5-dimethylamino-naphthalene-1-sulfonic acid (3-hydroxy-propyl)-amide | 81253-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-dimethylamino-naphthalene-1-sulfonic acid (3-hydroxy-propyl)-amide
• 英文别名: 5-(dimethylamino)-N-(3-hydroxypropyl)naphthalene-1-sulfonamide；3-Dansylamino-1-propanol
• CAS: 81253-23-8
• 化学式: C₁₅H₂₀N₂O₃S
• 分子量: 308.401
• InChiKey: LZBOWNLGEMJCJR-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  501.6±60.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-dimethylamino-naphthalene-1-sulfonic acid (3-hydroxy-propyl)-amide 在 2,6-二甲基吡啶 、 氨 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 5-dimethylamino-naphthalene-1-sulfonic acid [3-(4-amino-6-chloro-[1,3,5]triazin-2-yloxy)-propyl]-amide
  参考文献：
  名称：

  通过一维氢键基团的共价浇铸定义的双链低聚物

  摘要：

  由单体分子前体组成的氢键胶带用于定义相关低聚物设计的结构参数，这些低聚物以预定的组装模式编码。将这种“共价铸造”策略应用于由 2-amino-4,6-dichlorotriazine 表达的一维 H 键基序，可以设计出高亲和力双链分子链。二聚体、三聚体和四聚体双链体低聚物是通过迭代合成方案制备的，该方案涉及低聚（氨基三嗪）的顺序同源性。通过 (1)H NMR 稀释实验、等温滴定量热法 (ITC)、蒸汽压渗透法 (VPO) 在溶液中建立了同源低聚物的组装模式和链间亲和力，交叉杂交实验涉及通过薄层色谱法 (TLC) 分析染料标记的链，并通过 X 射线晶体学分析在固态下进行。从单体延伸到二聚体再到三聚体，每个单体的结合自由能 (-Delta G 度/n) 显着增加，表明强大的积极合作效应。Nanomolar 结合亲和力 (K(d) = 1.44 +/- 0.50 nM) 由 ITC 在 1,2-二氯乙烷中在

  DOI：

  10.1021/ja012696h
• 作为产物：
  描述：

  丹酰氯 、 3-氨基-1-丙醇 在 碳酸氢钠 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.0h， 以79%的产率得到5-dimethylamino-naphthalene-1-sulfonic acid (3-hydroxy-propyl)-amide
  参考文献：
  名称：

  组合Dansyl库及其在pH敏感型探针中的应用。

  摘要：

  在这里，我们报告第一个48成员，基于dansyl的组合荧光库。从探针的电子和结构性质，我们分析了它们的光学性质和化学产率，平均为49％。检查分子的pH响应，并且DS-2和DS-45显示出蓝移，而DS-7和DS-40显示出随pH增加的波长红移。最后，通过处理SNU-2292细胞来研究细胞通透性。我们的结果证明了该文库在生物传感器，生物成像和pH指示剂中的潜在应用。

  DOI：

  10.2174/1386207319666160408150203

文献信息

• Discovery of a Turn-On Fluorescent Probe for Myeloid Cell Leukemia-1 Protein
  作者：Tingting Liu、Yuqi Gao、Xiaomeng Zhang、Yichao Wan、Lupei Du、Hao Fang、Minyong Li

  DOI：10.1021/acs.analchem.7b01148

  日期：2017.11.7

  The environment-sensitive probe 2 with turn-on switch for Mcl-1 protein was developed herein. After careful evaluation, this small molecule fluorescent probe revealed a selective binding affinity with Mcl-1 protein with a Ki value of 2.6 μM and can be well applied to imaging Mcl-1 protein or detecting the cellular distribution of Mcl-1 protein inhibitors. Compared with other imaging approaches, such

  本文开发了具有Mcl-1蛋白开启开关的环境敏感探针2。经过仔细评估，该小分子荧光探针显示出与Mcl-1蛋白的选择性结合亲和力，其K i值为2.6μM，可以很好地应用于成像Mcl-1蛋白或检测Mcl-1蛋白抑制剂的细胞分布。与其他成像方法（例如免疫荧光和基于荧光蛋白的技术）相比，这种荧光方法是快速，方便和可负担的，特别是因为不再需要清洗程序。这种对环境敏感的“关闭”设计策略可能为开发Bcl-2家族蛋白小分子荧光探针提供了一个案例。
• Zn2+ fluorescent chemosensors and the influence of their spacer length on tuning Zn2+ selectivityElectronic supplementary information (ESI) available: job plot, partial 1H NMR spectra of free 3 and the 3–Zn2+ complex, Ca2+ and Mg2+ interference for Zn2+ sensing of 3, Kd measurements, and buffer preparation. See http://www.rsc.org/suppdata/p2/b2/b200462c/
  作者：Tae Woo Kim、Jung-hyun Park、Jong-In Hong

  DOI：10.1039/b200462c

  日期：2002.4.29

  Zn2+ fluorescent chemosensors based on the chelation-enhanced fluorescence (CHEF) mechanism were prepared and fine-tuning of their Zn2+ selectivity was achieved by control of the spacer length. The fluorescence emission response to metal ions shows a fluorescence decrease for Co2+, Cu2+ and Ni2+ and an increase for Ca2+, Cd2+ and Zn2+. Maximum Zn2+ selectivity over Ca2+ and Cd2+ was achieved with 3. The basic binding properties (stoichiometry, apparent dissociation constant, and pH dependence) were measured by fluorescence spectroscopy. Analysis of the Job plot for the 3–Zn2+ complex indicates the formation of a 1 ∶1 complex. The apparent dissociation constant Kd was determined as 0.98 (±0.43) nM for 3–Zn2+ at pH 7.5 [50 mM HEPES buffer I = 0.1 (NaNO3)]. The plateaus in the fluorescence intensity of 2 and the 2–Zn2+ complex in regions with a pH exceeding 7 imply that the fluorescence measurements should be little affected by physiological pH changes.

  基于配位增强荧光（CHEF）机制的Zn2+荧光化学传感器被制备出来，并通过控制间隔基长度实现了对Zn2+选择性的精细调节。对金属离子的荧光发射响应显示，Co2+、Cu2+和Ni2+使荧光减弱，而Ca2+、Cd2+和Zn2+使荧光增强。在3号传感器中实现了对Zn2+的最大选择性，优于Ca2+和Cd2+。基本结合特性（化学计量比、表观解离常数和pH依赖性）通过荧光光谱法测量。3号传感器与Zn2+的Job图分析表明形成了1:1的复合物。表观解离常数Kd在pH 7.5时为0.98（±0.43）nM [50 mM HEPES缓冲液，I = 0.1 (NaNO3)]。在pH超过7的区域，2号传感器及其与Zn2+的复合物的荧光强度平稳，表明荧光测量受生理pH变化的影响不大。
• Astemizole-based turn-on fluorescent probes for imaging hERG potassium channel
  作者：Xiaomeng Zhang、Tingting Liu、Beilei Wang、Yuqi Gao、Pan Liu、Minyong Li、Lupei Du

  DOI：10.1039/c8md00562a

  日期：——

  Based on the scaffold of astemizole, three novel turn-on fluorescent probes (N1–N3) for human ether-a-go-go-related gene (hERG) potassium channel were developed herein.

  基于astemizole的支架，本研究开发了三种新型用于人类ether-a-go-go相关基因（hERG）钾通道的开启型荧光探针（N1-N3）。
• Fluorophore-Labeled <i>S</i>-Nitrosothiols
  作者：Xinchao Chen、Zhong Wen、Ming Xian、Kun Wang、Niroshan Ramachandran、Xiaoping Tang、H. Bernhard Schlegel、Bulent Mutus、Peng George Wang

  DOI：10.1021/jo015658p

  日期：2001.9.1

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.
• New Excursions Into the Synthesis and Medicinal Chemistry of the Disulfide Bond
  作者：Roger Hunter*、Catherine Kaschula、Nashia Stellenboom、Jonathan Cotton、M. Iqbal Parker

  DOI：10.1080/10426507.2012.736107

  日期：2013.11.1

  The presentation discusses two themes of current interest in my research group in conjunction with a garlic mimics program. The first involves a new one-pot methodology for preparing unsymmetrical disulfides in high yield using 1-chlorobenzotriazole (BtCl) as oxidant, which can be applied to a range of functional types. The second part of the lecture will discuss the synthesis of derivatives of the garlic-derived natural product ajoene, in conjunction with an anti-cancer screening program. The synthesis has been used to prepare a fluorescently tagged derivative of the natural product that has been used to investigate localization and mode of action within the cancer cell using confocal laser scanning microscopy.