N-(8-氨基辛基)-5-二甲基氨基萘-1-磺酰胺 | 77840-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-(8-氨基辛基)-5-二甲基氨基萘-1-磺酰胺
• 英文名称: 5-dimethylamino-naphthalene-1-sulfonic acid (8-amino-octyl)-amide
• 英文别名: 1-Naphthalenesulfonamide, N-(8-aminooctyl)-5-(dimethylamino)-；N-(8-aminooctyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 77840-23-4
• 化学式: C₂₀H₃₁N₃O₂S
• 分子量: 377.551
• InChiKey: AAFRRFPQYFHXCI-UHFFFAOYSA-N

物化性质

• 沸点：
  536.5±60.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(8-氨基辛基)-5-二甲基氨基萘-1-磺酰胺 在 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 (2S,3S,4R,5R)-5-{6-[8-(5-Dimethylamino-naphthalene-1-sulfonylamino)-octylamino]-purin-9-yl}-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide
  参考文献：
  名称：

  腺苷受体的荧光探针：N6-丹磺酰基氨基烷基取代的NECA衍生物的合成与生物学。

  摘要：

  描述了用于腺苷受体的新的荧光配体。这些化合物是通过在NECA（一种强力的腺苷激动剂）的N6位插入带有增加碳链长度（3至12）的烷基间隔基的丹磺氨基烷基部分而获得的。其中，具有C6烷基间隔基的化合物被证明是最令人感兴趣的化合物，显示出对A1受体亚型的显着选择性。此外，在荧光显微镜检测中，它被证明能够在小脑皮层的分子层水平上观察和定位该受体亚型。

  DOI：

  10.1016/s0960-894x(98)00582-4
• 作为产物：
  描述：

  丹酰胺 在 一水合肼 、 lithium hexamethyldisilazane 作用下， 以 乙醇 为溶剂， 反应 52.5h， 生成 N-(8-氨基辛基)-5-二甲基氨基萘-1-磺酰胺
  参考文献：
  名称：

  腺苷受体的荧光探针：N6-丹磺酰基氨基烷基取代的NECA衍生物的合成与生物学。

  摘要：

  描述了用于腺苷受体的新的荧光配体。这些化合物是通过在NECA（一种强力的腺苷激动剂）的N6位插入带有增加碳链长度（3至12）的烷基间隔基的丹磺氨基烷基部分而获得的。其中，具有C6烷基间隔基的化合物被证明是最令人感兴趣的化合物，显示出对A1受体亚型的显着选择性。此外，在荧光显微镜检测中，它被证明能够在小脑皮层的分子层水平上观察和定位该受体亚型。

  DOI：

  10.1016/s0960-894x(98)00582-4

文献信息

• Fluorescence Anisotropy and Mobility of Dansyl Fluorophore in Labelled Homologous Alkanes
  作者：Drahomír Výprachtický、Veronika Pokorná、Jan Pecka、František Mikeš

  DOI：10.1135/cccc19991369

  日期：——

  Using the steady-state and time-resolved fluorescence anisotropy, the mobility of 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) fluorophore in homologous 1-[2-acetamido-3-(1H-indol-3-yl)propanamido]-n-[5-(dimethylamino)naphthalene-1-sulfonamido]alkanes 1 was studied in binary solvents glycerol-water. Steady-state fluorescence data were evaluated by the generalized Perrin equation and the micro-Brownian motion of dansyl fluorophore was described by means of average characteristics (rotational relaxation times) of the rotational relaxation spectrum. The rotational relaxation time of "fast" motions caused by torsional vibrations of single bonds within the rotational-isomeric states decreases with increasing number of methylene groups in homologous compounds. The rotational relaxation time of "slow" motions due to conformational changes of the chain between the tryptophane and dansyl fluorophore remains at first approximately constant with increasing number of methylene groups but increases considerably for long aliphatic chains. The observed decrease in the rate of conformational changes of a long aliphatic chain is probably due to intramolecular interaction of parts of the methylene chain in a medium with high water content. The values of activation enthalpy ∆H^≠ and activation entropy ∆S^≠ calculated from experimental data corroborate such interpretation. Time-resolved anisotropy of dansyl fluorophore at a particular binary solvent composition confirmed the shape of rotational relaxation spectrum and the measured rotational correlation times have been discussed. The time-dependent decays of anisotropy supported our previous interpretation in terms of intramolecular association of the long aliphatic chain in polar medium.

  使用稳态和时间分辨荧光各向异性，研究了5-(二甲氨基)萘磺酰（丹磺）荧光物质在同系列1-[2-乙酰胺基-3-(1H-吲哚-3-基)丙酰胺基]-n-[5-(二甲氨基)萘磺酰胺基]烷烃1中在二元溶剂甘油-水中的运动性。稳态荧光数据通过广义Perrin方程进行评估，丹磺荧光物质的微布朗运动通过旋转弛豫谱的平均特性（旋转弛豫时间）描述。由于同系列化合物中甲基烷基数目增加而引起的由单键扭转振动引起的“快速”运动的旋转弛豫时间随之减少。由于色氨酸和丹磺荧光物质之间链条的构象变化引起的“慢速”运动的旋转弛豫时间，起初随着甲基烷基数目的增加大致保持恒定，但对于长链脂肪烃来说会显著增加。观察到长链脂肪烃构象变化速率的减少可能是由于在水含量较高的介质中甲基链部分之间的分子内相互作用所致。从实验数据计算得到的活化焓ΔH≠和活化熵ΔS≠的值支持这种解释。在特定二元溶剂组成下，丹磺荧光物质的时间分辨各向异性证实了旋转弛豫谱的形状，并讨论了测得的旋转相关时间。各向异性的时间依赖衰减支持了我们先前在极性介质中关于长链脂肪烃分子内缔合的解释。
• Solvatochromic characteristics of dansyl molecular probes bearing alkyl diamine chains
  作者：Sorin Mocanu、Gabriela Ionita、Iulia Matei

  DOI：10.1016/j.saa.2020.118413

  日期：2020.8

  n-diamine chains of different length (DA1.n, n = 2-8, 10, 12) was characterized in terms of the absorptive and emissive features in solvents of different polarity and hydrogen bond donor/hydrogen bond acceptor character. The probes show solvent-dependent absorption, a feature that is uncommon among dansyl derivatives. The dual emission of DA1.n probes is strong in non-aqueous solvents and is influenced by the

  一系列带有不同长度的线性烷基-1，n-二胺链（DA1.n，n = 2-8，10，12）的基于丹磺酰基的荧光探针的特征在于在不同溶剂中的吸收和发射特征极性和氢键供体/氢键受体特性。探针显示出溶剂依赖性吸收，这在丹磺酰基衍生物中并不常见。DA1.n探针的双重发射在非水溶剂中很强，并且受链长和与溶剂的相互作用的影响。在Kamlet-Taft和Catalán溶剂变色模型的基础上，合理化了溶剂对光谱参数的影响，以量化极性驱动和氢键相互作用的程度。对两个模型预测的结果进行了比较讨论。在基态下，DA1。n个探针充当氢键受体。在激发态下，氢键作用较弱，溶质与溶剂的相互作用受溶剂极性增加的控制，该极性导致发射的大红移。与先前报道的相应的双丹磺酰荧光探针系列（2DA1.n）的光谱特征进行了比较。
• Fluorescent Probes for Cytochrome P450 Structural Characterization and Inhibitor Screening
  作者：Alexander R. Dunn、Anna-Maria A. Hays、David B. Goodin、C. David Stout、Richard Chiu、Jay R. Winkler、Harry B. Gray

  DOI：10.1021/ja0271678

  日期：2002.9.1

  We have synthesized two luminescent probes (D-4-Ad and D-8-Ad) that target cytochrome P450cam. D-4-Ad luminescence is quenched by Förster energy transfer upon binding (Kd = 0.83 muM) but is restored when the probe is displaced from the active site by camphor. In contrast, D-8-Ad (Kd approximately 0.02 muM) is not displaced from the enzyme, even in the presence of a large excess of camphor. The 2.2 A resolution crystal structure of the D-8-Ad:P450cam complex reveals extensive hydrophobic contacts between the probe and the enzyme, which result from the conformational flexibility of the B', F, and G helices. Probes with properties similar to those of D-4-Ad potentially could be useful for screening P450 inhibitors.
• Method of local rheological measurement by fluorescent microscopy and a new fluorescent probe for polyacrylamide polymer molecules
  申请人：Warshawsky Abraham

  公开号：US20050233468A1

  公开（公告）日：2005-10-20

  The present invention is directed to a complex comprising of a polymer and a fluorescent probe, a method for its preparation and use thereof for measuring dynamics of single molecules in a polymeric solution.
• [EN] METHOD OF LOCAL RHEOLOGICAL MEASUREMENTS BY FLUORESCENT MICROSCOPY AND A NEW FLUORESCENT PROBE FOR POLYACRYLAMIDE POLYMER MOLECULES<br/>[FR] PROCEDE DE MESURE RHEOLOGIQUE LOCALE PAR MICROSCOPIE DE FLUORESCENCE, ET NOUVELLES SONDES FLUORESCENTES POUR MOLECULES DE POLYACRYLAMIDE
  申请人：YEDA RES & DEV

  公开号：WO2003062349A1

  公开（公告）日：2003-07-31

  The present invention is directed to a complex comprising of a polymer and a fluorescent probe, a method for its preparation and use thereof for measuring dynamics of single molecules in a polymeric solution.