Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo

Mayumi Okamoto, Shun Kobayashi, Hiroshi Ikeuchi, Shunji Yamada, Korehito Yamanouchi, Kazumichi Nagasawa, Shun Maekawa, Takashi Kato, Isao Shimizu

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    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.

    Original languageEnglish
    Pages (from-to)845-849
    Number of pages5
    JournalSteroids
    Volume77
    Issue number8-9
    DOIs
    Publication statusPublished - 2012 Jul

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    Keywords

    • BODIPY
    • Estrogen receptor
    • Uterus

    ASJC Scopus subject areas

    • Biochemistry
    • Clinical Biochemistry
    • Endocrinology
    • Molecular Biology
    • Organic Chemistry
    • Pharmacology

    Cite this

    Okamoto, M., Kobayashi, S., Ikeuchi, H., Yamada, S., Yamanouchi, K., Nagasawa, K., Maekawa, S., Kato, T., & Shimizu, I. (2012). Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo. Steroids, 77(8-9), 845-849. https://doi.org/10.1016/j.steroids.2012.04.011