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Chemical Compound Review

CHLOROBIPHENYL     1-chloro-2-phenyl-benzene

Synonyms: Chlorodiphenyl, Chlorodwufenol, Arochlor-1254, PCB 1, AROCLOR 1232, ...
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Disease relevance of Monochlorobiphenyl

  • We report that chlorobiphenyl vancomycin analogues that are incapable of binding substrates nevertheless inhibit E. coli PBP1b, which shows that these compounds interact directly with the enzyme [1].
  • None of the compounds was mutagenic in the Ames assay with Salmonella typhimurium TA-98 and TA-100 strains, either in the absence or in the presence of the S-9 liver fraction from Arochlor 1254 treated rats [2].
  • These bacteria have the potential to interact metabolically because Pseudomonas sp. B13(FR1) can metabolize chlorobenzoate produced by Burkholderia sp. LB400 when grown on chlorobiphenyl [3].
  • These experiments were conducted with a 10-microm marine scuticociliate (Uronema sp.), bacterial prey (Halomonas halodurans), and a suite of 21 CB congeners spanning a range of aqueous solubilities [4].
  • This work provides proof of concept that a Rhodococcus strain constructed to grow on a PCB would grow in nonsterile soil if the appropriate chlorobiphenyl is available [5].

High impact information on Monochlorobiphenyl


Chemical compound and disease context of Monochlorobiphenyl


Biological context of Monochlorobiphenyl

  • Twenty-four chlorobiphenyl congeners have been measured along a pollution gradient both in sponges and seawater [11].
  • A liver homogenate (S9) prepared from Arochlor 1254 induced male Sprague-Dawley rats was employed to mediate the biotransformation of the promutagen [12].
  • The highest Arochlor 1254 concentration that did not cause observed effects (NOEC) on cell growth was 100 (48 h) and 25 ppb (96 h) [13].
  • The susceptibility of the dinoflagellate Lingulodinium polyedrum to Arochlor 1254, a commercial mixture of polychlorinated biphenyl (PCB) congeners was examined through toxicity bioassays based on cell survival and measures of oxidative balance and adaptive response to PCB stress [13].
  • Detection of by-side CBs in technical Halowaxes demonstrate clearly that those formulations apart from a massive introduction of dioxin-like CNs become in the past also an early source of environmental pollution with CBs, which proceeded for around 20-30 years use of original CB formulations [14].

Anatomical context of Monochlorobiphenyl

  • PC12 cells were incubated with hydroxylated PCB (4(OH)-2',3,3',4',5'-penta chlorobiphenyl, OH-PCB) at a final concentration from 10(-8) to 10(-5)M [15].
  • A fingerprint of chlorobiphenyl composition in the samples examined was virtually the same for human adipose tissue taken in 1990 from the coastal city of Gdańsk and in 1979 from the inland province of Skierniewice, in spite of geographic variations and sampling intervals [16].

Associations of Monochlorobiphenyl with other chemical compounds


Gene context of Monochlorobiphenyl

  • These data indicate that regular meals of lower trophic level fish, such as whitefish from the Great Lakes, may distort steady-state human chlorobiphenyl profiles with respect to certain lightly chlorinated or labile chlorobiphenyls [22].
  • It was also shown that when dextran solution or dextran solution with addition of Intralipid to the same concentration as the total lipid concentration in blood, were used as perfusion medium, there was no placental transport of the chlorobiphenyl [23].

Analytical, diagnostic and therapeutic context of Monochlorobiphenyl

  • Clean-up and separation of chlorobiphenyl isomers after synthesis by Cadogan coupling using preparative high-performance liquid chromatography [24].
  • In rat pretreated with Arochlor 1254, Vmax was 52 pmol/min/mg protein, whereas oral administration of ABZ increased the intestinal sulphoxidation of the drug, Vmax being 103 pmol/min/mg protein [25].
  • Furthermore, it was shown that the placental transport of the chlorobiphenyl was strongly dependent on the albumin concentration, but independent of the gamma-globulin concentration in the perfusion medium [23].
  • Bromo and chlorobiphenyl metabolism: gas chromatography mass spectrometric identification of urinary metabolites and the effects of structure on their rates of excretion [26].


  1. Vancomycin analogues active against vanA-resistant strains inhibit bacterial transglycosylase without binding substrate. Chen, L., Walker, D., Sun, B., Hu, Y., Walker, S., Kahne, D. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  2. Derivatives of beta-adrenergic antagonists. N-Nitrosopropranolol and N-hydroxypropranolol and its aldonitrone. Zhang, S., Powell, M.L., Nelson, W.L., Wirth, P.J. J. Med. Chem. (1983) [Pubmed]
  3. Role of commensal relationships on the spatial structure of a surface-attached microbial consortium. Nielsen, A.T., Tolker-Nielsen, T., Barken, K.B., Molin, S. Environ. Microbiol. (2000) [Pubmed]
  4. Importance of passive diffusion in the uptake of polychlorinated biphenyls by phagotrophic protozoa. Kujawinski, E.B., Farrington, J.W., Moffett, J.W. Appl. Environ. Microbiol. (2000) [Pubmed]
  5. Development of a Rhodococcus recombinant strain for degradation of products from anaerobic dechlorination of PCBs. Rodrigues, J.L., Maltseva, O.V., Tsoi, T.V., Helton, R.R., Quensen, J.F., Fukuda, M., Tiedje, J.M. Environ. Sci. Technol. (2001) [Pubmed]
  6. In vitro metabolism of 4-chlorobiphenyl by control and induced rat liver microsomes. Wyndham, C., Safe, S. Biochemistry (1978) [Pubmed]
  7. Some dietary fibers increase elimination of orally administered polychlorinated biphenyls but not that of retinol in mice. Kimura, Y., Nagata, Y., Buddington, R.K. J. Nutr. (2004) [Pubmed]
  8. Cloning of bacterial genes specifying degradation of 4-chlorobiphenyl from Pseudomonas putida OU83. Khan, A., Walia, S. Appl. Environ. Microbiol. (1989) [Pubmed]
  9. Cloning of a gene cluster encoding biphenyl and chlorobiphenyl degradation in Pseudomonas pseudoalcaligenes. Furukawa, K., Miyazaki, T. J. Bacteriol. (1986) [Pubmed]
  10. Genotoxic effects of N-nitrosodicyclohexylamine in isolated human lymphocytes. Westphal, G.A., Müller, M.M., Herting, C., Bünger, J., Hallier, E. Arch. Toxicol. (2001) [Pubmed]
  11. Marine sponges as biomonitor of polychlorobiphenyl contamination: concentration and fate of 24 congeners. Perez, T., Wafo, E., Fourt, M., Vacelet, J. Environ. Sci. Technol. (2003) [Pubmed]
  12. Quantitative analysis of cytotoxicity and mutagenicity of benzo[a]pyrene in mammalian cells (CHO/HGPRT system). Machanoff, R., O'Neill, J.P., Hsie, A.W. Chem. Biol. Interact. (1981) [Pubmed]
  13. PCB-induced oxidative stress in the unicellular marine dinoflagellate Lingulodinium polyedrum. Leitão, M.A., Cardozo, K.H., Pinto, E., Colepicolo, P. Arch. Environ. Contam. Toxicol. (2003) [Pubmed]
  14. By-side impurities in chloronaphthalene mixtures of the Halowax series: all 209 chlorobiphenyls. Noma, Y., Ishikawa, Y., Falandysz, J., Jecek, L., Gulkowska, A., Miyaji, K., Sakai, S. Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering. (2004) [Pubmed]
  15. Low dose hydroxylated PCB induces c-Jun expression in PC12 cells. Shimokawa, N., Miyazaki, W., Iwasaki, T., Koibuchi, N. Neurotoxicology (2006) [Pubmed]
  16. Congener-specific data of polychlorinated biphenyl residues in human adipose tissue in Poland. Falandysz, J., Yamashita, N., Tanabe, S., Tatsukawa, R. Sci. Total Environ. (1994) [Pubmed]
  17. Congener-specific carbon isotopic analysis of technical PCB and PCN mixtures using two-dimensional gas chromatography-isotope ratio mass spectrometry. Horii, Y., Kannan, K., Petrick, G., Gamo, T., Falandysz, J., Yamashita, N. Environ. Sci. Technol. (2005) [Pubmed]
  18. Expression of cytochrome P450s and microsomal epoxide hydrolase in primary cultures of human umbilical vein endothelial cells. Farin, F.M., Pohlman, T.H., Omiecinski, C.J. Toxicol. Appl. Pharmacol. (1994) [Pubmed]
  19. The metabolic activation of 2-naphthylamine to mutagens in the Ames test. Tong, S., Smith, J., Manson, D., Gorrod, J.W., Ioannides, C. Anticancer Res. (1986) [Pubmed]
  20. Mutagenic interactions of model chemical mixtures. Donnelly, K.C., Claxton, L.D., Huebner, H.J., Capizzi, J.L. Chemosphere (1998) [Pubmed]
  21. Anthraflavic acid is a potent and specific inhibitor of cytochrome P-448 activity. Ayrton, A.D., Lewis, D.F., Ioannides, C., Walker, R. Biochim. Biophys. Acta (1987) [Pubmed]
  22. Concentrations and frequencies of polychlorinated biphenyl congeners in a Native American population that consumes Great Lakes fish. Gerstenberger, S.L., Dellinger, J.A., Hansen, L.G. J. Toxicol. Clin. Toxicol. (2000) [Pubmed]
  23. Influence of albumin concentration in the foetal circulation on the placental transfer of 2,2',4,4',5,5'-hexachlorobiphenyl in the guinea pig. Kihlström, I. Acta pharmacologica et toxicologica. (1982) [Pubmed]
  24. Clean-up and separation of chlorobiphenyl isomers after synthesis by Cadogan coupling using preparative high-performance liquid chromatography. Seymour, M.P., Duncan, I.W., Jefferies, T.M., Notarianni, L.J. J. Chromatogr. (1986) [Pubmed]
  25. Small intestinal sulphoxidation of albendazole. Villaverde, C., Alvarez, A.I., Redondo, P., Voces, J., Del Estal, J.L., Prieto, J.G. Xenobiotica (1995) [Pubmed]
  26. Bromo and chlorobiphenyl metabolism: gas chromatography mass spectrometric identification of urinary metabolites and the effects of structure on their rates of excretion. Sparling, J., Fung, D., Safe, S. Biomed. Mass Spectrom. (1980) [Pubmed]
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