Çevredeki Alkifenoller ve Canlı Organizmalara Olan Zararlı Etkileri

Yıl 2009, Cilt: 2 Sayı: 1, 49 - 58, 01.03.2009

C Uğuz M İşcan İ Togan

Öz

Anahtar Kelimeler

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Alkylphenols in the Environment and Their Adverse Effects on Living Organisms

Öz

Alkilfenol bileşikleri (AFEO) iyonic olmayan yüzey aktif maddesi olarak deterjanlarda, ot ve böcek ilaçlarında, kozmeiklerde, plastik eşyalarda emülsifikatörlerde, boyalarda ve hatta uçak yakıtlarında çok yaygın kullanılan östrojenik endokrin sistem bozuculardır. Alkilfenol adı verilen AFEO bilişiklerinin türevlerinin hem suda hem de karada yaşayan canlılara zararlı etkileri olduğu rapor edilmiştir. Ayrıca, bunların hem östrojenik, hem toksik hem de karinojenik etkileri olduğu ortaya konmuştur. Bu nedenle, AFEO bileşikleriri ve türevlerinin doğadaki varoluşları, yapıları, biyolojik bozunumları, biyolojik birikimleri, metbolize edilme yolları ve insan dahil bütün canlı organizmalara olan zararlı etkileri karmaşık literatür taranarak potnsiyel zararlı etkileri anlaşılmaya çalışılmıştır. Bu literatür taraması ile doğada bulunan AFEO bileşikleri ve türevlerinin miktarlarının öldürücü dozlarda olmadığı anlaşılmıştır. Fakat, bu bileşiklerin ve türevlerinin öldürücü olmayan dozlarının da insan dahil bütün canlı organizmalarda hem östrojenik hem de karsinojenik etkilerinin olduğu ortaya konmuştur

Anahtar Kelimeler

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Kaynakça

• Nimrod AC, Benson WH (1996) Environmental estrogenic effects of akylphenol etoxylates. Crit Rev Toxicol, 26(3): 335-364.
• Sharpe RM (2001) Hormones and testis development and the possible adverse effects of environmental chemicals. Toxicol Lett, 120:221-232.
• Kris-Etherton PM, Hecker KD, Bonanome A, Coval SM, Binkoski AE, Hilpert KFA, Griel E, Etherton TD (2002) Bioactive compounds in foods: their role in the prevention of cardiovascular disease and cancer. American J Med, 113(9) Supp. (2): 71-88.
• McLachlan JA (1993) Functional toxicology: a new approach to detect biologically active xenobiotics. Environ Health Perspect, 101: 386-387.
• Colborn T, Clement C (1992) Chemically-induced alterations in sexual and functional development: the wildlife/human connection. Princeton, NJ: Princeton Sci Publications.
• Skakkebaek NE, Rajpert-De Meyts E, Main KM (2001) Testicular dysgenesis syndrome: an increasingly common developmental disorder with environmental aspects. Hum Reprod, 16: 972-978.
• Ademollo N, Ferrara F, Delise M, Fabietti F, Funari E (2008) Nonylphenol and octylphenol in human breast milk. Environ Internat, 34: 984-987.
• Dórea José G (2009) Alkylphenols and other pollutants contaminate human milk as well as cow's milk: formula feeding cannot abate exposure in nursing infants. Environ Internat, 35(2):451.
• Marselos M, Tomatis L (1992a) Diethylstilboestrol I: pharmacology, toxicology, and carcinogenicity in experimental animals. Eur J Canc, 29 :149-155.
• Marselos M, Tomatis L (1992b) Diethystilbestrol II: pharmacology toxicology, and carcinogenicity in experimental animals. Eur J Canc, 29:518-520.
• Rogan WJ, Gladen BC, McKinney JD, Careras N, Hardy P, Thullen J, Tinglestad J, Tully M (1987) Polychlorinated bihenyls (PCBs) and dichlorodiphenyl dichlorethane (DDE) in human milk: Effects on growth, morbidity and duration of lactation. Am J Public Health, 77:1294-1297.
• Kutz FW, Wood WH, Bottimore DP (1991) Organochlorine pesticides and polichlorinated biphenyls in human adipose tissue. Rev Environ Contam Toxicol, 120: 1-82.
• Guenther K, Heinke V, Thiele B, Kleist E, Prast H, Raecker T (2002) Endocrine disrupting nonylphenols are ubiquitous in food. Environ Sci Technol, 36:1676–80.
• Yang DK, Ding WH (2005) Determination of alkylphenolic residues in fresh fruits and vegetables by extractive steam distillation and gas chromatog- raphy–mass spectrometry. J Chromat A, 1088: 200–4.
• Ye X, Kuklenyik ZL, Needham LL, Calafat AM (2006). Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography–isotope dilution tandem mass spectrometry. J Chromat B, 831:110–5.
• Lu YY, Chen ML, Sung FC, Wang PSG, Mao IF (2007). Daily intake of 4-nonylphenol in Taiwanese, Environ, 33: 903-910.
• Soares A, Guieysse B, Jefferson B, Cartmell E, Lester JN (2008) Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Internat, 34: 1033–1049.
• Colborn T (1993) Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ Health Perspect, 101(5): 378-384.
• Safe SH (1995) Environmental and dietary estrogens in human health: is there a problem? Environ Health Perspect, 103:346-351.
• Department of the Environment (1993). Uses, fate and entry to the environment of NP ethoxylates, Final report.
• Jobling S, Sumpter JP (1993) Detergent components in sewage are weakly oestrogenic to fish: An in vitro study using rainbow trout (Onchorynchus mykiss) hepatocytes. Aquat Toxicol, 27: 361-372.
• Reinscheid UM (2009) Determination of the absolute configuration of two estrogenic nonylphenols in solution by chiroptical methods. J Mol Struct, 918(1-3):14-18.
• Skakkebaek NE, Meyts ERD, Jorgensen N, Carlsen E, Petersen PM., Giwercman A, Andersen AG, Jensen TK, Andersson AM, Muller J (1998) Germ cell cancer and disorders of spermatogenesis: an environmental connection? APMIS, 106 (1): 3-11.
• Veeramachaneni DNR (2000) Deteriorating trends in male reproduction: idiopathic or environmental?, Anim Reprod Sci, 60-61(2): 121-130.
• Brody JG, Moysich KB, Humblet O, Attfeild KR, Beehler GP, Rudel RA (2007) Environmental pollutants and breast cancer. Cancer, 109(12):2667–2711.
• Hughes PJ, McLellan H, Lowes DA, Khan SZ, Bilmen JG, Tovey SC, Godfrey RE, Michell RH, Kirk CJ, Michelangeli F (2000) Estrogenic alkylphenols induce cell death by inhibiting testis endoplasmic reticulum Ca2+ pumps. Biochem Biophy Res Commun, 277:568-574.
• Gong Y and Han XD (2006) Nonylphenol-induced oxidative stress and cytotoxicity in testicular Sertoli cells. Reprod Toxicol, 22:623-30.
• Gong Y, Pan XP, Huang Y, Gao ZS, Yu HX, Han X (2008) NP-induced biophysical and biochemical alterations of rat testicular Sertoli cell membranes related to disturbed intracellular Ca2+ homeostasis. Toxicol Let, 183(1-3):10-20.
• Tang H, Wang Y, Xie L, Mao O, Won SJ, Galvan V, Kunlin Jin K (2009) Effect of neural precursor proliferation level on neurogenesis in rat brain during aging and after focal ischemia. Neurobiol Aging, 30(2):299308.
• Montgomery-Brown J, Reinhard M (2003) Occurrence and Behavior of Alkylphenol Polyethoxylates in the Environment. Environ Eng Sci, 20(5): 471-486.
• Naylor CG, Mieure JP, Adams WJ, Weeks JA, Castaldi FJ, Ogle LD, Romano RR (1992) Alkylphenol Ethoxylate in the Environment. J American Oil Chem Soc, 69(7): 695-703.
• Brunner PH, Capli S, Marcomini A, Giger W (1988) Occurrence and behavior of linear alkylbenzene sulphonates, nonylphenol, nonylphenol mono- and nonylphenol diethoxylates in sewage and sewage sludge treatment. Water Res, 22: 1465-1472.
• Warhurst AM (1995) An environmental assessment of alkylphenol ethoxylates and alkylphenols. , Friends of the Earth, Edinburgh.
• Ahel M, McEvoy J, Giger W (1993) Bioaccumulation of the lipophilic metabolites of nonionic surfactants in freshwater organisms. Environ Pollut, 79: 243-248.
• Ahel M. and Giger W (1993) Partitioning of alkylphenols and alkylphenol polyethoxylates between water and organic solvents. Chemos, 26: 1471-1478.
• Ahel M, Giger W, Koch M (1994a) Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment. 1. Occurrence and transforma- tion in sewage treatment. Water Res, 28: 1131-1142.
• Ahel M, Giger W, Schaffner C (1994b) Behaviour of alkylphenol polyethoxylate surfactant in the aquatic environment. 2. Occurrence and transfor- mation in rivers. Water Res, 28: 1143-1152.
• Tyler CR, Jobling S, Sumpter JP (1998) Endocrine disruption in wildlife: A critical review of the evidence. Crit Rev Toxicol, 28: 319-361.
• Bennie DT, Sullivan CA, Lee HB, Peart TE, Maguire RJ (1997) Occurrence of alkylphenols and mono- and diethoxylates in natural waters of the Laurentian Great Lakes basin and the upper St. Lawrence River. Sci Tot Environ, 193: 263-275.
• CIR (Cosmetic Ingredient Review) (1996) Final amended report on nonoxynol-1, -2, -3, -4, -5, -6, -7, and -8. The Cosmetic, Toiletry, and Fragrance Association, Washington, D.C. June 4.
• Ahel M, Hrsak D, Giger W (1994c) Aerobic transformation of short-chain alkylphenol polyethoxylates by mixed bacterial cultures. Arch Environ Contam Toxicol, 26: 540-548.
• Hawrelak M, Bennett E, Metcalfe C (1999) The environmental fate of the primary degradation products of alkylphenol ethoxylate surfactants in recycled paper Sludge. Chemos, 39(5): 745-752.
• Ahel M, Scully FE, Hoigne J and Giger W (1994d) Photochemical degradation of nonylphenol and nonylphenol polyethoxylates in natural waters. Chemos, 28: 1361-1368.
• Marcomini A, Pojana G, Sfriso A, Quiroga AJM ( 2000) Behavior of anionic surfactants and their persistent metabolites in the Venice Lagoon, Italy. Environ Toxicol Chem, 19(8): 2000-2007.
• Talmage SS (1994) Environmental and human safety of major surfactants-alcohol ethoxylates and alkylphenol ethoxylates, In: The Soap and Deter- gent Association, Lewis Publication, Boca Raton, FL.
• Soto MA, Justicia H, Wray JW, Sonnenschein C (1991) p-Nonylphenol: an estrogenic xenobiotic released from “modified” polystyrene. Environ Health Perspect, 92: 167-173.
• Bolt HM, Janning P, Michna H (2001) Comparative assessment of endocrine modulators with oestrogenic activity: I. Definition of a hygienebased margin of safety (HBMOS) for xeno-oestrogens against the background of European developments. Arch Toxicol, 74: 649–662.
• Renner R (1997) European bans on surfactant trigger transatlantic debate. Environ Sci Tech, 31:316-320.
• Blankenship AL, Coady K (2005). Nonylphenol. In Encyclopedia of Toxicology, 2nd ed. (P.Wexler, Ed.), Vol. 3, pp. 260–263. Elsevier Academic Press, Oxford.
• Blackburn MA, Waldock MJ (1995) Concentrations of alkylphenols in rivers and estuaries in England and wales. Water Res, 29(7): 1623-1629.
• Blackburn MA, Kirby SJ, Waldock MJ (1999) Concentrations of alkylphenol polyethoxylates entering UK estuaries. Mar Pollut Bullet, 38: 109-118.
• Junk GA, Richard JJ, Grieser MD, Witiak D, Witiak JL, Arguello MD, Vick R, Svec, HJ, Fritz, JS, Calder GV (1974) Use of macroreticular resins in the analysis of water for trace organic contaminants, J Chromat A, 99: 745-762.
• Gilbert J, Startin JR, McGuinness JD (1986) Compositional analysis of commercial PVC bottles and studies of aspects and overall migration into foods and simulants. Food Addit Contam. 3(2): 133-144.
• Hale RC, Smith CL, De Fur PO, Harvey E, Bush EO, La Guardia MJ, Vadas GG (2000) NPs in sediments and effluents associated with diverse wastewater outfalls. Environ Toxicol Chem, 19(41):946-952.
• Jobling S, Sheahan D, Osborne JA, Matthissen P, Sumpter JP (1996) Inhibition of testicular growth in rainbow trout (Onchorynchus mykiss) ex- posed to estrogenic akylphenolic chemicals. Environ Toxicol Chem, 15(2): 194-202.
• O’Halloran SL, Liber K, Gang JA, Knuth ML (1999) Effects of repeated exposure to-NP on the zooplankton community in littoral enclosures. Environ Toxicol Chem, 18(3): 386-393.
• Daston GP, Gooch JW, Breslin WJ, Shuey DL, Nikiforov AI, Fico TA, Gorsuch J (1997) Environmental estrogens and reproductive health: A discussion of the human and environmental data. Reprod Toxic Rev, 11(4): 465-481.
• Lewis SK, Lech JJ (1996) Uptake, disposition, and persistence of nonylphenol from water in rainbow trout (Oncorhynchus mykiss). Xenobiot, 26: 813-819.
• Ekelund R, Bergman A, Granmo A, Berggren M (1990) Bioaccumulation of 4-nonylphenol in marine animals A re-evaluation. Environ Poll, 64: 107-120.
• Thibaut R, Debrauwer L, Rao D, Cravedi JP (1998) Metabolism of [3H]-4-n-nonylphenol in rainbow trout. Mar Environ Res, 46(1-5): 12521-524.
• Thibaut R, Debrauwer L, Rao D, Cravedi JP (1998)Metabolism of [3H]-4-n-nonylphenol in rainbow trout, Mar Environ Res, 46(1-5): 12521-524.
• Thibaut R, Debrauwer L, Rao D, Cravedi JP (1999) Urinary metabolites of 4-n-nonylphenol in rainbow trout (Oncorhynchus mykiss). Sci Tot Environ, 233(1-3): 193-200.
• Arukwe A, Nilsen BM, Karin B, Goksoyr A (1999) Immunohistochemical analysis of the vitellogenin response in the liver of Atlantic salmon exposed to environmental oestrogens. Biomarkers, 4:373–380
• Arukwe A, Goksİyr A, Thibaut R, Cravedi JP (2000). Metabolism and organ distribution of nonylphenol in Atlantic salmon (Salmo salar). Marine Environ Res, 50(1-5): 141-145.
• Pedersen RT, Hill EM (2000) Identification of novel metabolites of the xenoestrogen 4-tert-octylphenol in primary rat hepatocytes. Chem-Biol Interact, 128: 189-209.
• Coldham NG, Sivapathasundaram S, Dave M, Ashfield LA, Pottinger TG, Goodall C, Sauer MJ (1998) Biotransformation, tissue distribution, and persistence of 4-nonylphenol residues in juvenile rainbow trout (Oncorhynchus mykiss). Drug Metab Dispos, 26: 347-354.
• Ferreira-Leach AMR, Hill EM (2001) Bioconcentration and distribution of 4-tert-octylphenol residues in tissues of the rainbow trout (Oncorhynchus mykiss). Mar Environ Res, 51(1): 75-89.
• White R, Jobling S, Hoare SA, Sumpter JP, Parker MG (1994) Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135: 175-182.
• Legler J (1999) Development of a stably transfected estrogen receptor-mediated luciferase reporter gene assaying the human T47D breast cancer cell
• line. Toxicol Sci, 48(1): 55-56.
• Gong Y, WuJ, HuangY, Shena S, Han X (2009) Nonylphenol induces apoptosis in rat testicular Sertoli cells via endoplasmic reticulum stres. Toxicol Let, 186: 84–95.
• Sheahan D, Haries J (1992) Effects of trace organic in fish, a joint study between the Directorate of Fisheries Research of the Ministry of Agricul- ture, Fisheries and Food , Brunel University and the Water Reassert Center.
• Sharpe RM, Skakkebaek NE (1993) Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet, 341: 1392-1395.
• Wolf MS Toniolo P, Lee EW, Rivera M, Dubin N (1993) Blood levels of organochlorin residues and risk of breast cancer. J Natl Cancer Inst, 85: 648-52.
• Vetillard A, Bailhache T (2006). Effects of 4-n-nonylphenol and tamoxifen on salmon gonadotropin-releasing hormone, estrogen receptor, and vitellogenin gene expression in Juvenile Rainbow Trout. Toxicol Sci, 92: 537–544.
• Giesy JP, Pierens SL, Snyder EM, Miles-Richardson S, Kramer VJ, Snyder SA, Nichols KM, Villeneuve DA (2000) Effects of 4-nonylphenol on fecundity and biomarkers of estrogenicity in fathead minnows (Pimphales promelas). Environ Toxicol Chemist, 19(5): 1368-1377.
• Sonnenschein C, Soto AM (1998) An updated review of environmental estrogen and androgen mimics and antagonists. J Steroid Biochem Mol Biol, 165: 143-150.
• Arukwe A, Goksoyr A (1998) Xenobiotics, xenoestrogens and reproduction disturbances in fish. Sarsia, 83: 225-241.
• Desbrow C, Routledge E, Sheehan D, Waldock M, Sumpter J (1996) The identification and assessment of estrogenic substances in sewage treatment works effluents P2-,490/7. Riohouse, Bristol: Environment Agency.
• Lech JJ, Lewis SK, Ren LF (1996) In vivo estrogenic activity of nonylphenol in rainbow trout. Fund Appl Toxicol, 30: 229-232.
• Christiansen LB, Pedersen KL, Korsgaard B, Bjerresgaard P (1998a) Estrogenicity of xenobiotics in rainbow trout (Oncorhynchus mykiss) using in vivo synthesis of vitellogenin as a biomarker. Mar Environ Res, 46: 137-140.
• Korsgaard B, Pederson KL (1998) Vitellogenin in Zoarces viviparus: purification, quantification by ELISA and induction by estradiol -17ß and 4- nonylphenol. Comp Biochem Physiol, 120: 159-166.
• Sumpter JP, Jobling S (1995) Vitellogenesis as a biomarker of estrogenic contamination in the aquatic environment. Environ Health Perspect, 103: 173- 178.
• Harries JE, Sheahan DA, Jobling S, Matthiessen P, Neall P, Sumpter JP, Tylor T, Zaman N. (1997) Estrogenic activity in five United King- dom rivers detected by measurement of vitellogenesis in caged male trout. Environ Toxicol Chem, 16: 534-542.
• Islinger M, Pawlowski S, Hollert H., Völkl A, Braunbeck T (1999). Measurement of vitellogenin-mRNA in primary cultures of rainbow trout hepatocytes in a non-radioactive dot blot/RNAse protection assay. Sci Total Environ, 233: 109-122.
• Gimeno S, Komen H, Gerritsen A,, Bowmer T (1998) Feminization of common carp, Cyprinus carpio, exposed to 4-tert-pentylphenol during sexual differentiation. Aquat Toxicol, 43(2-3): 77-92.
• Arukwe, A., Knudson, Gorksoyr, A (1997a) Fish zona radiata (egg-shell) protein: a sensitive biomarker for environmental estrogens. Environ Health Perspect, 105: 418-422.
• Mommsen TP, Walsh PJ (1988) Vitellogenesis and oocytes assembly. In: Hoar, W. S., Randall, D. J. (Eds.), Fish Physiol. The physiology of devel- oping fish. Part. A Eggs and Larvae, 11, 347-406.
• Oppen-Berntsen DO, Hyllner SJ, Haux C, Helvik JV, Walther BT (1992) Eggshell zona radiata-proteins from cod (Gadus morhua): extra-ovarian origin and induction by estradiol-17ß. Int J Dev Biol, 36: 247-254.
• Lee C, Na JG, Lee KC, Park K (2003) Choriogenin mRNA induction in male medaka, Oryzias latipes as a biomarker of endocrine disruption. Aquat Toxicol, 61(3-4): 233-41.
• Nice HE (2005) Sperm motility in the Pacific oyster (Crassostrea gigas) is affected by nonylphenol. Mar Pollut Bull, 50: 1668–1674.
• Le Gac F, Thomas J, Mourot B, Loir M (2001). In vivo and in vitro effects of prochloraz and nonylphenol ethoxylates on trout spermatogenesis. Aquatic Toxicol, 53 (3-4): 187-200.
• Lahnsteiner F, Berger B, Grubinger F, Weismann T (2005) The effect of 4-nonylphenol on semen quality, viability of gametes, fertilization success, and embryo and larvae survival in rainbow trout (Oncorhynchus mykiss). Aquatic Toxico, 71(4): 297-306.
• Arslan OC, Parlak H, Oral R, Katalay S (2007). The effects of nonylphenol and octylphenol on embryonic development of sea srchin (Paracentrotus lividus). Arch Environ Contam Toxicol, 53: 214-21994.
• Ashfield LA, Pottinger TG, Sumpter JP (1998) Exposure of female juvenile rainbow trout to alkylphenolic compounds results in modifications to growth and ovosomatic index. Environ Toxicol Chem, 17: 679–686.
• Adeoya-Osiguwa SA, Markoulaki S, Pocock V, Milligan SR, Fraser LR (2003) 17ß-Estradiol and environmental estrogens significantly affect mammalian sperm function. Hum Reprod, 18(1): 100-107.
• Fraser LR, Beyret E, Milligan, SR, Adeoya-Osiguwa SA (2006) Effects of estrogenic xenobiotics on human and mouse spermatozoa. Human Reprod, 21: 1184-1193.
• Schreck CB (1974) Hormonal treatment and sex manipulation in fishes. Control of Sex in Fishes. pp. 84-106. Virginia Polytechnic Institute and State University Sea Grant Extension Division, Blacksburg, Virginia.
• Hunter GA, Donaldson EM (1983). Hormonal sex control and its application to fish culture. In Fish Physiology. (W.S., Hoar, D.J. Randall, and E.M. Donaldson, eds.)Vol. 9B, pp. 223-303. Academic press, New York.
• Shelton WL, Hopkins KD, Jensen G (1978) Use of hormones to produce monosex tilapia. In Culture of exotic fishes symposium proceedings Fish Culture Section. (R. O. Smitherman, W. L. Shelton, and J. L. Grover, eds) pp. 10-33. Ed., American Fisheries Society, Auburn, Alabama.
• Piferrer F, Baker II, Donaldson EM (1993). Effects of natural synthetic, aromatizable, and non aromatizable androgens on the resulting of coho salmon (Onchorhynchus tshawytscha). Gen Comp Endocrinol, 91: 59-65.
• van den Hurk, Slof GA (1981) A morphological experimental study of gonadal sex differentiation in the rainbow trout, Salmo gairdneri. Cell Tis Res, 218: 487-497.
• Garret GP (1989) Hormonal sex control of largemouth bass. The progressive Fish-Culturist, 51: 146-148.
• Gray MA, Metcalfe CD (1997) Induction of testis-ova in Japanese medaka (Oryzias latipes) exposed to p-nonylphenol. Environ Toxicol Chem, 16: 1082-1086.
• Metcalfe CD, Metcalfe TL, Kiparissis Y, Koenig BG, Khan, C, Hughes RJ, Croley TR, March RE, Potter T (2001) Estrogenic potency of chemicals detected in sewage treatment plant effluents as determined by in vivo assays with Japanese medaka (Oryzias latipes). Environ Toxicol Chem, 20(2): 297-308.
• Henderson BE, Ross RR, Pike M (1993) Hormonal chemoprevention of cancer in women. Science, 259: 633-638.
• Safe S, Connor K, Gaido K (1998) Methods for xenoestrogen testing. Toxicol Lett, 102(103): 665-670.
• SafeSH, GaidoK (1998) Phytoestrogens and anthropogenic estrogenic compounds. Environ Toxicol Chem, 17(1): 119–126.
• Mellanen P, Petänen T, Lehtimäki J, Mäkelä S, Bylund G, Hombolm B, Mannila E, Oikari A, Santti R (1996) Wood-derived estrogens, studies in vitro with breast cancer cell lines and in vivo in trout. Toxicol Appl Pharmacol, 136: 381-388.
• Banerjee SK, Roy D (1996) Is exposure of cells to environmental estrogen-like chemicals able to induce telemoric associations? Proc Am Assoc Cancer Res. 37:457-462.
• Gilliland FD, Key CR (1995) Male genital cancers. Cancer, 75: 295-315.
• Argese E, Marcomini A, Miana P, Bettiol C, Perin G (1994) Submitochondrial particle response to linear alkylbenzen sulfonates, nonylphenol polyethoxylates and their biodegradation derivatives. Environ Toxicol Chem, 13: 737-742.
• Mcleese DW, Zitko V, Sergeant DB, Burridge L, Metcalfe CD (1981) Lethality and accumulation of alkylphenols in aquatic fauna. Chemosphere, 10: 723-730.
• Chavpil M, Eskelson CD, Stiffel V, Owen JA, Droegmuller W (1980) Studies of nonoxynol-9. II. Intravaginal absorption, distribution, metabolism and excretion in rats and rabbits. Contracept, 22: 325-331.
• Buttar HS, Swierenga SHH, Matula TL (1986) Evaluation of the cytotoxicity and genotoxicity of the spermicides nonoxynol-9 and octoxynol-9. Toxicol Lett, 31: 65-73.
• Walter BA, Agha BJ , Digens GA (1998) Disposition of [14C] nonoxynol-9 after intravenous or vaginal administration to female Spraugue-Dawley rats. Toxicol Appl Pharmacol, 96: 258-270.
• Jick H, Walker AM, Rothman KJ, Hunter JR, Homes LB, Watkins RN, D’Ewart DC, Danford A, Madsen S (1981) Vaginal spermicides and congenital disorders. JAMA, 245: 1329-1981.
• Long SD, Wareen AJ, Little JB (1982) Effect of nonoxynol-9, a detergent with spermicidal activity, on malignant transformation in vitro. Carcinogen, 3: 553.
• Preston-Martin S, Pike MC, Ross RK, Jones PA, Henderson BE (1990) Increased cell divisions a cause of human cancer. Canc Res, 50: 7415-7421.
• Atkinson A, Roy D (1995a) In vivo genotoxicity of bisphenol A. Environ Mutagen, 26: 60-66.
• Atkinson A, Roy D (1995b) In vitro conversion of estrogenic compound bisphenol A to binding metabolites. Biochem Biophys Res Commun, 210: 424-433.
• Atienzar A, Billinghurst Z, Depledge MH (2002) 4-n-Nonylphenol and 17-β estradiol may induce common DNA effects in developing barnacle larvae. Environ Pollut, 120: 735–738.
• Ruggeri B, Ubaldi M, Lourdusamy A, Soverchia L, Ciccocioppo R. Hardiman G, Baker ME, Palermo F, Polzonetti-Magni AM (2008) Variation of the genetic expression pattern after exposure to estradiol-17β and 4-nonylphenol in male zebrafish (Danio rerio). Gen Comp Endoc, 158(1): 138-144.
• Kortner TM, Rocha E, Arukwe A (2009) Previtellogenic oocyte growth and transcriptional changes of steroidogenic enzyme genes in immature female Atlantic cod (Gadus morhua L.) after exposure to the androgens 11-ketotestosterone and testosterone. Comp. Biochem Physiol Part A, 152: 304– 313.
• Sung HH, Ye YZ (2009) Effect of nonylphenol on giant freshwater prawn (Macrobrachium rosenbergii) via oral treatment: Toxicity and messenger RNA expression of hemocyte genes. Aquat Toxicol, 91: 270–277.
• Burkhardt-Holm P, Peter A, Segner H (2002) Decline of fish catch in Switzerland. Aquatic Science, 64: 36–54.
• Miles-Richardson SR, Pierens SL, Nichols KM, Kramer VJ, Snyder EM, Snyder SA, Render JA, Fitzgerald SD, Giesy JP (1999) Effects of waterborne exposure to 4-nonylphenol and nonylphenol ethoxylate on secondary sex characteristics and gonads of fathead minnows (Pimephales promelas). Environ Res, 80 (2):122-S137.
• Uğuz C, İşcan M, Ergüven A, Togan İ. (2003) The bioaccumulation and its adverse effects on the liver of rainbow trout (Onchorynchus mykiss). Environ Res, 92: 262-270.
• Lee PC, Patra SC, Stelloh CT, Lee W, Struve M. (1996) Interaction of nonylphenol and hepatic CYP1Ain rats. Biochem Pharmacol, 52: 885-889.
• Landi S (2000) Mammalian class theta GST and differential susceptibility to carcinogens: a review. Mutat Res, 463: 247–283.
• Cakmak G, Uğuz, C, Togan İ, Severcan, F (2003) Rainbow trout livers exposed to nonylphenol display extensive structural and compositional changes on infrared spectroscopy. Appl Spectros, 57: 835–841.