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Chemical Compound Review:

CHEMBL14658 1,2,3-trichloro-5-(3,4,5...

Synonyms: AG-F-09798, HSDB 3948, PCB 169, AC1L1VCX, LS-44407, ...

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Disease relevance of PCB 169

Toxicity of 3,4,5,3',4',5'-hexachlorobiphenyl to mink [1].
The most active compounds were the coplanar PCB congeners, 3,3',4,4',5-penta- and 3,3',4,4',5,5'-hexachlorobiphenyl; for example, their ED50 values for body weight loss were 3.25 and 15.1 mumol/kg, respectively [2].

High impact information on PCB 169

The antisera used in the RIAs were produced against two forms of cytochrome P-448 isolated from livers of rats treated with 3,4,5,3',4',5'-hexachlorobiphenyl (3,4,5-HCB) and 3-methylcholanthrene (3-MC), referred to as cytochromes P-448HCB and P-448MC, respectively [3].
The cytotoxic T lymphocyte (CTL) response to allogeneic P815 tumor in C57bl/6 mice is dose-dependently suppressed after treatment with 3,3',4,4',5,5'-hexachlorobiphenyl (HxCB) [4].
We established that the porphyrinogenic effect of PCBs exhibits a sharply defined structure-activity relationship in that only 3,4,3',4'-tetrachlorobiphenyl and 3,4,5,3',4',5'-hexachlorobiphenyl produced a marked accumulation of uroporphyrin [5].
On days 7-21 of gestation, Sprague-Dawley rats were orally administered 3 or 30 mug/kg/d of 3,3',4,4',5-pentachlorobiphenyl (PCB126) or 3,3',4,4',5,5'-hexachlorobiphenyl (PCB169) daily [6].
Effects on CYP1B1 expression and 4-MeOE(1/2) formation were less pronounced; only TCDD caused an induction, whereas PCB 169 was a potent and selective inhibitor of 4-MeOE(1/2) formation (IC(50) 0.7 and 2.2 nM PCB 169 in MCF-7 and MCF-10A cells, respectively) [7].

Biological context of PCB 169

At a longer pretreatment time (48 h), both a non-ortho (I-169 = 3,3',4,4',5,5'-hexachlorobiphenyl) and mono-ortho PCB congener(s) (e.g. I-156) markedly increased the hepatic 3H-uptake (190%), a probable effect of an induction of hepatic binding sites for TCDF [8].

Anatomical context of PCB 169

MAb 1-12-3 recognized P-450E induced by 3,3',4,4',5,5'-hexachlorobiphenyl and by polychlorinated biphenyl mixtures in scup, and a single band induced by BNF or 3-methylcholanthrene (MC) in microsomes of other teleosts, including two trout species, killifish and winter flounder [9].
These isozymes (P-448HCB and P-448MC) were isolated from liver microsomes of rats treated with 3,4,5,3',4',5'-hexachlorobiphenyl (HCB) and 3-MC, respectively [10].
Suppression of allograft immunity by 3,4,5,3',4',5'-hexachlorobiphenyl. I. Effects of exposure on tumor rejection and cytotoxic T cell activity in vivo [11].
Suppression of allograft immunity by 3,4,5,3',4',5'-hexachlorobiphenyl. II. Effects of exposure on mixed lymphocyte reactivity and induction of suppressor cell activity in vitro [12].
For each method, the rank order in potency was TCDD > or = TCDF > PCB 126 > PCB 81 > PCB 77 > PCB 169 in chicken, pheasant, and turkey hepatocytes [13].

Associations of PCB 169 with other chemical compounds

Suppression of male-specific cytochrome P450 2c and its mRNA by 3,4,5,3',4',5'-hexachlorobiphenyl in rat liver is not causally related to changes in serum testosterone [14].
2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD), 2,3,4,7,8-pentachlorodibenzofuran (PCDF), 3,3',4,4',5-pentachlorobiphenyl (PCB 126), and 3,3'4,4',5,5'-hexachlorobiphenyl (PCB 169) concentration dependently induced 2-MeOE(1/2) formation and ethoxyresorufin-O-deethylation (EROD) activity through induced CYP1A1 expression in MCF-7 and MCF-10A cells [7].
Uptake and depuration of PCB 77, PCB 169, and hexachlorobenzene by zebra mussels (Dreissena polymorpha) [15].
Prostaglandin-E2 (PGE2) was investigated for its role in suppression of splenic cytotoxic T lymphocyte (CTL) activity following exposure to 3,3',4,4',5,5'-hexachlorobiphenyl (HxCB) in mice [16].
The effects of 2,2',4,4',5,5'-hexachlorobiphenyl (2,4,5-HCB) or 3,3',4,4',5,5'-hexachlorobiphenyl (3,4,5-HCB) on hepatic ornithine decarboxylase (ODC) induction by dexamethasone were investigated [17].

Gene context of PCB 169

The effects of two substituted polychlorinated biphenyls, the 3,4,5,3',4,5' (PCB-169) and the 2,3,4,2',4',5' (PCB-138) forms, were examined on the expression of c-myc, c-jun, c-ras, and jun-b in 3T3-L1 cells [18].
A comparison of the cytochrome P-450 species induced by mirex and 3,4,5,3',4',5'-hexachlorobiphenyl in hepatic microsomes of the mouse [19].
Previous studies have shown that the generation of cytotoxic T lymphocytes (CTL) following allogeneic tumor challenge is suppressed in Ah-responsive C57Bl/6 mice treated with a single oral dose of the toxic, Ah receptor-binding 3,4,5,3',4',5'-hexachlorobiphenyl (HxCB) [20].

Analytical, diagnostic and therapeutic context of PCB 169

The oral administration of 3,4,5,3',4',5'-hexachlorobiphenyl for 3 weeks to mice caused a marked accumulation of porphyrins in the liver of C57BL/6 and C57Bl/10 mice but not in the liver of ddY mice [21].
Serum PCB-126, but not PCB-169, was correlated with body mass index (Spearman's r = 0.40, p = 0.002) [22].
Separation and quantitation of 3,3',4,4'-tetrachlorobiphenyl and 3,3',4,4',5,5'-hexachlorobiphenyl in aroclors using florisil column chromatography and gas-liquid chromatography [23].

References

Toxicity of 3,4,5,3',4',5'-hexachlorobiphenyl to mink. Aulerich, R.J., Bursian, S.J., Evans, M.G., Hochstein, J.R., Koudele, K.A., Olson, B.A., Napolitano, A.C. Arch. Environ. Contam. Toxicol. (1987) [Pubmed]
Polychlorinated biphenyls: correlation between in vivo and in vitro quantitative structure-activity relationships (QSARs). Leece, B., Denomme, M.A., Towner, R., Li, S.M., Safe, S. Journal of toxicology and environmental health. (1985) [Pubmed]
Immunochemical evidence for two 3-methylcholanthrene-inducible forms of cytochrome P-448 in rat liver microsomes using a double-antibody radioimmunoassay procedure. Luster, M.I., Lawson, L.D., Linko, P., Goldstein, J.A. Mol. Pharmacol. (1983) [Pubmed]
Polychlorinated biphenyl-induced immune suppression: castration, but not adrenalectomy or RU 38486 treatment, partially restores the suppressed cytotoxic T lymphocyte response to alloantigen. De Krey, G.K., Baecher-Steppan, L., Deyo, J.A., Smith, B., Kerkvliet, N.I. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
Toxicity of polychlorinated biphenyl with special reference to porphyrin metabolism. Sano, S., Kawanishi, S., Seki, Y. Environ. Health Perspect. (1985) [Pubmed]
Effects of maternal exposure to 3,3',4,4',5-pentachlorobiphenyl (PCB126) or 3,3',4,4',5,5'-hexachlorobiphenyl (PCB169) on testicular steroidogenesis and spermatogenesis in male offspring rats. Yamamoto, M., Narita, A., Kagohata, M., Shirai, M., Akahori, F., Arishima, K. J. Androl. (2005) [Pubmed]
Effects of several dioxin-like compounds on estrogen metabolism in the malignant MCF-7 and nontumorigenic MCF-10A human mammary epithelial cell lines. van Duursen, M.B., Sanderson, J.T., van der Bruggen, M., van der Linden, J., van den Berg, M. Toxicol. Appl. Pharmacol. (2003) [Pubmed]
Liver accumulation of 2,3,7,8-tetrachloro-[3H]dibenzofuran in mice: modulation by treatments with polychlorinated biphenyls. Darnerud, P.O., Törnwall, U., Bergman, A., Brandt, I. Chem. Biol. Interact. (1993) [Pubmed]
Specificity and cross-reactivity of monoclonal and polyclonal antibodies against cytochrome P-450E of the marine fish scup. Kloepper-Sams, P.J., Park, S.S., Gelboin, H.V., Stegeman, J.J. Arch. Biochem. Biophys. (1987) [Pubmed]
Differential metabolism of acetanilide versus ethoxycoumarin and benzo[a]pyrene by two 3-methylcholanthrene-inducible forms of rat liver cytochrome P-450. Sundheimer, D.W., Caveness, M.B., Goldstein, J.A. Arch. Biochem. Biophys. (1983) [Pubmed]
Suppression of allograft immunity by 3,4,5,3',4',5'-hexachlorobiphenyl. I. Effects of exposure on tumor rejection and cytotoxic T cell activity in vivo. Kerkvliet, N.I., Baecher-Steppan, L. Immunopharmacology (1988) [Pubmed]
Suppression of allograft immunity by 3,4,5,3',4',5'-hexachlorobiphenyl. II. Effects of exposure on mixed lymphocyte reactivity and induction of suppressor cell activity in vitro. Kerkvliet, N.I., Baecher-Steppan, L. Immunopharmacology (1988) [Pubmed]
Cytochrome P4501A induction in avian hepatocyte cultures: a promising approach for predicting the sensitivity of avian species to toxic effects of halogenated aromatic hydrocarbons. Kennedy, S.W., Lorenzen, A., Jones, S.P., Hahn, M.E., Stegeman, J.J. Toxicol. Appl. Pharmacol. (1996) [Pubmed]
Suppression of male-specific cytochrome P450 2c and its mRNA by 3,4,5,3',4',5'-hexachlorobiphenyl in rat liver is not causally related to changes in serum testosterone. Yeowell, H.N., Waxman, D.J., LeBlanc, G.A., Linko, P., Goldstein, J.A. Arch. Biochem. Biophys. (1989) [Pubmed]
Uptake and depuration of PCB 77, PCB 169, and hexachlorobenzene by zebra mussels (Dreissena polymorpha). Brieger, G., Hunter, R.D. Ecotoxicol. Environ. Saf. (1993) [Pubmed]
Polychlorinated biphenyl-induced suppression of cytotoxic T lymphocyte activity: role of prostaglandin-E2. De Krey, G.K., Baecher-Steppan, L., Fowles, J.R., Kerkvliet, N.I. Toxicol. Lett. (1994) [Pubmed]
Effects of two hexachlorobiphenyl isomers on ornithine decarboxylase induction: inhibitory effects correlate with aryl hydrocarbon hydroxylase activity. Potter, C.L., Sipes, I.G., Russell, D.H. Life Sci. (1985) [Pubmed]
Modulation of proto-oncogene expression by polychlorinated biphenyls in 3T3-L1 cell line. Gribaldo, L., Sacco, M.G., Casati, S., Zucchi, I., Dosanjh, M.K., Catalani, P., Marafante, E. J. Toxicol. Environ. Health Part A (1998) [Pubmed]
A comparison of the cytochrome P-450 species induced by mirex and 3,4,5,3',4',5'-hexachlorobiphenyl in hepatic microsomes of the mouse. Peppriell, J. Environmental research. (1980) [Pubmed]
Role of the Ah locus in suppression of cytotoxic T lymphocyte activity by halogenated aromatic hydrocarbons (PCBs and TCDD): structure-activity relationships and effects in C57Bl/6 mice congenic at the Ah locus. Kerkvliet, N.I., Baecher-Steppan, L., Smith, B.B., Youngberg, J.A., Henderson, M.C., Buhler, D.R. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1990) [Pubmed]
Role of inhibition of uroporphyrinogen decarboxylase in PCB-induced porphyria in mice. Seki, Y., Kawanishi, S., Sano, S. Toxicol. Appl. Pharmacol. (1987) [Pubmed]
Coplanar PCBs and the relative contribution of coplanar PCBs, PCDDs, and PCDFs to the total 2,3,7,8-TCDD toxicity equivalents in human serum. Kang, D., Tepper, A., Patterson, D.G. Chemosphere (1997) [Pubmed]
Separation and quantitation of 3,3',4,4'-tetrachlorobiphenyl and 3,3',4,4',5,5'-hexachlorobiphenyl in aroclors using florisil column chromatography and gas-liquid chromatography. Kamops, L.R., Trotter, W.J., Young, S.J., Smith, A.C., Roach, J.A., Page, S.W. Bulletin of environmental contamination and toxicology. (1979) [Pubmed]

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