Biological Evaluation of Styrene Oligomers for Endocrine-disrupting Effects. (II).

Azuma, Yukimasa; Nobuhara, Yoichi; Date, Katsuhiro; Ohno, Katsutoshi; Tanaka, Kazunori; Hirano, Seishiro; Kobayashi, Kazuhiro; Sakurai, Takanobu; Chiba, Masaru; Yamada, Toshihiro

doi:10.3358/shokueishi.41.109

Cited by 18 publications

(6 citation statements)

References 17 publications

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“…However, styrene oligomers were reported to have no endocrine disruptive effect both in a MCF-7 cell proliferation assay (10) and in a radioisotope (RI) receptor competitive-binding assay using rat estrogen receptor (10,11). Therefore, we tested 11 styrene oligomers including those found in food (4,5) in a proliferation assay at an optimal initial cell concentration using human breast tumor, highly estrogen-sensitive MCF-7 cells.…”

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confidence: 99%

Certain styrene oligomers have proliferative activity on MCF-7 human breast tumor cells and binding affinity for human estrogen receptor.

Ohyama

Nagai²,

Tsuchiya³

2001

Environ Health Perspect

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Polystyrene used for food containers, such as takeout food containers, coffee cups, meat trays, soup bowls, and salad boxes (1), contains high levels of styrene dimers (90-1,030 µg/g) and styrene trimers (650-20,770 µg/g) as impurities (2,3). These styrene oligomers migrate from the polystyrene containers into the containers' contents (4-6). When polystyrene containers containing vegetable oil were treated by heating in a microwave oven or were incubated for 24 hr at 20°C, a styrene dimer, 2,4-diphenyl-1-butene (SD-2; 0-1.6 ng/cm 2 ) and styrene trimers 2,4,6-triphenyl-1-hexene (ST-1; 1.3-69.7 ng/cm 2 ), 1a-phenyl-4a-(1´-phenylethyl)tetralin (ST-2; 9.2-156 ng/cm 2 ), 1a-phenyl-4e-(1´-phenylethyl)tetralin (ST-3; 18.1-501 ng/cm 2 ), 1e-phenyl-4a-(1´-phenylethyl)tetralin (ST-4; 13.9-294 ng/cm 2 ), and 1e-phenyl-4e-(1´-phenylethyl)tetralin (ST-5; 18.7-306 ng/cm 2 ) migrated into the vegetable oil (4). When instant foods such as Chinese noodles, Japanese noodles, buckwheat noodles, chow mein, spaghetti, and rice were packed in polystyrene containers, styrene trimers ST-1 (0-8.1 µg/cup), ST-2 + ST-3 (0-13.8 µg/cup), ST-4 (0-5.2 µg/cup), and ST-5 (0-8.4 µg/cup) migrated (0-33.8 µg total styrene oligomers detected in a cup) from the containers into the foods after cooking in the cups, but the dimers did not (5). The maximum quantity of styrene trimers that migrated from containers to foods was higher than that of bisphenol A leached from the lacquer coating of vegetable cans (4-23 µg/can) (7).Colborn et al. (8) designated styrene dimers and trimers as endocrine disrupters in the Wingspread statement, and the Environmental Agency, Government of Japan, cited styrene dimers and trimers as compounds suspected of having endocrinedisruptive effects in its Strategic Programs on Environmental Endocrine Disrupters (9). However, styrene oligomers were reported to have no endocrine disruptive effect both in a MCF-7 cell proliferation assay (10) and in a radioisotope (RI) receptor competitive-binding assay using rat estrogen receptor (10,11). Therefore, we tested 11 styrene oligomers including those found in food (4,5) in a proliferation assay at an optimal initial cell concentration using human breast tumor, highly estrogen-sensitive MCF-7 cells. We also examined the binding potency of these styrene oligomers to human estrogen receptor α (hERα) in a non-RI receptor competitivebinding assay. Materials and MethodsChemicals. The styrene dimers 1,3-diphenyl propane (SD-1), SD-2, cis-1,2-diphenyl cyclobutane (SD-3), and trans-1,2-diphenyl cyclobutane (SD-4) and styrene trimers ST-1, ST-2, ST-3, ST-4, ST-5, 1e,3e,5a-triphenylcyclohexane (ST-6), and 1e,3e,5e-triphenylcyclohexane (ST-7) were purchased from Hayashi Pure Chemical Industry. (Osaka, Japan). The positive control, 17β-estradiol (E 2 ), was obtained from Calbiochem (Richmond, CA, USA). The chemical structures of these compounds are shown in Figure 1, and the purity of the compounds is summarized in Table 1.Solvent for styrene oligomers. Styrene oligomers and E 2 were dissolved ...

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confidence: 99%

Certain styrene oligomers have proliferative activity on MCF-7 human breast tumor cells and binding affinity for human estrogen receptor.

Ohyama

Nagai²,

Tsuchiya³

2001

Environ Health Perspect

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“…Colborn et al (8) designated styrene dimers and trimers as endocrine disrupters in the Wingspread statement, and the Environmental Agency, Government of Japan, cited styrene dimers and trimers as compounds suspected of having endocrinedisruptive effects in its Strategic Programs on Environmental Endocrine Disrupters (9). However, styrene oligomers were reported to have no endocrine disruptive effect both in a MCF-7 cell proliferation assay (10) and in a radioisotope (RI) receptor competitive-binding assay using rat estrogen receptor (10,11). Therefore, we tested 11 styrene oligomers including those found in food (4,5) in a proliferation assay at an optimal initial cell concentration using human breast tumor, highly estrogen-sensitive MCF-7 cells.…”

mentioning

confidence: 99%

Certain Styrene Oligomers Have Proliferative Activity on MCF-7 Human Breast Tumor Cells and Binding Affinity for Human Estrogen Receptor a

Ohyama¹,

Nagai²,

Tsuchiya³

2001

Environmental Health Perspectives

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To examine the estrogenic activities of styrene oligomers, we carried out cell proliferation assays with estrogen-sensitive MCF-7 cells and competitive binding assays to human estrogen receptor [alpha] (hER[alpha]). The styrene oligomers tested were 1,3-diphenyl propane (SD-1), 2,4-diphenyl-1-butene (SD-2), cis-1,2-diphenyl cyclobutane (SD-3), trans-1,2-diphenyl cyclobutane (SD-4), 2,4,6-triphenyl-1-hexene (ST-1), 1a-phenyl-4a-(1'-phenylethyl)tetralin (ST-2), 1a-phenyl-4e-(1'-phenylethyl)tetralin (ST-3), 1e-phenyl-4a-(1'-phenylethyl)tetralin (ST-4), 1e-phenyl-4e-(1'-phenylethyl)tetralin (ST-5), 1e,3e,5a-triphenylcyclohexane (ST-6), and 1e,3e,5e-triphenylcyclohexane (ST-7). In the MCF-7 cell proliferation assay, styrene trimers (ST-1, ST-3, ST-4, and ST-5) had the highest proliferative activities of the compounds tested. The relative potency of these chemicals was 0.0002-0.0015%, which was comparable with that of bisphenol A (0.0001-0.0025%), and their relative proliferative effect was 51-104%. Styrene dimers (SD-3 and SD-4) also significantly increased the cell yields. However, SD-1, SD-2, ST-2, ST-6, and ST-7 had insignificant proliferative activities. The competitive binding assay revealed the binding affinity of some styrene oligomers for hER[alpha]. The order of their binding potency for hER[alpha] was as follows: ST-4 > ST-2 > ST-3 > ST-5 > ST-1 > SD-3 > SD-4 > SD-2 > SD-1. ST-6 and ST-7 did not appear to bind to hER[alpha]. The present studies indicate that styrene dimers SD-3 and SD-4 and styrene trimers ST-1, ST-3, ST-4, and ST-5 have estrogenic activity on MCF-7 cells and binding affinity for hER[alpha]. These compounds might be endocrine disrupters.

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“…In a series of studies on the safety of PS food containers (), we have proved that one unknown compound was 1-phenyl-4-(2-phenylethyl)tetralin (NST-12) (), and eluted SD and ST showed no endocrine-disrupting action by in vivo and in vitro assays, which were compared in detail by Andersen et al and EDSTAC (Endocrine Disruptor Screening and Testing Advisory Committee) ( − ). However, another unknown compound ( 1 ) has not been identified or tested for bioassays.…”

Section: Introductionmentioning

confidence: 99%

Identification, Determination, and Biological Evaluation of a Novel Styrene Trimer Contained in Polystyrene Food Containers. 2

Hirano¹,

Tanaka²,

Date³

et al. 2001

J. Agric. Food Chem.

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An unidentified styrene trimer (ST) isolated from the acetonitrile extract of polystyrene (PS) food containers was characterized as (1S*,6R*,7S*,8S*,11R*)-6,11-diphenyltricyclo[6,2,2,0(2,7)]dodeca-2,9-diene. The content and migration of this compound in PS food containers were determined by GC-MS (SIM). Furthermore, an endocrine-disrupting effect was tested using in vitro and in vivo assays of the compound. In conclusion, it seems that the compound does not present the effect.

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Biological Evaluation of Styrene Oligomers for Endocrine-disrupting Effects. (II).

Cited by 18 publications

References 17 publications

Certain styrene oligomers have proliferative activity on MCF-7 human breast tumor cells and binding affinity for human estrogen receptor.

Certain styrene oligomers have proliferative activity on MCF-7 human breast tumor cells and binding affinity for human estrogen receptor.

Certain Styrene Oligomers Have Proliferative Activity on MCF-7 Human Breast Tumor Cells and Binding Affinity for Human Estrogen Receptor a

Identification, Determination, and Biological Evaluation of a Novel Styrene Trimer Contained in Polystyrene Food Containers. 2

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