2-((1-(2-azidoethyl)-1H-1,2,3-triazol-4-yl)methyl)-3',6'-bis(diethylamino)spiro-[isoindoline-1,9'-xanthen]-3-one | 1353015-42-5

• 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: 2-((1-(2-azidoethyl)-1H-1,2,3-triazol-4-yl)methyl)-3',6'-bis(diethylamino)spiro-[isoindoline-1,9'-xanthen]-3-one
• 英文别名: 2-((1-(2-azidoethyl)-1H-1,2,3-triazol-4-yl)methyl)-3',6'-bis(diethylamino)spiro[isoindoline-1,9'-xanthen]-3-one；2-[[1-(2-Azidoethyl)triazol-4-yl]methyl]-3',6'-bis(diethylamino)spiro[isoindole-3,9'-xanthene]-1-one
• CAS: 1353015-42-5
• 化学式: C₃₃H₃₇N₉O₂
• 分子量: 591.716
• InChiKey: WOBSZNMJARSPFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(2-丙炔基氧)-TEMPO 、 2-((1-(2-azidoethyl)-1H-1,2,3-triazol-4-yl)methyl)-3',6'-bis(diethylamino)spiro-[isoindoline-1,9'-xanthen]-3-one 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以74%的产率得到
  参考文献：
  名称：

  New Rhodamine Nitroxide Based Fluorescent Probes for Intracellular Hydroxyl Radical Identification in Living Cells

  摘要：

  The synthesis, characteristics, and biological applications of a series of new rhodamine nitroxide fluorescent probes that enable imaging of hydroxyl radicals (center dot OH) In living cells are described. These probes are highly selective for center dot OH in aqueous solution, avoiding interference from other reactive oxygen species (ROS), and they facilitate center dot OH imaging in biologically active samples. The robust nature of these probes (high specificity and selectivity, and facile synthesis) offer distinct advantages over previous methods for center dot OH detection.

  DOI：

  10.1021/ol202816m
• 作为产物：
  描述：

  3',6'-bis(diethylamino)-2-(prop-2-yn-1-yl)spiro[isoindoline-1,9'-xanthen]-3-one 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 12.0h， 生成 2-((1-(2-azidoethyl)-1H-1,2,3-triazol-4-yl)methyl)-3',6'-bis(diethylamino)spiro-[isoindoline-1,9'-xanthen]-3-one
  参考文献：
  名称：

  New Rhodamine Nitroxide Based Fluorescent Probes for Intracellular Hydroxyl Radical Identification in Living Cells

  摘要：

  The synthesis, characteristics, and biological applications of a series of new rhodamine nitroxide fluorescent probes that enable imaging of hydroxyl radicals (center dot OH) In living cells are described. These probes are highly selective for center dot OH in aqueous solution, avoiding interference from other reactive oxygen species (ROS), and they facilitate center dot OH imaging in biologically active samples. The robust nature of these probes (high specificity and selectivity, and facile synthesis) offer distinct advantages over previous methods for center dot OH detection.

  DOI：

  10.1021/ol202816m

文献信息

• Determination of intracellular pH using sensitive, clickable fluorescent probes
  作者：Nazmiye B. Yapici、Srinivas Rao Mandalapu、Teng-Leong Chew、Satya Khuon、Lanrong Bi

  DOI：10.1016/j.bmcl.2012.02.021

  日期：2012.4

  We synthesized and evaluated a series of acidic fluorescent pH probes exhibiting robust pH dependence, high sensitivity and photostability, and excellent cell membrane permeability. Titration analyses indicated that probe 3 could increase its fluorescence intensity 800-fold between pH 8.0 and 4.1. Additionally, its pK(a) value is optimal for intracellular probing of acidic organelles. Fluorescent imaging of HepG2 and Hela cells further revealed that probe 3 demonstrates outstanding capacity for monitoring of intracellular [H+] levels. The easily accessible terminal alkyne/azido function groups of these probes offer the possibility of rapidly constructing sensor molecule libraries using 'click' chemistry. Published by Elsevier Ltd.
• [EN] LYSOSOMAL TARGETING PROBES<br/>[FR] SONDES DE CIBLAGE LYSOSOMAL
  申请人：UNIV MICHIGAN TECH

  公开号：WO2014058535A1

  公开（公告）日：2014-04-17

  Described herein are compounds that may selectively stain lysosomes in cells, which may be used in methods of selectively staining and selectively detecting lysosomes in cells. The compounds are fluorescently labelled carbohydrates in which one or two monosaccharides selected from the group mannose, N- acetyl glucosamine, fucose, galactose and sialic acid are linked via a linker to a fluorescent probe such as rhodamine or cyanine or related probes.