Estradiol dimers as a new class of steroid sulfatase reversible inhibitors

被引：14
|
作者：
Fournier, Diane
Poirier, Donald [1 ]
机构：
[1] CHUQ CHUL Res Ctr, Div Med Chem, Oncol & Mol Endocrinol Lab, Quebec City, PQ G1V 4G2, Canada
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 03期
基金：
加拿大健康研究院;
关键词：
Sulfatase; Steroid; Inhibitor; Dimer; Enzyme; Cancer; ESTRONE SULFATASE; BREAST-CANCER; MODULATORS; ENZYMES; TISSUE;
D O I：
10.1016/j.bmcl.2008.12.047
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of estradiol dimers was synthesized or selected from compounds available in our laboratory and tested for inhibition against steroid sulfatase. Dimers linked by their C17 position, compounds 7 and 8, showed inhibitory potency similar (56% and 54% at 1 mu M) to that of our best previously reported reversible inhibitor EM-690 (62% at 1 mu M). Docking experiment seems to indicate that C17-C17 dimers bind in a similar way to EM-690 whereas C16-O3 and C16-C16 dimers bind in an upside-down position. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：693 / 696
页数：4
相关论文
共 50 条
  • [1] Steroid sulfatase inhibitors
    Poirier, D
    Ciobanu, LC
    Maltais, R
    EXPERT OPINION ON THERAPEUTIC PATENTS, 1999, 9 (08) : 1083 - 1099
  • [2] Steroid sulfatase inhibitors
    Nussbaumer, P
    Billich, A
    MEDICINAL RESEARCH REVIEWS, 2004, 24 (04) : 529 - 576
  • [3] Steroid sulfatase inhibitors
    Potter, BVL
    Woo, LWL
    Purohit, A
    Reed, MJ
    DRUG DISCOVERY TODAY, 1996, 1 (07) : 308 - 308
  • [4] Steroid sulfatase inhibitors
    Horvath, A
    Billich, A
    EXPERT OPINION ON THERAPEUTIC PATENTS, 2005, 15 (11) : 1541 - 1553
  • [5] Steroid sulfatase inhibitors
    Nussbaumer, P
    Billich, A
    EXPERT OPINION ON THERAPEUTIC PATENTS, 2003, 13 (05) : 605 - 625
  • [6] Nortropinyl-arylsulfonylureas as novel, reversible inhibitors of human steroid sulfatase
    Nussbaumer, P
    Geyl, D
    Horvath, A
    Lehr, P
    Wolff, B
    Billich, A
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (21) : 3673 - 3677
  • [7] Steroid derivatives as inhibitors of steroid sulfatase
    Mostafa, Yaser A.
    Taylor, Scott D.
    JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2013, 137 : 183 - 198
  • [8] Structure-activity relationships of 17α-derivatives of estradiol as inhibitors of steroid sulfatase
    Boivin, RP
    Luu-The, V
    Lachance, R
    Labrie, F
    Poirier, D
    JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (23) : 4465 - 4478
  • [9] Chemical synthesis and evaluation of 17α-alkylated derivatives of estradiol as inhibitors of steroid sulfatase
    Fournier, Diane
    Poirier, Donald
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) : 4227 - 4237
  • [10] N-acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase
    Lehr, P
    Billich, A
    Wolff, B
    Nussbaumer, P
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) : 1235 - 1238
12345