title: Regioselective deuterium labeling of estrone and catechol estrogen metabolites.
abstract: Increased exposure to estrogens and estrogen metabolites is linked with increased rates of breast, ovarian and other human cancers. Metabolism of estrogen can led to formation of electrophilic o-quinones capable of binding to DNA. In order to gain insight into the mechanism of estrogen-induced DNA damage, estrone and catechol estrogens derived from estrone, have been regioselectively labeled with deuterium at the 1-position. Estrone-1-d, estrone-1,2,4-d3, 4-hydroxyestrone-1-d and 2-hydroxyestrone-1-d have been synthesized with or without deuteriums at the 16-position. The key labeling step involves deuterated trifluoroacetic acid exchange catalyzed by t-butyl alcohol. This economical, straightforward labeling technique makes available a range of estrone compounds containing deuterium at the 1-position.
authors.affiliation: Department of Chemistry, University of Nebraska at Omaha, 6001 Dodge Street, Omaha, NE 68182-0109, United States. Electronic address: dstack@unomaha.edu.
authors.forename: Douglas E
authors.initials: DE
authors.lastname: Stack
authors.affiliation: Department of Chemistry, University of Nebraska at Omaha, 6001 Dodge Street, Omaha, NE 68182-0109, United States.
authors.forename: Justin
authors.initials: J
authors.lastname: Ritonya
authors.affiliation: Department of Chemistry, University of Nebraska at Omaha, 6001 Dodge Street, Omaha, NE 68182-0109, United States.
authors.forename: Scott
authors.initials: S
authors.lastname: Jakopovic
authors.affiliation: Department of Chemistry, University of Nebraska at Omaha, 6001 Dodge Street, Omaha, NE 68182-0109, United States.
authors.forename: Brittney
authors.initials: B
authors.lastname: Maloley-Lewis
mesh_terms: D002396:Catechols / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D004970:Estrone / Q000737:chemistry*; D007553:Isotope Labeling; D015394:Molecular Structure
chemical_list: D002396:Catechols; D004970:Estrone; D003903:Deuterium; C034221:catechol
keywords: Catechol estrogen; Deuterium labeled; Estrone; Regioselective