fluorescein monoacetate | 7262-41-1

• 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 monoacetate
• 英文别名: 3'-O-acetylfluorescein；6'-acetoxy-3'-hydroxy-spiro[phthalan-1,9'-xanthen]-3-one；6'-Acetoxy-3'-hydroxy-spiro[phthalan-1,9'-xanthen]-3-on；(6'-Hydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate
• CAS: 7262-41-1
• 化学式: C₂₂H₁₄O₆
• 分子量: 374.35
• InChiKey: SIOSUSOSPIZPGV-UHFFFAOYSA-N

物化性质

• 熔点：
  215 °C
• 沸点：
  608.4±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoyl chloride 、 fluorescein monoacetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以50 mg的产率得到6'-O-(N-maleoyl-β-alanyl)-3'-O-acetylfluorescein
  参考文献：
  名称：

  General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

  摘要：

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.016
• 作为产物：
  描述：

  乙酸酐 、 荧光素 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以40%的产率得到fluorescein monoacetate
  参考文献：
  名称：

  General strategy for the preparation of membrane permeable fluorogenic peptide ester conjugates for in vivo studies of ester prodrug stability

  摘要：

  To study ester prodrug stability properties in living cells we have conjugated fluorogenic esters to the cell membrane permeable peptide Arg(9). The desired conjugates are prepared by coupling N-maleoyl amino acid esters of monoalkylated fluoresceins or fluorescein to TyrArg(9)Cys. The photophysical properties of the monoalkylated fluorescein derivatives are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.016

文献信息

• Promiscuous G-protein compositions and their use
  申请人：Negulescu Paul

  公开号：US20060008855A1

  公开（公告）日：2006-01-12

  Disclosed are compositions and methods for their use, such as in identifying G-protein coupled receptors and ligands and compounds that modulate signal transduction. The compositions and methods employ promicuous G-proteins. Activation of the promiscous G-protein can be detected in a variety of assays, including assays in which activation is indicated by a change in fluorescence emission of a sample that contains the composition.

  揭示了用于识别G蛋白偶联受体、配体以及调节信号转导的化合物的组合物和使用它们的方法。这些组合物和方法利用了多功能G蛋白。可以通过各种测定方法检测多功能G蛋白的激活，包括在激活导致含有该组合物的样品的荧光发射变化的测定中。
• Substrates for beta-lactamase and uses thereof
  申请人：Tsien Y. Roger

  公开号：US20070184513A1

  公开（公告）日：2007-08-09

  Substrates for β-lactamase of the general formula I in which one of X and Y is a fluorescent donor moiety and the other is a quencher (which may or may not re-emit); R′ is selected from the group consisting of H, lower (i.e., alkyl of 1 to about 5 carbon atoms) and (CH 2 ) n OH, in which n is 0 or an integer from 1 to 5; R″ is selected from the group consisting of H, physiologically acceptable metal and ammonium cations, CHR 2 OCO(CH 2 ) n CH 3 , —CHR 2 OCOC (CH 3 ) 3 , acylthiomethyl, acyloxy-alpha -benzyl, delta-butyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, beta-morpholinoethyl, dialkylaminoethyl, acyloxyalkyl, dialkylaminocarbonyloxymethyl and aliphatic, in which R 2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO 2 and CH 2 ; and Z′ and Z″ are linkers for the fluorescent donor and quencher moieties. Methods of assaying β-lactamase activity and monitoring expression in systems using β-lactamase as a reporter gene also are disclosed.

  通式I的β-内酰胺酶底物，其中X和Y中的一个是荧光给体基团，另一个是猝灭剂（可以或不可以再发射）；R'从H，较低的（即1到约5个碳原子的烷基）和（CH2）nOH中选择，其中n为0或1到5的整数；R"从H，生理上可接受的金属和铵阳离子，CHR2OCO（CH2）nCH3，—CHR2OCOC（CH3）3，酰硫甲基，酰氧-α-苯甲基，δ-丁酰内酯，甲氧羰氧甲基，苯基，甲硫氧甲基，β-吗啡啉乙基，二烷基氨基乙基，酰氧烷基，二烷基氨基羰氧甲基和脂肪族中选择，其中R2从H和较低的烷基中选择；A从S，O，SO，SO2和CH2中选择；Z'和Z"是荧光给体和猝灭剂基团的连接器。还公开了评估β-内酰胺酶活性和使用β-内酰胺酶作为报告基因监测表达的方法。
• Method for detection of peritoneal inflammation or infection
  申请人：ABBOTT LABORATORIES

  公开号：EP0178501A1

  公开（公告）日：1986-04-23

  Peritoneal inflammation or infection can be detected in a patient by assaying a peritoneal lavage sample from the patient for lysosomal enzymes. This is done by combining the lavage sample with a leukocyte lysing agent and a chromogenic or fluorogenic enzyme substrate specific for lysosomat enzymes. The lysosomal enzymes can then be measured, and the inflammation or infection detected, by measuring the color or fluorescence developed in the sample by action of the enzymes of the substrate.

  腹膜炎症或感染可通过化验患者腹腔灌洗液样本中的溶酶体酶来检测。具体做法是将灌洗液样本与白细胞裂解剂和溶酶体酶特异性显色或荧光酶底物结合。然后，通过测量底物中酶的作用在样本中形成的颜色或荧光，就可以测量溶酶体酶，并检测炎症或感染。
• Methods for separating malignant cells from clinical specimens
  申请人：ANALYTICAL BIOSYSTEMS CORPORATION

  公开号：EP0277837A2

  公开（公告）日：1988-08-10

  Fragments of a biopsy sample on the order of about 50 to 5000 cells are preferred for establishing viable tumor cell cultures for purposes such as establishing cell lines, chemotherapeutic assays and the like. Such fragments retain the three-dimensional cellular structure or organization of the original tumor and, therefore, can be cultured more readily. To obtain such fragments suitable for culturing, the biopsy sample can be enzymatically digested in a proteolytic or nucleolytic enzyme, such as collagenase, or by mechanical dissociation, or both where necessary. The fragments can then be suspended in an aqueous medium so that non-aggregated cells (e.g., red blood cells, lymphocytes, macrophages) and cellular debris will form a supernatant while the remaining fragments containing aggregated tumor cells are deposited in a sediment layer. Preferably, the medium is an isotonic tissue culture medium and decantation is conducted at least twice; first in a serum-containing medium and then, secondly, in a serum-free medium. Fragments containing living tumor cells can be selected by fluorochromasia, that is, by contacting the sedimented layer with a fluorogenic substrate such that viable tumor cells take up and hydrolyse the substrate, and then exhibit fluorescence. Cytotoxicity assay protocols employing tumor cell aggregates prepared by the present techniques are also disclosed.

  活检样本中细胞数量在 50 至 5000 个之间的片段更适合用于建立有活力的肿瘤细胞培养物，如建立细胞系、化疗试验等。这种片段保留了原始肿瘤的三维细胞结构或组织，因此更易于培养。为获得适于培养的此类片段，活检样本可在蛋白水解酶或核酸水解酶（如胶原酶）中进行酶解，或通过机械解离，必要时也可同时进行酶解和机械解离。然后将碎片悬浮在水性培养基中，使非聚集细胞（如红细胞、淋巴细胞、巨噬细胞）和细胞碎片形成上清液，而含有聚集肿瘤细胞的剩余碎片沉积在沉淀层中。培养基最好是等渗组织培养基，倾析至少进行两次；第一次在含血清培养基中，第二次在无血清培养基中。含活肿瘤细胞的片段可通过荧光染色法选出，即用含氟底物接触沉淀层，使有活力的肿瘤细胞吸收并水解底物，然后发出荧光。此外，还公开了采用本技术制备的肿瘤细胞聚集体的细胞毒性检测方案。
• Compositions comprising substantially pure fluorescein
  申请人：Alcon Research, Ltd.

  公开号：EP2481741A1

  公开（公告）日：2012-08-01

  The invention is directed to substantially pure fluorescein, substantially pure fluorescein compositions and to pharmaceutical compositions for use in angiography. A substantially pure fluorescein is provided which is low in colour, low in sodium chloride content, and substantially free of pyridine. Fluorescein comprised in the composition is defmed as substantially pure if there are no detectable fluorescein-related substance impurities, or if a single fluorescein-related substance impurity is detected, it is present in an amount no greater than 0.1 % by weight, or if multiple fluorescein-related substance impurities are detected, they are present in aggregate in an amount no greater than 0.6% by weight, and wherein said fluorescein-related substance impurities comprise; synthetic impurities arising from the reaction of resorcinol with succinic acid (as an impurity in the phthalic acid precursor for fluorescein); isomers, oxidation products, dimerization products, and decomposition products of fluorescein.

  本发明涉及用于血管造影术的基本纯荧光素、基本纯荧光素组合物和药物组合物。本发明提供了一种色度低、氯化钠含量低且基本不含吡啶的高纯度荧光素。如果不存在可检测到的荧光素相关物质杂质，或如果检测到单个荧光素相关物质杂质，其含量不超过 0.1%（按重量计），或如果检测到多个荧光素相关物质杂质，其总含量不超过 0.6% （按重量计），其中所述荧光素相关物质杂质包括；间苯二酚与琥珀酸反应产生的合成杂质（作为荧光素邻苯二甲酸前体中的杂质）；荧光素的异构体、氧化产物、二聚化产物和分解产物。