title: Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo.
abstract: C7α-substituted estradiols bind to estrogen receptors in cell nuclei, yet these derivatives remain little used in bioimaging. Here, we describe a fluorescent derivative of estradiol (E2) with a boron-dipyrromethene (BODIPY) moiety attached to C7α, synthesized by olefin metathesis reaction of 7α-allylestradiol and 9-decenyl-BODIPY. In ovariectomized rats and non-ovariectomized mice, E2-BODIPY promoted the growth of uterine tissue similar to the effect of estradiol. Twenty-four hours after subcutaneous injection of E2-BODIPY in non-ovariectomized mice, we observed fluorescence of E2-BODIPY in the nuclei of uterine epithelial cells. Our findings suggest that fluorescence microscopy can localize this derivative in E2-responsive cells during normal development and tumorigenesis in vivo.
authors.affiliation: Department of Applied Chemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku-ku, Tokyo, Japan. okamoto@aoni.waseda.jp
authors.forename: Mayumi
authors.initials: M
authors.lastname: Okamoto
authors.forename: Shun
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Ikeuchi
authors.forename: Shunji
authors.initials: S
authors.lastname: Yamada
authors.forename: Korehito
authors.initials: K
authors.lastname: Yamanouchi
authors.forename: Kazumichi
authors.initials: K
authors.lastname: Nagasawa
authors.forename: Shun
authors.initials: S
authors.lastname: Maekawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Kato
authors.forename: Isao
authors.initials: I
authors.lastname: Shimizu
mesh_terms: D000818:Animals; D001896:Boron Compounds / Q000737:chemistry*; D004958:Estradiol / Q000737:chemistry*; D005260:Female; D051379:Mice; D008856:Microscopy, Fluorescence / Q000379:methods*; D010052:Ovariectomy; D051381:Rats; D014599:Uterus / Q000378:metabolism
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D004958:Estradiol