N-(6-(diethylamino)-9-(2-(piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium 2,2,2-trifluoroacetate | 1100365-01-2

• 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: N-(6-(diethylamino)-9-(2-(piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium 2,2,2-trifluoroacetate
• CAS: 1100365-01-2
• 化学式: C₂F₃O₂*C₃₂H₃₉N₄O₂
• 分子量: 624.703
• InChiKey: FYJBDZAJXQCTIB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(6-(diethylamino)-9-(2-(piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium 2,2,2-trifluoroacetate 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.5h， 生成 (R)-2-(6-(4-(2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl)benzoyl)piperazin-1-yl)-6-oxohexanamido)-3-((5-((2-mercaptoethyl)amino)-5-oxopentyl)amino)-3-oxopropane-1-sulfonate
  参考文献：
  名称：

  Conversion of S-phenylsulfonylcysteine residues to mixed disulfides at pH 4.0: utility in protein thiol blocking and in protein-S-nitrosothiol detection

  摘要：

  一种被称为硫代亚砜开关的协议，其特点是在pH 4.0下，依次阻断蛋白质巯基并将蛋白质-S-亚硝基硫醇转化为带有荧光探针的混合二硫化物。

  DOI：

  10.1039/c4ob00995a
• 作为产物：
  描述：

  罗丹明B 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 N-(6-(diethylamino)-9-(2-(piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Cell‐Penetrating Peptide‐Bismuth Bicycles**

  摘要：

  Cell‐penetrating peptides (CPPs) play a significant role in the delivery of cargos into human cells. We report the first CPPs based on peptide‐bismuth bicycles, which can be readily obtained from commercially available peptide precursors, making them accessible for a wide range of applications. These CPPs enter human cells as demonstrated by live‐cell confocal microscopy using fluorescently labelled peptides. We report efficient sequences that demonstrate increased cellular uptake compared to conventional CPPs like the TAT peptide (derived from the transactivating transcriptional activator of human immunodeficiency virus 1) or octaarginine (R8), despite requiring only three positive charges. Bicyclization triggered by the presence of bismuth(III) increases cellular uptake by more than one order of magnitude. Through the analysis of cell lysates using inductive coupled plasma mass spectrometry (ICP‐MS), we have introduced an alternative approach to examine the cellular uptake of CPPs. This has allowed us to confirm the presence of bismuth in cells after exposure to our CPPs. Mechanistic studies indicated an energy‐dependent endocytic cellular uptake sensitive to inhibition by rottlerin, most likely involving macropinocytosis.

  DOI：

  10.1002/anie.202318615

文献信息

• Ratiometric Fluorescence Detection of Pathogenic Bacteria Resistant to Broad-Spectrum β-Lactam Antibiotics
  作者：Junxiang Zhang、Yang Shen、Sarah L. May、Daniel C. Nelson、Shuwei Li

  DOI：10.1002/anie.201107810

  日期：2012.2.20

  Identification of bacteria: A methoxyimino cephalosporin derivative containing a pair of fluorescence resonance energy transfer (FRET) fluorophores was synthesized. This probe displays selective cleavage toward different types of β‐lactamases, thereby providing a rapid assay to distinguish bacterial cells that are either sensitive or resistant to broad‐spectrum β‐lactam antibiotics (see picture).

  细菌的鉴定：合成了含有一对荧光共振能量转移（FRET）荧光团的甲氧基亚氨基头孢菌素衍生物。该探针显示出对不同类型的β-内酰胺酶的选择性切割，从而提供了一种快速分析方法，以区分对广谱β-内酰胺抗生素敏感或耐药的细菌细胞（见图）。
• Synthesis of a Toolbox of Clickable Rhodamine B Derivatives
  作者：Pierangelo Gobbo、Mark Workentin、Praveen Gunawardene、Wilson Luo

  DOI：10.1055/s-0034-1380191

  日期：——

  An efficient method for the large-scale preparation of rhodamine B clickable derivatives has been developed. Starting from inexpensive rhodamine B as the starting material it was possible to functionalize the carboxylic functionality of rhodamine B with an azide, a strained-alkyne, a substituted triphenylphosphine, a thiol, and a maleimide. Through the synthetic strategy it was possible to obtain stable and pure clickable rhodamine compounds that can be readily used not only for chemoselectively probing biomolecules, but also for materials science.