4-羧基宾夕法尼亚绿 | 879288-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 4-羧基宾夕法尼亚绿
• 英文名称: 4-carboxy-Pennsylvania Green
• 英文别名: 4-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-3-methylbenzoic acid
• CAS: 879288-14-9
• 化学式: C₂₁H₁₂F₂O₅
• 分子量: 382.32
• InChiKey: XUNQGAYPSJNQMX-UHFFFAOYSA-N

物化性质

• 沸点：
  626.4±55.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-羧基宾夕法尼亚绿 在 N-羟基丁二酰亚胺 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 26.0h， 生成 N-[4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoyl]-β-alanyl-N-(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)-β-alaninamide
  参考文献：
  名称：

  The Pennsylvania Green Fluorophore: A Hybrid of Oregon Green and Tokyo Green for the Construction of Hydrophobic and pH-Insensitive Molecular Probes

  摘要：

  Fluorescent small molecules are powerful tools for exploring cellular biology. As a more hydrophobic, photostable, and less pH-sensitive alternative to fluorescein, we synthesized Pennsylvania Green, a bright, monoanionic fluorophore related to Oregon Green and Tokyo Green. Comparison of membrane probes comprising N-alkyl-3 beta-cholesterylamine linked to 4-carboxy-Tokyo Green (pK(a) similar to 6.2) and 4-carboxy-Pennsylvania Green (pK(a) similar to 4.8) revealed that only Pennsylvania Green was highly fluorescent in acidic early and recycling endosomes within living mammalian cells.

  DOI：

  10.1021/ol052655g
• 作为产物：
  描述：

  4-氟间苯二酚 在 氢氧化钾 、 甲烷磺酸 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 31.0h， 生成 4-羧基宾夕法尼亚绿
  参考文献：
  名称：

  A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with O⁶-Benzylguanine Derivatives

  摘要：

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.

  DOI：

  10.1021/ol7015093

文献信息

• SELECTIVE FLUORESCENT PROBE FOR ALDEHYDE DEHYDROGENASE
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20200199092A1

  公开（公告）日：2020-06-25

  High aldehyde dehydrogenase 1A1 (ALDH1A1) activity has emerged as a reliable marker for the identification of both normal and cancer stem cells. Herein, is presented AlDeSense, a turn-on green fluorescent probe for aldehyde dehydrogenase 1A1 (ALDH1A1) and Ctrl-AlDeSense, a matching non-responsive reagent. AlDeSense exhibits a 20-fold fluorescent enhancement when treated with ALDH1A1. Through the application of surface marker antibody staining, tumorsphere assays, and assessment of tumorigenicity, the disclosed results show that cells exhibiting high AlDeSense signal intensity have properties of cancer stem cells. Herein, is also reported the development of a red congener, red-AlDeSense. Importantly, red-AlDeSense represents one of only a few examples of a turn-on sensor in the red region using the d-PeT quenching mechanism.

  高乙醛脱氢酶1A1（ALDH1A1）活性已成为识别正常和癌干细胞的一个可靠标志。本文介绍了一种名为AlDeSense的针对乙醛脱氢酶1A1（ALDH1A1）的开启型绿色荧光探针，以及一个相应的无响应试剂Ctrl-AlDeSense。当用ALDH1A1处理时，AlDeSense的荧光强度可增强20倍。通过表面标记抗体染色、肿瘤球体试验和肿瘤生成能力的评估，所披露的结果显示，表现出高AlDeSense信号强度的细胞具有癌干细胞的特性。本文还报告了一种红色类似物，即red-AlDeSense的开发。重要的是，red-AlDeSense是使用d-PeT淬灭机制在红色区域进行开启型传感的少数几个例子之一。
• A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with <i>O</i><i>⁶</i>-Benzylguanine Derivatives
  作者：Laurie F. Mottram、Ewa Maddox、Markus Schwab、Florent Beaufils、Blake R. Peterson

  DOI：10.1021/ol7015093

  日期：2007.9.1

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.
• The Pennsylvania Green Fluorophore: A Hybrid of Oregon Green and Tokyo Green for the Construction of Hydrophobic and pH-Insensitive Molecular Probes
  作者：Laurie F. Mottram、Siwarutt Boonyarattanakalin、Rebecca E. Kovel、Blake R. Peterson

  DOI：10.1021/ol052655g

  日期：2006.2.1

  Fluorescent small molecules are powerful tools for exploring cellular biology. As a more hydrophobic, photostable, and less pH-sensitive alternative to fluorescein, we synthesized Pennsylvania Green, a bright, monoanionic fluorophore related to Oregon Green and Tokyo Green. Comparison of membrane probes comprising N-alkyl-3 beta-cholesterylamine linked to 4-carboxy-Tokyo Green (pK(a) similar to 6.2) and 4-carboxy-Pennsylvania Green (pK(a) similar to 4.8) revealed that only Pennsylvania Green was highly fluorescent in acidic early and recycling endosomes within living mammalian cells.