Measurement of estrogenic activity of chemicals for the development of new dental polymers

Hashimoto, Yoshiya; Moriguchi, Y; Oda, Hiroshi; Kawaguchi, Minoru; Miyazaki, Kôji; Nakamura, Masaaki

doi:10.1016/s0887-2333(01)00046-7

Cited by 89 publications

(67 citation statements)

References 8 publications

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“…13) This might be due to the difference in the tested alkylphenols and/or bioassay method. Hashimoto et al 24) reported that the difference in the bioassay method affected the sensitivity of the estrogenic activity.…”

Section: Relationship Between Estrogenic Activity and Structure Of Nomentioning

confidence: 99%

Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay

Shioji

Tsunoi

Kobayashi

et al. 2006

JOURNAL OF HEALTH SCIENCE

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Various branched isomers of 4-nonylphenol (NP) and, in addition, the other 4-alkylphenols (APs) were synthesized and their estrogenic activities were assessed using the yeast two-hybrid system. We investigated the relationships between the structure of the nonyl group of NP isomers and their estrogenic activities based on the following five factors: the length of the main alkyl chain, the degree of branching on the α-carbon, the degree of bulkiness, the position of the branch, and the cyclic structure in the nonyl group. An appropriate length of the main alkyl chain was essential for the estrogenic activity. A small effect of the branching on the α-carbon was observed. The importance of the bulkiness and position of the branch in the nonyl group was suggested from the results of the synthesized NP isomers possessing the high estrogenic activities. The bulkiness on the β-carbon was the most important factor for the high estrogenic activity. The investigation of the cyclic structure also indicated the significance of the bulkiness around the β-carbon. The bulkiness on the γ-carbon was also suggested to be an important factor. The metabolic effect of the synthesized APs on the estrogenic activity was also examined using a liver S9. The estrogenic activities of the selected APs were either reduced or lost. In addition, GC-MS analyses of the commercial NP and synthesized NP isomers revealed that the nine synthesized NP isomers were included in the commercial NP.

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Section: Relationship Between Estrogenic Activity and Structure Of Nomentioning

confidence: 99%

Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay

Shioji

Tsunoi

Kobayashi

et al. 2006

JOURNAL OF HEALTH SCIENCE

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“…BPB showed considerably higher estrogenic activity than BPA in the yeast two-hybrid assay. 33) This compound also exhibited significant increase of MCF-7 cell growth in the E-screen test 40,41) as well as greater luciferase activity in MCF-7 cells. 34) Moderate binding affinity to ER was also reported in Sprague-Dawley rat uterine cytosol.…”

Section: )mentioning

confidence: 90%

“…42) In in vitro assay using a yeast two-hybrid system BPF was identified as the most estrogenic compound among the tested chemicals that were present in food packaging material or used in dentistry. 40,43) BPF has also exhibited estrogenic activity in yeast recombinant gene assay. 44) In human cells, the proliferative response of MCF-7 cells (EScreen assay) increased in a concentration dependent manner.…”

Section: )mentioning

confidence: 99%

“…44) In human cells, the proliferative response of MCF-7 cells (EScreen assay) increased in a concentration dependent manner. 14,40,43,45) The latter authors showed that, according to the respective median effective concentration (EC 50 ) values for proliferation of MCF-7 cell, BPF was more pronounced than BPA. Moderate binding affinities of BPF to ER in MCF-7 cell, 34) HeLa cell, 42) HepG2 cell, 46) and SpragueDawley rat uterine cytosol 35) were reported.…”

Section: )mentioning

confidence: 99%

“…It was first reported that BPS had no estrogenic activity using the yeast two-hybrid system. 33) Several authors, however, reported that BPS possessed estrogenic activity in MCF-7 cell 40,43) as well as weak estrogenic transcriptional activities in human MELN cells derived from MCF-7 cells. 36) Since the basic structural features which have been linked to ER binding, 48) in particular the presence of a para hydroxyl group on each of the phenol rings, are shared by both BPA and BPS, BPS also may have modulatory effects toward ER binding potency.…”

Section: )mentioning

confidence: 99%

See 2 more Smart Citations

Endocrine Disruption Potentials of Bisphenol A Alternatives - Are Bisphenol A Alternatives Safe from Endocrine Disruption?

Ji¹,

Choi²

2013

Korean Journal of Environmental Health Sciences

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Objectives: Although a great body of knowledge is available on the toxicity of bisphenol A (BPA), little is known about that of BPA alternatives, such as bisphenol analogues (BPs) or Tritan TM copolyesters. This review provides a summary of the available information on the toxicity of BPs and three components of Tritan TM, with a special focus on endocrine disruption. Methods:We collected from the literature a battery of in vitro and in vivo assay data developed to assess endocrine disruption of four BPs (bisphenol AF, B, F, and S) and three major components of Tritan TM ((di-methylterephthalate (DMT), 1,4-cyclohexanedimethanol (CHDM), and 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD)).Results: Several alternative compounds were identified as possessing comparable or even greater endocrinedisrupting effects than BPA in in vitro and in vivo studies.Conclusions: Potential endocrine disruption of BPA alternatives requires further studies on health consequences in experimental animals and in humans following longer term exposure.

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The Bisphenol A analogue Bisphenol S binds to K‐Ras4B – implications for ‘BPA‐free’ plastics

et al. 2016

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K-Ras4B is a small GTPase that belongs to the Ras superfamily of guanine nucleotide-binding proteins. GTPases function as molecular switches in cells and are key players in intracellular signalling. Ras has been identified as an oncogene and is mutated in more than 20% of human cancers. Here, we report that Bisphenol S binds into a binding pocket of K-Ras4B previously identified for various low molecular weight compounds. Our results advocate for more comprehensive safety studies on the toxicity of Bisphenol S, as it is frequently used for Bisphenol A-free food containers.

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Measurement of estrogenic activity of chemicals for the development of new dental polymers

Cited by 89 publications

References 8 publications

Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay

Estrogenic Activity of Branched 4-Nonylphenol Isomers Examined by Yeast Two-Hybrid Assay

Endocrine Disruption Potentials of Bisphenol A Alternatives - Are Bisphenol A Alternatives Safe from Endocrine Disruption?

The Bisphenol A analogue Bisphenol S binds to K‐Ras4B – implications for ‘BPA‐free’ plastics

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