fluorescein-5-isothiocyanate | 3012-71-3

• 物质功能分类: 原料药 - 诊断用药 - 器官功能检查剂
• 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-5-isothiocyanate
• 英文别名: fluorescein isothiocyanate；fluoresceinisothiocyanate；Fluoresceinisothiocyanat；FITC-NCS；FITC；2-(3-Hydroxy-6-oxoxanthen-9-yl)-4-isothiocyanatobenzoic acid
• CAS: 3012-71-3
• 化学式: C₂₁H₁₁NO₅S
• 分子量: 389.388
• InChiKey: WLJPEKSIBAZDIU-UHFFFAOYSA-N

物化性质

• 沸点：
  741.1±60.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36/37,S45
• 危险类别码：
  R36,R42/43
• WGK Germany：
  3
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-氨基丙基三乙氧基硅烷 、 fluorescein-5-isothiocyanate 反应 24.0h， 生成 2-(3-Hydroxy-6-oxoxanthen-9-yl)-4-(3-triethoxysilylpropylcarbamothioylamino)benzoic acid
  参考文献：
  名称：

  Spectroscopy of Fluorescein (FITC) Dyed Colloidal Silica Spheres

  摘要：

  We have measured the absorption spectrum, the emission spectrum, the emission lifetime, and the photostability of fluorescein isothiocyanate (FITC) incorporated inside colloidal silica spheres as a function of the dye concentration in the spheres, while minimizing scattering effects. Six batches of stable, monodisperse particles were synthesized with FITC up to high densities of 0.03 M. At dye concentrations above 0.001 M, we observe a large: red shift of 10 nm in the absorption and the emission spectra, as well as a strong reduction of the lifetime. At the same time, the photostability of the dye is considerably improved. These effects are caused by an increased energy transfer between the dye molecules as their concentration increases. Several excitation quenching models are examined, namely annihilation quenching, surface quenching, and a fractal distribution of quenchers. None of the models that assume a homogeneous distribution of FITC provide a sufficient explanation of the observed effects. It is suggested that the dye molecules tend to form clusters during the synthesis of the colloidal spheres. It is concluded that colloids with a low dye concentration are useful for photonic applications, whereas high dye concentrations are interesting for optical experiments in colloid science.

  DOI：

  10.1021/jp983241q

文献信息

• Nanoscale Biodegradable Organic–Inorganic Hybrids for Efficient Cell Penetration and Drug Delivery
  作者：Sebastian Hörner、Sascha Knauer、Christina Uth、Marina Jöst、Volker Schmidts、Holm Frauendorf、Christina Marie Thiele、Olga Avrutina、Harald Kolmar

  DOI：10.1002/anie.201606065

  日期：2016.11.14

  carrier was significantly more potent than cell‐penetrating peptides (CPPs) and displayed low toxicity. It efficiently delivered a covalently attached cytotoxic drug, doxorubicin, to living tumor cells. As the uptake of fluorescently labeled carrier remained in the presence of serum, the system could be considered particularly attractive for the in vivo delivery of therapeutics.

  我们报告了对新型，高效，可生物降解的杂交分子转运蛋白的全面研究。为此，我们设计了一系列可穿透细胞的立方八聚倍半硅氧烷（COSS），并通过共聚焦显微镜和流式细胞术研究了细胞摄取情况。胍基团的空间排列紧密的COSS在纳摩尔浓度的HeLa细胞中显示出快速的吸收动力学和细胞渗透性。在细菌，酵母和古细菌中也观察到有效吸收。基于COSS的载体比穿透细胞的肽（CPPs）更有力，并且毒性低。它有效地将共价结合的细胞毒性药物阿霉素递送至活体肿瘤细胞。由于在血清中仍保留对荧光标记载体的吸收，
• Oligo-Asp Tag/Zn(II) Complex Probe as a New Pair for Labeling and Fluorescence Imaging of Proteins
  作者：Akio Ojida、Kei Honda、Daisuke Shinmi、Shigeki Kiyonaka、Yasuo Mori、Itaru Hamachi

  DOI：10.1021/ja0618604

  日期：2006.8.1

  specific protein in complicated biological systems, a peptide tag incorporated into the protein and a complementary small molecular probe are required. Although a variety of peptide tag/probe pairs have been developed as molecular tools for protein analyses, the availability of pairs suitable for real-time imaging of proteins is still limited. We now report a new peptide tag/artificial probe pair composed

  为了在复杂的生物系统中完成对特定蛋白质的选择性标记，需要掺入蛋白质中的肽标签和互补的小分子探针。尽管已经开发了多种肽标签/探针对作为蛋白质分析的分子工具，但适用于蛋白质实时成像的对的可用性仍然有限。我们现在报告了一个新的肽标签/人工探针对，由可遗传编码的低聚天冬氨酸序列（D4 标签，(D4)n，n = 1-3）和相应的多核 Zn(II) 复合物 (Zn(II)- DpaTyrs）。Zn(II)-DpaTyr 探针与 D4 标签的强结合亲和力是多重配位键和多价效应的结果。用等温滴定量热法定量测定。
• Hydrophobic Interactions in Donor-Disulphide-Acceptor (DSSA) Probes Looking Beyond Fluorescence Resonance Energy Transfer Theory
  作者：Shilpa Kammaradi Sanjeeva、Swathi Korrapati、Chandrasekhar B. Nair、P. V. Subba Rao、Phani Kumar Pullela、U. Vijayalakshmi、Ramamoorthy Siva

  DOI：10.1007/s10895-014-1414-z

  日期：2014.7

  Donor –linker –acceptor (DSSA) is a concept in fluorescence chemistry with acceptor being a fluorescent compound (FRET) or quencher. The DSSA probes used to measure thiol levels in vitro and in vivo. The reduction potential of these dyes are in the range of −0.60 V, much lower than the best thiol reductant reported in literature, the DTT (−0.33 V). DSSA disulphide having an unusually low reduction potential compared to the typical thiol reductants is a puzzle. Secondly, DSSA probes have a cyclized rhodamine ring as acceptor which does not have any spectral overlap with fluorescein, but quenches its absorbance and fluorescence. To understand the structural features of DSSA probes, we have synthesized DSSANa and DSSAOr. The calculated reduction potential of these dyes suggest that DSSA probes have an alternate mechanism from the FRET based quenching, namely hydrophobic interaction or dye to dye quenching. The standard reduction potential change with increasing complexity and steric hindrance of the molecule is small, suggesting that ultra- low Eo’ has no contribution from the disulphide linker and is based on structural interactions between fluorescein and cyclized rhodamine. Our results help to understand the DSSA probe quenching mechanism and provide ways to design fluorescent probes.

  供体-连接体-受体（DSSA）是荧光化学中的一个概念，受体是一种荧光化合物（FRET）或淬灭剂。DSSA 探针用于测量体外和体内的硫醇水平。这些染料的还原电位在 -0.60 V 范围内，远低于文献报道的最佳硫醇还原剂 DTT（-0.33 V）。与典型的硫醇还原剂相比，DSSA 二硫化物具有异常低的还原电位，这是一个谜。其次，DSSA 探针有一个环化的罗丹明环作为受体，它与荧光素没有任何光谱重叠，却能淬灭荧光素的吸光度和荧光。为了了解 DSSA 探针的结构特征，我们合成了 DSSANa 和 DSSAOr。计算得出的这些染料的还原电位表明，DSSA 探针具有与基于 FRET 的淬灭机制不同的另一种机制，即疏水作用或染料间淬灭。标准还原电位随分子复杂性和立体阻碍的增加而变化很小，这表明超低 Eo'没有来自二硫键的贡献，而是基于荧光素和环化罗丹明之间的结构相互作用。我们的研究结果有助于理解 DSSA 探针的淬灭机制，并为设计荧光探针提供了方法。
• Permeation through Phospholipid Bilayers, Skin-Cell Penetration, Plasma Stability, and CD Spectra of<i>α</i>- and<i>β</i>-Oligoproline Derivatives
  作者：Beata Kolesinska、Dominika J. Podwysocka、Magnus A. Rueping、Dieter Seebach、Faustin Kamena、Peter Walde、Markus Sauer、Barbara Windschiegl、Mira Meyer-Ács、Marc Vor der Brüggen、Sebastian Giehring

  DOI：10.1002/cbdv.201200393

  日期：2013.1

  translocation rates of cell-penetrating peptides (CPPs) across lipid bilayers. Cell penetration is observed with mouse (3T3) and human foreskin fibroblasts (HFF; Figs. 5 and 6-8, resp.). The stabilities of oligoprolines in heparin-stabilized human plasma increase with decreasing chain lengths (Figs. 9-11). Time- and solvent-dependent CD spectra of most of the oligoprolines (Figs. 13 and 14) show changes that

  在对氨基酸脯氨酸在生命化学中所起的特殊作用进行了调查之后，讨论了含聚阳离子脯氨酸的肽的细胞穿透特性，以及Giralt小组（J.Am. Soc。2002，124，8876），据此，荧光素标记的十四碳脯氨酸被大鼠肾细胞（NRK-49F）缓慢吸收。在这里，我们描述了我们先前提到的（Chem。Biodiversity 2004，1，1111）六-β（3）-Pro衍生物穿透成纤维细胞的观察结果的细节，并且我们提出了对寡聚L-和oligo-D-α-脯氨酸，以及不带有和带有荧光标记的oligo-β（2）h-和oligo-β（3）h-脯氨酸（1-8;图1）。用nanoFAST生物芯片技术检测到无蛋白质磷脂双层的渗透（图2-4）。首次将这种方法用于定量测定跨脂质双层的细胞穿透肽（CPP）的转运速率。用小鼠（3T3）和人包皮成纤维细胞（HFF；图5和6-8，分别）观察到细胞渗透。肝素稳定的人血浆中寡脯氨酸的稳
• METHODS OF USE FOR CAR T CELLS
  申请人：Seattle Children's Hospital (dba Seattle Children's Research Institute)

  公开号：US20190224237A1

  公开（公告）日：2019-07-25

  The present disclosure relates to methods of treating a patient with a cancer by administering to the patient a composition comprising CAR T cells wherein the CAR T cells comprise a CAR and the CAR comprises an E2 anti-fluorescein antibody fragment, and administering to the patient a small molecule linked to a targeting moiety by a linker. The disclosure also relates to compositions for use in such methods.

  本公开涉及通过向患者注射包含CAR T细胞的组合物来治疗癌症的方法，其中CAR T细胞包括CAR，并且CAR包括E2抗荧光素抗体片段，并向患者注射通过链接剂与靶向部分相连的小分子。该公开还涉及用于这些方法的组合物。