fluorescein-5-thiosemicarbazide | 1216446-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: fluorescein-5-thiosemicarbazide
• 英文别名: 5-(aminocarbamothioylamino)-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• CAS: 1216446-90-0
• 化学式: C₂₁H₁₅N₃O₅S
• 分子量: 421.433
• InChiKey: MEUCHQDLZYLNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  fluorescein-5-thiosemicarbazide 、 葡萄糖 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 2.5h， 以80%的产率得到
  参考文献：
  名称：

  One-pot fluorescent labeling of saccharides with fluorescein-5-thiosemicarbazide for imaging polysaccharides transported in living cells

  摘要：

  A simple and efficient procedure for the fluorescent labeling of saccharides is a prerequisite step for imaging the transport of polysaccharides in living cells. We report a one-pot strategy for the fluorescent labeling of saccharides with fluorescein-5-thiosemicarbazide (FTSC), which introduces the thiosemicarbazide group of FTSC to the aldehyde group at the reducing end of saccharides to form stable amino derivatives via reductive amination. The Glc-FTSC derivative was characterized by HPLC-MS, HRESIMS and NMR spectroscopy. Saccharides were quantitatively labeled with FTSC at 75 degrees C for 1 h under optimum reaction conditions. Fluorescence studies illustrated that the conjugation of FTSC to saccharides did not change its florescence properties (lambda(ex) = 495 nm, lambda(em) = 517 nm), presenting desirable compatibility with commonly used fluorescence equipment. Polysaccharide AAG-FTSC derivatives exhibited rather low levels of cytotoxicity against rat thymus cells, and the fluorescent labeling procedure had slight impact on their anti-tumor activity. Results indicate that the assay neither introduces discernible cytotoxicity against living cells nor obviously alters the functional activities of polysaccharides, and provides a convenient, highly efficient fluorescent labeling approach for imaging the transport of polysaccharides in living cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.014

文献信息

• [EN] METHODS FOR THE SITE-SELECTIVE COUPLING OF A FIRST AGENT TO A SECOND AGENT<br/>[FR] PROCÉDÉS DE COUPLAGE SITE-SÉLECTIF D'UN PREMIER AGENT À UN DEUXIÈME AGENT
  申请人：UNIV GENT

  公开号：WO2017001204A1

  公开（公告）日：2017-01-05

  The present invention relates to a method for site-selective coupling of a first agent to a second agent, comprising the steps of: contacting a first agent comprising at least one furan moiety with an activation signal and with a second agent comprising at least one hydrazine moiety or at least one hydroxylamine moiety, thereby activating said furan moiety to an activated furan moiety; and reacting said activated furan moiety with the hydrazine moiety or the hydroxylamine moiety, thereby site-selectively coupling said first agent to said second agent.

  本发明涉及一种用于将第一试剂与第二试剂进行位点选择性偶联的方法，包括以下步骤：将至少含有一个呋喃基团的第一试剂与激活信号和至少含有一个肼基团或至少含有一个羟胺基团的第二试剂接触，从而将该呋喃基团激活为活化的呋喃基团；并将该活化的呋喃基团与肼基团或羟胺基团反应，从而将该第一试剂与该第二试剂进行位点选择性偶联。
• New fluorescent macrolide derivatives for studying interactions of antibiotics and their analogs with the ribosomal exit tunnel
  作者：A. G. Tereshchenkov、A. V. Shishkina、V. V. Karpenko、V. A. Chertkov、A. L. Konevega、P. S. Kasatsky、A. A. Bogdanov、N. V. Sumbatyan

  DOI：10.1134/s0006297916100138

  日期：2016.10

  substance. With the synthesized fluorescent tylosin derivatives, the dissociation constants for ribosome complexes with several known antibiotics and macrolide analogs previously obtained were determined. It was found that the fluorescent tylosin derivatives containing BODIPY FL and NBD groups could be used to screen the binding of novel antibiotics to bacterial ribosomes in the macrolide-binding site

  合成了大环内酯类抗生素的新型荧光衍生物，该衍生物与带有罗丹明，荧光素，Alexa Fluor 488，BODIPY FL和硝基苯并恶二唑（NBD）残基的泰乐菌素有关。这些化合物与70S大肠杆菌核糖体的复合物的形成通过在恒定浓度的荧光物质下根据核糖体量测量荧光偏振来研究。用合成的荧光泰乐菌素衍生物，测定核糖体与几种先前已知的抗生素和大环内酯类似物的复合物的解离常数。发现含有BODIPY FL和NBD基团的荧光泰乐菌素衍生物可用于在大环内酯结合位点筛选新型抗生素与细菌核糖体的结合。
• Late‐Stage Functionalization of Histidine in Unprotected Peptides
  作者：Anaïs F. M. Noisier、Magnus J. Johansson、Laurent Knerr、Martin A. Hayes、William J. Drury、Eric Valeur、Lara R. Malins、Ranganath Gopalakrishnan

  DOI：10.1002/anie.201910888

  日期：2019.12.19

  late-stage functionalization (LSF) of peptides represents a valuable strategy for the design of potent peptide pharmaceuticals by enabling rapid exploration of chemical diversity and offering novel opportunities for peptide conjugation. While the C(sp2 )-H activation of tryptophan (Trp) is well documented, the resurgence of radical chemistry is opening new avenues for the C-H functionalization of other

  肽的后期功能化（LSF）通过快速探索化学多样性并提供肽结合的新机会，代表了有效肽药物设计的重要策略。虽然色氨酸（Trp）的C（sp2）-H激活已得到充分证明，但自由基化学的复兴正在为其他芳香族侧链的CH功能化开辟新途径。本文中，我们报道了利用广泛范围的脂族亚磺酸盐作为自由基前体在组氨酸（His）的C2处LSF的第一个例子。在这项工作中，通过在水介质中对复杂的未保护肽进行烷基化，证明了对组氨酸功能化的出色选择性。最后，此方法已扩展为可安装酮柄，
• Singlet Oxygen-Induced Furan Oxidation for Site-Specific and Chemoselective Peptide Ligation
  作者：Eirini Antonatou、Kurt Hoogewijs、Dimitris Kalaitzakis、Andreas Baudot、Georgios Vassilikogiannakis、Annemieke Madder

  DOI：10.1002/chem.201601113

  日期：2016.6.13

  chemoselective ligation methodology has been developed for the facile construction of peptide‐based fluorescent probes. Furan‐containing peptides were activated by singlet oxygen and covalently engaged by nitrogen nucleophiles to yield stable conjugates. Singlet oxygen was compatible with sensitive amino acid residues within the peptides and a range of fluorophores, bearing different functionalities, were successfully

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• BIFUNCTIONAL HYDROXY-BISPHOSPHONIC ACID DERIVATIVES
  申请人：Egorov Maxim

  公开号：US20140086843A1

  公开（公告）日：2014-03-27

  The present invention relates to a bifunctional hydroxy-bisphosphonic acid derivative of formula (I) below: or a pharmaceutically-acceptable salt thereof, a method for producing the same, pharmaceutical compositions containing the same, and the use thereof as a medicament, as well as a compound of formula (II) below: or a pharmaceutically-acceptable salt thereof, and the use thereof for producing a vectorized molecule of therapeutic or diagnostic purpose.

  本发明涉及以下式子(I)的双功能羟基双膦酸衍生物或其药学上可接受的盐，以及制备该衍生物的方法，含有该衍生物的药物组合物以及其作为药物的用途，以及以下式子(II)的化合物或其药学上可接受的盐，以及用于生产用于治疗或诊断目的的载体化分子的用途。