The DOI matches its Crossref record; 22 of the 22 references it cites were found in a registry or an index.
The estrogenicity of bisphenol A-related diphenylalkanes with various substituents at the central carbon and the hydroxy groups.
Open accessAbstract
The chemical structure of hydroxylated diphenylalkanes or bisphenols consists of two phenolic rings joined together through a bridging carbon. This class of endocrine disruptors that mimic estrogens is widely used in industry, particularly in plastics. Bisphenol F, bisphenol A, fluorine-containing bisphenol A (bisphenol AF), and other diphenylalkanes were found to be estrogenic in a bioassay with MCF7 human breast cancer cells in culture (E-SCREEN assay). Bisphenols promoted cell proliferation and increased the synthesis and secretion of cell type-specific proteins. When ranked by proliferative potency, the longer the alkyl substituent at the bridging carbon, the lower the concentration needed for maximal cell yield; the most active compound contained two propyl chains at the bridging carbon. Bisphenols with two hydroxyl groups in the para position and an angular configuration are suitable for appropriate hydrogen bonding to the acceptor site of the estrogen receptor. Our data suggest that estrogenicity is influenced not only by the length of the substituents at the bridging carbon but also by their nature. Because diphenylalkane derivatives are widespread and their production and use are increasing, potential exposure of humans to estrogenic bisphenols is becoming a significant issue. The hazardous effects of inadvertent exposure to bisphenol-releasing chemicals in professional workers and the general populations therefore deserve investigation.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., & Boyd, M. R. (1990) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/82.13.1107 · Cited by 9,766
Developmental effects of endocrine-disrupting chemicals in wildlife and humans.
Colborn, T., vom Saal, F. S., & Soto, A. M. (1993) · Environmental Health Perspectives · doi:10.1289/ehp.93101378 · Cited by 3,445
Soto, A. M., Sonnenschein, C., Chung, K. L., Fernandez, M. F., Olea, N., & Serrano, F. O. (1995) · Environmental Health Perspectives · doi:10.1289/ehp.95103s7113 · Cited by 1,720
Self-citationBisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving
Krishnan, A. V., Stathis, P., Permuth, S. F., Tokes, L., & Feldman, D. I. (1993) · Endocrinology · doi:10.1210/en.132.6.2279 · Cited by 1,613
p-Nonyl-phenol: an estrogenic xenobiotic released from "modified" polystyrene.
Soto, A. M., Justicia, H., Wray, J. W., & Sonnenschein, C. (1991) · Environmental Health Perspectives · doi:10.1289/ehp.9192167 · Cited by 1,082
Chemically-induced alterations in sexual and functional development : the wildlife/human connection
Colborn, T., & Clement, C. (1992) · Medical Entomology and Zoology · Cited by 1,046
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. (1996) · Environmental Health Perspectives · doi:10.1289/ehp.96104298 · Cited by 1,041
Self-citationXenoestrogens released from lacquer coatings in food cans.
Brotons, J. A., Olea-Serrano, M. F., Villalobos, M., Pedraza, V, & Olea, N. (1995) · Environmental Health Perspectives · doi:10.1289/ehp.95103608 · Cited by 942
Self-citationNagel, S. C., vom Saal, F. S., Thayer, K. A., Dhar, M. G., Boechler, M., & Welshons, W. V. (1997) · Environmental Health Perspectives · doi:10.1289/ehp.9710570 · Cited by 793
Synthetic strogenic Agents without the Phenanthrene Nucleus
DODDS, E. C., & LAWSON, W. (1936) · Nature · doi:10.1038/137996a0 · Cited by 610
The Environmental Estrogen Bisphenol A Stimulates Prolactin Release in Vitro and in Vivo
Steinmetz, R. (1997) · Endocrinology · doi:10.1210/en.138.5.1780 · Cited by 519
Structural Features of Alkylphenolic Chemicals Associated with Estrogenic Activity
Routledge, E. J., & Sumpter, J. P. (1997) · Journal of Biological Chemistry · doi:10.1074/jbc.272.6.3280 · Cited by 493
Developmental Effects of Endocrine-Disrupting Chemicals in Wildlife and Humans
Colborn, T., Saal, F. S. V., & Soto, A. M. (1993) · Environmental Health Perspectives · doi:10.2307/3431890 · Cited by 435
The E-screen assay: a comparison of different MCF7 cell stocks.
Villalobos, M., Olea, N., Brotons, J. A., Olea-Serrano, M. F., Ruiz de Almodovar, J. M., & Pedraza, V (1995) · Environmental Health Perspectives · doi:10.1289/ehp.95103844 · Cited by 263
Self-citationThe role of estrogens on the proliferation of human breast tumor cells (MCF-7)
Soto, A. M., & Sonnenschein, C. (1985) · Journal of Steroid Biochemistry · doi:10.1016/0022-4731(85)90265-1 · Cited by 253
Connor, K., Ramamoorthy, K., Moore, M., Mustain, M., Chen, I., Safe, S., Zacharewski, T., Gillesby, B., Joyeux, A., & Balaguer, P. (1997) · Toxicology and Applied Pharmacology · doi:10.1006/taap.1997.8169 · Cited by 241
An"in culture"bioassay to assess the estrogenicity of xenobiotics (E-SCREEN)
Soto, A. M. (1992) · Medical Entomology and Zoology · Cited by 212
The developmental toxicity of bisphenol A in rats and mice*1
MORRISSEY, R. (1987) · Fundamental and Applied Toxicology · doi:10.1016/0272-0590(87)90142-4 · Cited by 199
Colerangle, J. B., & Roy, D. (1997) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/s0960-0760(96)00130-6 · Cited by 137
Editorial: Estrogens from Plastic—Are We Being Exposed?
Feldman, D. I. (1997) · Endocrinology · doi:10.1210/endo.138.5.5213 · Cited by 78
Lewis, D. F. V., Parker, M. G., & King, R. J. B. (1995) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/0960-0760(94)00151-b · Cited by 41
Importance of A-ring substitution of estrogens for the physiology and pharmacology of reproduction
Knüppen, R., Ball, P., & Emons, G. (1986) · Journal of Steroid Biochemistry · doi:10.1016/0022-4731(86)90050-6 · Cited by 17
Cited by
Rochester, J. R., & Bolden, A. L. (2015) · Environmental Health Perspectives · doi:10.1289/ehp.1408989 · Cited by 1,524
Blair, R. M. (2000) · Toxicological Sciences · doi:10.1093/toxsci/54.1.138 · Cited by 806
Meerts, I. A., Letcher, R. J., Hoving, S., Marsh, G., Bergman, A., Lemmen, J. G., van der Burg, B., & Brouwer, A. (2001) · Environmental Health Perspectives · doi:10.1289/ehp.01109399 · Cited by 732
Acute toxicity, mutagenicity, and estrogenicity of bisphenol‐A and other bisphenols
Chen, M., Ike, M., & Fujita, M. (2002) · Environmental Toxicology · doi:10.1002/tox.10035 · Cited by 508
NTP‐CERHR expert panel report on the reproductive and developmental toxicity of bisphenol A
Chapin, R. E., Adams, J., Boekelheide, K., Gray, L. E., Hayward, S. W., Lees, P. S. J., McIntyre, B. S., Portier, K. M., Schnorr, T. M., Selevan, S. G., et al. (2008) · Birth Defects Research Part B: Developmental and Reproductive Toxicology · doi:10.1002/bdrb.20147 · Cited by 506
Metadata
- Authors
- Perez, P., Pulgar, R., Olea-Serrano, F., Villalobos, M., Rivas, A., Metzler, M., Pedraza, V, & Olea, N.
- Venue
- Environmental Health Perspectives
- Publisher
- American Chemical Society (ACS)
- Published
- 1998-03
- Volume
- 106
- Issue
- 3
- Pages
- 167-174
- ISSN
- 0091-6765 (ISSN-L)
- 1552-9924
- OpenAlex
- W2087919607
- Cited by
- 254
- References
- 22
- FWCI
- 13.70
- Type
- journal article
- Language
- en
- Open access
- gold
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
