Publication Year



Chemistry, computational chemistry, estrogen, environmental mimic


Chemistry | Medicine and Health Sciences | Organic Chemistry | Physical Sciences and Mathematics


17B-estradiol (E2) is the most potent of all natural estrogens. It plays a vital role in several physiological processes which include sexual differentiation, cell proliferation, and early neuronal development. E2 exerts its role by binding to its receptor protein, the estrogen receptor-a (ER). The bound ER-(E2) complex then functions as a transcription factor. However, the ER exhibits a low specificity for ligand interaction. This is demonstrated by the fact that several environmental agents, known as estrogen mimics, have been shown to induce estrogenic activity in the presence of the ER. In this paper, computational chemistry techniques were employed to compare and analyze eight estrogen mimics: diethystibestrol (DES), bis-(2-ethylhexyl)phthalate (DEHP), butylbenzyl phthalate (BBP), di-n-butyl phthalate (DBP), octylphenol (OP), nonylphenol (NP), 4-nonylphenoxycarboxylic acid (NP1EC), and 4-nonylphenoxydiethoxylate (NP2EO). The goal of this comparison was to determine parameters that may govern ligand-binding to the ER. While the presence of a phenolic OH group, the magnitude and direction of the dipole moment vector, and the presence of partially charged atoms on the aromatic ring appear to be important structural features, the most essential parameters appear to be the presence of an aromatic ring and the presence of an adequate apolar surface area.

Department 1 Awarding Honors Status