N-[2-(3,4-dihydroxyphenyl)ethyl]biotinamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N-[2-(3,4-dihydroxyphenyl)ethyl]biotinamide
• 英文别名: N-biotinyl-2-(3,4-dihydroxyphenyl)ethylamine；N-biotinyl-dopamine；N-Biotinyl Dopamine；5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-(3,4-dihydroxyphenyl)ethyl]pentanamide
• 化学式: C₁₈H₂₅N₃O₄S
• 分子量: 379.48
• InChiKey: PDZDPPBGYITTEH-NUTKFTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-biotinyl-2-(3,4-dibenzyloxyphenyl)ethylamine 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 30.0 ℃ 、7.0 MPa 条件下， 反应 2.0h， 以78%的产率得到N-[2-(3,4-dihydroxyphenyl)ethyl]biotinamide
  参考文献：
  名称：

  通过自组装纳米粒子-囊泡水凝胶将磁脉冲转化为细胞反应

  摘要：

  用磁性纳米粒子交联囊泡会产生 MNPV，这是一种自组装的“纳米药丸”，可以通过交变磁场 (AMF) “解锁”，释放储存在囊泡内的化学信使。当 MNPV 与水凝胶基质中的细胞共同固定时，暴露于 AMF 磁信号会释放化学信使，然后诱导细胞反应。

  DOI：

  10.1002/anie.201103469

文献信息

• Heterodimers of Nanoparticles:  Formation at a Liquid−Liquid Interface and Particle-Specific Surface Modification by Functional Molecules
  作者：Hongwei Gu、Zhimou Yang、Jinhao Gao、C. K. Chang、Bing Xu

  DOI：10.1021/ja045220h

  日期：2005.1.1

  On the basis of a fundamental property of nanoparticles, the self-assembling at a liquid-liquid interface to form "colloidosomes", a heterogeneous reaction takes place on the exposed surface of the nanoparticles to produce the heterodimers of two distinct nanospheres, which can be modified by two different functional molecules in a particle-specific manner.

  基于纳米粒子的一个基本特性，即在液-液界面自组装形成“胶体”，纳米粒子的暴露表面发生异质反应，产生两个不同纳米球的异二聚体，可以是由两种不同的功能分子以特定于颗粒的方式修饰。
• Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand–receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution
  作者：Shin Aoki、Nanako Matsuo、Kengo Hanaya、Yasuyuki Yamada、Yoshiyuki Kageyama

  DOI：10.1016/j.bmc.2009.03.031

  日期：2009.5

  The ability of avidin (Avn) to form strong complex with biotin (Btn) is frequently used in the detection and isolation of biomolecules in biochemical, analytical, and medicinal research. The fact that the binding is nealy irreversible, however, constitutes a drawback in term of the isolation and purification of intact biomolecules. We recently found that 8-quinolinyl esters of aromatic or aliphatic sulfonic acids undergo photolysis when irradiated at 300-330 nm in aqueous solution at neutral pH. In this work, a biotin-dopamine (BD) conjugate containing a photocleavable 8-quinolinyl benzenesulfonate (QB) linker, BDQB, was designed and synthesized for use in the efficient recovery of dopamine-protein (e.g., antibody) complexes from an Avn-Btn system. The complexation of BDQB with a primary anti-dopamine antibody (anti-dopamine IgG(1) from mouse) on an Avn-coated plate was confirmed by an enzyme-linked immunosorbent assay ( ELISA) utilizing a secondary antibody (anti-IgG(1) antibody) conjugated with horseradish peroxidase (HRP). Upon the photoirradiation (at 313 nm) of the BDQB-IgG(1) complex, the release of dopamine-IgG(1) complex was confirmed by ELISA. Characterization of the resulting photoreleased dopamine anti-dopamine IgG(1) complex was performed by SDS-PAGE and Western blot. (C) 2009 Elsevier Ltd. All rights reserved.
• Conversion of Magnetic Impulses into Cellular Responses by Self-Assembled Nanoparticle-Vesicle Hydrogels
  作者：Felicity de Cogan、Andrew Booth、Julie E. Gough、Simon J. Webb

  DOI：10.1002/anie.201103469

  日期：2011.12.16

  Crosslinking vesicles with magnetic nanoparticles produced MNPVs, self‐assembled “nanopills” that can be “unlocked” by an alternating magnetic field (AMF), releasing chemical messengers stored within the vesicles. When MNPVs are co‐immobilized with cells in a hydrogel matrix, exposure to an AMF magnetic signal releases the chemical messengers, which then induce a cellular response.

  用磁性纳米粒子交联囊泡会产生 MNPV，这是一种自组装的“纳米药丸”，可以通过交变磁场 (AMF) “解锁”，释放储存在囊泡内的化学信使。当 MNPV 与水凝胶基质中的细胞共同固定时，暴露于 AMF 磁信号会释放化学信使，然后诱导细胞反应。