17β-estradiol-3-dansyl | 100821-85-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17β-estradiol-3-dansyl
• 英文别名: DNS-β-estradiol；3-O-dansyl estradiol；E2-Dansyl；3-Dansylestradiol；[(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] 5-(dimethylamino)naphthalene-1-sulfonate
• CAS: 100821-85-0；30808-48-1
• 化学式: C₃₀H₃₅NO₄S
• 分子量: 505.678
• InChiKey: HPCHMBPQUJEXLJ-XDLBVFQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  雌二醇 、 丹酰氯 在 Duolite A-102D 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以92%的产率得到17β-estradiol-3-dansyl
  参考文献：
  名称：

  A convenient derivatization with anion exchange resin catalysts for high-performance liquid chromatographic analysis. I. Derivatization of estrogens with dansyl chloride.

  摘要：

  阴离子交换树脂Duolite A-101D、A-102D和A-109被应用于雌激素与丹酯氯（DNS-Cl）的荧光衍生化，以便进行高效液相色谱分析。通过将雌激素与DNS-Cl的混合溶液在丙酮中通过填有Duolite A-102D（OH-形式）的小柱，衍生化过程迅速且高效，产生了相应的DNS-雌激素，产率极高。这种使用树脂柱的程序具有实用价值，并可适用于其他分析样品的衍生化。

  DOI：

  10.1248/cpb.33.5092

文献信息

• Simultaneous quantitation of testosterone and estradiol in human cell line (H295R) by liquid chromatography/positive atmospheric pressure photoionization tandem mass spectrometry
  作者：F. Zhang、D. L. Rick、L. H. Kan、A. W. Perala、D. R. Geter、M. J. Lebaron、M. J. Bartels

  DOI：10.1002/rcm.5208

  日期：2011.10.30

  lack of selectivity. In the current study, a rapid and sensitive liquid chromatography/positive atmospheric pressure photoionization tandem mass spectrometry method (LC/APPI-MS/MS) has been developed and validated for the simultaneous quantitation of testosterone and estradiol in the H295R cell line. Briefly, the media from cultured cells was extracted with dichloromethane (CH(2)Cl(2)) containing internal

  自1990年代初以来，环境污染物与内分泌系统的可能相互作用一直是环境问题。为了检查这些相互作用，监管机构已引入测试指南来筛选可能的内分泌活性化合物。这些准则之一是EPA的OPPTS 890.1550 [类固醇生成（人类细胞系H295R）]。该指南要求对各种生物测试系统中的两种主要生物标志物（睾丸激素和雌二醇）进行定量。传统的定量方法，如放射免疫测定（RIA）和酶联免疫吸附测定（ELISA）已用于定量低水平的类固醇。但是，这些方法具有缺点，例如放射性安全性，抗体可用性，每种生物标记物的单独检测方法以及缺乏选择性。在目前的研究中 已经开发了一种快速灵敏的液相色谱/正气压光电离串联质谱法（LC / APPI-MS / MS），并已验证该方法可同时定量H295R细胞系中的睾丸激素和雌二醇。简而言之，用含有睾丸激素-d（3）和雌二醇-（13）C（3）内标的二氯甲烷（CH（2）Cl（2））提取培养细胞
• Effects of Room Temperature Ionic Liquids on Fluorescence Characteristics of 17β-estradiol and its Derivative
  作者：Xuedong Wang、Yanyan Li、Xiwei Du、Zhenkun Lin、Changjiang Huang

  DOI：10.1007/s10895-011-0853-z

  日期：2011.7

  their effects on derivatization reaction or derivatives. In this study, we reported that the effects of four different RTILs, i.e., [EMIM]PF6, [BMIM]PF6, [HMIM]PF6 and [OMIM]PF6, on fluorescence spectra of 17 β-estradiol (E2), and its derivatization solvent dansyl chloride (DNSCl) and the derivative. [BMIM]PF6 had a significant quenching effect on the fluorescence intensity of E2, suggesting the formation

  以往的报道很少关注 RTILs（室温离子液体）及其对衍生反应或衍生物的影响。在本研究中，我们报道了四种不同的 RTILs，即 [EMIM]PF 6、[BMIM]PF 6、[HMIM]PF 6和 [OMIM]PF 6对 17 β-雌二醇 (E2 )，及其衍生溶剂丹磺酰氯 (DNSCl) 及其衍生物。[BMIM]PF 6对E2的荧光强度有显着的淬灭作用，表明[BMIM]PF 6 /E2复合物的形成以及可能在更疏水的微环境中埋藏的E2分子。估计的 Stern-Volmer 猝灭常数 ( Ksv = 0.3519) 证明 [BMIM]PF 6引起的 E2 淬火是一个动态淬火过程。在咪唑鎓阳离子中具有不同烷基链长度的四种RTIL导致对E2的不同猝灭强度如下：[EMIM]PF 6 > [BMIM]PF 6 > [HMIM]PF 6 > [OMIM]PF 6。在 5 mg L -1的 DNSCl 下，[BMIM]PF
• High-sensitivity determination of estrogens in fish plasma using chemical derivatization upstream UHPLC–MSMS
  作者：Ugo Bussy、Yu-Wen Chung-Davidson、Tyler J. Buchinger、Ke Li、Weiming Li

  DOI：10.1016/j.steroids.2017.04.003

  日期：2017.7

  This article describes the development and validation of a sensitive LC-MSMS method for determination of estrogen in fish plasma. Dansyl chloride derivatization of the phenol functional group in estrogen was used to enhance the response to atmospheric pressure ionization leading to improve the sensitivity. Individual C-13 internal standards were selected after comparison with deuterated standards. Liquid-liquid extraction (ethyl acetate or methyl tert-butyl ether) and protein precipitation (acetonitrile, methanol or acetone) were compared for the extraction and clean-up of estrogens from fish plasma. Ethyl acetate was selected as the best alternative with recovery ranging from 61 to 96% and matrix effect ranging from 88 to 106%. Limits of quantification ranged from 0.5 to 1 pg/mL showing a gain in sensitivity of 10,000 times over electrospray ionization of underivatized estrogens. Accuracy and precision were validated over three consecutive days and the method was applied to measure estrogen in sea lamprey (Petromyzon marinus) and lake trout (Salvelinus namaycush) plasma. Estrone and estriol were detected in fish below 1 ng/mL in plasma, justifying the need of a highly sensitive LC-MSMS quantification method.
• CARTONI, GIAMPAOLO;COCCIOLI, FRANCO;CAMILLI, LUCIA, ANN. CHIM., 80,(1990) N-10, C. 453-460
  作者：CARTONI, GIAMPAOLO、COCCIOLI, FRANCO、CAMILLI, LUCIA

  DOI：——

  日期：——