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

    Research output: Contribution to journalArticle

    11 Citations (Scopus)

    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

    Fingerprint

    Boron
    Bioassay
    Optical Imaging
    Biological Assay
    Estradiol
    Fluorescence
    Derivatives
    Imaging techniques
    Fluorescence microscopy
    Alkenes
    Subcutaneous Injections
    Cell Nucleus
    Fluorescence Microscopy
    Estrogen Receptors
    Rats
    Carcinogenesis
    Epithelial Cells
    Cells
    dipyrromethene
    Tissue

    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., ... 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

    Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo. / Okamoto, Mayumi; Kobayashi, Shun; Ikeuchi, Hiroshi; Yamada, Shunji; Yamanouchi, Korehito; Nagasawa, Kazumichi; Maekawa, Shun; Kato, Takashi; Shimizu, Isao.

    In: Steroids, Vol. 77, No. 8-9, 07.2012, p. 845-849.

    Research output: Contribution to journalArticle

    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, vol. 77, no. 8-9, pp. 845-849. https://doi.org/10.1016/j.steroids.2012.04.011
    Okamoto M, Kobayashi S, Ikeuchi H, Yamada S, Yamanouchi K, Nagasawa K et al. Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo. Steroids. 2012 Jul;77(8-9):845-849. https://doi.org/10.1016/j.steroids.2012.04.011
    Okamoto, Mayumi ; Kobayashi, Shun ; Ikeuchi, Hiroshi ; Yamada, Shunji ; Yamanouchi, Korehito ; Nagasawa, Kazumichi ; Maekawa, Shun ; Kato, Takashi ; Shimizu, Isao. / Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo. In: Steroids. 2012 ; Vol. 77, No. 8-9. pp. 845-849.
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