells led to a significant enhancement of the amount of 8-hydroxydeoxyguanosine (8-OH-dG) in DNA [17].
• The calculated kappa accounts for the dielectric response of CT salts based on substituted TTF's (tetrathiafulvalene) and substituted CA's (chloranil) [18].

Gene context of Reranil

• The longest wavelength band of the spectra of BQ(2)(-) and the chloranil dianion (CL(2)(-)) is assigned to the (1)B(3u) <-- (1)A(g) band mainly contributed from an intramolecular charge-transfer (CT) configuration [19].
• This indicates a covalent modification of the rat liver DT-diaphorase by tetrachloro-p-benzoquinone [20].
• The presence of bovine serum albumin (BSA) in the incubation mixture protects DT-diaphorase against the inactivation by tetrachloro-p-benzoquinone, probably by interacting with the quinone [20].

Analytical, diagnostic and therapeutic context of Reranil

• NADPH was shown to reduce tetrachloro-1,4-benzoquinone (TCBQ) to tetrachloro-1,4-benzene diol which was identified on the basis of cochromatography with synthetic standard in a reverse phase HPLC system, electronic absorption spectroscopy, and mass spectrometry [21].

References