| 1354688-43-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 1354688-43-9
• 化学式: C₃₇H₃₉N₂O₃*ClO₄
• 分子量: 659.179
• InChiKey: YIJXZICNIPCEQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  47.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  145.02
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成 1-(6'-(diethylamino)-3-oxo-4'-(2-(1,3,3-trimethylindolin-2-ylidene)ethylidene)-1',2',3',4'-tetrahydrospiro[isoindoline-1,9'-xanthen]-2-yl)thiourea
  参考文献：
  名称：

  A Unique Class of Near-Infrared Functional Fluorescent Dyes with Carboxylic-Acid-Modulated Fluorescence ON/OFF Switching: Rational Design, Synthesis, Optical Properties, Theoretical Calculations, and Applications for Fluorescence Imaging in Living Animals

  摘要：

  Fluorescence imaging is one of the most powerful techniques for monitoring biomolecules in living systems. Fluorescent sensors with absorption and emission in the near-infrared (NIR) region are favorable for biological imaging . applications in living animals, as NIR light leads to minimum photodamage, deep tissue penetration, and minimum background autofluorescence interference. Herein, we have introduced a new strategy to design NIR functional dyes with the carboxylic-acid-controlled fluorescence on off switching mechanism by the spirocyclization. Based on the design strategy, we have developed a series of Changsha (CS1-6) NIR fluorophores, a unique new class of NIR functional fluorescent dyes, bearing excellent photophysical properties including large absorption extinction coefficients, high fluorescence quantum yields, high brightness, good photostability, and sufficient chemical stability. Significantly, the new CS1-6 NIR dyes are superior to the traditional rhodamine dyes with both absorption and emission in the NIR region while retaining the rhodamine-like fluorescence ON-OFF switching mechanism. In addition, we have performed quantum chemical calculations with the B3LYP exchange functional employing 6-31G* basis sets to shed light on the structure-optical properties of the new CS1-6 NIR dyes. Furthermore, using CS2 as a platform, we further constructed the novel NIR fluorescent TURN-ON sensor 7, which is capable of imaging endogenously produced HCIO in the living animals, demonstrating the value of our new CS NIR functional fluorescent dyes. We expect that the design strategy may be extended for development of a wide variety of NIR functional dyes with a suitable fluorescence-controlled mechanism for many useful applications in biological studies.

  DOI：

  10.1021/ja209292b
• 作为产物：
  描述：

  环己酮 在 硫酸 、 乙酸酐 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  A Unique Class of Near-Infrared Functional Fluorescent Dyes with Carboxylic-Acid-Modulated Fluorescence ON/OFF Switching: Rational Design, Synthesis, Optical Properties, Theoretical Calculations, and Applications for Fluorescence Imaging in Living Animals

  摘要：

  Fluorescence imaging is one of the most powerful techniques for monitoring biomolecules in living systems. Fluorescent sensors with absorption and emission in the near-infrared (NIR) region are favorable for biological imaging . applications in living animals, as NIR light leads to minimum photodamage, deep tissue penetration, and minimum background autofluorescence interference. Herein, we have introduced a new strategy to design NIR functional dyes with the carboxylic-acid-controlled fluorescence on off switching mechanism by the spirocyclization. Based on the design strategy, we have developed a series of Changsha (CS1-6) NIR fluorophores, a unique new class of NIR functional fluorescent dyes, bearing excellent photophysical properties including large absorption extinction coefficients, high fluorescence quantum yields, high brightness, good photostability, and sufficient chemical stability. Significantly, the new CS1-6 NIR dyes are superior to the traditional rhodamine dyes with both absorption and emission in the NIR region while retaining the rhodamine-like fluorescence ON-OFF switching mechanism. In addition, we have performed quantum chemical calculations with the B3LYP exchange functional employing 6-31G* basis sets to shed light on the structure-optical properties of the new CS1-6 NIR dyes. Furthermore, using CS2 as a platform, we further constructed the novel NIR fluorescent TURN-ON sensor 7, which is capable of imaging endogenously produced HCIO in the living animals, demonstrating the value of our new CS NIR functional fluorescent dyes. We expect that the design strategy may be extended for development of a wide variety of NIR functional dyes with a suitable fluorescence-controlled mechanism for many useful applications in biological studies.

  DOI：

  10.1021/ja209292b

文献信息

• pH-activatable near-infrared fluorescent probes for detection of lysosomal pH inside living cells
  作者：Giri K. Vegesna、Jagadeesh Janjanam、Jianheng Bi、Fen-Tair Luo、Jingtuo Zhang、Connor Olds、Ashutosh Tiwari、Haiying Liu

  DOI：10.1039/c4tb00475b

  日期：——

  fluorescent probes (A, B, C and D) have been synthesized, characterized, and evaluated for detection of lysosomal pH inside living cells. The fluorescent probes display highly sensitive and selective fluorescent response to acidic pH as the acidic pH results in drastic structural changes from spirocyclic (non-fluorescent) forms to ring-opening (fluorescent) forms of the fluorescent probes. The fluorescence

  已经合成，表征和评估了四种近红外荧光探针（A，B，C和D）以检测活细胞内的溶酶体pH。荧光探针显示出对酸性pH的高度敏感和选择性的荧光响应，因为酸性pH导致荧光探针从螺环（非荧光）形式到开环（荧光）形式发生剧烈的结构变化。从pH 7.4到4.2 ，荧光探针（B，C和D）的荧光强度显着增加200倍以上。带有N的荧光探针D-（2-羟乙基）乙酰胺残基具有灵敏度高，光稳定性好，细胞膜通透性好，pH依赖性强，自发荧光背景低的优点。它已成功应用于选择性溶酶体染色并检测正常内皮细胞和乳腺癌细胞内的溶酶体pH值变化。
• Targeted theranostics: Near-infrared triterpenoic acid-rhodamine conjugates as prerequisites for precise cancer diagnosis and therapy
  作者：Niels Heise、Florian Lehmann、René Csuk、Thomas Mueller

  DOI：10.1016/j.ejmech.2023.115663

  日期：2023.11

  significantly reduced toxicity for non-malignant cells. This study focuses on the development of triterpenoic acid-rhodamine conjugates with fluorescence shifted to the near-infrared (NIR) region for theranostic applications in cancer research. Spectral analysis revealed emission wavelengths around λ = 760 nm, enabling stronger signals and deeper tissue penetration. The conjugates were evaluated using

  五环三萜酸已显示出作为合成高细胞毒性药物的起始材料的巨大潜力，并且对非恶性细胞的毒性显着降低。本研究重点开发三萜酸-罗丹明缀合物，其荧光转移到近红外 (NIR) 区域，用于癌症研究中的治疗诊断应用。光谱分析显示发射波长约为 λ = 760 nm，可实现更强的信号和更深的组织穿透。使用 SRB 测定对肿瘤细胞系和非恶性成纤维细胞进行评估，显示出低纳摩尔活性和高选择性，与已知的罗丹明 B 对应物类似。额外的染色实验证明了它们作为线粒体的作用方式。