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Chemical Compound Review:

CHEMBL344161 1,2-dichloro-4-(3,4- dichlorophenyl)benzene

Synonyms: SureCN137915, CCRIS 8592, CHEBI:1367, PCB 77, AG-F-09125, ...

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Disease relevance of PCB 77

However, cytocidal toxicity of 2-FAA was substantially potentiated by either 3-methylcholanthrene [(MCA) CAS: 56-49-5] or 3,3',4,4'-tetrachlorobiphenyl [(TCBP) CAS: 32598-13-3], an MCA-type PCB [1].
3,3',4,4'-Tetrachlorobiphenyl (tetraCB) binds to the aryl hydrocarbon receptor (AhR), and several reports have demonstrated that AhR agonists exhibit antiestrogenic and antitumorigenic activities in human breast cancer cells, the rodent uterus and breast [2].
On the first day of lactation, material rats were treated with a single low dose of 5 mg/kg body weight of 3,3',4,4'-tetrachlorobiphenyl (TCB) or 2,2',4,4',5,5'-hexachlorobiphenyl (HCB) or with a combination of both congeners [3].
Importantly, the animals with elevated serum levels of 3,3',4,4'-TCB, 3,3',4,4',5-PnCB and an increased total serum TEQ had a high prevalence of endometriosis, and the severity of disease correlated with the serum concentration of 3,3,',4,4'-TCB [4].
Cytosol from rats with carcinogen-generated liver neoplasms and livers induced with 3,3',4,4'-tetrachlorobiphenyl and 2,2',4,4',5,5'-hexachlorobiphenyl had more GST activity toward CDNB than cytosol from normal rat liver [5].

Psychiatry related information on PCB 77

These results document effects of PCB 77 on maternal behavior and serve to raise questions about the importance of maternal contributions to the developmental effects of this and similar contaminants [6].

High impact information on PCB 77

2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) and 3,3',4,4'-tetrachlorobiphenyl (TCB), two ubiquitous environmental pollutants, accelerate thymocyte maturation, and eventually lead to thymus atrophy [7].
Here we present evidence that 3,4,3',4'-tetrachlorobiphenyl (TCB) (PCB77), a PCB with high toxicity and significant bioaccumulation, can act as an estrogen with actions mediated through the estrogen receptor [8].
Structure-toxicity studies suggest that the coplanar PCBs, namely, 3,3',4,4'-tetrachlorobiphenyl (tetraCB), 3,3',4,4',5-pentaCB, 3,3',4,4',5,5'-hexaCB, and their monoortho analogs are Ah-receptor agonists and contribute significantly to the toxicity of the PCB mixtures [9].
Microsomal cytochrome P-450 1A (CYP1A) in a vertebrate model (the teleost fish scup) is inactivated by the aryl hydrocarbon receptor agonist 3,3',4,4'-tetrachlorobiphenyl (TCB) [10].
We investigated CYP1A expression and activity in porcine aorta endothelial cells (PAEC) exposed in culture to the AhR agonists 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), 3,3',4,4'-tetrachlorobiphenyl (TCB), benzo[a]pyrene (BP), or beta-naphthoflavone (BNF) [11].

Chemical compound and disease context of PCB 77

The pharmacokinetics of 2,2',5,5'-tetrachlorobiphenyl and 3,3',4,4'-tetrachlorobiphenyl and its relationship to toxicity [12].
Chronic toxicity and bioaccumulation of 2,5,2',5'- and 3,4,3',4'-tetrachlorobiphenyl and Aroclor 1242 in the amphipod Hyalella azteca [13].
4. The results of this study show that PCB 126 elicits some TCDD-like reproductive effects after in utero exposure, while the reproductive effects of in utero exposure to PCB 77 on male offspring may be attributed to the neonatal hypothyroidism induced by the substance during early fetal development [14].
The toxicity of tetrachlorobenzyltoluenes (Ugilec 141) and polychlorobiphenyls (Aroclor 1254 and PCB-77) compared in Ah-responsive and Ah-nonresponsive mice [15].
This paper discusses the use of gas chromatography/mass spectrometry negative chemical ionization (GC/MS-NCI) to quantify congeners of highly suspected toxicity such as IUPAC #77 (3,3',4,4'-tetrachlorobiphenyl) and #126 (3,3',4,4',5-pentachlorobiphenyl) [16].

Biological context of PCB 77

In contrast, exposure of the cells to 3,4,3',4'-tetrachlorobiphenyl, a planar polycyclic aromatic hydrocarbon inducer of P-450, resulted in preferential increased hydroxylation at the 2- and 3-positions of biphenyl [17].
In vivo/in vitro comparison of the pharmacokinetics and pharmacodynamics of 3,3',4,4'-tetrachlorobiphenyl (PCB77) [18].
This study investigated the effect of dietary micelle composition and 3,4,3',4'-tetrachlorobiphenyl (TCB) exposure upon the subsequent systemic bioavailability and intestinal metabolism of [(14)C]-TCB in a catfish in situ intestinal preparation [19].
Time-mated Sprague-Dawley rats were dosed with PCB 77 (3,3',4,4'-tetrachlorobiphenyl), 2 or 8 mg/kg/day; PCB 126 (3,3',4,4',5-pentachlorobiphenyl), 0.25 or 1.0 micrograms/kg/day; TCDD, 0.025 or 0.1 micrograms/kg/day; or corn oil vehicle via gavage on gestation days 10-16 [20].
These results indicate long-term effects of maternal exposure to PCB 77 on emotional and motor functions [21].

Anatomical context of PCB 77

Evidence was obtained for a microsomal bilirubin-degrading system that could be induced in the liver by treating either rats or chick embryos with TCDD, beta-naphthoflavone, or 3,4,3',4'-tetrachlorobiphenyl (3,4-TCB) in vivo [22].
The ability of 3,3',4,4'-tetrachlorobiphenyl to stimulate bilirubin degradation by liver microsomes from rats treated with a polycyclic aromatic hydrocarbon-type inducer has been confirmed and extended to another planar biphenyl, 3,3',4,4',5,5'-hexachlorobiphenyl [23].
Gastric epithelial cell proliferation in monkeys fed 3,4,3',4'-tetrachlorobiphenyl [24].
Altered growth control of rat hepatocytes after treatment with 3,4,3',4'-tetrachlorobiphenyl in vivo and in vitro [25].
Study of the separate and combined effects of the non-planar 2,5,2',5'- and the planar 3,4,3',4'-tetrachlorobiphenyl in liver and lymphocytes in vivo [26].

Associations of PCB 77 with other chemical compounds

Cultures of chick-embryo hepatocytes were used to study the mechanism by which 3,4,3',4'-tetrachlorobiphenyl and 2,4,5,3',4'-pentabromobiphenyl cause accumulation of uroporphyrin [27].
In the presence of 3,4,3',4'-tetrachlorobiphenyl, an inhibitor of haem synthesis at the uroporphyrinogen decarboxylase step, synergistic induction of 5-aminolaevulinate synthase was observed with all the alcohols except ethanol [28].
In rodent microsomes, uroporphyrinogen oxidation required the addition of NADPH, whereas chick liver microsomes required both NADPH and 3,3',4,4'-tetrachlorobiphenyl [29].
Male Sprague-Dawley rats were injected i.p. with corn oil, 2,2',4,4',5,5'-hexachlorobiphenyl (PCB-153, 30, 150, or 300 micromol/kg), 3,3',4,4'-tetrachlorobiphenyl (PCB-77, 30, 150, or 300 micromol/kg), or both PCBs (each 30 or 150 micromol/kg) [30].
The 3,4,3',4'-tetrachlorobiphenyl and 3,4,5,3',4',5'-hexachlorobiphenyl strongly inhibit uroporphyrinogen decarboxylase directly at two steps, i.e. first in the formation of hexacarboxylic porphyrinogen III from heptacarboxylic porphyrinogen III and second in the formation of heptacarboxylic porphyrinogen III from uroporphyrinogen III [31].

Gene context of PCB 77

Induction and post-transcriptional suppression of hepatic cytochrome P450 1A1 by 3,3',4,4'-tetrachlorobiphenyl [32].
This study also shows that the AhR agonists benzo[a]pyrene, 3,3',4,4'-tetrachlorobiphenyl, chrysin, 6-methyl-1,3,8-trichlorodibenzofuran, and 3,3'-diindolylmethane also induce ERalpha-dependent transactivation [33].
3,3',4,4'-Tetrachlorobiphenyl did not increase COX-2 mRNA levels [34].
For this purpose, catfish were exposed in vivo to the pgp inducer vincristine (VIN), and the xenobiotics beta-naphthoflavone (BNF), benzo[a]pyrene (BaP), and 3,4,3',4'-tetrachlorobiphenyl (TCB) [35].
Using fluorescence polarization, we firstly assayed whether PCB 77 (3,3',4,4'-tetrachlorobiphenyl), PCB 153 (2,2',4,4',5,5'-hexachlorobiphenyl) and PCB 156 (2,3,3',4,4',5-hexachlorobiphenyl) were able to bind to the alpha isoform of ER, recently found to be involved in angiogenesis [36].

Analytical, diagnostic and therapeutic context of PCB 77

METHODS: Six rats received an intraperitoneal injection of 3,4,3',4'-tetrachlorobiphenyl (300 mumol/kg) in soyabean oil [37].
In the experimental setup, primary cultures of salmon hepatocytes isolated by a two-step perfusion method were exposed for 48 h to nonylphenol (NP; 5 muM) and 3,3',4,4'-tetrachlorobiphenyl (TCB; 1 muM), singly and combined, in the absence or presence of antagonists [38].
The exposure of cell cultures to 3,3',4,4'-tetrachlorobiphenyl (TCB) (a non-ortho-subtituted planar congener) does not alter PLA(2) activity [39].
The distribution of radiolabeled 3,4,3',4'-tetrachlorobiphenyl (TCB) and TCB-induced effects on serum and adrenal gland retinoid content, and adrenal gland morphology was studied by liquid scintillation counting, high performance liquid chromatography, light microscopic autoradiography, and transmission electron microscopy [40].
The environmental pollutant 3,3',4,4'-tetrachlorobiphenyl (TCB) leads to thymic atrophy and immunosuppression, the former possibly causing the latter [41].

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