N-{2-[bis(2-aminoethyl)amino]ethyl}-5-(dimethylamino)naphthalene-1-sulfonamide | 330163-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-{2-[bis(2-aminoethyl)amino]ethyl}-5-(dimethylamino)naphthalene-1-sulfonamide
• 英文别名: N-[2-[bis(2-aminoethyl)amino]ethyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 330163-12-7
• 化学式: C₁₈H₂₉N₅O₂S
• 分子量: 379.527
• InChiKey: VPSGKEWOHGGUMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-{2-[bis(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1.00 g的产率得到
  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：

  三(2-氨基乙基)胺 、 丹酰氯 以 二氯甲烷 为溶剂， 生成 N-{2-[bis(2-aminoethyl)amino]ethyl}-5-(dimethylamino)naphthalene-1-sulfonamide
  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

文献信息

• Monitoring inorganic pyrophosphatase activity with the fluorescent dizinc(<scp>ii</scp>) complex of a macrocycle bearing one dansylamidoethyl antenna
  作者：Ana Cruz、Ara Núñez-Montenegro、Pedro Mateus、Rita Delgado

  DOI：10.1039/d0dt01673j

  日期：——

  The dizinc(II) complexes of L were used for the recognition of anions by fluorescence spectroscopy (L is a heteroditopic hexaazamacrocycle with two diethylenetriamine coordination heads with 2-methylpyridyl and dansylamido ethyl arms, and m-xylyl spacers). The protonation of L and stability constants of its zinc(II) complexes were determined in aqueous solution, at 298.2 ± 0.1 K and I = 0.10 ± 0.01

  所述dizinc（II）配合物的大号被用于通过荧光光谱法识别阴离子（大号是heteroditopic hexaazamacrocycle与2-甲基吡啶基二乙烯三胺2协调头和dansylamido乙基臂，和米-二甲苯间隔物）。在水溶液中测定了L的质子化及其锌（II）配合物的稳定常数，在KNO 3中为298.2±0.1 K和I = 0.10±0.01M 。在2：1 Zn 2+ / L在比例上，双核复合物显然占主导地位。单独的配体不会随pH值的增加而显示荧光变化，但是在Zn 2+的存在下，发射在pH≥7.5时达到最大值，此时95％的配体为双核络合物形式。发射与[Zn 2 H -1 L ] 3+物种形成同时出现，这表明后者的络合物​​对应于金属促进的丹磺酰胺NH的去质子化。[Zn 2 H -1 L ] 3+络合物用于识别在pH 7.5和2mM PIPPS缓冲于298.2 K的水溶液中的磷酸根和多磷
• 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