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Chemical Compound Review

Bisphenol     4-[2-(4-hydroxyphenyl)propan- 2-yl]phenol

Synonyms: Rikabanol, Diano, DIAN, Bisphenol-A, Bisphenol A, ...
 
 
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Disease relevance of Biphenol A

  • Here we tested the effect of probucol and its metabolite bisphenol on aortic lipid (per)oxidation and atherogenesis in Watanabe heritable hyperlipidemic (WHHL) rabbits [1].
  • An important and controversial health concern is whether low-dose exposures to hormonally active environmental estrogens, such as bisphenol A, can promote human diseases, including prostate cancer [2].
  • A role for sulfation-desulfation in the uptake of bisphenol a into breast tumor cells [3].
  • Bisphenol-A (BPA), one of the most common environmental endocrine disrupters, has been extensively evaluated for toxicity in a variety of tests in rodents, including developmental and reproductive toxicity, and carcinogenicity [4].
  • Perinatal exposure to low doses of bisphenol A affects body weight, patterns of estrous cyclicity, and plasma LH levels [5].
 

Psychiatry related information on Biphenol A

 

High impact information on Biphenol A

  • We observed that TSPs of the xenoestrogens (e.g., genistein or bisphenol A) were clearly different from the TSP of 17beta-estradiol; namely, the former strongly enhanced expression of genes involved in mitochondrial oxidative phosphorylation, whereas the latter showed minimal effects [10].
  • We found that the antiangiogenic effects of rosiglitazone were reversed by either bisphenol A diaglycidyl ether, a PPARgamma antagonist, or iberiotoxin, a maxi-K channel blocker [11].
  • Bisphenol a exposure causes meiotic aneuploidy in the female mouse [12].
  • Self-diffusion rates of lipids and trapped bisphenol A (BPA) are determined in various sizes of confined but fluid membranes by high-field-gradient NMR at 600 MHz [13].
  • However, bisphenol A, another EDC, had no effect on PXR-mediated transcription, although this chemical significantly enhanced ER-mediated transcription [14].
 

Chemical compound and disease context of Biphenol A

 

Biological context of Biphenol A

  • The ERK phosphorylation induced by PPARgamma agonists is not blocked by the PKC inhibitors GF109203X and Ro31-8220, the PI3K inhibitor wortmannin, the Ras inhibitor FPTI, the negative mutant of Ras, or the PPARgamma antagonist bisphenol A diglycidil ether [20].
  • Inhibition of testicular steroidogenesis by the xenoestrogen bisphenol A is associated with reduced pituitary luteinizing hormone secretion and decreased steroidogenic enzyme gene expression in rat Leydig cells [21].
  • Hydrolysis of bisphenol A diglycidylether by epoxide hydrolases in cytosolic and microsomal fractions of mouse liver and skin: inhibition by bis epoxycyclopentylether and the effects upon the covalent binding to mouse skin DNA [22].
  • In contrast, addition of a phenolic anti-oxidant, bisphenol (BP), prior to H/R injury, inhibited ROS production and gene regulation and significantly decreased neuronal cell apoptosis [23].
  • Bisphenol A eliminates brain and behavior sex dimorphisms in mice: how low can you go [24]?
 

Anatomical context of Biphenol A

  • UGT activities towards both bisphenol A and diethylstilboestrol were distributed mainly in the liver but were also observed at substantial levels in the kidney and testis [25].
  • Perinatal exposure to bisphenol-A alters peripubertal mammary gland development in mice [26].
  • UGT activity towards bisphenol A in liver microsomes and in UGT2B1 expressed in yeast AH22 cells (22.9 and 0.58 nmol/min per mg of microsomal proteins respectively) was higher than that towards diethylstilboestrol (75.0 and 4.66 pmol/min per mg of microsomal proteins respectively) [25].
  • Bisphenol A in combination with insulin can accelerate the conversion of 3T3-L1 fibroblasts to adipocytes [27].
  • In this study, we investigated the (anti)estrogenic potencies of several PBDE congeners, three hydroxylated PBDEs (HO-PBDEs), and differently brominated bisphenol A compounds in three different cell line assays based on estrogen receptor (ER)-dependent luciferase reporter gene expression [28].
 

Associations of Biphenol A with other chemical compounds

  • Partial agonists [ICI 3188, tri(4-hydroxyphenyl)chloroethylene, and bisphenol] each had bis(4-hydroxyphenol) substitutions at the ethylene double bond and stimulated prolactin synthesis only to about 50% of the maximal response observed with E2 [29].
  • Specifically, we observed that the environmental estrogen bisphenol A was a potent agonist in stimulating ER transcriptional activity, whereas it exhibited little uterotropic activity [30].
  • Estrogenic chemicals, as for instance nonylphenol, bisphenol A, o, p'-DDT and 2',4',6'-trichloro-4-biphenylol stimulate the transcriptional activity of ER alpha and ER beta at concentrations of 100-1000 nM [31].
  • In contrast to bisphenol A, tamoxifen significantly increased uterine weight, but minimally induced ER reporter activity in this tissue [30].
  • Thus, time-pregnant CD-1 mice were fed diethylstilbestrol (DES), bisphenol A (BPA), and aroclor (aroclor 1016) at an average concentration of 100 ng/kg/day, 50 microg/kg/day, and 50 microg/kg/day, respectively, during Days 16-18 of gestation [32].
 

Gene context of Biphenol A

  • E2, bisphenol A, and NP inhibited MCP-1 messenger RNA expression in MCF-7 cells [33].
  • Transient transfection assay using dioxin-response element (DRE)-linked luciferase revealed that bisphenol A reduced transformation of the aryl hydrocarbons (Ah) receptor to a form capable of specifically binding to the DRE sequence in the promoter of the Cyp1a-1 gene [19].
  • Dietary bisphenol A prevents ovarian degeneration and bone loss in female mice lacking the aromatase gene (Cyp19 ) [34].
  • Low-level bisphenol A increases production of glial fibrillary acidic protein in differentiating astrocyte progenitor cells through excessive STAT3 and Smad1 activation [35].
  • Additionally, we investigated the inhibitory effect of bisphenol A on CYP2C19-mediated S-mephenytoin 4-hydroxylation [36].
 

Analytical, diagnostic and therapeutic context of Biphenol A

References

  1. Dissociation of atherogenesis from aortic accumulation of lipid hydro(pero)xides in Watanabe heritable hyperlipidemic rabbits. Witting, P., Pettersson, K., Ostlund-Lindqvist, A.M., Westerlund, C., Wâgberg, M., Stocker, R. J. Clin. Invest. (1999) [Pubmed]
  2. Developmental exposure to estradiol and bisphenol a increases susceptibility to prostate carcinogenesis and epigenetically regulates phosphodiesterase type 4 variant 4. Ho, S.M., Tang, W.Y., Belmonte de Frausto, J., Prins, G.S. Cancer Res. (2006) [Pubmed]
  3. A role for sulfation-desulfation in the uptake of bisphenol a into breast tumor cells. Stowell, C.L., Barvian, K.K., Young, P.C., Bigsby, R.M., Verdugo, D.E., Bertozzi, C.R., Widlanski, T.S. Chem. Biol. (2006) [Pubmed]
  4. Prenatal and neonatal exposure to bisphenol-A enhances the central dopamine D1 receptor-mediated action in mice: enhancement of the methamphetamine-induced abuse state. Suzuki, T., Mizuo, K., Nakazawa, H., Funae, Y., Fushiki, S., Fukushima, S., Shirai, T., Narita, M. Neuroscience (2003) [Pubmed]
  5. Perinatal exposure to low doses of bisphenol A affects body weight, patterns of estrous cyclicity, and plasma LH levels. Rubin, B.S., Murray, M.K., Damassa, D.A., King, J.C., Soto, A.M. Environ. Health Perspect. (2001) [Pubmed]
  6. Exposure to a low dose of bisphenol A during fetal life or in adulthood alters maternal behavior in mice. Palanza, P.L., Howdeshell, K.L., Parmigiani, S., vom Saal, F.S. Environ. Health Perspect. (2002) [Pubmed]
  7. Prenatal exposure to bisphenol A impairs sexual differentiation of exploratory behavior and increases depression-like behavior in rats. Fujimoto, T., Kubo, K., Aou, S. Brain Res. (2006) [Pubmed]
  8. Chronic exposure to low doses bisphenol A interferes with pair-bonding and exploration in female Mongolian gerbils. Razzoli, M., Valsecchi, P., Palanza, P. Brain Res. Bull. (2005) [Pubmed]
  9. Lack of maternal dietary exposure effects of bisphenol A and nonylphenol during the critical period for brain sexual differentiation on the reproductive/endocrine systems in later life. Takagi, H., Shibutani, M., Masutomi, N., Uneyama, C., Takahashi, N., Mitsumori, K., Hirose, M. Arch. Toxicol. (2004) [Pubmed]
  10. Importance of dosage standardization for interpreting transcriptomal signature profiles: evidence from studies of xenoestrogens. Shioda, T., Chesnes, J., Coser, K.R., Zou, L., Hur, J., Dean, K.L., Sonnenschein, C., Soto, A.M., Isselbacher, K.J. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  11. Antiangiogenic Effect of Rosiglitazone Is Mediated via Peroxisome Proliferator-activated Receptor {gamma}-activated Maxi-K Channel Opening in Human Umbilical Vein Endothelial Cells. Kim, K.Y., Cheon, H.G. J. Biol. Chem. (2006) [Pubmed]
  12. Bisphenol a exposure causes meiotic aneuploidy in the female mouse. Hunt, P.A., Koehler, K.E., Susiarjo, M., Hodges, C.A., Ilagan, A., Voigt, R.C., Thomas, S., Thomas, B.F., Hassold, T.J. Curr. Biol. (2003) [Pubmed]
  13. Limited slowdown of endocrine-disruptor diffusion in confined fluid lipid membranes. Okamura, E., Wakai, C., Matubayasi, N., Sugiura, Y., Nakahara, M. Phys. Rev. Lett. (2004) [Pubmed]
  14. Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription. Masuyama, H., Hiramatsu, Y., Kunitomi, M., Kudo, T., MacDonald, P.N. Mol. Endocrinol. (2000) [Pubmed]
  15. Estrogenicity of resin-based composites and sealants used in dentistry. Olea, N., Pulgar, R., Pérez, P., Olea-Serrano, F., Rivas, A., Novillo-Fertrell, A., Pedraza, V., Soto, A.M., Sonnenschein, C. Environ. Health Perspect. (1996) [Pubmed]
  16. The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups. Perez, P., Pulgar, R., Olea-Serrano, F., Villalobos, M., Rivas, A., Metzler, M., Pedraza, V., Olea, N. Environ. Health Perspect. (1998) [Pubmed]
  17. A physiologically based approach to the study of bisphenol A and other estrogenic chemicals on the size of reproductive organs, daily sperm production, and behavior. vom Saal, F.S., Cooke, P.S., Buchanan, D.L., Palanza, P., Thayer, K.A., Nagel, S.C., Parmigiani, S., Welshons, W.V. Toxicology and industrial health. (1998) [Pubmed]
  18. Pulmonary hemorrhage and edema due to inhalation of resins containing tri-mellitic anhydride. Herbert, F.A., Orford, R. Chest (1979) [Pubmed]
  19. Down-regulation of murine Cyp1a-1 in mouse hepatoma Hepa-1c1c7 cells by bisphenol A. Jeong, H.G., Kimand, J.Y., Choi, C.Y. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  20. Superoxide anion-dependent Raf/MEK/ERK activation by peroxisome proliferator activated receptor gamma agonists 15-deoxy-delta(12,14)-prostaglandin J(2), ciglitazone, and GW1929. Huang, W.C., Chio, C.C., Chi, K.H., Wu, H.M., Lin, W.W. Exp. Cell Res. (2002) [Pubmed]
  21. Inhibition of testicular steroidogenesis by the xenoestrogen bisphenol A is associated with reduced pituitary luteinizing hormone secretion and decreased steroidogenic enzyme gene expression in rat Leydig cells. Akingbemi, B.T., Sottas, C.M., Koulova, A.I., Klinefelter, G.R., Hardy, M.P. Endocrinology (2004) [Pubmed]
  22. Hydrolysis of bisphenol A diglycidylether by epoxide hydrolases in cytosolic and microsomal fractions of mouse liver and skin: inhibition by bis epoxycyclopentylether and the effects upon the covalent binding to mouse skin DNA. Bentley, P., Bieri, F., Kuster, H., Muakkassah-Kelly, S., Sagelsdorff, P., Stäubli, W., Waechter, F. Carcinogenesis (1989) [Pubmed]
  23. Protective effect of a synthetic anti-oxidant on neuronal cell apoptosis resulting from experimental hypoxia re-oxygenation injury. Rayner, B.S., Duong, T.T., Myers, S.J., Witting, P.K. J. Neurochem. (2006) [Pubmed]
  24. Bisphenol A eliminates brain and behavior sex dimorphisms in mice: how low can you go? vom Saal, F.S. Endocrinology (2006) [Pubmed]
  25. Glucuronidation of the environmental oestrogen bisphenol A by an isoform of UDP-glucuronosyltransferase, UGT2B1, in the rat liver. Yokota, H., Iwano, H., Endo, M., Kobayashi, T., Inoue, H., Ikushiro, S., Yuasa, A. Biochem. J. (1999) [Pubmed]
  26. Perinatal exposure to bisphenol-A alters peripubertal mammary gland development in mice. Muñoz-de-Toro, M., Markey, C.M., Wadia, P.R., Luque, E.H., Rubin, B.S., Sonnenschein, C., Soto, A.M. Endocrinology (2005) [Pubmed]
  27. Bisphenol A in combination with insulin can accelerate the conversion of 3T3-L1 fibroblasts to adipocytes. Masuno, H., Kidani, T., Sekiya, K., Sakayama, K., Shiosaka, T., Yamamoto, H., Honda, K. J. Lipid Res. (2002) [Pubmed]
  28. In vitro estrogenicity of polybrominated diphenyl ethers, hydroxylated PDBEs, and polybrominated bisphenol A compounds. Meerts, I.A., Letcher, R.J., Hoving, S., Marsh, G., Bergman, A., Lemmen, J.G., van der Burg, B., Brouwer, A. Environ. Health Perspect. (2001) [Pubmed]
  29. Estrogen-stimulated prolactin synthesis in vitro. Classification of agonist, partial agonist, and antagonist actions based on structure. Jordan, V.C., Lieberman, M.E. Mol. Pharmacol. (1984) [Pubmed]
  30. Development of an ER action indicator mouse for the study of estrogens, selective ER modulators (SERMs), and Xenobiotics. Nagel, S.C., Hagelbarger, J.L., McDonnell, D.P. Endocrinology (2001) [Pubmed]
  31. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Kuiper, G.G., Lemmen, J.G., Carlsson, B., Corton, J.C., Safe, S.H., van der Saag, P.T., van der Burg, B., Gustafsson, J.A. Endocrinology (1998) [Pubmed]
  32. Reproductive malformation of the male offspring following maternal exposure to estrogenic chemicals. Gupta, C. Proc. Soc. Exp. Biol. Med. (2000) [Pubmed]
  33. Molecular analysis of the inhibition of monocyte chemoattractant protein-1 gene expression by estrogens and xenoestrogens in MCF-7 cells. Inadera, H., Sekiya, T., Yoshimura, T., Matsushima, K. Endocrinology (2000) [Pubmed]
  34. Dietary bisphenol A prevents ovarian degeneration and bone loss in female mice lacking the aromatase gene (Cyp19 ). Toda, K., Miyaura, C., Okada, T., Shizuta, Y. Eur. J. Biochem. (2002) [Pubmed]
  35. Low-level bisphenol A increases production of glial fibrillary acidic protein in differentiating astrocyte progenitor cells through excessive STAT3 and Smad1 activation. Yamaguchi, H., Zhu, J., Yu, T., Sasaki, K., Umetsu, H., Kidachi, Y., Ryoyama, K. Toxicology (2006) [Pubmed]
  36. Inhibition of drug-metabolizing enzyme activity in human hepatic cytochrome P450s by bisphenol A. Niwa, T., Tsutsui, M., Kishimoto, K., Yabusaki, Y., Ishibashi, F., Katagiri, M. Biol. Pharm. Bull. (2000) [Pubmed]
  37. Identification of estrogenic tamoxifen metabolite(s) in tamoxifen-resistant human breast tumors. Wiebe, V.J., Osborne, C.K., McGuire, W.L., DeGregorio, M.W. J. Clin. Oncol. (1992) [Pubmed]
  38. Simultaneous measurement of urinary bisphenol A and alkylphenols by automated solid-phase extractive derivatization gas chromatography/mass spectrometry. Kuklenyik, Z., Ekong, J., Cutchins, C.D., Needham, L.L., Calafat, A.M. Anal. Chem. (2003) [Pubmed]
  39. Male-specific suppression of hepatic microsomal UDP-glucuronosyl transferase activities toward sex hormones in the adult male rat administered bisphenol A. Shibata, N., Matsumoto, J., Nakada, K., Yuasa, A., Yokota, H. Biochem. J. (2002) [Pubmed]
  40. Determination of bisphenol A and related aromatic compounds released from bis-GMA-based composites and sealants by high performance liquid chromatography. Pulgar, R., Olea-Serrano, M.F., Novillo-Fertrell, A., Rivas, A., Pazos, P., Pedraza, V., Navajas, J.M., Olea, N. Environ. Health Perspect. (2000) [Pubmed]
 
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