5-(2,4-二硝基苯胺基)戊酸 | 28166-04-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 5-(2,4-二硝基苯胺基)戊酸
• 英文名称: 5-amino-(2,4-dinitrobenzene)-pentanoic acid
• 英文别名: N-(2,4-dinitrophenyl)-5-aminopentanoic acid；δ-(2,4-Dinitroanilino)-valeriansaeure；DNP-δ-Aminovaleriansaeure；5-(2,4-Dinitroanilino)pentanoic acid
• CAS: 28166-04-3
• 化学式: C₁₁H₁₃N₃O₆
• 分子量: 283.241
• InChiKey: CBDRAWLLQJRWIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  167.5-169.5 °C(Solv: acetone (67-64-1))
• 沸点：
  528.5±50.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(2,4-二硝基苯胺基)戊酸 在 copper(ll) sulfate pentahydrate 、 1-羟基苯并三唑 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 THPTA 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  In vivo programming of endogenous antibodies via oral administration of adaptor ligands

  摘要：

  Vaccination is a reliable method of prophylaxis and a crucial measure for public health. However, the majority of vaccines cannot be administered orally due to their degradation in the harsh gut environment or inability to cross the GI tract. In this study, we report the first proof-of-concept study of orally producible chemically programmed antibodies via specific conjugation of adaptor ligands to endogenous antibodies, in vivo. Pre-immuniztion with 2,4-dinitrophenyl (DNP), or the reactive hapten, 1,3-diketone (DK), or a novel reactive hapten, vinyl sulfone (VS) in mice, followed by oral administration of adaptor ligands composed of the hapten and biotin to the pre-immunized mice resulted in successful in vivo formation of the biotin-hapten-antibody complexes within 2 h. Pharmacokinetic evaluations revealed that apparent serum concentrations of programmed antibodies were up to 144 nM and that the serum half-lives reached up to 34.4 h. These findings show promise for the future development of orally bioavailable drug-hapten-antibody complexes as a strategy to quickly and easily modulate immune targets for aggressive pathogens as well as cancer. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.010
• 作为产物：
  描述：

  1-氯-2,4-二硝基苯 、 5-氨基颉草酸 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以84%的产率得到5-(2,4-二硝基苯胺基)戊酸
  参考文献：
  名称：

  In vivo programming of endogenous antibodies via oral administration of adaptor ligands

  摘要：

  Vaccination is a reliable method of prophylaxis and a crucial measure for public health. However, the majority of vaccines cannot be administered orally due to their degradation in the harsh gut environment or inability to cross the GI tract. In this study, we report the first proof-of-concept study of orally producible chemically programmed antibodies via specific conjugation of adaptor ligands to endogenous antibodies, in vivo. Pre-immuniztion with 2,4-dinitrophenyl (DNP), or the reactive hapten, 1,3-diketone (DK), or a novel reactive hapten, vinyl sulfone (VS) in mice, followed by oral administration of adaptor ligands composed of the hapten and biotin to the pre-immunized mice resulted in successful in vivo formation of the biotin-hapten-antibody complexes within 2 h. Pharmacokinetic evaluations revealed that apparent serum concentrations of programmed antibodies were up to 144 nM and that the serum half-lives reached up to 34.4 h. These findings show promise for the future development of orally bioavailable drug-hapten-antibody complexes as a strategy to quickly and easily modulate immune targets for aggressive pathogens as well as cancer. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.010

文献信息

• [EN] CYCLODEXTRIN LABELS FOR IMMUNOASSAY AND BIOCHEMICAL ANALYSIS
  申请人：KOSAK, Kenneth, M.

  公开号：WO1991005605A1

  公开（公告）日：1991-05-02

  (EN) The invention provides new compositions and methods for qualitative and quantitative immunoassay employing cyclodextrin (CD), labels. The labels comprise a CD ''host'' molecule that includes a fluorescent or chemiluminescent ''guest'' molecule, with a ''coupling group'' available on the CD. The labels are used for labeling various substances such as ligands, antigens, and antibodies, to provided tracers for use in immunoassays and other ligand binding assays. Methods are disclosed for competitive, and noncompetitive ''sandwich'' type assays, as well as heterogeneous and homogeneous assays. The invention provides the following properties and advantages: 1) safer, nonradioactive tracers; 2) potentially higher signal efficiency and longer shelf life; 3) coupling groups for one-step labeling; 4) chemiluminescent detection for more sensitivity; 5) multiple CD labels for efficient labeling; 6) chemical/physical similarity for easier synthesis and use; 7) different colored labels with similar properties; 8) methods are readily automated for high volume applications. The invention also provides catalytic CD labels and methods.(FR) De nouvelles compositions et de nouvelles méthodes permettent de procéder à des essais immunitiares avec des marqueurs en cyclodextrine (CD). Les marqueurs comprennent une molécule ''hôte'' de CD qui contient une molécule ''invitée'' fluorescente ou chimioluminescente, avec un ''groupe de couplage'' agencé sur la CD. Les marqueurs sont utiles pour marquer diverses substances, telles que ligands, antigènes et anticorps, qui servent d'indicateurs lors d'essais immunitaires et d'autres essais par liaison avec des ligands. On décrit des procédés d'essais de type compétitif et non compétitif en ''sandwich'', ainsi que des essais hétérogènes et homogènes. Les propriétés et les avantages de l'invention sont: 1) indicateurs sûrs non radioactifs; 2) des signaux d'une efficacité potentiellement supérieure et une plus longue durée de conservation; 3) des groupes de couplage pour des marquages en une seule étape; 4) une détection chimioluminescente plus sensible; 5) des marqueurs multiples en CD qui assurent un marquage efficace; 6) similarité chimique/physique, qui facilite la synthèse et l'utilisation; 7) des marqueurs de couleurs différentes avec des propriétés similaires; 8) des procédés faciles à automatiser, pour des applications à des volumes importants. L'invention concerne également des procédés et des marqueurs en CD par catalyse.
• In vivo programming of endogenous antibodies via oral administration of adaptor ligands
  作者：Masanobu Nagano、Nancy Carrillo、Nobumasa Otsubo、Wataru Hakamata、Hitoshi Ban、Roberta P. Fuller、Nasir K. Bashiruddin、Carlos F. Barbas

  DOI：10.1016/j.bmc.2017.09.010

  日期：2017.11

  Vaccination is a reliable method of prophylaxis and a crucial measure for public health. However, the majority of vaccines cannot be administered orally due to their degradation in the harsh gut environment or inability to cross the GI tract. In this study, we report the first proof-of-concept study of orally producible chemically programmed antibodies via specific conjugation of adaptor ligands to endogenous antibodies, in vivo. Pre-immuniztion with 2,4-dinitrophenyl (DNP), or the reactive hapten, 1,3-diketone (DK), or a novel reactive hapten, vinyl sulfone (VS) in mice, followed by oral administration of adaptor ligands composed of the hapten and biotin to the pre-immunized mice resulted in successful in vivo formation of the biotin-hapten-antibody complexes within 2 h. Pharmacokinetic evaluations revealed that apparent serum concentrations of programmed antibodies were up to 144 nM and that the serum half-lives reached up to 34.4 h. These findings show promise for the future development of orally bioavailable drug-hapten-antibody complexes as a strategy to quickly and easily modulate immune targets for aggressive pathogens as well as cancer. (C) 2017 Elsevier Ltd. All rights reserved.