메뉴 건너뛰기




Volumn 70, Issue 9, 2008, Pages 1694-1698

The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

Author keywords

Crystal structure; Dihedral angle; Dioxin like PCBs; Environmental contaminants

Indexed keywords

COMPUTATION THEORY; CRYSTAL STRUCTURE; DERIVATIVES; PHASE TRANSITIONS;

EID: 38349006102     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2007.07.017     Document Type: Article
Times cited : (29)

References (35)
  • 1
    • 0001590401 scopus 로고
    • Internal rotation of biphenyl in solution studied by IR and NMR spectra
    • Akiyama M., Watanabe T., and Kakihana M. Internal rotation of biphenyl in solution studied by IR and NMR spectra. J. Phys. Chem. 90 (1986) 1752-1755
    • (1986) J. Phys. Chem. , vol.90 , pp. 1752-1755
    • Akiyama, M.1    Watanabe, T.2    Kakihana, M.3
  • 2
    • 0002305877 scopus 로고
    • Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 1. The molecular structure and normal coordinate analysis of normal biphenyl and perdeuterated biphenyl
    • Almenningen A., Bastiansen O., Fernholt L., Cyvin B.N., Cyvin S.J., and Samdal S. Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 1. The molecular structure and normal coordinate analysis of normal biphenyl and perdeuterated biphenyl. J. Mol. Struct. 128 (1985) 59-76
    • (1985) J. Mol. Struct. , vol.128 , pp. 59-76
    • Almenningen, A.1    Bastiansen, O.2    Fernholt, L.3    Cyvin, B.N.4    Cyvin, S.J.5    Samdal, S.6
  • 3
    • 0013101601 scopus 로고
    • Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 3. Structure of 4-fluoro-, 4,4′-difluoro-, 4-chloro- and 4,4′-dichlorobiphenyl
    • Almenningen A., Bastlansen O., Gundersen S., Samdal S., and Skancke A. Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 3. Structure of 4-fluoro-, 4,4′-difluoro-, 4-chloro- and 4,4′-dichlorobiphenyl. J. Mol. Struct. 128 (1985) 95-114
    • (1985) J. Mol. Struct. , vol.128 , pp. 95-114
    • Almenningen, A.1    Bastlansen, O.2    Gundersen, S.3    Samdal, S.4    Skancke, A.5
  • 4
    • 0012262014 scopus 로고
    • Crystal and molecular structure of 2,7-dichlorodibenzo-p-dioxin
    • Boer F.P., and North P.P. Crystal and molecular structure of 2,7-dichlorodibenzo-p-dioxin. Acta Cryst. B28 (1972) 1613-1618
    • (1972) Acta Cryst. , vol.B28 , pp. 1613-1618
    • Boer, F.P.1    North, P.P.2
  • 5
    • 0001478781 scopus 로고
    • Crystal and molecular structure of 2,3,7,8-tetrachlorodibenzo-p-dioxin
    • Boer F.P., Van Remoortere F.P., North P.P., and Neuman M.A. Crystal and molecular structure of 2,3,7,8-tetrachlorodibenzo-p-dioxin. Acta Cryst. B28 (1972) 1023-1029
    • (1972) Acta Cryst. , vol.B28 , pp. 1023-1029
    • Boer, F.P.1    Van Remoortere, F.P.2    North, P.P.3    Neuman, M.A.4
  • 6
    • 0040609614 scopus 로고
    • 4,4′-Dichlorobiphenyl: crystal packing in para-substituted biphenyls
    • Brock C.P., Kuo M.-S., and Levy H.A. 4,4′-Dichlorobiphenyl: crystal packing in para-substituted biphenyls. Acta Cryst. B34 (1978) 981-985
    • (1978) Acta Cryst. , vol.B34 , pp. 981-985
    • Brock, C.P.1    Kuo, M.-S.2    Levy, H.A.3
  • 8
    • 0011710980 scopus 로고
    • Identification and crystal structure of a hydropericardium-producing factor: 1,2,3,7,8,9-hexachlorodibenzo-p-dioxin
    • Cantrell J.S., Webb N.C., and Mabis A.J. Identification and crystal structure of a hydropericardium-producing factor: 1,2,3,7,8,9-hexachlorodibenzo-p-dioxin. Acta Cryst. B25 (1969) 150-156
    • (1969) Acta Cryst. , vol.B25 , pp. 150-156
    • Cantrell, J.S.1    Webb, N.C.2    Mabis, A.J.3
  • 9
    • 0024429103 scopus 로고
    • Structural analysis by diffraction of polychlorinated dioxins and dibenzofurans
    • Cantrell J.S., Beiter T.A., and Tomlin D. Structural analysis by diffraction of polychlorinated dioxins and dibenzofurans. Chemosphere 19 (1989) 155-160
    • (1989) Chemosphere , vol.19 , pp. 155-160
    • Cantrell, J.S.1    Beiter, T.A.2    Tomlin, D.3
  • 10
    • 0020606139 scopus 로고
    • Polychlorinated biphenyls as phenobarbitone-type inducers of microsomal enzymes. Structure-activity relationships for a series of 2,4-dichloro-substituted congeners
    • Denomme M.A., Bandiera S., Lambert I., Copp L., Safe L., and Safe S. Polychlorinated biphenyls as phenobarbitone-type inducers of microsomal enzymes. Structure-activity relationships for a series of 2,4-dichloro-substituted congeners. Biochem. Pharmacol. 32 (1983) 2955-2963
    • (1983) Biochem. Pharmacol. , vol.32 , pp. 2955-2963
    • Denomme, M.A.1    Bandiera, S.2    Lambert, I.3    Copp, L.4    Safe, L.5    Safe, S.6
  • 11
    • 0842341771 scopus 로고
    • Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model
    • Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107 (1985) 3902-3909
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
  • 12
    • 33645242725 scopus 로고    scopus 로고
    • Intestinal bioavailability and biotransformation of 3,3′,4,4′-tetrachlorobiphenyl (CB 77) in in situ preparations of channel catfish following dietary induction of CYP1A
    • Doi A.M., Lou Z., Holmes E., Venugopal C.S., Nyagode B., James M.O., and Kleinow K.M. Intestinal bioavailability and biotransformation of 3,3′,4,4′-tetrachlorobiphenyl (CB 77) in in situ preparations of channel catfish following dietary induction of CYP1A. Aquat. Toxicol. 77 (2006) 33-42
    • (2006) Aquat. Toxicol. , vol.77 , pp. 33-42
    • Doi, A.M.1    Lou, Z.2    Holmes, E.3    Venugopal, C.S.4    Nyagode, B.5    James, M.O.6    Kleinow, K.M.7
  • 13
    • 0018138305 scopus 로고
    • 2,3,7,8-Tetrachlorodibenzofuran in a commercially available 99% pure polychlorinated biphenyl isomer identified as the inducer of hepatic cytochrome P-448 and aryl hydrocarbon hydroxylase in the rat
    • Goldstein J.A., Hass J.R., Linko P., and Harvan D.J. 2,3,7,8-Tetrachlorodibenzofuran in a commercially available 99% pure polychlorinated biphenyl isomer identified as the inducer of hepatic cytochrome P-448 and aryl hydrocarbon hydroxylase in the rat. Drug Metab. Dispos. 6 (1978) 258-264
    • (1978) Drug Metab. Dispos. , vol.6 , pp. 258-264
    • Goldstein, J.A.1    Hass, J.R.2    Linko, P.3    Harvan, D.J.4
  • 14
    • 0003414118 scopus 로고
    • Kluwer Academic Publishers, Holland
    • Hahn T. International Tables for Crystallography. Mathematical, Physical and Chemical Tables vol. C (1992), Kluwer Academic Publishers, Holland
    • (1992) Mathematical, Physical and Chemical Tables , vol.C
    • Hahn, T.1
  • 17
    • 0024213953 scopus 로고
    • The crystal structure of octachlorodibenzodioxin: experimental and calculated
    • Koester C.J., Huffman J.C., and Hites R.A. The crystal structure of octachlorodibenzodioxin: experimental and calculated. Chemosphere 17 (1988) 2419-2422
    • (1988) Chemosphere , vol.17 , pp. 2419-2422
    • Koester, C.J.1    Huffman, J.C.2    Hites, R.A.3
  • 18
    • 0024359153 scopus 로고
    • Further studies on metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl in rats: identification of minor metabolites in rat feces
    • Koga N., Beppu M., Ishida C., and Yoshimura H. Further studies on metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl in rats: identification of minor metabolites in rat feces. Xenobiotica 19 (1989) 1307-1318
    • (1989) Xenobiotica , vol.19 , pp. 1307-1318
    • Koga, N.1    Beppu, M.2    Ishida, C.3    Yoshimura, H.4
  • 20
    • 0036147457 scopus 로고    scopus 로고
    • The three-dimensional structure of 3,3′,5′-trichloro-4-methoxybiphenyl, a "coplanar" polychlorinated biphenyl (PCB) derivative
    • Lehmler H.-J., Parkin S., and Robertson L.W. The three-dimensional structure of 3,3′,5′-trichloro-4-methoxybiphenyl, a "coplanar" polychlorinated biphenyl (PCB) derivative. Chemosphere 46 (2002) 485-488
    • (2002) Chemosphere , vol.46 , pp. 485-488
    • Lehmler, H.-J.1    Parkin, S.2    Robertson, L.W.3
  • 21
    • 31744452397 scopus 로고    scopus 로고
    • 2,2′,3,3′,6-Pentachlorobiphenyl (PCB 84)
    • Lehmler H.J., Robertson L.W., and Parkin S. 2,2′,3,3′,6-Pentachlorobiphenyl (PCB 84). Acta Cryst. E61 (2005) o3025-o3026
    • (2005) Acta Cryst. , vol.E61
    • Lehmler, H.J.1    Robertson, L.W.2    Parkin, S.3
  • 22
    • 33947531892 scopus 로고    scopus 로고
    • Influence of fluoro-substitution on the planarity of 4-chlorobiphenyl (PCB 3)
    • Luthe G., Swenson D.C., and Robertson L.W. Influence of fluoro-substitution on the planarity of 4-chlorobiphenyl (PCB 3). Acta Cryst. B 63 (2007) 319-327
    • (2007) Acta Cryst. B , vol.63 , pp. 319-327
    • Luthe, G.1    Swenson, D.C.2    Robertson, L.W.3
  • 23
    • 0004753619 scopus 로고
    • 3,3′,5,5′-Tetrachloro-4,4′-dihydroxybiphenyl. A coplanar polychlorinated biphenyl in the solid state
    • McKinney J.D., and Singh P. 3,3′,5,5′-Tetrachloro-4,4′-dihydroxybiphenyl. A coplanar polychlorinated biphenyl in the solid state. Acta Cryst. C44 (1988) 558-562
    • (1988) Acta Cryst. , vol.C44 , pp. 558-562
    • McKinney, J.D.1    Singh, P.2
  • 24
    • 0023067127 scopus 로고
    • Polychlorinated biphenyls and related compound interactions with specific binding sites for thyroxine in rat liver nuclear extracts
    • McKinney J., Fannin R., Jordan S., Chae K., Rickenbacher U., and Pedersen L. Polychlorinated biphenyls and related compound interactions with specific binding sites for thyroxine in rat liver nuclear extracts. J. Med. Chem. 30 (1987) 79-86
    • (1987) J. Med. Chem. , vol.30 , pp. 79-86
    • McKinney, J.1    Fannin, R.2    Jordan, S.3    Chae, K.4    Rickenbacher, U.5    Pedersen, L.6
  • 25
    • 0007891926 scopus 로고    scopus 로고
    • Structure elucidation of polychlorinated biphenyls by X-ray analysis
    • Miao X., Chu S., Xu X., and Jin X. Structure elucidation of polychlorinated biphenyls by X-ray analysis. Chin. Sci. Bull. 42 (1997) 1803-1806
    • (1997) Chin. Sci. Bull. , vol.42 , pp. 1803-1806
    • Miao, X.1    Chu, S.2    Xu, X.3    Jin, X.4
  • 26
    • 0020582855 scopus 로고
    • Immunochemical quantitation of cytochrome P-450 isozymes and epoxide hydrolase in liver microsomes from polychlorinated or polybrominated biphyenyl-treated rats. A study of structure-activity relationships
    • Parkinson A., Safe S.H., Robertson L.W., Thomas P.E., Ryan D.E., Reik L.M., and Levin W. Immunochemical quantitation of cytochrome P-450 isozymes and epoxide hydrolase in liver microsomes from polychlorinated or polybrominated biphyenyl-treated rats. A study of structure-activity relationships. J. Biol. Chem. 258 (1983) 5967-5976
    • (1983) J. Biol. Chem. , vol.258 , pp. 5967-5976
    • Parkinson, A.1    Safe, S.H.2    Robertson, L.W.3    Thomas, P.E.4    Ryan, D.E.5    Reik, L.M.6    Levin, W.7
  • 28
    • 0028235721 scopus 로고
    • Polychlorinated biphenyls (PCBs): environmental impact, biochemical and toxic responses, and implications for risk assessment
    • Safe S.H. Polychlorinated biphenyls (PCBs): environmental impact, biochemical and toxic responses, and implications for risk assessment. Crit. Rev. Toxicol. 24 (1994) 87-149
    • (1994) Crit. Rev. Toxicol. , vol.24 , pp. 87-149
    • Safe, S.H.1
  • 29
    • 0032437889 scopus 로고    scopus 로고
    • Environmental xenobiotics and the antihormones cyproterone acetate and spironolactone use the nuclear hormone pregnenolone X receptor to activate the CYP3A23 hormone response element
    • Schuetz E.G., Brimer C., and Schuetz J.D. Environmental xenobiotics and the antihormones cyproterone acetate and spironolactone use the nuclear hormone pregnenolone X receptor to activate the CYP3A23 hormone response element. Mol. Pharmacol. 54 (1998) 1113-1117
    • (1998) Mol. Pharmacol. , vol.54 , pp. 1113-1117
    • Schuetz, E.G.1    Brimer, C.2    Schuetz, J.D.3
  • 30
    • 33748296412 scopus 로고    scopus 로고
    • The Ullmann coupling reaction: a new approach to tetraarylstannanes
    • Shaikh N.S., Parkin S., and Lehmler H.-J. The Ullmann coupling reaction: a new approach to tetraarylstannanes. Organometallics 25 (2006) 4207-4214
    • (2006) Organometallics , vol.25 , pp. 4207-4214
    • Shaikh, N.S.1    Parkin, S.2    Lehmler, H.-J.3
  • 32
    • 0037745545 scopus 로고    scopus 로고
    • Crystallographic analysis of a hydroxylated polychlorinated biphenyl (OH-PCB) bound to the catalytic estrogen binding site of human estrogen sulfotransferase
    • Shevtsov S., Petrotchenko E.V., Pedersen L.C., and Negishi M. Crystallographic analysis of a hydroxylated polychlorinated biphenyl (OH-PCB) bound to the catalytic estrogen binding site of human estrogen sulfotransferase. Environ. Health Perspect 111 (2003) 884-888
    • (2003) Environ. Health Perspect , vol.111 , pp. 884-888
    • Shevtsov, S.1    Petrotchenko, E.V.2    Pedersen, L.C.3    Negishi, M.4
  • 33
    • 0141507433 scopus 로고
    • 2,2′,4,4′,6,6′-Hexachlorobiphenyl
    • Singh P., and McKinney J.D. 2,2′,4,4′,6,6′-Hexachlorobiphenyl. Acta Cryst. B35 (1979) 259-262
    • (1979) Acta Cryst. , vol.B35 , pp. 259-262
    • Singh, P.1    McKinney, J.D.2
  • 34
    • 0000349260 scopus 로고
    • Crystal and energy-refined structures of 2,2′,4,4′,5,5′-hexachlorobiphenyl
    • Singh P., Pedersen L.G., and McKinney J.D. Crystal and energy-refined structures of 2,2′,4,4′,5,5′-hexachlorobiphenyl. Acta Cryst. C42 (1986) 1172-1175
    • (1986) Acta Cryst. , vol.C42 , pp. 1172-1175
    • Singh, P.1    Pedersen, L.G.2    McKinney, J.D.3
  • 35
    • 33745978718 scopus 로고    scopus 로고
    • 2,2′,3,4,4′,5,5′-Heptachlorobiphenyl (PCB 180)
    • Vyas S.M., Parkin S., and Lehmler H.J. 2,2′,3,4,4′,5,5′-Heptachlorobiphenyl (PCB 180). Acta Cryst. E E62 (2006) o2905-o2906
    • (2006) Acta Cryst. E , vol.E62
    • Vyas, S.M.1    Parkin, S.2    Lehmler, H.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.