3-[(2Z)-2-[2-[2-chloro-3-[(E)-2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-3,3-dimethylindol-1-yl]propane-1-sulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[(2Z)-2-[2-[2-chloro-3-[(E)-2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-3,3-dimethylindol-1-yl]propane-1-sulfonate
• 化学式: C₃₆H₄₂ClN₂O₆S₂
• 分子量: 698.324
• InChiKey: BSKLXINCNWPCNL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(2Z)-2-[2-[2-chloro-3-[(E)-2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-3,3-dimethylindol-1-yl]propane-1-sulfonate 在 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  一种近红外花菁类比色荧光探针及其制备方法和应用

  摘要：

  本发明公开了一种近红外花菁类比色荧光探针及其制备方法和应用，该探针的结构式如式(I)所示。该荧光探针在无水乙醇和PBS缓冲液的混合溶液中，利用荧光和紫外可见吸收光谱可识别检测N2H4。该探针对N2H4的识别具有高选择性和灵敏度，抗干扰能力强，而且具有非常低的检测限；所述荧光探针可以应用于环境污染或生物体外以及生物体内抗结核药物代谢物N2H4的检测。

  公开号：

  CN113234068B
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 sodium acetate 、 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 25.0h， 生成 3-[(2Z)-2-[2-[2-chloro-3-[(E)-2-[3,3-dimethyl-1-(3-sulfonatopropyl)indol-1-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-3,3-dimethylindol-1-yl]propane-1-sulfonate
  参考文献：
  名称：

  A dual functional probe: sensitive fluorescence response to H₂S and colorimetric detection for SO₃²⁻

  摘要：

  在这项研究中，我们开发了一种新的双功能探针，NIR-DNP，用于区分检测H₂S和SO₃²⁻。

  DOI：

  10.1039/c6ra15065a

文献信息

• Phototriggered Secretion of Membrane Compartmentalized Bioactive Agents
  作者：Robert M. Hughes、Christina M. Marvin、Zachary L. Rodgers、Song Ding、Nathan P. Oien、Weston J. Smith、David S. Lawrence

  DOI：10.1002/anie.201609731

  日期：2016.12.23

  compartments in the dark, as exemplified by their retention in the interior of erythrocytes. Subsequent illumination drives the secretion of the bioactive species from red blood cells. Photorelease is triggered by wavelengths in the red, far-red, and near-IR regions, which can be pre-assigned by affixing a fluorophore with the desired excitation wavelength to the Cbl-bioagent conjugate. Pre-assigned wavelengths

  描述了一种从膜封闭的仓库中光活化释放生物活性化合物（BODIPY，秋水仙碱，紫杉醇和甲氨蝶呤）的策略。我们已经发现，通过光可裂解的连接体通过共价附于钴胺素（Cbl），可使膜可渗透的生物试剂变得膜不可渗透。这些Cbl-生物试剂结合物被囚禁在黑暗中的脂质封闭的隔室内，以其在红细胞内部的滞留为例。随后的照明驱动了红细胞中生物活性物质的分泌。光释放由红色，远红色和近红外区域中的波长触发，可以通过将具有所需激发波长的荧光团固定到Cbl-bioagent共轭物中来预先分配光。
• Near-Infrared Heavy-Atom-Modified Fluorescent Dyes for Base-Calling in DNA-Sequencing Applications Using Temporal Discrimination
  作者：James H. Flanagan,、Clyde V. Owens、Sarah E. Romero、Emanuel Waddell、Shaheer H. Kahn、Robert P. Hammer、Steven A. Soper

  DOI：10.1021/ac980018g

  日期：1998.7.1

  A series of near-IR fluorescent dyes were prepared which contained an intramolecular heavy atom for altering the fluorescence lifetimes to produce a set of probes appropriate for base-calling in a single-lane DNA sequencing format. The heavy-atom modification consisted of an intramolecular halogen situated on a remote section of the chromophore in order to minimize the perturbation on the lifetimes and fluorescence quantum yields. In addition, the dye series possessed an isothiocyanate functional group to allow facile attachment to sequencing primers. The unconjugated dyes showed similar absorption and emission maxima (λabs = 765−768 nm; λem = 794−798 nm) as well as fluorescence quantum yields that were invariant, within experimental error, with the heavy atom. However, the lifetimes of these dyes were found to vary with the identity of the halogen substitution (I, τf = 947 ps; F, τf = 843 ps, measured in methanol), with an average variation within the dye series of 35 ps. The spectroscopic properties of the free dyes and the dyes conjugated to sequencing primers on the 5‘-end of the oligonucleotide were determined in a DNA-sequencing matrix (denaturing gels containing formamide). The results indicated slight differences in the fluorescence properties of the free dyes compared to those of the dye/primer conjugates in this particular matrix. Inspection of the ground-state absorption spectra showed significant aggregation for the free dyes in this solution, but the conjugated dyes exhibited no sign of aggregation due to the highly anionic nature of the oligonucleotide. The fluorescence lifetimes of the dye/primer conjugates demonstrated lifetimes which ranged from 735 to 889 ps, with an average variation of 51 ps, an adequate difference to allow facile discrimination of these dyes in DNA-sequencing conditions. In addition, the free solution electrophoretic mobilities of the native heavy-atom-modified dyes were found to be very similar. When the dye/primer conjugates were electrophoresed in a cross-linked polyacrylamide gel electrophoresis capillary column, they comigrated, indicating that, in single-lane sequencing applications, when utilizing these dyes, no postrun corrections would be required to correct for dye-dependent mobility shifts.

  我们制备了一系列近红外荧光染料，这些染料含有一个分子内重金属原子，可改变荧光寿命，从而产生一组适合单道 DNA 测序格式中碱基调用的探针。重原子修饰包括位于发色团偏远部分的分子内卤素，以尽量减少对荧光寿命和荧光量子产率的干扰。此外，染料系列还具有异硫氰酸酯官能团，可以方便地连接到测序引物上。非共轭染料显示出相似的吸收和发射最大值（λabs = 765-768 nm；λem = 794-798 nm）以及荧光量子产率，这些量子产率在实验误差范围内与重原子无关。然而，研究发现这些染料的寿命随卤素取代物的特性而变化（I，τf = 947 ps；F，τf = 843 ps，在甲醇中测量），染料系列内的平均变化为 35 ps。在 DNA 测序基质（含有甲酰胺的变性凝胶）中测定了游离染料和与寡核苷酸 5'- 端测序引物共轭的染料的光谱特性。结果表明，在这种特定基质中，游离染料的荧光特性与染料/引物共轭物的荧光特性略有不同。对基态吸收光谱的检测显示，游离染料在该溶液中出现了明显的聚集现象，但由于寡核苷酸的高阴离子性质，共轭染料没有出现聚集的迹象。染料/引物共轭物的荧光寿命从 735 到 889 ps 不等，平均变化为 51 ps，这种差异足以让这些染料在 DNA 测序条件下被轻松区分。此外，还发现原生重原子修饰染料的自由溶液电泳迁移率非常相似。当染料/原体共轭物在交联聚丙烯酰胺凝胶电泳毛细管柱中电泳时，它们会结合在一起，这表明在单道测序应用中，当使用这些染料时，无需进行运行后校正来纠正染料依赖性迁移率偏移。
• Fabrication of a water-soluble near-infrared fluorescent probe for selective detection and imaging of dipeptidyl peptidase IV in biological systems
  作者：Xiumei Guo、Shuai Mu、Jian Li、Yintang Zhang、Xiaoyan Liu、Haixia Zhang、Hong Gao

  DOI：10.1039/c9tb02301a

  日期：——

  Dipeptidyl peptidase IV (DPP-IV) is a transmembrane glycoprotein known to regulate T cell activation, which is related to various pathological processes and has become a potential target to treat type 2 diabetes mellitus.

  二肽基肽酶IV（DPP-IV）是一种跨膜糖蛋白，已知能调节T细胞激活，与各种病理过程相关，并已成为治疗2型糖尿病的潜在靶点。
• Activity‐based Photoacoustic Probes Reveal Elevated Intestinal MGL and FAAH Activity in a Murine Model of Obesity
  作者：Melissa Y. Lucero、Sarah H. Gardner、Anuj K. Yadav、Austin Borri、Zhenxiang Zhao、Jefferson Chan

  DOI：10.1002/anie.202211774

  日期：2022.11.2

  Activity-based sensing probes and whole-body photoacoustic imaging have enabled the selective detection of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH) activity in the context of obesity and gastrointestinal tract inflammation.

  基于活性的传感探针和全身光声成像能够在肥胖和胃肠道炎症的背景下选择性检测单酰基甘油脂肪酶（MGL）和脂肪酸酰胺水解酶（FAAH）活性。
• Naked‐Eye Readout of Analyte‐Induced NIR Fluorescence Responses by an Initiation–Input–Transduction Nanoplatform
  作者：Dailiang Zhang、Linlin Wang、Xi Yuan、Yijun Gong、Hongwen Liu、Jing Zhang、Xiaobing Zhang、Yanlan Liu、Weihong Tan

  DOI：10.1002/anie.201911113

  日期：2020.1.7

  Fluorescence visualization (FV) in the near-infrared (NIR) window promises to break through the signal-to-background ratio (SBR) bottleneck of traditional visible-light-driven FV methods. However, straightforward NIR-FV has not been realized, owing to the lack of methods to readily transduce NIR responses into instrument-free, naked eye-recognizable outputs. Now, an initiation-input-transduction platform

  近红外（NIR）窗口中的荧光可视化（FV）有望突破传统可见光驱动FV方法的信噪比（SBR）瓶颈。但是，由于缺乏将NIR响应轻松转换为无需仪器，肉眼可识别的输出的方法，因此尚未实现直接的NIR-FV。现在，提出了一种启动-输入-转导平台，该平台包括设计良好的NIR荧光团作为信号引发剂，以及掺杂镧系元素的纳米晶体作为便捷的NIR-FV的换能器。被分析物诱导的关闭NIR信号用作肉眼读出的传感器可见光的敏化开关。该设计可用于便携式，定量检测光气，并具有显着改善的SBR和灵敏度。通过进一步探索发起者，