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

被引：19

作者：

Okamoto, Mayumi ^{[1
,2
]}

Kobayashi, Shun ^{[1
]}

Ikeuchi, Hiroshi ^{[1
]}

Yamada, Shunji ^{[3
]}

Yamanouchi, Korehito ^{[3
]}

Nagasawa, Kazumichi ^{[4
]}

Maekawa, Shun ^{[4
]}

Kato, Takashi ^{[4
,5
]}

Shimizu, Isao ^{[1
,2
,4
]}

机构：

[1] Waseda Univ, Dept Appl Chem, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan

[2] Waseda Univ, Res Inst Sci & Engn, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan

[3] Waseda Univ, Dept Human Behav & Environm Sci, Sch Human Sci, Tokorozawa, Saitama 3591192, Japan

[4] Waseda Univ, Dept Biosci & Biomed Engn, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan

[5] Waseda Univ, Sch Educ, Dept Biol, Shinjuku Ku, Tokyo 1628480, Japan

来源：

STEROIDS | 2012年 / 77卷 / 8-9期

关键词：

BODIPY; Estrogen receptor; Uterus; BINDING AFFINITIES; ESTROGEN; MECHANISMS; LIGANDS; ASSAY;

D O I：

10.1016/j.steroids.2012.04.011

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

C7 alpha-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 C7 alpha, synthesized by olefin metathesis reaction of 7 alpha-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. (c) 2012 Elsevier Inc. All rights reserved.

引用

页码：845 / 849

页数：5

共 16 条

[1] An ultrahigh-throughput screening assay for estrogen receptor ligands
Allan, GF
Hutchins, A
Clancy, J
[J]. ANALYTICAL BIOCHEMISTRY, 1999, 275 (02) : 243 - 247
[2] The estrogen receptor relative binding affinities of 188 natural and xenochemicals: Structural diversity of ligands
Blair, RM
Fang, H
Branham, WS
Hass, BS
Dial, SL
Moland, CL
Tong, WD
Shi, LM
Perkins, R
Sheehan, DM
[J]. TOXICOLOGICAL SCIENCES, 2000, 54 (01) : 138 - 153
[3] ESTROGEN-RECEPTORS IN HUMAN NONTARGET TISSUES - BIOLOGICAL AND CLINICAL IMPLICATIONS
CIOCCA, DR
ROIG, LMV
[J]. ENDOCRINE REVIEWS, 1995, 16 (01) : 35 - 62
[4] A SYNTHESIS OF 7-ALPHA-SUBSTITUTED ESTRADIOLS - SYNTHESIS AND BIOLOGICAL EVALUATION OF A 7-ALPHA-PENTYL SUBSTITUTED BODIPY FLUORESCENT CONJUGATE AND A F-18 LABELED 7-ALPHA-PENTYLESTRADIOL ANALOG
FRENCH, AN
WILSON, SR
WELCH, MJ
KATZENELLENBOGEN, JA
[J]. STEROIDS, 1993, 58 (04) : 157 - 169
[5] High affinity 17α-substituted estradiol derivatives:: Synthesis and evaluation of estrogen receptor agonist activity
Kasiotis, KM
Mendorou, C
Haroutounian, SA
Alexis, MN
[J]. STEROIDS, 2006, 71 (03) : 249 - 255
[6] SURPRISING PLACES OF ESTROGENIC ACTIVITY
KORACH, KS
[J]. ENDOCRINOLOGY, 1993, 132 (06) : 2277 - 2278
[7] Synthesis and binding affinities of fluoroalkylated raloxifenes
Lee, KC
Moon, BS
Lee, JH
Chung, KH
Katzenellenbogen, JA
Chi, DY
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (17) : 3649 - 3658
[8] BODIPY dyes and their derivatives: Syntheses and spectroscopic properties
Loudet, Aurore
Burgess, Kevin
[J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4891 - 4932
[9] Mechanisms of estrogen action
Nilsson, S
Mäkelä, S
Treuter, E
Tujague, M
Thomsen, J
Andersson, G
Enmark, E
Pettersson, K
Warner, M
Gustafsson, JÅ
[J]. PHYSIOLOGICAL REVIEWS, 2001, 81 (04) : 1535 - 1565
[10] Novel monitoring strategies for xenoestrogens
Oosterkamp, AJ
Hock, B
Seifert, M
Irth, H
[J]. TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1997, 16 (10) : 544 - 553

← 1 2 →