TY - JOUR
T1 - Synthesis and bioassay of a boron-dipyrromethene derivative of estradiol for fluorescence imaging in vivo
AU - Okamoto, Mayumi
AU - Kobayashi, Shun
AU - Ikeuchi, Hiroshi
AU - Yamada, Shunji
AU - Yamanouchi, Korehito
AU - Nagasawa, Kazumichi
AU - Maekawa, Shun
AU - Kato, Takashi
AU - Shimizu, Isao
N1 - Funding Information:
The authors thank Prof. Robert Shiurba for discussions. Funding for this research was from the Global Center of Excellence (COE) program “Center for Practical Chemical Wisdom” by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT).
PY - 2012/7
Y1 - 2012/7
N2 - 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.
AB - 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.
KW - BODIPY
KW - Estrogen receptor
KW - Uterus
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U2 - 10.1016/j.steroids.2012.04.011
DO - 10.1016/j.steroids.2012.04.011
M3 - Article
C2 - 22542503
AN - SCOPUS:84861651774
SN - 0039-128X
VL - 77
SP - 845
EP - 849
JO - Steroids
JF - Steroids
IS - 8-9
ER -