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Journal of Environmental Science and Health, Part A
Toxic/Hazardous Substances and Environmental Engineering
Volume 46, 2011 - Issue 4
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ARTICLES

Chlorinated isomers of nonylphenol differ in estrogenic and androgenic activity

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Pages 329-336 | Received 06 Oct 2010, Published online: 18 Feb 2011

References

  • Fry , D. M. 1995 . Reproductive effects in birds exposed to pesticides and industrial chemicals . Environ. Health Persp. , 103 ( Suppl 7 ) : 165 – 171 .
  • Sumpter , J. P. 1995 . Feminized responses in fish to environmental estrogens . Toxicol. Lett. , 82–83 : 737 – 742 .
  • Rotchell , J. M. and Ostrander , G. K. 2003 . Molecular markers of endocrine disruption in aquatic organisms . J. Toxicol. Environ. Health B. , 6 ( 5 ) : 453 – 495 .
  • Roy , D. , Palangat , M. , Chen , C.-W. , Thomas , R. D. , Colerangle , J. , Atkinson , A. and Yan , Z.-J. 1997 . Biochemical and molecular changes at the cellular level in response to exposure to environmental estrogen-like chemicals . J. Toxicol. Environ. Health. , 50 ( 1 ) : 1 – 29 .
  • Grove , R. A. , Henny , C. J. and Kaiser , J. L. 2009 . Osprey: worldwide sentinel species for assessing and monitoring environmental contamination in rivers, lakes, reservoirs, and estuaries . J. Toxicol. Environ. Health B. , 12 ( 1 ) : 25 – 44 .
  • Toppari , J. , Larsen , J. C. , Christiansen , P. , Giwercman , A. , Grandjean , P. , Guillette , L. J. Jr. , Jegou , B. , Jensen , T. K. , Jouannet , P. , Keiding , N. , Leffers , H. , McLachlan , J. A. , Meyer , O. , Muller , J. , Rajpert-De Meyts , E. , Scheike , T. , Sharpe , R. , Sumpter , J. and Skakkebaek , N. E. 1996 . Male reproductive health and environmental xenoestrogens . Environ. Health Persp. , 104 ( Suppl 4 ) : 741 – 803 .
  • Swan , S. H. , Elkin , E. P. and Fenster , L. 2000 . The question of declining sperm density revisited: an analysis of 101 studies published 1934–1996 . Environ. Health Persp. , 108 ( 10 ) : 961 – 966 .
  • Goksoyr , A. 2006 . Endocrine disruptors in the marine environment: mechanisms of toxicity and their influence on reproductive processes in fish . J. Toxicol. Environ. Health A. , 69 ( 1–2 ) : 175 – 184 .
  • Phillips , K. P. and Tanphaichitr , N. 2008 . Human exposure to endocrine disrupters and semen quality . J. Toxicol. Environ. Health B. , 11 ( 3–4 ) : 188 – 220 .
  • Merzenich , H. , Zeeb , H. and Blettner , M. 2010 . Decreasing sperm quality: a global problem? . BMC Public Health , 10 : 24
  • Zacharewski , T. R. 1997 . In vitro bioassays for assessing estrogenic substances . Environ. Sci. Technol. , 31 ( 3 ) : 613 – 623 .
  • McKinney , J. D. and Waller , C. L. 1998 . Molecular determinants of hormone mimicry: halogenated aromatic hydrocarbon environmental agents . J. Toxicol. Environ. Health B. , 1 ( 1 ) : 27 – 58 .
  • Kwack , S. J. , Kwon , O. , Kim , H. S. , Kim , S. S. , Kim , S. H. , Sohn , K. H. , Lee , R. D. , Park , C. H. , Jeung , E. B. , An , B. S. and Park , K. L. 2002 . Comparative evaluation of alkylphenolic compounds on estrogenic activity in vitro and in vivo . J. Toxicol. Environ. Health A. , 65 ( 1–2 ) : 419 – 431 .
  • Svedenborg , E. , Pongratz , I. and Gustafsson , J. A. 2010 . Endocrine disruptors targeting ERbeta function . Int. J. Androl. , 33 ( 2 ) : 288 – 297 .
  • Mueller , G. C. and Kim , U. H. 1978 . Displacement of estradiol from estrogen receptors by simple alkyl phenols . Endocrinology. , 102 ( 5 ) : 1429 – 1435 .
  • White , R. , Jobling , S. , Hoare , S. A. , Sumpter , J. P. and Parker , M. G. 1994 . Environmentally persistent alkylphenolic compounds are estrogenic . Endocrinology. , 135 ( 1 ) : 175 – 182 .
  • Russ , A. S. , Vinken , R. , Schuphan , I. and Schmidt , B. 2005 . Synthesis of branched para-nonylphenol isomers: Occurrence and quantification in two commercial mixtures . Chemosphere , 60 ( 11 ) : 1624 – 1635 .
  • Kim , Y.-S. , Katase , T. , Sekine , S. , Inoue , T. , Makino , M. , Uchiyama , T. , Fujimoto , Y. and Yamashita , N. 2004 . Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography . Chemosphere , 54 ( 8 ) : 1127 – 1134 .
  • Thiele , B. , Heinke , V. , Kleist , E. and Guenther , K. 2004 . Contribution to the structural elucidation of 10 isomers of technical p-Nonylphenol . Environ. Sci. Technol. , 38 ( 12 ) : 3405 – 3411 .
  • Routledge , E. J. and Sumpter , J. P. 1997 . Structural features of alkylphenolic chemicals associated with estrogenic activity . J. Biol. Chem. , 272 ( 6 ) : 3280 – 3288 .
  • Tabira , Y. , Nakai , M. , Asai , D. , Yakabe , Y. , Tahara , Y. , Shinmyozu , T. , Noguchi , M. , Takatsuki , M. and Shimohigashi , Y. 1999 . Structural requirements of para-alkylphenols to bind to estrogen receptor . Eur. J. Biochem. , 262 ( 1 ) : 240 – 245 .
  • Preuss , T. G. , Gehrhardt , J. , Schirmer , K. , Coors , A. , Rubach , M. , Russ , A. , Jones , P. D. , Giesy , J. P. and Ratte , H. T. 2006 . Nonylphenol isomers differ in estrogenic activity . Environ. Sci. Technol. , 40 ( 16 ) : 5147 – 5153 .
  • Ahel , M. , Giger , W. and Koch , M. 1994 . Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment—I . Occurrence and transformation in sewage treatment. Water Res. , 28 ( 5 ) : 1131 – 1142 .
  • Ahel , M. , Giger , W. and Schaffner , C. 1994 . Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment—II . Occurrence and transformation in rivers. Water Res. , 28 ( 5 ) : 1143 – 1152 .
  • Shao , B. , Hu , J. , Yang , M. , An , W. and Tao , S. 2005 . Nonylphenol and nonylphenol ethoxylates in river water, drinking water, and fish tissues in the area of Chongqing, China . Arch. Environ. Contam. Toxicol. , 48 ( 4 ) : 467 – 473 .
  • Petrovic , M. , Eljarrat , E. , Lopez De Alda , M. J. and Barcelo , D. 2004 . Endocrine disrupting compounds and other emerging contaminants in the environment: a survey on new monitoring strategies and occurrence data . Anal. Bioanal. Chem. , 378 ( 3 ) : 549 – 562 .
  • Hu , J. Y. , Xie , G. H. and Aizawa , T. 2002 . Products of aqueous chlorination of 4-nonylphenol and their estrogenic activity . Environ. Toxicol. Chem. , 21 ( 10 ) : 2034 – 2039 .
  • Petrovic , M. , Barcelo , D. , Diaz , A. and Ventura , F. 2003 . Low nanogram per liter determination of halogenated nonylphenols, nonylphenol carboxylates, and their non-halogenated precursors in water and sludge by liquid chromatography electrospray tandem mass spectrometry . J. Am. Soc. Mass Spectrom. , 14 ( 5 ) : 516 – 527 .
  • Petrovic , M. , Diaz , A. , Ventura , F. and Barcelo , D. 2001 . Simultaneous determination of halogenated derivatives of alkylphenol ethoxylates and their metabolites in sludges, river sediments, and surface, drinking, and wastewaters by liquid chromatography-mass spectrometry . Anal. Chem. , 73 ( 24 ) : 5886 – 5895 .
  • Lee , B.-C. , Kamata , M. , Akatsuka , Y. , Takeda , M. , Ohno , K. , Kamei , T. and Magara , Y. 2004 . Effects of chlorine on the decrease of estrogenic chemicals . Water Res. , 38 ( 3 ) : 733 – 739 .
  • Kuruto-Niwa , R. , Nozawa , R. , Miyakoshi , T. , Shiozawa , T. and Terao , Y. 2005 . Estrogenic activity of alkylphenols, bisphenol S, and their chlorinated derivatives using a GFP expression system . Environ. Toxicol. and Pharmacol. , 19 ( 1 ) : 121 – 130 .
  • Vinken , R. , Schmidt , B. and Schäffer , A . 2002 . Synthesis of tertiary 14C-labelled nonylphenol isomers . J. of Labelled Compounds Radiopharmaceut. , 45 ( 14 ) : 1253 – 1263 .
  • Galve , R. , Nichkova , M. , Camps , F. , Sanchez-Baeza , F. and Marco , M. P. 2002 . Development and evaluation of an immunoassay for biological monitoring chlorophenols in urine as potential indicators of occupational exposure . Anal. Chem. , 74 ( 2 ) : 468 – 478 .
  • Routledge , E. J. and Sumpter , J. P. 1996 . Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen . Environ. Toxicol. Chem. , 15 ( 3 ) : 241 – 248 .
  • Rastall , A. C. , Neziri , A. , Vukovic , Z. , Jung , C , Mijovic , S. , Hollert , H. , Nikcevic , S. and Erdinger , L. 2004 . The identification of readily bioavailable pollutants in Lake Shkodra/Skadar using semipermeable membrane devices (SPMDs), bioassays and chemical analysis . Environ Sci Pollut. Res. Int. , 11 ( 4 ) : 240 – 253 .
  • Keiter , S. , Rastall , A. , Kosmehl , T. , Wurm , K. , Erdinger , L. , Braunbeck , T. and Hollert , H. 2006 . Ecotoxicological assessment of sediment, suspended matter and water samples in the upper Danube River. A pilot study in search for the causes for the decline of fish catches . Environ Sci. Pollut. Res. Int. , 13 ( 5 ) : 308 – 319 .
  • Moeder , M. , Martin , C. , Harynuk , J. , Gorecki , T. , Vinken , R. and Corvini , P. F.X. 2006 . Identification of isomeric 4-nonylphenol structures by gas chromatography-tandem mass spectrometry combined with cluster analysis . J. Chromatogr. A , 1102 ( 1–2 ) : 245 – 255 .
  • Sohoni , P. and Sumpter , J. P. 1998 . Several environmental oestrogens are also anti-androgens . J. Endocrinol. , 158 ( 3 ) : 327 – 339 .
  • Bitman , J. , Cecil , H. C. , Harris , S. J. and Fries , G. F. 1968 . Estrogenic activity of o p'-DDT in the mammalian uterus and avian oviduct . Science. , 162 ( 851 ) : 371 – 372 .
  • Kelce , W. R. , Stone , C. R. , Laws , S. C. , Gray , L. E. , Kemppainen , J. A. and Wilson , E. M. 1995 . Persistent DDT metabolite pp'-DDE is a potent androgen receptor antagonist . Nature. , 375 ( 6532 ) : 581 – 585 .
  • Tran , D. Q. , Klotz , D. M. , Ladlie , B. L. , Ide , C. F. , McLachlan , J. A. and Arnold , S. F. 1996 . Inhibition of progesterone receptor activity in yeast by synthetic chemicals . Biochem Biophys. Res. Commun. , 229 ( 2 ) : 518 – 523 .
  • Gundersen , J. L. 2001 . Separation of isomers of nonylphenol and select nonylphenol polyethoxylates by high-performance liquid chromatography on a graphitic carbon column . J. Chromatogr. A , 914 ( 1–2 ) : 161 – 166 .
  • Beresford , N. , Routledge , E. J. , Harris , C. A. and Sumpter , J. P. 2000 . Issues arising when interpreting results from an in vitro assay for estrogenic activity . Toxicol. Appl. Pharmacol. , 162 ( 1 ) : 22 – 33 .
  • Garcia-Reyero , N. , Requena , V. , Petrovic , M. , Fischer , B. , Hansen , P. D. , Diaz , A. , Ventura , F. , Barcelo , D. and Pina , B. 2004 . Estrogenic potential of halogenated derivatives of nonylphenol ethoxylates and carboxylates . Environ. Toxicol. Chem. , 23 ( 3 ) : 705 – 711 .

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