Oestrogenic activity of benzyl salicylate, benzyl benzoate and butylphenylmethylpropional (Lilial) in MCF7 human breast cancer cells in vitro

Journal of Applied Toxicology

Volumn 29, Issue 5, 2009, Pages 422-434

  Charles, A K ^a   Darbre, P D ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

Benzyl benzoate; Benzyl salicylate; Butylphenylmethylpropional; Cosmetic; Environmental oestrogen; Lilial; MCF7 human breast cancer cells

Indexed keywords

BENZYL BENZOATE; BUTYLPHENYLMETHYLPROPRIONAL; COSMETIC; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FULVESTRANT; PROTEIN P62; PROTEIN PS2; SALICYLIC ACID BENZYL ESTER; TRITIUM; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; BREAST CANCER; BREAST CARCINOGENESIS; CANCER CELL CULTURE; CELL PROLIFERATION; CELL STIMULATION; CELL STRAIN MCF 7; ESTROGEN ACTIVITY; GENE EXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY; PRIORITY JOURNAL; REPORTER GENE;

ALDEHYDES; BENZOATES; BINDING, COMPETITIVE; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL PROLIFERATION; COSMETICS; CYTOSOL; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTROGEN RECEPTOR MODULATORS; FEMALE; HUMANS; LIGANDS; MOLECULAR STRUCTURE; PROTEIN BINDING; RECOMBINANT PROTEINS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; SALICYLATES; TRANSFECTION;

EID: 67651146577     PISSN: 0260437X     EISSN: 10991263     Source Type: Journal    
DOI: 10.1002/jat.1429     Document Type: Article

References (99)

1. Adolfsson-Erici M, Pettersson M, Parkkonen J, Sturve J. 2002. Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden. Chemosphere 46: 1485-1489. (Pubitemid 34224476)
2. Allmyr M, Adolfsson-Erici M, McLachlan MS, Sandborgh-Englund G. 2006. Triclosan in plasma and milk from Swedish nursing mothers and their exposure via personal care products. Sci. Total Environ. 372: 87-93. (Pubitemid 44751071)
3. Arnau EG, Anderson KE, Bruze M, Frosch PJ, Johansen JD, Menne T, Rastogi SC, White IR, Lepoittevin J-P. 2000. Identification of Lilial® as a fragrance sensitizer in a perfume by bioassay-guided chemical fractionation and structure-activity relationships. Contact Dermatitis 43: 351-358.
4. Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM. 2000. The estrogen receptor binding affinities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol. Sci. 54: 138-153. (Pubitemid 30152465)
5. Brian JV, Harris CA, Scholze M, Backhaus T, Booy P, Lamoree M, Pojana G, Jonkers N, Runnalls T, Bonfa A, Marcomini A, Sumpter JP. 2005. Accurate prediction of the response of freshwater fish to a mixture of estrogenic chemicals. Environ. Health Perspect. 113: 721-728. (Pubitemid 40862184)
6. Bronaugh RL, Wester RC, Bucks D, Maibach HI, Sarason R. 1990. In vivo percutaneous absorption of fragrance ingredients in rhesus monkeys and humans. Food Chem. Toxicol. 28: 369-373. (Pubitemid 20226719)
7. Brzozowski AM, Pike ACW, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Ohman L, greene GL, Gustafsson JA, Carlquist M. 1997. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389: 753-758.
8. Buckley DA. 2007. Fragrance ingredient labelling in products on sale in the U.K. Br. J. Dermatol. 157: 295-300.
9. Byford JR, Shaw LE, Drew MGB, Pope GS, Sauer MJ, Darbre PD. 2002. Oestrogenic activity of parabens in MCF7 human breast cancer cells. J. Steroid Biochem. Mol. Biol. 80: 49-60. (Pubitemid 34178410)
10. Calafat AM, Slakman AR, Silva MJ, Herbert AR, Needham LL. 2004. Automated solid phase extraction and quantitative analysis of human milk for 13 phthalate metabolites. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 805: 49-56. (Pubitemid 38534402)
11. Chatelain E, Gabard B, Surber C. 2003. Skin penetration and sun protection factor of five UV filters: effect of the vehicle. Skin Pharmacol. Appl. Skin Physiol. 16: 28-35. (Pubitemid 36173467)
12. Daly RJ, Darbre PD. 1990. Cellular and molecular events in loss of estrogen sensitivity in ZR-75-1 and T-47-D human breast cancer cells. Cancer Res. 50: 5868-5875.
13. Darbre PD. 2003. Underarm cosmetics and breast cancer. J. Appl. Toxicol. 23: 89-95.
14. Darbre PD. 2006a. Environmental oestrogens, cosmetics and breast cancer. Best Pract. Res. Clin. Endocrinol. Metab. 20: 121-143. (Pubitemid 43328572)
15. Darbre PD. 2006b. Metalloestrogens: an emerging class of inorganic xenoestrogens with potential to add to the oestrogenic burden of the human breast. J. Appl. Toxicol. 26: 191-197.
16. Darbre PD, Daly RJ. 1989. Effects of oestrogen on human breast cancer cells in culture. Proc. R. Soc. Edinburgh 95B: 119-132.
17. Darbre PD, Harvey PW. 2008. Paraben esters: review of recent studies of endocrine toxicity, absorption, esterase and human exposure, and discussion of potential human health risks. J. Appl. Toxicol. 28: 561-578.
18. Darbre P, Yates J, Curtis SA, King RJB. 1983. Effect of estradiol on human breast cancer cells in culture. Cancer Res. 43: 349-354. (Pubitemid 13172841)
19. Darbre PD, Byford JR, Shaw LE, Horton RA, Pope GS, Sauer MJ. 2002. Oestrogenic activity of isobutylparaben in vitro and in vivo. J Appl. Toxicol. 22: 219-226. (Pubitemid 34830746)
20. Darbre PD, Byford JR, Shaw LE, Hall S, Coldham NG, Pope GS, Sauer MJ. 2003. Oestrogenic activity of benzylparaben. J. Appl. Toxicol. 23: 43-51.
21. Darbre PD, Aljarrah A, Miller WR, Coldham NG, Sauer MJ, Pope GS. 2004. Concentrations of parabens in human breast tumours. J. Appl. Toxicol. 24: 5-13. (Pubitemid 38181537)
22. Donovan M, Tiwary CM, Axelrod D, Sasco AJ, Jones L, Hajek R, Sauber E, Kuo J, Davis DL. 2007. Personal care products that contain estrogens or xenoestrogens may increase breast cancer risk. Med. Hypoth. 68: 756-766. (Pubitemid 46157081)
23. Duty SM, Ackerman RM, Calafat AM, Hauser R. 2005. Personal care product use predicts urinary concentrations of some phthalate monoesters. Environ. Health Perspect. 113: 1530-1535. (Pubitemid 41614907)
24. Exley C, Charles LM, Barr L, Martin C, Polwart A, Darbre PD. 2007. Aluminium in human breast tissue. J. Inorg. Biochem. 101: 1344-1346.
25. Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, Hass BS, Xie Q, Dial SL, Moland CL, Sheehan DM. 2001. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem. Res. Toxicol. 14: 280-294. (Pubitemid 32238488)
26. Flarend R, Bin T, Elmore D, Hem SL. 2001. A preliminary study of the dermal absorption of aluminium from antiperspirants using aluminium-26. Food Chem. Toxicol. 39: 163-168. (Pubitemid 32239355)
27. Frater G, Bajgrowicz JA, Kraft P. 1998. Fragrance chemistry. Tetrahedron 54: 7633-7703.
28. Gee RH, Charles A, Taylor N, Darbre PD. 2008. Oestrogenic and androgenic activity of triclosan in breast cancer cells. J. Appl. Toxicol. 28: 78-91.
29. Glover JF, Irwin JT, Darbre PD. 1988. Interaction of phenol red with estrogenic and antiestrogenic action on growth of human breast cancer cells ZR-75-1 and T-47-D. Cancer Res. 48: 3693-3697.
30. Gomez E, Pillon A, Fenet H, Rosain D, Duchesne MJ, Nicolas JC, Balaguer P, Casellas C. 2005. Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens and musks. J. Toxicol. Environ. Health A 68: 239-251. (Pubitemid 40130175)
31. Gordon RM, Unsworth K. 1943. The lethal action of benzyl benzoate, dimethylthianthrene (Mitigal) and tetraethylthiuram monosulfide (Tetmos) on the scabies producing mites, Notoedres sp. and Sarcoptes scabiei Var. Hominis, when tested in vitro. Ann. Trop. Med. 37: 195-199.
32. Green B, Leake RE. 1987. Steroid Hormones: A Practical Approach. IRL Press: Oxford.
33. Guillard O, Fauconneau B, Olichon D, Dedieu G, Deloncle R. 2004. Hyperaluminemia in a woman using an aluminium-containing antiperspirant for 4 years. Am. J. Med. 117: 956-959. (Pubitemid 40075565)
34. Hany J, Nagel R, Nachweis V. 1995. UV-Filtersubstanzen in muttermilch. Deut. Lebensmitt.-Rundshau 91: 341-345.
35. Harris CA, Henttu P, Parker MG, Sumpter JP. 1997. The estrogenic activity of phthalate esters in vitro. Environ. Health Perspect. 105: 802-811. (Pubitemid 27487770)
36. Harvey PW, Darbre P. 2004. Endocrine disrupters and human health: could oestrogenic chemicals in body care cosmetics adversely affect breast cancer incidence in women? A review of evidence and call for further research. J Appl. Toxicol. 24: 167-176. (Pubitemid 38801621)
37. Harville HM, Voorman R, Prusakiewicz JJ. 2007. Comparison of paraben stability in human and rat skin. Drug Metab. Lett. 1: 17-21.
38. Hashimoto Y, Kawaguchi M, Miyazaki K, Nakamura M. 2003. Estrogenic activity of tissue conditioners in vitro. Dental Mater. 19: 341-346.
39. Hayden JF, Barlow SA. 1972. Structure-activity relationships of organosiloxanes and the female reproductive system. Toxicol. Appl. Pharmacol. 21: 68-79.
40. Hayden CGJ, Roberts MS, Bensen HAE. 1997. Systemic absorption of sunscreen after topical application. Lancet 350: 863-864. (Pubitemid 27404352)
41. He B, Rhodes-Brower S, Miller MR, Munson AE, Germolec DR, Walker VR, Korach KS, Meade BJ. 2003. Octamethylcyclotetrasiloxane exhibits estrogenic activity in mice via ERα. Toxicol. Appl. Pharmacol. 192: 254-261. (Pubitemid 37311342)
42. Heneweer M, Muusse M, van der Berg M, Sanderson JT. 2005. Additive estrogenic effects of mixtures of frequently used UV filters on pS2-gene transcription in MCF-7 cells. Toxicol. Appl. Pharmacol. 208: 170-177. (Pubitemid 41377133)
43. Hihi AK, Wahli W. 1999. Structure and function of the estrogen reeptor. In Estrogens and Antiestrogens I, Oettel M, Schillinger E (eds). Springer: Berlin; 111-126.
44. Hossaini A, Larsen JJ and Larsen JC. 2000. Lack of oestrogenic effects of food preservatives (parabens) in uterotrophic assays. Food Chem. Toxicol. 38: 319-323. (Pubitemid 30155492)
45. Hovander L, Malmberg T, Athanasiadou M, Athanassiadis I, Rahm S, Bergman A, Klasson Wehler E. 2002. Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma. Arch. Environ. Contam. Toxicol. 42: 105-117. (Pubitemid 34260160)
46. International Fragrance Association. 1999. Code of Practice. IFRA: Geneva.
47. Inui M, Adachi T, Takenaka S, Inui H, Nakazawa M, Ueda M, Wata H, Mori C, Iguchi T, Miyatake K. 2003. Effect of UV screens and preservatives on vitellogenin and choriogenin production in male medaka (Oryzias latipes). Toxicology 194: 43-50. (Pubitemid 37421381)
48. Ishiwatari S, Suzuki T, Hitomi T, Yoshinl S, Matsukuma S, Tsuji T. 2007. Effects of methyl paraben on skin keratinocytes. J. Appl. Toxicol. 27: 1-9. (Pubitemid 46180780)
49. Janjua NR, Mogensen B, Andersson AM, Petersen JH, Henriksen M, Skakkebaek NE, Wulf HC. 2004. Systemic absorption of the sunscreens benzophenone-3, octyl-methoxycinnamate, and 3-(4-methylbenzylidene) camphor after whole-body topical application and reproductive hormone levels in humans. J. Invest. Dermatol. 123: 57-61. (Pubitemid 38833463)
50. Janjua NR, Mortensen GK, Andersson AM, Kongshoj B, Skakkebaek NE, Wulf HC. 2007. Systemic uptake of diethyl phthalate, dibutyl phthalate, and butyl paraben following whole-body topical application and reproductive and thyroid hormone levels in humans. Environ. Sci. Technol. 41: 5564-5570. (Pubitemid 47221785)
51. Janjua NR, Frederiksen H, Skakkebaek NE, Wulff HC, Andersson AM. 2008a. Urinary excretion of phthalates and paraben after repeated whole-body topical application in humans. Int. J. Androl. 31: 118-130. (Pubitemid 351341369)
52. Janjua NR, Kongshoj B, Andersson AM, Wulff HC. 2008b. Sunscreens in human plasma and urine after repeated whole-body topical application. J. Eur. Acad. Dermatol. Venereol. 22: 456-461.
53. Jimbo Y. 1983. Penetration of fragrance compounds through human epidermis. J. Dermatol. 10: 229-239.
54. Jin-Sung P, Lee BJ, Kang KS, Tai JH, Cho JJ, ChoMH, Inoue T, Lee YS. 2000. Hormonal effects of several chemicals in recombinant yeast, MCF7 cells and uterotropic assays in mice. Microbiol. Biotechnol. 10: 293-299.
55. Jobling S, Reynolds T, White R, Parker MG, Sumpter JP. 1995. A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environ. Health Perspect. 103: 582-587.
56. Kameda Y, Tamada M, Kanai Y, Masunaga S. 2007. Occurrence of organic UV filters in surface waters, sediments, and core sediments in Tokyo Bay - organic UV filters are new POPs? Organohalogen Compounds 69: 263-266.
57. Kannan K, Reiner JL, Yun SH, Perrotta EE, Tao L, Johnson-Restrepo B, Rodan BD. 2005. Polycyclic musk compounds in higher trophic level aquatic organisms and humans from the United States. Chemosphere 61: 693-700. (Pubitemid 41433386)
58. Klopman G, Chakravarti SK. 2003. Screening of high production volume chemicals for estrogen receptor binding activity (II) by the MultiCASE expert system. Chemosphere 51: 461-468. (Pubitemid 36286104)
59. Koda T, Umezu T, Kamata R, Morohoshi K, Ohta T, Morita M. 2005. Uterotrophic effects of benzophenone derivatives and p-hydroxybenzoate used in ultraviolet screens. Environ. Res. 98: 40-45. (Pubitemid 40254943)
60. Kortenkamp A. 2006. Breast cancer, oestrogens and environmental pollutants: a re-evaluation from a mixture perspective. Int. J. Androl. 29: 193-198.
61. Kuklenyik Z, Bryant XA, Needham LL, Calafat AM. 2007. SPE/SPME-GC/MS approach for measuring musk compounds in serum and breast milk. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 858: 177-183. (Pubitemid 47513612)
62. Kunz PY, Fent K. 2006a. Multiple hormonal activities of UV filters and comparison of in vivo and in vitro estrogenic activity of ethyl-4-aminobenzoate in fish. Aquat. Toxicol. 79: 305-324. (Pubitemid 44374762)
63. Kunz PY, Fent K. 2006b. Estrogenic activity of UV filter mixtures. Toxicol. Appl. Pharmacol. 217: 86-99.
64. Kyung-Sun-Kang, Cho SD, Lee YS. 2002. Additive estrogenic activites of the binary mixtures of four estrogenic chemicals in recombinant yeast expressing human estrogen receptor. J. Vet. Sci. 3: 1-5.
65. Lapczynski A, McGinty D, Jones L, Bhatia S, Letizia CS, Api AM. 2007 Fragrance material review on benzyl salicylate. Food Chem. Toxicol. 45: S362-S380. (Pubitemid 350181209)
66. Lemini C, Silva G, Timossi C, Luque D, Valverde A, Gonzalez-Marti M, Hernandez A, Rubio-Poo C, Chavez Lara B, Valezuela F. 1997. Estrogenic effects of p-hydroxybenzoic acid in CD1 mice. Environ. Res. 75: 130-134. (Pubitemid 28022906)
67. Lemini C, Jaimez R, Avila ME, Franco Y, Larrea F, Lemus AE. 2003. In vivo and in vitro estrogen bioactivities of alkyl parabens. Toxicol. Ind. Health. 19: 69-79. (Pubitemid 40036696)
68. Mannello F, Tonti GA, Darbre PD. 2008. Concentration of aluminium in breast cyst fluids collected from women affected by gross cystic breast disease. J. Appl. Toxicol. (in press).
69. Masiakowski P, Breathnach R, Bloch J, Gannon F, Krust A, Chambon P. 1982. Cloning of cDNA sequences of hormone-regulated genes from the MCF-7 human breast cancer cell line. Nucl. Acids Res. 10: 7895-7903.
70. Matsumura A, Ghosh A, Pope GS, Darbre PD. 2005. Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. J. Steroid Biochem. Mol. Biol. 94: 431-443. (Pubitemid 40616404)
71. McKim JM, Wilga PC, Breslin WJ, Plotzke KP, Gallavan RH, Meeks RG. 2001. Potential estrogenic and antiestrogenic activity of the cyclic siloxane ocatamethylcyclotetrasiloxane (D4) and the linear siloxane hexamethyldisiloxane (HMDS) in immature rats using the uterotrophic assay. Toxicol. Sci. 63: 37-46.
72. Merck Index. 2006. An Encyclopedia of Chemicals, Drugs and Biologicals, 14th edn. Merck Research Laboratories: NJ, USA.
73. Miller WR. 1996. Estrogen and Breast Cancer. Chapman and Hall: London.
74. Mori T, Iida M, Ishibashi H, Kohra S, Takao Y, Takemasa T, Arizono K. 2007. Hormonal activity of polycyclic musks evaluated by reporter gene assay. Environ. Sci. 14: 195-202.
75. Moss T, Howes D, Willimas FM. 2000. Percutaneous penetration and dermal metabolism of triclosan (2,4,4′-trichloro-2′-hydroxydiphenyl ether) Food Chem. Toxicol. 38: 361-370. (Pubitemid 30155497)
76. Nesaretnam K, Corcoran D, Dils RR, Darbre P. 1996. 3,4,3′,4′- Tetrachlorobiphenyl acts as an estrogen in vitro and in vivo. Mol.r Endocrinol. 10: 923-936. (Pubitemid 26268874)
77. Nishihara T, Nishikawa J, Kanayama T, Dakeyama F, Saito K, Imagawa M, Takatori S, Kitagawa Y, Hori S, Utsumi H. 2000. Estrogenic activites of 517 chemicals by yeast two-hybrid assay. J. Health Sci. 46: 282-298. (Pubitemid 30671081)
78. Okubo T, Yokoyama Y, Kano K, Kano I. 2001. ER-dependent estrogenic activity of parabens assessed by proliferation of human breast cancer MCF-7 cells and expression of ER á and PR. Food Chem. Toxicol. 39: 1225-1232. (Pubitemid 33030234)
79. Okubo T, Suzuki T, Yokoyama Y, Kano K, Kano I. 2003. Estimation of estrogenic and anti-estrogenic aactivities of some phthalate diesters and monoesters by MCF-7 cell proliferation assay in vitro. Biol. Pharm. Bull. 26: 1219-1224. (Pubitemid 40012597)
80. Osborne CK, Hobbs K, Trent JM. 1987. Biological differences among MCF-7 human breast cancer cell lines from different laboratories. Breast Cancer Res. Treatment 9: 111-121. (Pubitemid 17114724)
81. Payne J, Scholze M, Kortenkamp A. 2001. Mixtures of four organochlorines enhance human breast cancer cell proliferation. Environ. Health Perspect. 109: 391-397. (Pubitemid 32440278)
82. Pedersen KL, Pedersen SN, Christiansen LB, Korsgaard B, Bjerregaard P. 2000. The preservatives ethyl-, propyl-, and butylparaben are oestrogenic in an in vivo fish assay. Pharmacol. Toxicol. 86: 110-113. (Pubitemid 30158963)
83. Pike ACW. 2006. Lessons learnt from structural studies of the oestrogen receptor. Best Pract. Res. Clin. Endocrinol. Metab. 20: 1-14.
84. Prusakiewicz JJ, Ackermann C, Voorman R. 2006. Comparison of skin esterase activities from different species. Pharm. Res. 23: 1517-1524. (Pubitemid 43993815)
85. Pugazhendhi D, Pope GS, Darbre PD. 2005. Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines. J. Appl. Toxicol. 25: 301-309. (Pubitemid 41039568)
86. Pugazhendhi D, Sadler AJ, Darbre PD. 2007. Comparison of the global gene expression profiles produced by methylparaben, n-butylparaben and 17 β-oestradiol in MCF7 human breast cancer cells. J. Appl. Toxicol. 27: 67-77. (Pubitemid 46180788)
87. Rajapakse N, Silva E, Kortenkamp A. 2002. Combining xenoestrogens at levels below individual no-observed-effect concentrations dramatically enhances steroid hormone action. Environ. Health Perspect. 110: 917-921.
88. Reiner JL, Wong CM, Arcaro KF, Kannan K. 2007. Synthetic musk fragrances in human milk from the United States. Environ. Sci. Technol. 41: 3815-3820. (Pubitemid 46903185)
89. Routledge EJ, Parker J, Odum J, Ashby J, Sumpter JP. 1998. Some alkyl hydroxy benzoate preservatives (parabens) are estrogenic. Toxicol. Appl. Pharmacol. 153: 12-19. (Pubitemid 28563885)
90. Schlumpf M, Cotton B, Conscience M, Haller V, Steinmann B, Lichtensteiger W. 2001. In vitro and in vivo estrogenicity of UV screens. Environ. Health Perspect. 109: 239-244.
91. Schnuch A, Uter W, Geier J, Lessman H, Frosch PJ. 2007. Sensitization to 26 fragrances to be labeled according to current European regulation. Contact Dermatitis 57: 1-10.
92. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B. 2005. Interaction of polycyclic musks with the estrogen receptor (ER), androgen receptor (AR) and progesterone receptor (PR) in reporter gene assays. Toxicol. Sci. 83: 264-272. (Pubitemid 40227896)
93. Schulz WT, Sinks G D, Cronin MTD. 2002. Structure-activity relationships for gene activation oestrogenicity: evaluation of a diverse set of aromatic chemicals, Environ. Toxicol. 17: 14-23.
94. Silva E, Rajapakse N, Kortenkamp A. 2002. Something from 'nothing' - eight weak estrogenic chemicals combined at concentrations below NOECs produce significant mixture effects. Environ. Sci. Technol. 36: 1751-1756. (Pubitemid 34310943)
95. Simonich SL, Begley WM, Debaere G, Eckhoff WS. 2000. Trace analysis of fragrance materials in wastewater and treated wastewater. Environ. Sci. Technol. 34: 959-965. (Pubitemid 30155196)
96. Strange PG. 2008. Agonist binding, agonist affinity and agonist efficacy at G protein-coupled receptors. Br. J. Pharmacol. 153: 1353-1363.
97. Tinwell H, Ashby J. 2004. Sensitivity of the immature rat uterotrophic assay to mixtures of estrogens. Environ. Health Perspect. 112: 575-582. (Pubitemid 38500048)
98. Treffel P, Gabard B. 1996. Skin penetration and sun protection factor of ultraviolet filters from two vehicles. Pharm. Res. 13: 770-774. (Pubitemid 26160098)
99. Zareba G, Gelein R, Morrow PE, Utell MJ. 2002. Percutaneous absorption studies of octamethylcyclotetrasiloxane using the human skin/nude mouse model. Skin Pharmacol. Appl. Skin Physiol. 15: 184-194. (Pubitemid 34665225)