6-(2,4-二硝基苯胺基)己酸 N-琥珀酰亚氨基酯 | 82321-04-8

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-(2,4-二硝基苯胺基)己酸 N-琥珀酰亚氨基酯
• 中文别名: 6-(2,4-二硝基苯胺基)己酸-N-琥珀酰亚氨基酯；6-(2,4-二硝基苯胺基)己酸N-琥珀酰亚氨基酯；N-(2,4-二硝基苯基)-6-氨基己酸-N-琥伯酰亚胺
• 英文名称: 6-(2,4-dinitrophenyl)aminohexanoic acid succinimidyl ester
• 英文别名: N-Succinimidyl 6-(2,4-Dinitroanilino)hexanoate；(2,5-dioxopyrrolidin-1-yl) 6-(2,4-dinitroanilino)hexanoate
• CAS: 82321-04-8
• 化学式: C₁₆H₁₈N₄O₈
• 分子量: 394.341
• InChiKey: IYBNUJCDIAGXNX-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  591.8±60.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 海关编码：
  2925190090

制备方法与用途

生物活性

DNP-X (6-(2,4-二硝基苯基氨基己酸，琥珀酰亚胺酯)，经过琥珀酰亚胺酯修饰的 DNP-X 酸)，是一种用于开发可被 anti-DNP 抗体识别的探针的胺反应性构建块。同时，DNP-X (6-(2,4-二硝基苯基氨基己酸，琥珀酰亚胺酯) 也是一种与 Trp 或 Tyr 配对极好的胺反应性 FRET 淬灭剂。

反应信息

• 作为反应物：
  描述：

  6-(2,4-二硝基苯胺基)己酸 N-琥珀酰亚氨基酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 生成 N-{3-[5-fluoresceinisothiourea]propyl}-6-[(2,4-dinitrophenyl)amino]hexanamide
  参考文献：
  名称：

  Synthetic Mimics of Small Mammalian Cell Surface Receptors

  摘要：

  Receptors on the surface of mammalian cells promote the uptake of cell-impermeable ligands by receptor-mediated endocytosis. To mimic this process, we synthesized small molecules designed to project anti-dinitrophenyl antibody-binding motifs from the surface of living Jurkat lymphocytes. These synthetic receptors comprise N-alkyl derivatives of 3beta-cholesterylamine as the plasma membrane anchor linked to 2,4-dinitrophenyl (DNP) and structurally similar fluorescent 7-nitrobenz-2-oxa-1,3-diazole (NBD) headgroups. Insertion of two beta-alanine subunits between a DNP derivative and 3beta-cholesterylamine yielded a receptor that avidly associates with cell surfaces (cellular t(1/2) similar to 20 h). When added to Jurkat cells at 10 muM, this receptor enhanced uptake of an anti-DNP IgG ligand by similar to200-fold in magnitude and similar to400-fold in rate within 4 h (ligand internalization t(1/2) similar to 95 min at 37 degreesC). This non-natural receptor mimics many natural receptors by dynamically cycling between plasma membranes and intracellular endosomes (recycling t(1/2) similar to 3 min), targeting of protein ligands to proposed cholesterol and sphingolipid-enriched lipid raft membrane microdomains, and delivery of protein ligands to late endosomes/lysosomes. Quantitative dithionite quenching of fluorescent extracellular NBD headgroups demonstrated that other 3beta-cholesterylamine derivatives bearing fewer beta-alanines in the linker region or N-acyl derivatives of 3beta-cholesterylamine were less effective receptors due to more extensive trafficking to internal membranes. Synthetic cell surface receptors have potential applications as cellular probes, tools for drug delivery, and methods to deplete therapeutically important extracellular ligands.

  DOI：

  10.1021/ja046663o
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-(2,4-二硝基苯)-6-氨基己酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-(2,4-二硝基苯胺基)己酸 N-琥珀酰亚氨基酯
  参考文献：
  名称：

  通过Cu（I）催化的炔-叠氮化物[2 + 3]环加成反应对磁性纳米粒子进行表面改性。

  摘要：

  Cu（I）催化炔叠氮化物[2 + 3]环加成反应是将生物分子共价固定在磁性纳米颗粒（MNP）上的有效且正交的共轭反应。MNP表面上的叠氮基可提供更好的与烷基化分子的结合效率。此外，将C末端链化的蛋白位点特异性地固定在MNP上。通过位点特异性固定表现出的蛋白质结合活性高于通过随机酰胺键形成所表现出的蛋白质结合活性。

  DOI：

  10.1021/ol070588f

文献信息

• [EN] CONTROLLED DRUG RELEASE FROM SOLID SUPPORTS<br/>[FR] SUPPORTS SOLIDES POUR LA LIBÉRATION CONTRÔLÉE DE MÉDICAMENTS
  申请人：PROLYNX LLC

  公开号：WO2011140392A1

  公开（公告）日：2011-11-10

  The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

  这项发明涉及在医疗应用中有用的固体支持物，可提供药物的控制释放，如肽、核酸和小分子。这些药物通过一个通过受控β消除释放药物或前药的连接与固体支持物共价偶联。
• [EN] CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES<br/>[FR] LIBÉRATION CONTRÔLÉE À PARTIR DE CONJUGUÉS MACROMOLÉCULAIRES
  申请人：PROLYNX LLC

  公开号：WO2011140393A1

  公开（公告）日：2011-11-10

  The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

  这项发明涉及大分子载体和药物的共轭物，包括释放药物或前药的连接剂，通过速率控制的β-消除释放药物，以及制备和使用这些共轭物的方法。
• Synthetic mimics of mammalian cell surface receptors: method and compositions
  申请人：Peterson R. Blake

  公开号：US20060229235A1

  公开（公告）日：2006-10-12

  The present invention relates to new synthetic receptors. More particularly, the present invention relates to the use of the synthetic receptors for delivering a protein, peptide, drug, prodrug, lipid, nucleic acid, carbohydrate or small molecule into a target cell via receptor-mediated endocytosis. According to the invention, novel synthetic mimics of cell surface receptors have been designed and methods for use of the same are disclosed.

  本发明涉及新的合成受体。更具体地，本发明涉及利用合成受体通过受体介导的内吞作用将蛋白质、肽、药物、前药、脂质、核酸、碳水化合物或小分子输送到靶细胞中。根据本发明，已设计了细胞表面受体的新型合成模拟物，并公开了其使用方法。
• Surface Modification of Magnetic Nanoparticle via Cu(I)-Catalyzed Alkyne-azide [2 + 3] Cycloaddition
  作者：Po-Chiao Lin、Shau-Hua Ueng、Sheng-Chieh Yu、Mi-Dan Jan、Avijit Kumar Adak、Ching-Ching Yu、Chun-Cheng Lin

  DOI：10.1021/ol070588f

  日期：2007.5.1

  The Cu(I)-catalyzed alkyne-azide [2 + 3] cycloaddition has been demonstrated to be an effective and orthogonal conjugation reaction to covalently immobilize biomolecules on magnetic nanoparticles (MNPs). The azido group on the MNP surface provides better conjugation efficiency with alkynated molecules. Moreover, the C-terminal alkynated protein was site-specifically immobilized on MNP. The protein

  Cu（I）催化炔叠氮化物[2 + 3]环加成反应是将生物分子共价固定在磁性纳米颗粒（MNP）上的有效且正交的共轭反应。MNP表面上的叠氮基可提供更好的与烷基化分子的结合效率。此外，将C末端链化的蛋白位点特异性地固定在MNP上。通过位点特异性固定表现出的蛋白质结合活性高于通过随机酰胺键形成所表现出的蛋白质结合活性。
• MS/MS Simplification by 355 nm Ultraviolet Photodissociation of Chromophore-Derivatized Peptides in a Quadrupole Ion Trap
  作者：Jeffrey J. Wilson、Jennifer S. Brodbelt

  DOI：10.1021/ac071241t

  日期：2007.10.1

  Ultraviolet photodissociation (UVPD) of chromophore-modified peptides enhances the capabilities for de novo sequencing in a quadrupole ion trap mass spectrometer. Attachment of UV chromophores allows efficient photoactivation of not only the precursor ions but also any fragments that retain the chromophore functionality. For doubly protonated peptides, UVPD leads to a vast reduction in MS/MS complexity

  发色团修饰的肽的紫外光解离（UVPD）增强了四极离子阱质谱仪中从头测序的能力。紫外线发色团的附着不仅可以有效地激活前体离子，而且还可以保留任何保留发色团功能的碎片。对于双质子化肽，UVPD导致MS / MS复杂性大大降低。根据生色团的位置（即N端或C端），通过UVPD将碰撞激活解离时通常看到的b和y离子阵列还原为y或b离子的单个序列。磺化试剂Alexa Fluor 350（AF350）通过UVPD为单电荷和双电荷肽提供了最佳的总体结果。AF350的非磺化类似物7-氨基-4-甲基香豆素-3-乙酸 还通过UVPD简化了带双电荷但不带单电荷的肽的光谱。二硝基苯基肽还可以通过UVPD产生简化的光谱，尽管伴随一系列诊断性y离子有少量内部碎片。此MS / MS简化过程的成功源自暴露于后续激光脉冲时任何含发色团的片段的广泛二次断裂。能量可变的UVPD显示，不含生色团的y碎片离子的丰度随激光脉冲能量线性增