bis(3-ethylbenzothiazol-2-ylidene)squaraine | 1043454-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: bis(3-ethylbenzothiazol-2-ylidene)squaraine
• 英文别名: 4-[(3-Ethyl-1,3-benzothiazol-3-ium-2-yl)methylidene]-2-[(3-ethyl-1,3-benzothiazol-2-ylidene)methyl]-3-oxocyclobuten-1-olate
• CAS: 1043454-79-0
• 化学式: C₂₄H₂₀N₂O₂S₂
• 分子量: 432.567
• InChiKey: QGPLEIXNDHGZCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(3-ethylbenzothiazol-2-ylidene)squaraine 以 二氯甲烷 为溶剂， 生成 (4Z)-3-[bis(2-hydroxyethyl)amino]-4-[(3-ethyl-1,3-benzothiazol-3-ium-2-yl)methylidene]-2-[(Z)-(3-ethyl-1,3-benzothiazol-2-ylidene)methyl]cyclobut-2-en-1-one;iodide
  参考文献：
  名称：

  氨基鞘脂作为潜在的光动力剂：体外细胞毒性的合成和评估

  摘要：

  描述了在所谓的光疗窗（650-850 nm）内具有强吸收性的几种氨基方酸阳离子染料的合成。测试了它们在黑暗和光照条件下对几种人类肿瘤细胞系（乳腺癌，肺癌，宫颈癌和肝细胞癌）和非肿瘤猪肝原代细胞的细胞毒性。与在不存在光的情况下或多或少地扩展时相比，所有化合物在辐射下均显示出更多地抑制肿瘤细胞的生长，明显表现出光动力活性。对某些细胞系的光敏能力，以及一些合成的化合物对非肿瘤原代PLP2细胞的低毒性，使它们成为潜在的候选药物，成为PDT的光敏剂。

  DOI：

  10.1016/j.bmcl.2017.08.004
• 作为产物：
  描述：

  2-甲基苯并噻唑 以 乙腈 、 正丁醇 为溶剂， 生成 bis(3-ethylbenzothiazol-2-ylidene)squaraine
  参考文献：
  名称：

  氨基鞘脂作为潜在的光动力剂：体外细胞毒性的合成和评估

  摘要：

  描述了在所谓的光疗窗（650-850 nm）内具有强吸收性的几种氨基方酸阳离子染料的合成。测试了它们在黑暗和光照条件下对几种人类肿瘤细胞系（乳腺癌，肺癌，宫颈癌和肝细胞癌）和非肿瘤猪肝原代细胞的细胞毒性。与在不存在光的情况下或多或少地扩展时相比，所有化合物在辐射下均显示出更多地抑制肿瘤细胞的生长，明显表现出光动力活性。对某些细胞系的光敏能力，以及一些合成的化合物对非肿瘤原代PLP2细胞的低毒性，使它们成为潜在的候选药物，成为PDT的光敏剂。

  DOI：

  10.1016/j.bmcl.2017.08.004

文献信息

• New Synthetic Approach to Aminosquarylium Cyanine Dyes
  作者：P. F. Santos、L. V. Reis、J. P. Serrano、P. Almeida

  DOI：10.1055/s-2002-34226

  日期：——

  A novel synthesis of aminosquarylium cyanine dyes, based on the methylation of readily available squarylium dyes with methyl triflate, followed by nucleophilic substitution with appropriate aliphatic amines, was disclosed. By this procedure several new aminosquarylium cyanine dyes bearing benzothiazole, benzoselenazole and quinoline nuclei were prepared.

  公开了一种氨基方酸菁染料的新型合成方法，该方法基于容易获得的方酸菁染料与三氟甲磺酸甲酯的甲基化，然后用适当的脂肪胺进行亲核取代。通过该程序制备了几种带有苯并噻唑、苯并硒唑和喹啉核的新型氨基方酸菁染料。
• Host–guest assembly of squaraine dye in cucurbit[8]uril: its implication in fluorescent probe for mercury ions
  作者：Yongqian Xu、Matthew J. Panzner、Xiaopeng Li、Wiley J. Youngs、Yi Pang

  DOI：10.1039/c002219p

  日期：——

  The binding interactions between SQ2 squaraine dye and cucurbit[8]uril (CB8) effectively removes the aggregation of SQ2 in aqueous solution by forming a 1 : 1 inclusion complex. The resulting SQ2·CB8 complex exhibits highly selective fluorescence quenching by Hg2+ ions, as a result of the synergetic binding between CB8, SQ2 and metal cation.

  SQ2磺菁染料与瓜环[8]（CB8）之间的结合相互作用通过形成1: 1的包合复合物，有效地去除了SQ2在水溶液中的聚集。由此形成的SQ2·CB8复合物表现出对Hg2+离子的高度选择性荧光猝灭，这是由于CB8、SQ2与金属阳离子之间的协同结合作用所致。
• Molecular assembly of a squaraine dye with cationic surfactant and nucleotides: its impact on aggregation and fluorescence response
  作者：Yongqian Xu、Andrey Malkovskiy、Qiuming Wang、Yi Pang

  DOI：10.1039/c0ob01061h

  日期：——

  A novel fluorescent system has been assembled by using ATP, surfactant, and a squaraine dye in an aqueous buffer solution. In the system, a cationic surfactant such as cetyl trimethyl ammonium bromide (CTAB) forms a sphere-like micelle, whose positive charge at the surface of the micelle attracts the negatively charged ATP to form a unique organized nanostructure. Such an organized system is shown to interact with the squaraine dye (SQ) to perturb its aggregate structure, thereby generating the optical response. The nanostructure of the assembly has been characterized by dynamic light-scattering (DLS) and atomic force microscopy (AFM). The unique feature of the developed sensing system is that the analytes ATP form part of the assembly structure. The system utilizes forces such as electrostatic interaction and π–π stacking of the aromatic segment of ATP and SQ to achieve the selective detection of ATP.

  利用ATP、表面活性剂和方酸染料在含水缓冲溶液中组装了一种新型荧光系统。在该系统中，如十六烷基三甲基溴化铵（CTAB）等阳离子表面活性剂形成球状胶束，其表面正电荷吸引带负电的ATP，形成独特的组织化纳米结构。这种有序系统能与方酸染料（SQ）相互作用，扰乱其聚集结构，从而产生光学响应。通过动态光散射（DLS）和原子力显微镜（AFM）对组装的纳米结构进行了表征。开发出的传感系统的独特之处在于，待测物ATP构成了组装结构的一部分。该系统利用静电相互作用和ATP与SQ芳香片段的π-π堆积等作用力，实现了对ATP的选择性检测。
• Photochemistry of squaraine dyes. 6. Solvent hydrogen bonding effects on the photophysical properties of bis(benzothiazolylidene)squaraines
  作者：Suresh Das、K. George Thomas、R. Ramanathan、M. V. George、P. V. Kamat

  DOI：10.1021/j100153a033

  日期：1993.12

  The photophysical properties of two bis(benzothiazolylidene)squaraine dyes have been studied in aromatic hydrocarbon and alcoholic solvents. These dyes exhibit fluorescence quantum yields of 0.06-0.52 and excited singlet lifetimes of 0.48-2.5 ns in these solvents. Although the photophysical properties of the dyes are independent of solvent polarity in the hydrocarbon solvents, in alcoholic solvents a marked hyposchromic shift in the absorption and emission spectra and a reduction in lifetimes of excited state have been observed. These effects have been correlated with the hydrogen bond donating ability of the alcoholic solvents.
• Nakazumi, Hiroyuki; Natsukawa, Kazuki; Nakai, Kazuhisa, Angewandte Chemie, 1994, vol. 106, # 9, p. 1021 - 1023
  作者：Nakazumi, Hiroyuki、Natsukawa, Kazuki、Nakai, Kazuhisa、Isagawa, Kakuzo

  DOI：——

  日期：——