메뉴 건너뛰기




Volumn 282, Issue 3, 2011, Pages 88-93

Dicofol degradation to p,p'-dichlorobenzophenone - A potential antiandrogen

Author keywords

Antiandrogens; Degradation; Dicofol; Kelthane; Metabolism; P,p' Dichlorobenzophenone

Indexed keywords

4,4' DICHLOROBENZOPHENONE; ANTIANDROGEN; BENZOPHENONE DERIVATIVE; CHLOROFORM; CLUSTERIN; DICOFOL; HYDROXIDE; MESSENGER RNA; PROSTATE SPECIFIC ANTIGEN; UNCLASSIFIED DRUG;

EID: 79952311057     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2011.01.016     Document Type: Article
Times cited : (18)

References (36)
  • 1
    • 0022672051 scopus 로고
    • Gas chromatographic determination of organochlorine pesticides; contamination of dicofol, fenson, and tetradifon in fish and natural waters of a wet area beside the Mediterranean sea
    • Barbera J.C., Lopez F.J., Hernandez F., Medina J., Pastor A. Gas chromatographic determination of organochlorine pesticides; contamination of dicofol, fenson, and tetradifon in fish and natural waters of a wet area beside the Mediterranean sea. Bull. Environ. Contam. Toxicol. 1986, 36:211-218.
    • (1986) Bull. Environ. Contam. Toxicol. , vol.36 , pp. 211-218
    • Barbera, J.C.1    Lopez, F.J.2    Hernandez, F.3    Medina, J.4    Pastor, A.5
  • 2
    • 0014549738 scopus 로고
    • Storage, distribution, and metabolism of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol
    • Brown J.R., Hughes H., Viriyanondha S. Storage, distribution, and metabolism of 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol. Toxicol. Appl. Pharmacol. 1969, 15:30-37.
    • (1969) Toxicol. Appl. Pharmacol. , vol.15 , pp. 30-37
    • Brown, J.R.1    Hughes, H.2    Viriyanondha, S.3
  • 4
    • 0023027611 scopus 로고
    • Photochemical conversion of a dicofol impurity α-chloro-DDT, to DDE
    • Brown M.A., Ruzo L.O., Casida J.E. Photochemical conversion of a dicofol impurity α-chloro-DDT, to DDE. Bull. Environ. Contam. Toxicol. 1986, 37:791-796.
    • (1986) Bull. Environ. Contam. Toxicol. , vol.37 , pp. 791-796
    • Brown, M.A.1    Ruzo, L.O.2    Casida, J.E.3
  • 5
    • 0023637556 scopus 로고
    • Metabolism of a dicofol impurity α-chloro-DDT, but not dicofol or dechlorodicofol, to DDE in mice and a liver microsomal system
    • Brown M.A., Casida J.E. Metabolism of a dicofol impurity α-chloro-DDT, but not dicofol or dechlorodicofol, to DDE in mice and a liver microsomal system. Xenobiotica 1987, 17(10):1169-1174.
    • (1987) Xenobiotica , vol.17 , Issue.10 , pp. 1169-1174
    • Brown, M.A.1    Casida, J.E.2
  • 6
    • 0021393816 scopus 로고
    • Comparative study of thin film photodegradative rates for 36 pesticides
    • Chen Z.M., Zabik M.J., Leavitt R.A. Comparative study of thin film photodegradative rates for 36 pesticides. Ind. Eng. Chem. Prod. Res. Dev. 1984, 23:5-11.
    • (1984) Ind. Eng. Chem. Prod. Res. Dev. , vol.23 , pp. 5-11
    • Chen, Z.M.1    Zabik, M.J.2    Leavitt, R.A.3
  • 7
    • 0035203030 scopus 로고    scopus 로고
    • Dicofol stimulation of cell proliferation
    • Du K., Xu X. Dicofol stimulation of cell proliferation. Bull. Environ. Contam. Toxicol. 2001, 67:795-799.
    • (2001) Bull. Environ. Contam. Toxicol. , vol.67 , pp. 795-799
    • Du, K.1    Xu, X.2
  • 8
    • 8544235780 scopus 로고    scopus 로고
    • EPA RED, United States Environmental Protection Agency, EPA 783-R-98-018
    • EPA RED Dicofol, Reregistration Eligibility Decision 1998, United States Environmental Protection Agency, EPA 783-R-98-018.
    • (1998) Dicofol, Reregistration Eligibility Decision
  • 11
    • 0028129515 scopus 로고
    • Developmental abnormalities of the gonad and abnormal sex hormone concentrations in juvenile alligators from contaminated and control lakes in Florida
    • Guillette L.J., Gross T.S., Masson G.R., Matter J.M., Percival H.F., Woodward A.R. Developmental abnormalities of the gonad and abnormal sex hormone concentrations in juvenile alligators from contaminated and control lakes in Florida. Environ. Health Perspect. 1994, 102:680-688.
    • (1994) Environ. Health Perspect. , vol.102 , pp. 680-688
    • Guillette, L.J.1    Gross, T.S.2    Masson, G.R.3    Matter, J.M.4    Percival, H.F.5    Woodward, A.R.6
  • 12
    • 9944256403 scopus 로고    scopus 로고
    • Sensitive in vitro test systems to determine androgenic/antiandrogenic activity
    • Guth S.E., Böhm S., Mußler B.H., Eisenbrand G. Sensitive in vitro test systems to determine androgenic/antiandrogenic activity. Mol. Nutr. Food Res. 2004, 48(4):282-291.
    • (2004) Mol. Nutr. Food Res. , vol.48 , Issue.4 , pp. 282-291
    • Guth, S.E.1    Böhm, S.2    Mußler, B.H.3    Eisenbrand, G.4
  • 13
    • 0345517147 scopus 로고    scopus 로고
    • DDT metabolite bis(chlorophenyl) acetic acid: the neglected environmental contaminant
    • Heberer T., Dunnbier U. DDT metabolite bis(chlorophenyl) acetic acid: the neglected environmental contaminant. Environ. Sci. Technol. 1999, 33:2346-2361.
    • (1999) Environ. Sci. Technol. , vol.33 , pp. 2346-2361
    • Heberer, T.1    Dunnbier, U.2
  • 14
    • 79952315711 scopus 로고    scopus 로고
    • Lack of evidence for effects of dicofol on reproductive hormone function following dietary exposure in rats
    • Hoberman A.M., Shuey D.L., Foss J.A., Parker R.M., Hurt S.S. Lack of evidence for effects of dicofol on reproductive hormone function following dietary exposure in rats. Toxicologist 1999, 48(1-S):388-389.
    • (1999) Toxicologist , vol.48 , Issue.1 S , pp. 388-389
    • Hoberman, A.M.1    Shuey, D.L.2    Foss, J.A.3    Parker, R.M.4    Hurt, S.S.5
  • 15
    • 33646853277 scopus 로고    scopus 로고
    • Estrogenic activity of dicofol with the human estrogen receptor: isomer- and enantiomer-specific implications
    • Hoekstra P.F., Burnison B.K., Garrison A.W., Neheli T., Muir D.C. Estrogenic activity of dicofol with the human estrogen receptor: isomer- and enantiomer-specific implications. Chemosphere 2006, 64(1):174-177.
    • (2006) Chemosphere , vol.64 , Issue.1 , pp. 174-177
    • Hoekstra, P.F.1    Burnison, B.K.2    Garrison, A.W.3    Neheli, T.4    Muir, D.C.5
  • 16
    • 0033401814 scopus 로고    scopus 로고
    • Effect of dicofol formulation on estrous cycle and follicular dynamics in albino rats
    • Jadarmkunti U.C., Kaliwal B.B. Effect of dicofol formulation on estrous cycle and follicular dynamics in albino rats. J. Basic Clin. Physiol. Pharmacol. 1999, 10(4):305-314.
    • (1999) J. Basic Clin. Physiol. Pharmacol. , vol.10 , Issue.4 , pp. 305-314
    • Jadarmkunti, U.C.1    Kaliwal, B.B.2
  • 19
    • 0015079894 scopus 로고
    • Comparative metabolism of chlorobenzilate, chloropropylate, and bromopropylate acaricides by rat hepatic enzymes
    • Knowles C.O., Ahmad S. Comparative metabolism of chlorobenzilate, chloropropylate, and bromopropylate acaricides by rat hepatic enzymes. Can. J. Physiol. Pharmacol. 1971, 49:590-597.
    • (1971) Can. J. Physiol. Pharmacol. , vol.49 , pp. 590-597
    • Knowles, C.O.1    Ahmad, S.2
  • 20
    • 0033931562 scopus 로고    scopus 로고
    • Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rat
    • Lambright C., Ostby J., Bobseine K., Wilson V., Hotchkiss A.K., Mann P.C., Gray L.E. Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rat. Toxicol. Sci. 2000, 56:389-399.
    • (2000) Toxicol. Sci. , vol.56 , pp. 389-399
    • Lambright, C.1    Ostby, J.2    Bobseine, K.3    Wilson, V.4    Hotchkiss, A.K.5    Mann, P.C.6    Gray, L.E.7
  • 21
    • 0029985678 scopus 로고    scopus 로고
    • Reproductive and morphological effects of o,p'-dicofol on two generations of captive American kestrels
    • MacLellan K.N.M., Bird D.M., Fry D.M., Cowles J.L. Reproductive and morphological effects of o,p'-dicofol on two generations of captive American kestrels. Arch. Environ. Contam. Toxicol. 1996, 30:364-372.
    • (1996) Arch. Environ. Contam. Toxicol. , vol.30 , pp. 364-372
    • MacLellan, K.N.M.1    Bird, D.M.2    Fry, D.M.3    Cowles, J.L.4
  • 23
    • 33845555781 scopus 로고
    • Kinetic and thermodynamic study of the base-catalyzed oxidative cleavage of 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol
    • Nome F., Erbs W., Correia V.R. Kinetic and thermodynamic study of the base-catalyzed oxidative cleavage of 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol. J. Org. Chem. 1981, 46:3802-3804.
    • (1981) J. Org. Chem. , vol.46 , pp. 3802-3804
    • Nome, F.1    Erbs, W.2    Correia, V.R.3
  • 24
    • 18844429502 scopus 로고    scopus 로고
    • Late gestational exposure to the fungicide prochloraz delays the onset of parturition and causes reproductive malformations in male but not female rat offspring
    • Noriega N.C., Ostby J., Lambright C., Wilson V.S., Gray L.E. Late gestational exposure to the fungicide prochloraz delays the onset of parturition and causes reproductive malformations in male but not female rat offspring. Biol. Reprod. 2005, 72(6):1324-1335.
    • (2005) Biol. Reprod. , vol.72 , Issue.6 , pp. 1324-1335
    • Noriega, N.C.1    Ostby, J.2    Lambright, C.3    Wilson, V.S.4    Gray, L.E.5
  • 25
    • 0033363929 scopus 로고    scopus 로고
    • The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro
    • Ostby J., Kelce W.R., Lambright C., Wolf C.J., Mann P., Gray L.E. The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro. Toxicol. Ind. Health 1999, 15:80-93.
    • (1999) Toxicol. Ind. Health , vol.15 , pp. 80-93
    • Ostby, J.1    Kelce, W.R.2    Lambright, C.3    Wolf, C.J.4    Mann, P.5    Gray, L.E.6
  • 26
    • 47149116517 scopus 로고    scopus 로고
    • Degradation of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) by brown-rot fungi
    • Purnomo A.S., Kamei I., Kondo R. Degradation of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) by brown-rot fungi. J. Biosci. Bioeng. 2008, 105(6):614-621.
    • (2008) J. Biosci. Bioeng. , vol.105 , Issue.6 , pp. 614-621
    • Purnomo, A.S.1    Kamei, I.2    Kondo, R.3
  • 27
    • 0001897610 scopus 로고
    • Studies of the rearrangement of (trichloromethyl)carbinols to α-chloroacetic acids
    • Reeve W., McKee J.R., Brown R., Lakshmanan S., McKee G.A. Studies of the rearrangement of (trichloromethyl)carbinols to α-chloroacetic acids. Can. J. Chem. 1980, 58:485-493.
    • (1980) Can. J. Chem. , vol.58 , pp. 485-493
    • Reeve, W.1    McKee, J.R.2    Brown, R.3    Lakshmanan, S.4    McKee, G.A.5
  • 29
    • 0347298766 scopus 로고    scopus 로고
    • DDT-related compounds bound to the nonextractable particulate matter in sediments of the Teltow Canal, Germany
    • Schwarzbauer J., Ricking M., Littke R. DDT-related compounds bound to the nonextractable particulate matter in sediments of the Teltow Canal, Germany. Environ. Sci. Technol. 2003, 37:488-495.
    • (2003) Environ. Sci. Technol. , vol.37 , pp. 488-495
    • Schwarzbauer, J.1    Ricking, M.2    Littke, R.3
  • 30
    • 79952311750 scopus 로고
    • Water soluble metabolites of dicofol in mouse urine
    • Tabata K., Miyata T., Saito T. Water soluble metabolites of dicofol in mouse urine. Appl. Entomol. Zool. 1979, 14(4):490-493.
    • (1979) Appl. Entomol. Zool. , vol.14 , Issue.4 , pp. 490-493
    • Tabata, K.1    Miyata, T.2    Saito, T.3
  • 31
    • 0032693810 scopus 로고    scopus 로고
    • Screening of selected pesticides for oestrogen receptor activation in vitro
    • Vinggaard A.M., Hnida C., Larsen J.C. Screening of selected pesticides for oestrogen receptor activation in vitro. Food Addit. Contam. 1999, 16(12):533-542.
    • (1999) Food Addit. Contam. , vol.16 , Issue.12 , pp. 533-542
    • Vinggaard, A.M.1    Hnida, C.2    Larsen, J.C.3
  • 33
    • 0030498568 scopus 로고    scopus 로고
    • Interaction of environmental chemicals with the estrogen and progesterone receptors from the oviduct of the American alligator
    • Vonier P.M., Crain D.A., McLachlan J.A., Guillette L.J., Arnold S.F. Interaction of environmental chemicals with the estrogen and progesterone receptors from the oviduct of the American alligator. Environ. Health Perspect. 1996, 104(12):1318-1322.
    • (1996) Environ. Health Perspect. , vol.104 , Issue.12 , pp. 1318-1322
    • Vonier, P.M.1    Crain, D.A.2    McLachlan, J.A.3    Guillette, L.J.4    Arnold, S.F.5
  • 35
    • 17044384114 scopus 로고    scopus 로고
    • Fate of DDT-related compounds in Bohai Bay and its adjacent Haihe Basin, North China
    • Wan Y., Hu J., Liu J., An W., Tao S., Jia Z. Fate of DDT-related compounds in Bohai Bay and its adjacent Haihe Basin, North China. Mar. Pollut. Bull. 2005, 50:439-445.
    • (2005) Mar. Pollut. Bull. , vol.50 , pp. 439-445
    • Wan, Y.1    Hu, J.2    Liu, J.3    An, W.4    Tao, S.5    Jia, Z.6
  • 36
    • 0029123855 scopus 로고
    • Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamid
    • Wong C., Kelce W.R., Sar M., Wilson E.M. Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamid. J. Biol. Chem. 1995, 270:19998-20003.
    • (1995) J. Biol. Chem. , vol.270 , pp. 19998-20003
    • Wong, C.1    Kelce, W.R.2    Sar, M.3    Wilson, E.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.