N-(2-((2-aminoethyl)amino)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide | 52664-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-((2-aminoethyl)amino)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• 英文别名: DNSH-dienH；N-[2-(2-aminoethylamino)ethyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 52664-02-5
• 化学式: C₁₆H₂₄N₄O₂S
• 分子量: 336.458
• InChiKey: LVLAFEBHIMOGMI-UHFFFAOYSA-N

物化性质

• 沸点：
  532.8±60.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-((2-aminoethyl)amino)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以0.91 g的产率得到N-(2-((2-aminoethyl)amino)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide hydrochloride
  参考文献：
  名称：

  Synthesis and Characterization of Fluorescent Displacers for Online Monitoring of Displacement Chromatography

  摘要：

  One of the major impediments to the implementation of displacement chromatography for the purification of biomolecules is the need to collect fractions from the column effluent for time-consuming off line analysis. The ability to employ direct online monitoring of displacement chromatography would have significant implications for applications ranging from analytical to preparative bioseparations. To this end, a set of novel fluorescent displacers were rationally designed using known chemically selective displacers as a template. Fluorescent cores were functionalized with different charge moieties, creating a homologous library of displacers. These compounds were then tested on two protein pairs, alpha-chymotrypsinogen A/ribonuclease A and cytochrome c/lysozyme, using batch and column displacement experiments. Of the synthesized displacers, two were found to be highly selective while one was determined to be a high-affinity displacer. Column displacements using one of the selective displacers yielded complete separation of both protein pairs while facilitating direct online detection using UV and fluorescence detection. Saturation transfer difference NMR was also carried out to investigate the binding of the fluorescent displacers to proteins. The results indicated a selective binding between the selective displacers and (x-chymotrypsinogen A, while no binding was observed for ribonuclease A, confirming that protein-displacer binding is responsible for the selectivity in these systems. This work demonstrates the utility of fluorescent displacers to enable online monitoring of displacer breakthroughs while also acting as efficient displacers for protein purification.

  DOI：

  10.1021/ja806279x
• 作为产物：
  描述：

  丹酰氯 、 二乙烯三胺 以 乙腈 为溶剂， 反应 6.0h， 以72%的产率得到N-(2-((2-aminoethyl)amino)ethyl)-5-(dimethylamino)naphthalene-1-sulfonamide
  参考文献：
  名称：

  丹磺酰-二亚乙基三胺-硫脲共轭物作为水介质中 Hg2+离子的荧光化学剂量计

  摘要：

  制备了一种新的丹磺酰-二亚乙基三胺-硫脲偶联物 (DT) 作为 Hg2+ 离子的高选择性和灵敏荧光化学剂量计。一个 Hg2+ 诱导的脱硫反应紧随其后...

  DOI：

  10.1246/cl.140268

文献信息

• The Neglected Pt−N(sulfonamido) Bond in Pt Chemistry. New Fluorophore-Containing Pt(II) Complexes Useful for Assessing Pt(II) Interactions with Biomolecules
  作者：Anna Maria Christoforou、Patricia A. Marzilli、Luigi G. Marzilli

  DOI：10.1021/ic0606375

  日期：2006.8.1

  data establish that Pt(DNS-dien) has a Pt-C8 bond and a Pt-N(sulfonamido) bond. Pt(DNSH-dien)Cl and [Pt(DNSH-tren)Cl]Cl bind to N7 of 6-oxopurines (e.g., 5'-GMP, 3'-IMP, and 9-ethylguanine) and sulfur of methionine (met). Competition and challenge reactions for Pt(II) with met and 5'-GMP typically reveal that met binding is favored kinetically but that 5'-GMP binding is favored thermodynamically. This

  用DNSH-tren处理顺式Pt（Me2SO）2Cl2可得到[Pt（DNSH-tren）Cl] Cl和DNSH-dienH，在越来越基本的条件下，导致Pt（DNSH-dienH）Cl（2），Pt （DNSH-dien）Cl和Pt（DNS-dien）。（DNSH = 5-（二甲基氨基）萘-1-磺酰基，通过磺酰胺基与三（2-氨基乙基）胺（DNSH-tren）和二亚乙基三胺（DNSH-dienH）连接; DNSH-dienH中的H表示质子有时会丢失在Pt结合时，即dienH部分的磺酰胺NH和DNSH部分的H8）。三种中性DNSH-dienH-衍生的复合物分别是双官能的，单官能的和无官能的，并且随着丹磺酰基基团到Pt的距离的减小，荧光依次递减。2D NMR数据确定Pt（DNS-dien）具有Pt-C8键和Pt-N（磺酰胺基）键。Pt（DNSH-dien）Cl和[Pt（DNSH-tren）Cl] C
• Fluorescent Chemosensor for Organic Guests and Copper(II) Ion Based on Dansyldiethylenetriamine-Modified β-Cyclodextrin
  作者：Roberto Corradini、Arnaldo Dossena、Gianni Galaverna、Rosangela Marchelli、Anna Panagia、Giorgio Sartor

  DOI：10.1021/jo970349d

  日期：1997.9.1

  A modified cyclodextrin containing a dansyldiethylenetriamine metal-binding group (6-deoxy-6-N(N''-dansyldiethylenetriamino)-beta-cyclodextrin, CD-dien-DNS) was synthesized. The conformation of CD-dien-DNS was studied by 2D NMR (ROESY spectral in D2O, by circular dichroism, and by fluorescence. The results were compared with those previously obtained with the analogous 6-deoxy-6-N-(N'-dansylethylenediamino)-beta-cyclodextrin (CD-en-DNS) and were consistent with the self-inclusion of the dansyl group within the macrocycle cavity. However, the orientation of the dansyl group for CD-dien-DNS was found to be equatorial, whereas for CD-en-DNS it was axial, suggesting a dependence of the orientation of the dansyl group upon the length of the linker. In the presence of lipophilic organic molecules, CD-dien-DNS showed sensing properties similar to those observed for CD-en-DNS, suggesting a similar ''in-out'' movement of the dansyl group, due to competitive inclusion of the guest. Unlike CD-en-DNS, CD-dien-DNS was found to be a fluorescent chemosensor for copper(II) ion, with a linear response up to a 1:1 molar ratio, suggesting that a more flexible conformation of the linker and the presence of additional binding sites allow binding of the metal ion by the amino and sulfonamidate groups. Good selectivity for Cu(II), when compared with Fe(II), Co(II), Ni(II), and Zn(II), was observed. The CD-dien-DNS copper(II) complex was shown to behave as a chemosensor for bifunctional molecules, such as amino acids. In fact, upon addition of alanine, tryptophan, and thyroxine, the negligible fluorescence intensity of Cu(CD-dien-DNS) complex was ''switched on'', with a response dependent on the amino acid side chain.
• Synthesis and Characterization of Fluorescent Displacers for Online Monitoring of Displacement Chromatography
  作者：Christopher J. Morrison、Sun Kyu Park、Chester Simocko、Scott A. McCallum、Steven M. Cramer、J. A. Moore

  DOI：10.1021/ja806279x

  日期：2008.12.17

  One of the major impediments to the implementation of displacement chromatography for the purification of biomolecules is the need to collect fractions from the column effluent for time-consuming off line analysis. The ability to employ direct online monitoring of displacement chromatography would have significant implications for applications ranging from analytical to preparative bioseparations. To this end, a set of novel fluorescent displacers were rationally designed using known chemically selective displacers as a template. Fluorescent cores were functionalized with different charge moieties, creating a homologous library of displacers. These compounds were then tested on two protein pairs, alpha-chymotrypsinogen A/ribonuclease A and cytochrome c/lysozyme, using batch and column displacement experiments. Of the synthesized displacers, two were found to be highly selective while one was determined to be a high-affinity displacer. Column displacements using one of the selective displacers yielded complete separation of both protein pairs while facilitating direct online detection using UV and fluorescence detection. Saturation transfer difference NMR was also carried out to investigate the binding of the fluorescent displacers to proteins. The results indicated a selective binding between the selective displacers and (x-chymotrypsinogen A, while no binding was observed for ribonuclease A, confirming that protein-displacer binding is responsible for the selectivity in these systems. This work demonstrates the utility of fluorescent displacers to enable online monitoring of displacer breakthroughs while also acting as efficient displacers for protein purification.
• A Dansyl–Diethylenetriamine–Thiourea Conjugate as a Fluorescent Chemodosimeter for Hg²⁺ Ions in Water Media
  作者：Nguyen Khoa Hien、Phan Tu Quy、Nguyen Tien Trung、Vo Vien、Dang Van Khanh、Nguyen Thi Ai Nhung、Duong Tuan Quang

  DOI：10.1246/cl.140268

  日期：2014.7.5

  A new dansyl–diethylenetriamine–thiourea conjugate (DT) was prepared as a highly selective and sensitive fluorescent chemodosimeter for Hg2+ ions. A Hg2+-induced desulfurization reaction followed b...

  制备了一种新的丹磺酰-二亚乙基三胺-硫脲偶联物 (DT) 作为 Hg2+ 离子的高选择性和灵敏荧光化学剂量计。一个 Hg2+ 诱导的脱硫反应紧随其后...