3-(naphthalen-1-ylamino)propanoic acid | 6580-22-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(naphthalen-1-ylamino)propanoic acid
• CAS: 6580-22-9
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: WAALMSYGFMMLHS-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  452.6±28.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-1-ylamino)propanoic acid 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{5-[3-(2-methoxy-2-oxoethylamino)-3-oxopropylamino]-10-methyl-9H-benzo[a]phenoxazin-9-ylidine}ethanaminium chloride
  参考文献：
  名称：

  Fluorescence derivatisation of amino acids in short and long-wavelengths

  摘要：

  3-(Naphthalen-1-ylamino)propanoic acid was coupled to the amino group of the main and lateral chains of various amino acids in order to evaluate its applicability as a fluorescent derivatising reagent. The resulting amino acid derivatives are strongly fluorescent with a maximum emission of about 415 run. Condensation of these derivatives with 5-ethylamino-4-methyl-2-nitrosophenol hydrochloride resulted in the corresponding blue benzo[a]phenoxazinium conjugates, also revealing strong fluorescence in ethanol and water at physiological pH and good quantum yields, but with emission wavelengths between 644 and 657 nm, which was preferable in biological assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.070
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 3-(naphthalen-1-ylamino)propanoic acid
  参考文献：
  名称：

  40.合成氮杂类固醇的实验。第一部分

  摘要：

  DOI：

  10.1039/jr9530000192

文献信息

• Improved synthetic method of Benzo[a]pheno-selenazinium phototherapeutic agents
  作者：Xiuxiu Yue、Jing Xu、Xiaozhong Liu、Xiangzhi Song、James W. Foley

  DOI：10.1016/j.dyepig.2021.109154

  日期：2021.4

  Benzo[a]phenoselenazinium dyes are excellent photodynamic therapeutic agents that have a red absorption (660 nm), high singlet oxygen quantum yield (>0.8), and good water-solubility and liposolubility. Bis-(3-diethylaminophenyl) diselenide, the most important intermediate for the synthesis of benzo[a]phenoselenazinium dyes, is previously prepared in one pot through 3 steps, during which special care

  苯并[ a ]酚硒氮鎓染料是出色的光动力学治疗剂，具有红色吸收（660 nm），高单线态氧量子产率（> 0.8）以及良好的水溶性和脂溶性。双-（3-二乙基氨基苯基）二硒化物是合成苯并[ a ]酚硒基氮鎓染料的最重要中间体，以前需要在一锅中分三步进行制备，在此期间需要格鲁纳德试剂和有毒硒蒸气的制备。在这项工作中，我们使用CuO纳米粉将卤代苯胺与硒直接偶联，在温和的条件下以高产率获得纯的双-（3-二乙基氨基苯基）二硒化物（一步法），而无需柱色谱法。四种苯并[ a ]苯硒基氮鎓染料，使用改进的合成方法可以容易地制备5a-d；并研究了它们在活细胞中的光毒性。改进的方法可用于大规模合成苯并[ a ]苯并硒氮鎓染料，从而可能刺激这种光敏剂的光动力学研究。
• Survey of Redox-Active Moieties for Application in Multiplexed Electrochemical Biosensors
  作者：Di Kang、Francesco Ricci、Ryan J. White、Kevin W. Plaxco

  DOI：10.1021/acs.analchem.6b02376

  日期：2016.11.1

  Recent years have seen the development of a large number of electrochemical sandwich assays and reagentless biosensor architectures employing biomolecules modified via the attachment of a redox-active “reporter.” Here we survey a large set of potential redox reporters in order to determine which exhibits the best long-duration stability in thiol-on-gold monolayer-based sensors and to identify reporter “sets” signaling at distinct, nonoverlapping redox potentials in support of multiplexing and error correcting ratiometric or differential measurement approaches. Specifically, we have characterized the performance of more than a dozen potential reporters that are, first, redox active within the potential window over which thiol-on-gold monolayers are reasonably stable and, second, are available commercially in forms that are readily conjugated to biomolecules or can be converted into such forms in one or two simple synthetic steps. To test each of these reporters we conjugated it to one terminus of a single-stranded DNA “probe” that was attached by its other terminus via a six-carbon thiol to a gold electrode to form an “E-DNA” sensor responsive to its complementary DNA target. We then measured the signaling properties of each sensor as well as its stability against repeated voltammetric scans and against deployment in and reuse from blood serum. Doing so we find that the performance of methylene blue-based, thiol-on-gold sensors is unmatched; the near-quantitative stability of such sensors against repeated scanning in even very complex sample matrices is unparalleled. While more modest, the stability of sensors employing a handful of other reporters, including anthraquinone, Nile blue, and ferrrocene, is reasonable. Our work thus serves as both to highlight the exceptional properties of methylene blue as a redox reporter in such applications and as a cautionary tale–we wish to help other researchers avoid fruitless efforts to employ the many, seemingly promising and yet ultimately inadequate reporters we have investigated. Finally, we hope that our work also serves as an illustration of the pressing need for the further development of useful redox reporters.

  近年来，大量的电化学夹心分析法和无试剂生物传感器架构得到了发展，这些架构采用了通过附着氧化还原活性"报告基团"修饰的生物分子。本文综述了一系列潜在的氧化还原报告基团，旨在确定哪些报告基团在巯基-金单层传感器中具有最佳的长期稳定性，并识别在不同、非重叠氧化还原电位上发出信号的报告基团"组合"，以支持多重检测和校正比率或差分测量方法的错误。具体而言，我们对十几种潜在的报告基团进行了性能表征，这些报告基团首先在巯基-金单层的稳定电位窗口内具有氧化还原活性，其次以易于与生物分子偶联的形式商业化，或者可以通过一两个简单的合成步骤转化为这种形式。为了测试每个报告基团，我们将其与单链DNA"探针"的一端偶联，该探针的另一端通过六个碳的巯基连接到金电极上，形成了一个对互补DNA目标敏感的"E-DNA"传感器。然后，我们测量了每个传感器的信号特性以及其对抗重复循环伏安扫描和在血清中使用及重复使用的稳定性。通过这些测试，我们发现亚甲蓝基的巯基-金传感器性能无与伦比；即使在非常复杂的样品矩阵中，这种传感器对抗重复扫描的近似定量稳定性也是前所未有的。虽然较为有限，但使用少数其他报告基团（包括蒽醌、尼罗蓝和二茂铁）的传感器的稳定性是合理的。因此，我们的工作既突出了亚甲蓝在这些应用中作为氧化还原报告基团的卓越特性，也为其他研究人员提供了一个警示——我们希望帮助他们避免我们在调查看似有前景但最终不充分的报告基团时所经历的无用功。最后，我们希望我们的工作也展现了进一步开发有用的氧化还原报告基团的迫切需要。
• Synthesis and Evaluation of New Potential Benzo[a]phenoxazinium Photosensitizers for Anticancer Photodynamic Therapy
  作者：Juan Zhang、Wellington Tavares de Sousa Júnior、Victor Mello da Silva、Mosar Rodrigues、José Vasconcelos Morais、Jia-Li Song、Zhi-Qiang Cheng、João Longo、Ricardo Bentes Azevedo、Cheng-Shi Jiang、Luís Alexandre Muehlmann、Hua Zhang

  DOI：10.3390/molecules23061436

  日期：——

  The use of photodynamic therapy (PDT) and development of novel photosensitizers (PSs) for cancer treatment have received more and more attention nowadays. In the present work, five benzo[a]phenoxazinium derivatives have been prepared and evaluated for their in vitro anticancer photodynamic activity for the first time. They are red light absorbers and show low fluorescence quantum yield. Of these compounds

  光动力疗法（PDT）的使用和用于癌症治疗的新型光敏剂（PSs）的开发如今受到越来越多的关注。在目前的工作中，首次制备并评估了五种苯并 [a] 吩恶嗪鎓衍生物的体外抗癌光动力活性。它们是红光吸收剂并且显示出低的荧光量子产率。在这些化合物中，PS4 表现出更高的活性氧 (ROS) 生成量子产率。体外细胞分析表明，PS1 和 PS4 在黑暗中没有显着毒性，但在光活化后对鼠乳腺腺癌细胞 4T1 和正常鼠成纤维细胞 NIH-3T3 具有强烈毒性。更有趣的是，PS5 对 4T1 癌细胞特别有选择性，对非癌性 NIH-3T3 细胞几乎无光毒性。本报告中描述的结果表明，这些新的苯并 [a] 吩恶嗪衍生物是作为抗癌 PDT 的 PS 的潜在候选物。有必要进一步研究苯并 [a] 吩恶嗪用于抗癌 PDT。
• Intraduplex DNA-Mediated Electrochemistry of Covalently Tethered Redox-Active Reporters
  作者：Catrina G. Pheeney、Jacqueline K. Barton

  DOI：10.1021/ja408135g

  日期：2013.10.9

  Intraduplex DNA-mediated reduction is established as a general mechanism for the reduction of distally bound stacked redox-active species covalently tethered to DNA through flexible alkane linkages. Methylene Blue (MB), Nile Blue (NB), and Anthraquinone (AQ) were covalently tethered to DNA with three different covalent linkages. Using these reporters DNA electrochemistry was shown to be both DNA-mediated

  双链内 DNA 介导的还原被确立为减少远端结合的堆叠氧化还原活性物质通过灵活的烷烃键共价连接到 DNA 的一般机制。亚甲蓝 (MB)、尼罗蓝 (NB) 和蒽醌 (AQ) 通过三个不同的共价键共价连接到 DNA。使用这些报告基因的 DNA 电化学被证明是 DNA 介导的和内部双链体，而不是内部双链体。重要的是，通过 DNA π-stack 发生的电荷传输路径是通过使用介入的 AC 错配来打破这条路径来建立的。DNA 介导的 MB 减少主要通过双链内插入发生，这一事实是通过改变相邻双链 DNA 的接近度和完整性来确定的。
• Encapsulation and Release Mechanisms in Coordination Polymer Nanoparticles
  作者：Laura Amorín‐Ferré、Félix Busqué、José Luis Bourdelande、Daniel Ruiz‐Molina、Jordi Hernando、Fernando Novio

  DOI：10.1002/chem.201302662

  日期：2013.12.16

  compositionally and structurally equivalent coordination polymer particles through distinct encapsulation mechanisms: coordination and mechanical entrapment. The two types of particles delivered their fluorescent cargo with remarkably different kinetic profiles, which could be satisfactorily modeled considering degradation‐ and diffusion‐controlled release processes. This demonstrates that careful selection

  通过一种新的多学科方法研究了纳米级金属有机载体中客体包封和释放机制的相互作用及其对这些材料的药物传递动力学的影响。合成了两个经过合理设计的分子客体，包括共价束缚在配位邻苯二酚基团和受保护的非配位邻苯二酚基团上的红色荧光苯甲恶嗪染料。通过不同的包封机制：配位和机械截留，可将客体装载到组成和结构上等效的配位聚合物颗粒中。两种类型的粒子以非常不同的动力学特性传递其荧光物质，考虑到降解和扩散控制释放过程，可以令人满意地对其进行建模。