JBC Avanti Polar Lipids

HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
QUICK SEARCH:   [advanced]


     

This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Right arrow Citation Map
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Routledge, E. J.
Right arrow Articles by Sumpter, J. P.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Routledge, E. J.
Right arrow Articles by Sumpter, J. P.
Social Bookmarking
Add to CiteULike   Add to Complore   Add to Connotea   Add to Del.icio.us   Add to Digg   Add to Reddit   Add to Technorati  
What's this?

Volume 272, Number 6, Issue of February 7, 1997 pp. 3280-3288
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.

Structural Features of Alkylphenolic Chemicals Associated with Estrogenic Activity

(Received for publication, July 15, 1996, and in revised form, October 15, 1996)

Edwin J. Routledge and John P. Sumpter

From the Department of Biology and Biochemistry, Brunel University, Uxbridge, Middlesex UB8 3PH, United Kingdom

The ability of certain man-made chemicals to mimic the effects of natural steroid hormones and their potential to disrupt the delicate balance of the endocrine system in animals are of increasing concern. The growing list of reported hormone-mimics includes the alkylphenolic (AP) compounds, a small number of which have been reported to be weakly estrogenic. In their most basic form, APs are composed of an alkyl group, which can vary in size, branching, and position, joined to a phenolic ring. The aim of this project was to identify the important structural features responsible for the estrogenic activity of AP chemicals. This was achieved by incubating APs with different structural features in a medium containing a previously described estrogen-inducible strain of yeast (Saccharomyces cerevisiae) expressing the human estrogen receptor and comparing their activity spectrophotometrically by the resulting color change of the medium. The results were compared to the effects of the main natural estrogen 17beta -estradiol. The data indicate that both the position (para > meta > ortho) and branching (tertiary > secondary = normal) of the alkyl group affect estrogenicity. Optimal estrogenic activity requires a single tertiary branched alkyl group composed of between 6 and 8 carbons located at the para position on an otherwise unhindered phenol ring. The results are discussed in relation to the purity and composition of the chemicals tested.


Add to CiteULike CiteULike   Add to Complore Complore   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us   Add to Digg Digg   Add to Reddit Reddit   Add to Technorati Technorati    What's this?


This article has been cited by other articles:


Home page
 Toxicol SciHome page
S. C. Laws, S Yavanhxay, R. L. Cooper, and J. C. Eldridge
Nature of the Binding Interaction for 50 Structurally Diverse Chemicals with Rat Estrogen Receptors
Toxicol. Sci., November 1, 2006; 94(1): 46 - 56.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
P. Y. Kunz, T. Gries, and K. Fent
The Ultraviolet Filter 3-Benzylidene Camphor Adversely Affects Reproduction in Fathead Minnow (Pimephales promelas)
Toxicol. Sci., October 1, 2006; 93(2): 311 - 321.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
S. Cooper, J. R. Latendresse, D. R. Doerge, N. C. Twaddle, X. Fu, and K. B. Delclos
Dietary Modulation of p-Nonylphenol-Induced Polycystic Kidneys in Male Sprague-Dawley Rats
Toxicol. Sci., June 1, 2006; 91(2): 631 - 642.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
P. Y. Kunz, H. F. Galicia, and K. Fent
Comparison of In Vitro and In Vivo Estrogenic Activity of UV Filters in Fish
Toxicol. Sci., April 1, 2006; 90(2): 349 - 361.
[Abstract] [Full Text] [PDF]

Home page
 Appl. Environ. Microbiol.Home page
F. L. P. Gabriel, W. Giger, K. Guenther, and H.-P. E. Kohler
Differential Degradation of Nonylphenol Isomers by Sphingomonas xenophaga Bayram
Appl. Envir. Microbiol., March 1, 2005; 71(3): 1123 - 1129.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
Y.-W. Jung, E.-J. Hong, K.-C. Choi, and E.-B. Jeung
Novel Progestogenic Activity of Environmental Endocrine Disruptors in the Upregulation of Calbindin-D9k in an Immature Mouse Model
Toxicol. Sci., January 1, 2005; 83(1): 78 - 88.
[Abstract] [Full Text] [PDF]

Home page
 Biol. Reprod.Home page
E.-J. Hong, K.-C. Choi, and E.-B. Jeung
Induction of Calbindin-D9k Messenger RNA and Protein by Maternal Exposure to Alkylphenols During Late Pregnancy in Maternal and Neonatal Uteri of Rats
Biol Reprod, August 1, 2004; 71(2): 669 - 675.
[Abstract] [Full Text] [PDF]

Home page
 J. Exp. Biol.Home page
T. H. Rasmussen, T. K. Andreassen, S. N. Pedersen, L. T. M. Van der Ven, P. Bjerregaard, and B. Korsgaard
Effects of waterborne exposure of octylphenol and oestrogen on pregnant viviparous eelpout (Zoarces viviparus) and her embryos in ovario
J. Exp. Biol., December 15, 2002; 205(24): 3857 - 3876.
[Abstract] [Full Text] [PDF]

Home page
 Toxicol SciHome page
S.'i. Yoshihara, M. Makishima, N. Suzuki, and S. Ohta
Metabolic Activation of Bisphenol A by Rat Liver S9 Fraction
Toxicol. Sci., August 1, 2001; 62(2): 221 - 227.
[Abstract] [Full Text] [PDF]

Home page
 J. Pharmacol. Exp. Ther.Home page
R. Elsby, J. L. Maggs, J. Ashby, D. Paton, J. P. Sumpter, and B. K. Park
Assessment of the Effects of Metabolism on the Estrogenic Activity of Xenoestrogens: A Two-Stage Approach Coupling Human Liver Microsomes and a Yeast Estrogenicity Assay
J. Pharmacol. Exp. Ther., April 13, 2001; 296(2): 329 - 337.
[Abstract] [Full Text]

Home page
 Toxicol Ind HealthHome page
S. Oishi
Effects of butylparaben on the male reproductive system in rats
Toxicology and Industrial Health, February 1, 2001; 17(1): 31 - 39.
[Abstract] [PDF]

Home page
 J. Biol. Chem.Home page
R. M. Harris, R. H. Waring, C. J. Kirk, and P. J. Hughes
Sulfation of "Estrogenic" Alkylphenols and 17beta -Estradiol by Human Platelet Phenol Sulfotransferases
J. Biol. Chem., January 7, 2000; 275(1): 159 - 166.
[Abstract] [Full Text] [PDF]

Home page
 J. Exp. Biol.Home page
K Kinnberg, B Korsgaard, P Bjerregaard, and A Jespersen
Effects of nonylphenol and 17beta-estradiol on vitellogenin synthesis and testis morphology in male platyfish Xiphophorus maculatus
J. Exp. Biol., January 1, 2000; 203(2): 171 - 181.
[Abstract] [PDF]

Home page
 Proc. Natl. Acad. Sci. USAHome page
B. Moosmann and C. Behl
The antioxidant neuroprotective effects of estrogens and phenolic compounds are independent from their estrogenic properties
PNAS, August 3, 1999; 96(16): 8867 - 8872.
[Abstract] [Full Text] [PDF]

Home page
 EndocrinologyHome page
G. G. J. M. Kuiper, J. G. Lemmen, B. Carlsson, J. C. Corton, S. H. Safe, P. T. van der Saag, B. van der Burg, and J.-A. Gustafsson
Interaction of Estrogenic Chemicals and Phytoestrogens with Estrogen Receptor {beta}
Endocrinology, October 1, 1998; 139(10): 4252 - 4263.
[Abstract] [Full Text] [PDF]

Home page
 Am. J. Physiol. Renal Physiol.Home page
J. H. M. Charuk, A. A. Grey, and R. A. F. Reithmeier
Identification of the synthetic surfactant nonylphenol ethoxylate: a P-glycoprotein substrate in human urine
Am J Physiol Renal Physiol, June 1, 1998; 274(6): F1127 - F1139.
[Abstract] [Full Text] [PDF]


HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
 All ASBMB Journals   Molecular and Cellular Proteomics 
 Journal of Lipid Research   ASBMB Today 
Copyright © 1997 by the American Society for Biochemistry and Molecular Biology.