1-hexadecyl-2-(2-hydroxy-5-nitro-styryl)-3,3-dimethyl-3H-indolium betaine

• 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: 1-hexadecyl-2-(2-hydroxy-5-nitro-styryl)-3,3-dimethyl-3H-indolium betaine
• 英文别名: 6-[2-(1-Hexadecyl-3,3-dimethylindol-2-ylidene)ethylidene]-4-nitrocyclohexa-2,4-dien-1-one；6-[2-(1-hexadecyl-3,3-dimethylindol-2-ylidene)ethylidene]-4-nitrocyclohexa-2,4-dien-1-one
• 化学式: C₃₄H₄₈N₂O₃
• 分子量: 532.767
• InChiKey: KMFRTOQATOCARR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-hexadecyl-2-(2-hydroxy-5-nitro-styryl)-3,3-dimethyl-3H-indolium betaine 以 various solvent(s) 为溶剂， 生成 1'-hexadecyl-3',3'-dimethyl-6-nitro-1',3'-dihydrospiro[chromene-2,2'-indole]
  参考文献：
  名称：

  二恶烷-水混合物和自组装表面活性剂聚集体中的表面活性螺并苯并吡喃部分的光致变色

  摘要：

  1'-十六烷基-3'，3'-二甲基-6-硝基螺[2H-1-苯并吡喃-2,2'-二氢吲哚]（SP-16）在胶束自组装表面活性剂聚集体中的光化学和物理化学性质调查。为了比较1,4-二恶烷-水混合物中1'，3'，3'-三甲基-6-硝基螺[2H-1-苯并吡喃-2,2'-二氢吲哚]（SP-1）的性质，在较小程度上，还检查了一些纯有机溶剂。在所有研究的介质中，SP-16和SP-1在用紫外线照射时均会发生异源裂解。该过程可以热逆转或通过可见光照射逆转。紫外线照射产生的螺并苯并吡喃开放形式是溶剂变色的。开放形式的立体异构体贡献的复杂相互作用使溶剂变色现象的分析复杂化，尤其是对于胶束系统。在所有媒体中 SP-16和SP-1的开放形式的热脱色遵循单一的一级动力学。在胶束系统中，一阶速率常数是根据界面溶剂和电荷稳定作用以及空间位阻来解释的。在pH值的中低范围内，pH值引起的SP-16和SP-1的开放形式的UV-

  DOI：

  10.1039/ft9908603613
• 作为产物：
  描述：

  生成 1-hexadecyl-2-(2-hydroxy-5-nitro-styryl)-3,3-dimethyl-3H-indolium betaine
  参考文献：
  名称：

  Photoswitchable Nanoparticles for Triggered Tissue Penetration and Drug Delivery

  摘要：

  We report a novel nanoparticulate drug delivery system that undergoes reversible volume change from 150 to 40 nm upon phototriggering with UV light. The volume change of these monodisperse nanoparticles comprising spiropyran, which undergoes reversible photoisomerization, and PEGylated lipid enables repetitive dosing from a single administration and enhances tissue penetration. The photo-switching allows particles to fluoresce and release drugs inside cells when illuminated with UV light. The mechanism of the light-induced size switching and triggered-release is studied. These particles provide spatiotemporal control of drug release and enhanced tissue penetration, useful properties in many disease states including cancer.

  DOI：

  10.1021/ja211888a

文献信息

• Determination of Critical Aggregation Concentrations of Self-Assembling Lipids in Nonpolar Organic Media Using Spiropyrans as Photochromic Probes
  作者：Hiroshi Hachisako、Hiroki Nakayama、Hirotaka Ihara

  DOI：10.1246/cl.1999.1165

  日期：1999.11

  Critical aggregation concentrations of organic gel-forming lipids in nonpolar organic media such as benzene were found to be determined by measuring the first-order rate constants of merocyanine-to-spiropyran thermal isomerizations for spiropyrans added as probes.

  发现在非极性有机介质（如苯）中形成有机凝胶的脂质的临界聚集浓度是通过测量作为探针添加的螺吡喃的部花青到螺吡喃热异构化的一级速率常数来确定的。
• Photochromic transformations of amphiphilic spiropyran in acetonitrile solutions and at the air/water interface
  作者：D. A. Ivakhnenko、A. V. Shokurov、G. V. Lyubimova、N. L. Zaichenko、V. V. Arslanov、O. A. Raitman

  DOI：10.1007/s11172-018-2368-0

  日期：2018.12

  The results of a study of the photochromic properties of 1´-hexadecyl-3´,3´-dimethyl-6-nitro-1´,3´-dihydrospiro[chromene-2,2´-indole] (SP) are presented. The kinetic characteristics of photophysical processes occurring in acetonitrile solution of SP upon irradiation with UV light and during dark relaxation are determined. It is shown that spiropyran modified at the nitrogen atom by a long-chain hydrocarbon

  介绍了 1'-十六烷基-3',3'-二甲基-6-硝基-1',3'-二氢螺[色烯-2,2'-吲哚] (SP) 的光致变色特性的研究结果。测定了在紫外光照射和暗弛豫期间在 SP 的乙腈溶液中发生的光物理过程的动力学特性。结果表明，在氮原子上被长链烃基修饰的螺吡喃在溶解状态下表现出光致变色特性，直接光致变色的速率超过暗弛豫速率一个数量级。进行了溶解态和二维态 SP 光反应的比较研究。获得的结果为这种光致变色在使用朗缪尔单层技术获得的薄膜器件中的应用开辟了广阔的前景。
• Photochemical Switching of Electrochemical Process by Spiropyran LB Films
  作者：Katsuhiko Nishiyama、Masamichi Fujihira

  DOI：10.1246/cl.1987.1443

  日期：1987.7.5

  Photoelectrochemical control of the ion-blocking ability of the Langmuir–Blodgett (LB) film as an ion gate was demonstrated on a gold optically semi-transparent electrode (Au OTE) coated with multilayers containing photoresponsive amphiphilic compounds. When UV light was irradiated upon the modified Au OTE, this LB film became more compact to block permeation of ions into and out of the LB film and therefore inhibited electrochemical reactions of the redox active species in solution. On the other hand, when visible light was irradiated, this layer became more loose and redox species could penetrate the LB film.

  在涂有多层光响应性两亲化合物的金光学半透明电极（Au OTE）上，展示了Langmuir-Blodgett（LB）膜作为离子闸的离子阻挡能力的光电化学控制。当紫外线照射到经过改性的Au OTE上时，LB膜变得更致密，从而阻止离子进出LB膜，并因此抑制溶液中氧化还原活性物质的电化学反应。另一方面，当可见光照射时，该层变得更松散，氧化还原物质可以穿透LB膜。
• High and rapid response in photo-induced potential changes across a poly(vinyl chloride)/spirobenzopyran membrane
  作者：Jun-ichi Anzai、Akihiko Ueno、Tetsuo Osa

  DOI：10.1039/c39840000688

  日期：——

  Photo-induced potential changes of more than 100mV were attained with rapid response time (about 20 s)across a poly(vinyl Chloride)/spirobenzopyran membrane.

  跨越聚氯乙烯/螺并苯并吡喃膜的快速响应时间（约20 s）获得了超过100mV的光诱导电势变化。
• Comparison of the photochromism of a spirobenzopyran derivative in unilamellar surfactant vesicles and solvent-cast surfactant films
  作者：Calum J. Drummond、D. Neil Furlong、George Georgaklis

  DOI：10.1039/ft9908603913

  日期：——

  been examined in a number of different aqueous unilamellar surfactant vesicle solutions and solvent-cast surfactant film matrices. The thermal decolouration of SP-16 in solvent cast dihexadecylphosphate (DHP) films and unilamellar dimyristoyl phosphatidylcholine (DMPC) vesicles exhibits single first-order kinetics. In DHP vesicles and solvent-cast DMPC films the thermal decolouration deviates from single

  已大量研究了1'-十六烷基-3'，3'-二甲基-6-硝基螺[2H-1-苯并吡喃-2,2'-二氢吲哚]（SP-16）的光诱导性花菁形式的热脱色不同的单层表面活性剂囊泡水溶液和溶剂型表面活性剂薄膜基质的制备。SP-16在溶剂流延的二十六烷基磷酸酯（DHP）薄膜和单层的二豆油基磷脂酰胆碱（DMPC）囊泡中的热脱色表现出单一的一级动力学。在DHP囊泡和溶剂浇铸的DMPC薄膜中，热脱色与单个一阶行为不同。这两个系统中的热脱色通过两个一级速率过程的叠加来很好地描述。囊泡DHP介质中的双重一级动力学已归因于SP-16的花菁部分在囊泡内的两个居住位点之间分配，可能是表面活性剂/水界面区域和烃链结构域。DMPC薄膜中的双重一级动力学已被归因于部分花青种群与磷脂酰胆碱头基络合，而另一部分种群位于烃链结构域。在溶剂浇铸的聚（二烯丙基二甲基铵）二十六烷基磷酸酯（DHPP）膜中，SP-16的热脱色与单个一阶行为不同