Toxicity of Ortho-Phenylphenol (OPP) and Sodyum Ortho-Phenylphenate (SOPP)

Yıl 2020, Cilt: 8 Sayı: 1, 18 - 29, 30.04.2020

Selinay Başak Erdemli Köse Fatma Kocasarı

https://doi.org/10.24998/maeusabed.701208

Cited By: 2

Öz

Ortho-phenylphenol (OPP) and its sodium (SOPP) salt have been used world-wide for decades as fungicides and disinfectants. OPP is generally used as a hospital and household disinfectant, whereas SOPP is used as a fungicide, which post-harvest treatment of citrus fruits and vegatables for the prevention of mold. Due to widespread use, including many consumer applications, the fate of OPP in the mammalian organism has been the subject of numerous investigations over many years. The aim of this review is to give information about OPP and SOPP including metabolism, general toxicity, carcinogenicity and genotoxicity.

Anahtar Kelimeler

Ortho-Phenylphenol, Sodyum ortho-Phenylphenate, Toxicity

Kaynakça

• Appel, K.E., 2000. The carcinogenicity of the biocide ortho-phenylphenol. Archives of Toxicology 74, 61-71.
• Bajaj, K.L., Miller, I.R., Bhatia, I.S., 1976. Metabolism of 2-hydroxybiphenyl & 4-hydroxybiphenyl in albino mice. Indian Journal of Experimental Biology 14, 329-331.
• Balakrishan, S., Eastmond, D.A., 2006. Micronuclei and cell proliferation as early biological markers of orho-phenylphenol-induced changes in the bladder of male F344 rats. Food and Chemical Toxicology 44, 1340-1347.
• Balakrishnan, S., Uppala, P.T., Rupa, D.S., Hasegawa, L., Eastmond, D.A., 2002. Detection of micronuclei, cell proliferation and hyperploidy in bladder epithelial cells of rats treated with o-phenylphenol. Mutagenesis 17, 89-93.
• Bomhard, E., 1991. Preventol O extra (Schuppen) – Untersuchungenzur akuten dermalen Toxizitaet an maennlichen und weiblichen Wistar-Ratten. Bayer AG, Report No.19831.
• Bomhard, E.M., Brendler-Schwaab, S.Y., Freyberger, A., Herbold, B.A., Leser, K.H., Richter, M., 2002. o-Phenylphenol and its sodium and potassium salts: a toxicological assessment. Critical Reviews in Toxicology 32, 551-625.
• Brusick, D., 2005. Analysis of genotoxicity and the carcinogenic mode of action for ortho-phenylphenol. Environmental and Molecular Mutagenesis 45, 460-481.
• Christenson, W.R., Whale, B.S., Bartels, M.J., Cohen, S.M., 1996. Technical grade orthophenylphenol: A 32P-postlabeling study to examine the potential for the formation of DNA adducts in the urinary bladder of male rats. The Dow Chemical Inc. Laboratory Project I.D. 94-972-AV.
• DPR, 2007. Ortho-Phenylphenol and sodium ortho-phenylphenate Risk Characterization Document Dietary Exposure. California Environmental Protection Agency, ABD.
• Ernst, W., 1965. Umwandlung und Ausscheidung von 2-hydroxydiphenyl bei der Ratte. Arzneimittelforschung 15, 632-636. Fujii, T., Hiraga, K., 1985. Carcinogenicitytesting of sodium ortho-phenylphenate in F344 rats. Journal of Saitama Medical School 12, 277-287.
• Fujii, T., Nakamura, K., Hiraga, K., 1987. Effects of pH on the carcinogenicity of o-phenylphenol and sodium ophenylphenate in the rat urinary bladder. Food and Chemical Toxicology 25, 359-362.
• Fukushima, S., Hasegawa, R., Kurata, Y., Okuda, M., Hatano, A., Ito, N., 1982. Histopathological and ultrastructural analysis of urinary bladder lesions in animals induced by sodium o-phenylphenate. Proceedings of Japan Cancer Association (41th Annual Meeting, 314, (abstract).
• Fukushima, S., Inoue, T., Uwagawa, S., Shibata, M.A., Ito, N., 1989. Cocarcinogenic effects of NaHCO3 on ophenylphenol-induced rat bladder carcinogenesis. Carcinogenesis 10, 1635-1640.
• Gilbert, K.S., 1994. Dowicidetm1 antimicrobial; primary dermal irritation study in New Zealand White rabbits. Dow Chemical, Report No. K-001024–057b.
• Gilbert, K.S., Crissman, J.W., 1994. Dowicidetm1 antimicrobial; acute oral toxicity study in Fischer 344 rats. Dow Chemical, Report No. K-001024–057a.
• Grossman, J., 1995. What's hiding under the sink: dangers of household pesticides. Environmental Health Perspectives 103, 550-554.
• Hasegawa, R., Nakaji, Y., Kurokawa, Y., Tobe, M., 1989. Acute toxicity tests on 113 environmental chemicals. The science reports of the research institutes, Tohoku University, 36, 1–4.
• Hasegawa, R., Takahashi, S., Asamoto, M., Shirai, T., Fukushima, S., 1990. Species differences in sodium o-phenylphenate induction of urinary bladder lesions. Cancer Letters 50, 87-91.
• Hiraga, K., Fujii, T., 1981. Induction of tumors of the urinary system in F344 rats by dietary administration of sodium o-phenylphenate. Food and Cosmetics Toxicology 19, 303-310.
• Hiraga, K., Fujii, T., 1984. Induction of tumors of the urinary bladder in F344 rats by dietary administration of o-phenylphenol. Food and Chemical Toxicology 22, 865-870.
• Honma, Y., Kakizoe, T., Komatsu, H., Niijima, T., Sugimura, T., 1983. Increased agglutinability of bladder epithelial cells by concanavalin A in rats fed several biphenyl derivatives. Journal of Cancer Research and Clinical Oncology 106, 176-178.
• Hussain, T., Tan, B., Yin, Y., Blachier, F., Tossou, M.C., Rahu N., 2016. Oxidative stress and inflammation: What polyphenols can do for us? Oxid Med Cell Longevity, Article ID 7432797. doi: 10.1155/2016/7432797.
• Inoue, S., Yamamoto, K., Kawanishi, S., 1990. DNA damage induced by metabolites of o phenylphenol in the presence of copper(II) ions. Chemical Research in Toxicology 3, 144-149.
• Jang, H., Nde, C., Toghrol, F., Bentley, W.E., 2008. Microarray analysis of toxicogenic effects of ortho-phenylphenol in Staphylococcus aureus. BMC Genomics 9, 411.
• Kawachi, T., Yahagi, T., Kada, T., Tazima, Y., Ishidate, M., Sasaki, M., Sugiyama, T., 1981. Cooperative programme on short-term assays for carcinogenicity in Japan. IARC Scientific Publications 27, 323-330.
• Kojima, A., Fujita, H., Hiraga, K., 1983. Mutagenicity of ophenylphenol (OPP) in the microbial system. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 34, 319-324.
• Kojima, A., Hiraga, K., 1978. Mutagenicity of citrus fungicides in microbial system. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 29, 83-85.
• Kwok, E.S.C., Eastmond, D.A., 1997. Effects of pH on nonenzymatic oxidation of phenyl-hydroquinone: potential role in urinary bladder carcinogenesis induced by ophenylphenol in Fischer 344 rats. Chemical Research in Toxicology 10, 742-749.
• Kwok, E.S.C., Silva, M.H., 2013. Re-evaluation of Developmental and Reproductive Toxicity of Ortho-Phenylphenol (OPP) and Sodium Ortho-Phenylphenate (SOPP). Cell and Developmental Biology 2(3), 1-12.
• Lambert, A.C., 1992. Mechanisms of genotoxicity induced by the ortho-phenylphenol metabolites phenylhydroquinone and phenylbenzoquinone. Master Thesis, Univercity of California Riverside.
• Lambert, A.C., Eastmond, D.A., 1994. Genotoxic effects of the o-phenylphenol metabolites phenylhydroquinone and phenylbenzo-quinone in V79 cells. Mutation Research 322, 243-256.
• Landry, T.D., Stebbins, K.E., Battjes, J.E., 1992. Orthophenylphenol: acute aerosol inhalation toxicity study in Fischer 344 rats. Dow Chemical, Report No. K-001024–049.
• Li J, Yang G, Wang S, Jiang L, Liu X, Geng C, Zhong L, Chen M., 2012. The protective effects of hydroxytyrosol against ortho-phenylphenol-induced DNA damage in HepG2 cells. Toxicology Mechanisms and Methods 22(6), 432-437.
• Lyr, H., 1995. Aromatic hydrocarbon fungicides and their mechanism of action. In: Modern selective fungicides. Gustav Fischer, pp 75-98.
• Maertins, T., 1988. Preventol ON: Untersuchungen zum Reiz-/Aetzpotential an Haut und Auge (Kaninchen) nach OECD-Richtlinie No. 404 und 405. Bayer AG Report- No. 16951.
• Mihail, F., Kimmerle, G., 1977. Preventol O und Preventol ON: Bestimmung der Inhalations-toxizitaet. Bayer AG, Report.
• Morimoto, K., Sato, M., Fukuoka, M., Hasegawa, R., Takahashi, T., Tsuchiya, T., Tanaka, A., Takahashi, A., Hayashi, Y., 1989. Correlation between the DNA damage in urinary bladder epithelium and the urinary 2– phenyl-1,4–benzoquinone levels from F344 rats fed sodium o-phenylphenate in the diet. Carcinogenesis 10, 1823–1827.
• Murata, M., Moriya, K., Inoue, S., Kawanishi, S., 1999. Oxidative damage to cellular and isolated DNA by metabolites of a fungicide ortho-phenylphenol. Carcinogenesis 20(5), 851-857.
• Nakagawa, Y., Tayama, K., 1988. Effect of buthionine sulfoximine on ortho-phenylphenol-induced hepato- and nephrotoxic potential in male rats. Archives of Toxicology 62, 452-457.
• Nakagawa, Y., Tayama, S., 1996. Induction of 8–hydroxy-2´-deoxyguanosine in CHO-KL cells exposed to phenylhydroquinone, a metabolite of ortho-phenylphenol. Cancer Letters 101, 227–232.
• Nakamura, K., Iguchi, S., Ikeda, T., Hiraga, K., 1981. Subacute toxicity of o-phenylphenol by food administration to male rats. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 32, 33-39.
• Nakao, T., Ushiyama, K., Kabashima, J., Nagai, F., Nakagawa, A., Ohno, T., Ichikawa, H., Kobayashi, H., Hiraga, K., 1983. The metabolic profile of sodium o-phenylphenate after subchronic oral administration to rats. Food and Chemical Toxicology 21, 325-329.
• Nde, C.W., Jang, H.J., Toghrol, F., Bentley, W.E., 2008. Toxicogenomic response of Pseudomonas aeruginosa to ortho-phenylphenol. BMC Genomics 9, 473.
• Norris, J.M., 1971a. Product chemistry, acute toxicological organisms data for Dowicide-1 antimicrobial. Dow Chemical Company, DPR Vol. 129-0044.
• Norris, J.M., 1971b. Toxicology and residue data on Dowicide A antimicrobial. Dow Chemical Company, DPR Vol. 50438-0007.
• NTP, 1986. Technical report on the toxicology and carcinogenesis studies of ortho phenylphenol (CAS No. 90–43–7) alone and with 7,12–dimethylbenz(a)anthracene (CAS No. 57–97–6) in Swiss CD-1 mice dermal studies). NIH Publication No. 85–2557, NTP 84–099, US Department of Health and Human Services, NTP TR 301.
• Oehme, F.W., 1971. Comparative toxicity of o-phenylphenol and an o-phenolphenol containing disinfectant. Toxicology and Applied Pharmacology 19, 412.
• Ogata, A., Ando, H., Kubo, Y., Hiraga, K., 1979. Acute oral toxicity of sodium o-phenylphenate (OPP-Na) in mice. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 30, 54-56.
• Okuda, M., 1986. Pathological analysis of the carcinogenic effect of sodium o-phenylphenol and o-phenylphenol in the urinary bladder of rats and mice. Journal of the Nagoya City University Medical Association 37, 157-184.
• Pathak, D.N., Roy, D., 1992. Examination of microsomal cytochrome P450–catalyzed in vitro activation of ophenylphenol to DNA binding metabolite(s) by 32P postlabeling technique. Carcinogenesis 13, 1593-1597.
• Pathak, D.N., Roy, D., 1993. In vivo genotoxicity of sodium ortho-phenylphenol: phenylbenzoquinone is one of the DNA-binding metabolite(s) of sodium orthophenylphenol. Mutation Research 286, 309-319.
• Pauluhn, J., 1983. Preventol ON extra: Untersuchungen auf hautund schleimhautreizende Wirkung. Bayer AG, Report.
• Reid TM, DeBord DG, Cheever KL, Savage RE Jr., 1998. Mutagenicity of N-OH-MOCA (4-amino-4'-hydroxylamino-bis-3,3'-dichlorodiphenylmethane) and PBQ (2-phenyl-1,4-benzoquinone) in human lymphoblastoid cells. Toxicology Letters 95(3), 205-210.
• Reitz, R.H., Fox, T.R., Quast, J.F., Hermann, E.A., Watanabe, P.G., 1983. Molecular mechanisms involved in the toxicity of o-phenylphenol and its sodium salt. Chemico-Biological Interactions 43, 99-119.
• Reitz, R.H., Fox, T.R., Quast, J.F., Hermann, E.A., Watanabe, P.G., 1984. Biochemical factors involved in the effects of orthophenylphenol (OPP) and sodium orthophenylphenate (SOPP) on the urinary tract of male F44 rats. Toxicology and Applied Pharmacology 73, 345-349.
• Roy, D., 1990. Cytochrome P-450 catalyzed redox cycling of orthophenylphenol. Biochemistry International 22, 849-857.
• Savides, M.C., Oehme, F.W., 1980. Urinary metabolism of orally administered ortho-phenylphenol in dogs and cats. Toxicology 17, 355-363.
• Schreiber, G., 1981. Pruefung von Peventol O extra auf Schleimhautreizwirkung. Fraunhofer-Institut für Toxikologie und Aerosolforschung.
• Selim, M., 1996. A single dose open label study to investigate the absorption and excretion of 14C/13C-labeled ortho-phenylphenol formulation after dermal application to healthy volunteers. Pharma Bio-Research Clinics BV, Assen, Netherlands, Report No. P0995002.
• Shibata, M.A., Hagiwara, A., Tamano, S., Fukushima, S., Ito, N., 1985. Subchronic toxicity study of sodiumo-phenylphenate in mice. Toxicology Letters 25, 239-246.
• St. John, M.K., Arnold, L.L., Cano, M., Johansson, S.L., Cohen, S.M., 2001. Dietary Effects of ortho-Phenylphenol and Sodium ortho-Phenylphenate on Rat Urothelium. Toxicological Sciences 59(2), 346-351.
• Suberg, H., 1983. Preventol O extra (OPP): Untersuchung auf primaere Reiz-/Aetzwirkung an der Kaninchenhaut. BAYER AG Institut für Toxikologie, Report.
• Suzuki, H., Suzuki, N., Sasaki, M., Hiraga, K., 1985. Orthophenylphenol mutagenicity in a human cell strain. Mutation Research 156, 123-127.
• Tadi-Uppala., P., Hasegawa, L., Rupa, D.S., Eastmond, D.A., 1996. Detection of micronuclei and cell proliferation in the rat bladder induced by the fungicides o-phenylphenol and sodium ortho phenylphenate. Carcinogenesis 37, 127-128 (abstract).
• Taniguchi, Y., Morimoto, J., Okada, K., Imai, S., Tsubura, Y., 1981. Toxicological study of sodium orthophenylphenate (OPP-Na) in rats. II. Acute oral toxicity in Fischer 344 DuCrj rats. Journal of the Nara Medical Association 32, 709-714.
• Tayama, K., Iguchi, S., Hiraga, K., 1979. Acute oral toxicity of sodium o-phenylphenol (OPP-Na) in rats. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 30, 57-65.
• Tayama, K., Iguchi, S., Sasaki, M., Hiraga, K., 1983. Acute oral toxicity of o-phenylphenol (OPP) in mice. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 34, 325-328.
• Tayama, S., Kamiya, N., Nakagawa, Y., 1989. Genotoxic effects of o-phenylphenol metabolites in CHO-K1 cells. Mutation Research 223, 23-33.
• Tayama, S., Nakagawa, Y., 1991. Sulfhydryl compounds inhibit the cyto- and genotoxicity of o phenylphenol metabolites in CHO-K1 cells. Mutation Research 259, 1-12.
• Thyssen, J., 1982. Preventol O extra: Gewerbetoxikologische Untersuchungen. Bayer AG, Report No. 10541.a
• Ushiyama, K., Kabashima, J., Nakao, T., 1982. Metabolism of 2-phenylphenol (OPP) in rats: metabolic profile of OPP in rats fed dietary for long period. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 33, 455-457.
• Ushiyama, K., Kabashima, J., Nakao, T., 1983. Metabolism of o-phenylphenol sodium salt (OPPNa) in rats: dose response of metabolic profile of OPP. Annual Report of the Tokyo Metropolitan Research Laboratory of Public Health 34, 297-298.
• Ushiyama, K., Nagai, F., Nakagawa, A., Kano, I., 1992. DNA adduct formation by o-phenyphenol metabolite in vivo and in vitro. Carcinogenesis 13, 1469-1473.
• WHO, 2003. 2-Phenylphenol and its sodium salt in drinking-water. Background document for preparation of WHO Guidelines for drinking-water quality. Geneva, World Health Organization (WHO/SDE/WSH/03.04/69).
• Wick, L.Y., Gschwend, P.M., 1998. Source and chemodynamic behavior of diphenyl sulfone and ortho- and para-hydroxybiphenyl in a small lake receiving discharges froman adjacent superfund site. Environmental Science & Technology 32, 1319-1328.