estrone-3-oxyacetyl-Arg-Gly-Asp-Ser-OH

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: estrone-3-oxyacetyl-Arg-Gly-Asp-Ser-OH
• 英文别名: estrone-3-oxyacetyl-Arg-Gly-Asp-Ser；(3S)-4-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-3-[[2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]acetyl]amino]pentanoyl]amino]acetyl]amino]-4-oxobutanoic acid
• 化学式: C₃₅H₄₉N₇O₁₁
• 分子量: 743.814
• InChiKey: WEXFBNZRZCBVJV-PPXSHVBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  302
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  雌酚酮 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium ethanolate 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 19.0h， 生成 estrone-3-oxyacetyl-Arg-Gly-Asp-Ser-OH
  参考文献：
  名称：

  Improved Anti-Osteoporosis Potency and Reduced Endometrial Membrane Hyperplasia During Hormone Replacement Therapy with Estrogen−RGD Peptide Conjugates

  摘要：

  To improve the specificity and potency of estrogen replacement therapy therapeutics while also minimizing the side effects such as bone resorption and thickening of the uterine wall, a series of novel estrogen-derived conjugates estradiol-3-RGD, estradiol-17-RGD, and estrone-3-RGD peptides have been prepared. In a mouse model, intraperitoneal (i.p.) administration of these estrogen-RGD peptide conjugates resulted in decreased serum concentrations of calcium and alkaline phosphatase, as well as increased levels of calcium, phosphorus, and minerals in the mouse femur. Furthermore, the anti-osteoporosis action of these conjugates followed a dose-dependent manner and was accompanied with no observable effects on endometrial cell hyperplasia. In addition to all of these compounds exhibiting biological activity when administered by the i.p. route, we were particularly pleased to note that the estradiol-3-RGD and estradiol-17-RGD conjugates were both orally active.

  DOI：

  10.1021/jm070242a

文献信息

• 3D QSAR of novel estrogen–RGD peptide conjugates: Getting insight into structural dependence of anti-osteoporosis activity and side effect of estrogen in ERT
  作者：Ming Zhao、Jiangyuan Liu、Xiaoyi Zhang、Li Peng、Chunyu Li、Shiqi Peng

  DOI：10.1016/j.bmc.2009.03.057

  日期：2009.5

  To explore the structural dependence of the oral potency and side effect of estrogen-RGD peptide conjugates, here six novel conjugates were prepared via introducing RGD-tetrapeptides into both 3- and 17-positions of estradiol, and introducing RGD-octapeptides into 3-position of estrone. In an ovariectomized mouse model they exhibited higher anti-osteoporosis activity and lower side effect than estrogen. For 3D QSAR analysis the anti-osteoporosis activities of nine known conjugates estrogen-RGD tetrapeptide conjugates were also provided. Using Cerius(2) module their 3D QSAR analysis was performed, four equations with high r(2) values were established, and the structural dependence of the oral potency and side effect of them was elucidated. (C) 2009 Elsevier Ltd. All rights reserved.