Pennsylvania Green succinimidyl ester | 952053-74-6

• 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: Pennsylvania Green succinimidyl ester
• 英文别名: 1-{[4-(2,7-difluoro-6-hydroxy-3-oxo-xanthen-9-yl)-3-methylbenzoyl]oxy}pyrrolidine-2,5-dione；pennsylvania green N-hydroxysuccinimide ester；2,5-dioxopyrrolidin-1-yl 4-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-3-methylbenzoate；4-carboxy-Pennsylvania Green NHS ester；4-carboxy-pennsylvania green succinimidyl ester；(2,5-Dioxopyrrolidin-1-yl) 4-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-3-methylbenzoate；(2,5-dioxopyrrolidin-1-yl) 4-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-3-methylbenzoate
• CAS: 952053-74-6
• 化学式: C₂₅H₁₅F₂NO₇
• 分子量: 479.393
• InChiKey: VCFSUWBIAQIMNW-UHFFFAOYSA-N

物化性质

• 熔点：
  225-230 °C
• 沸点：
  701.0±70.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Pennsylvania Green succinimidyl ester 在 potassium carbonate 、 苯硫酚 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 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-ylamino}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 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.0h， 生成 Pennsylvania Green succinimidyl ester
  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

• Fluorescent mimics of cholesterol that rapidly bind surfaces of living mammalian cells
  作者：David Hymel、Sutang Cai、Qi Sun、Rebecca S. Henkhaus、Chamani Perera、Blake R. Peterson

  DOI：10.1039/c5cc06325f

  日期：——

  Novel analogues of cholesterol are rapidly and massively incorporated into the plasma membrane of living mammalian cells through a receptor-mediated pathway.

  新型类固醇类似物通过受体介导的途径迅速大量地被纳入活体哺乳动物细胞的质膜中。
• [EN] METHODS OF MAKING AND USING NANOSTRUCTURES<br/>[FR] PROCÉDÉS DE FABRICATION ET D'UTILISATION DE NANOSTRUCTURES
  申请人：UNIV MINNESOTA

  公开号：WO2013109939A1

  公开（公告）日：2013-07-25

  The invention provides methods for attaching drugs, dyes or radiolabels to bis-MTX. This method can be used to prepare bis-MTX analogs that can be used to deliver agents, such as nanoparticles, drugs, dyes or radiolabels, to cells.

  这项发明提供了将药物、染料或放射性标记物附着到双甲氨蝶呤（bis-MTX）的方法。这种方法可用于制备可用于将纳米颗粒、药物、染料或放射性标记物传递给细胞的双甲氨蝶呤类似物。
• Multivalent Soluble Antigen Arrays Exhibit High Avidity Binding and Modulation of B Cell Receptor-Mediated Signaling to Drive Efficacy against Experimental Autoimmune Encephalomyelitis
  作者：Brittany L. Hartwell、Chad J. Pickens、Martin Leon、Cory Berkland

  DOI：10.1021/acs.biomac.7b00335

  日期：2017.6.12

  (CuAAC)) rather than a hydrolyzable oxime bond to attach PLP and LABL to HA. We explored cSAgAPLP:LABL B cell engagement and modulation of BCR-mediated signaling in vitro through flow cytometry binding and calcium flux signaling assays. Indeed, cSAgAPLP:LABL exhibited higher avidity B cell binding and greater dampening of BCR-mediated signaling than hydrolyzable SAgAPLP:LABL. Furthermore, cSAgAPLP:LABL

  迫切需要抗原特异性免疫疗法（ASIT），该疗法可在自身免疫疾病中诱导选择性耐受，同时避免有害的整体免疫抑制。多价可溶性抗原阵列（SAgA PLP：LABL）由透明质酸（HA）线性聚合物主链与多份自身抗原（PLP）和细胞粘附抑制剂（LABL）肽共移植组成，旨在诱导对特定多发性硬化的耐受性（MS）自身抗原。先前的研究确定了可水解的SAgA PLP：LABL，使用可降解的接头来编码肝脏和肝癌，在体内实验性自身免疫性脑脊髓炎（EAE）中具有治疗性，并与B细胞表现出抗原特异性结合，靶向B细胞受体（BCR），并在体外减弱了BCR介导的信号传导。我们的结果表明持续的BCR参与是SAgA PLP：LABL的治疗机制，因此我们使用不可水解的缀合化学方法开发了新版的SAgA分子，认为它可以增强和维持分子在细胞表面的作用，从而提高功效。“ Click SAgA”（cSAgA PLP：LABL）使用水解稳定的共价
• [EN] SYNTHETIC CHOLESTERYLAMINE-LINKER DERIVATIVES FOR AGENT DELIVERY INTO CELLS<br/>[FR] DÉRIVÉS SYNTHÉTIQUES DE CHOLESTÉRYLAMINE-LIEUR POUR L'ADMINISTRATION INTRACELLULAIRE D'AGENTS
  申请人：UNIV KANSAS

  公开号：WO2011019942A3

  公开（公告）日：2011-07-14
• 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.