methyl 3-(3-ethylureido)propanoate

• 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
• 英文名称: methyl 3-(3-ethylureido)propanoate
• 英文别名: Methyl 3-(ethylcarbamoylamino)propanoate
• 化学式: C₇H₁₄N₂O₃
• mdl: MFCD14586855
• 分子量: 174.2
• InChiKey: IRABKEKREKLIOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(3-ethylureido)propanoate 在 lithium hydroxide monohydrate 、 sodium acetate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 50.67h， 生成 acetoxymethyl 3-((E)-5-((2E,4E)-4-(1-(3-(acetoxymethoxy)-3-oxopropyl)-3,3-trimethylindilin-2-ylidene)but-2-en-1-ylidene)-3-ethyl-2,4,6-trioxotetrahydropyrimidine-1(2H)-yl)propanoate
  参考文献：
  名称：

  Membrane-Permeant, Environment-Sensitive Dyes Generate Biosensors within Living Cells

  摘要：

  Dyes with environment-sensitive fluorescence have proven useful to study the spatiotemporal dynamics of protein activity in living cells. When attached to proteins, their fluorescence can reflect protein conformational changes, post-translational modifications, or protein interactions. However, the utility of such dye-protein conjugates has been limited because it is difficult to load them into cells. They usually must be introduced using techniques that perturb cell physiology, limit throughput, or generate fluorescent vesicles (e.g., electroporation, microinjection, or membrane transduction peptides). Here we circumvent these problems by modifying a proven, environment-sensitive biosensor fluorophore so that it can pass through cell membranes without staining intracellular compartments and can be attached to proteins within living cells using unnatural amino acid (UAA) mutagenesis. Reactive groups were incorporated for attachment to UAAs or small molecules (mero166, azide; mero167, alkyne; mero76, carboxylic acid). These dyes are bright and fluoresce at long wavelengths (reaching epsilon = 100 000 M-1 cm(-1), phi = 0.24, with excitation 565 nm and emission 594 nm). The utility of mero166 was demonstrated by in-cell labeling of a UAA to generate a biosensor for the small GTPase Cdc42. In addition, conjugation of mero166 to a small molecule produced a membrane-permeable probe that reported the localization of the DNA methyltransferase G9a in cells. This approach provides a strategy to access biosensors for many targets and to more practically harness the varied environmental sensitivities of synthetic dyes.

  DOI：

  10.1021/jacs.8b09841
• 作为产物：
  描述：

  3-氨基丙酸甲酯盐酸盐 、 异氰酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.75h， 以58%的产率得到methyl 3-(3-ethylureido)propanoate
  参考文献：
  名称：

  Membrane-Permeant, Environment-Sensitive Dyes Generate Biosensors within Living Cells

  摘要：

  Dyes with environment-sensitive fluorescence have proven useful to study the spatiotemporal dynamics of protein activity in living cells. When attached to proteins, their fluorescence can reflect protein conformational changes, post-translational modifications, or protein interactions. However, the utility of such dye-protein conjugates has been limited because it is difficult to load them into cells. They usually must be introduced using techniques that perturb cell physiology, limit throughput, or generate fluorescent vesicles (e.g., electroporation, microinjection, or membrane transduction peptides). Here we circumvent these problems by modifying a proven, environment-sensitive biosensor fluorophore so that it can pass through cell membranes without staining intracellular compartments and can be attached to proteins within living cells using unnatural amino acid (UAA) mutagenesis. Reactive groups were incorporated for attachment to UAAs or small molecules (mero166, azide; mero167, alkyne; mero76, carboxylic acid). These dyes are bright and fluoresce at long wavelengths (reaching epsilon = 100 000 M-1 cm(-1), phi = 0.24, with excitation 565 nm and emission 594 nm). The utility of mero166 was demonstrated by in-cell labeling of a UAA to generate a biosensor for the small GTPase Cdc42. In addition, conjugation of mero166 to a small molecule produced a membrane-permeable probe that reported the localization of the DNA methyltransferase G9a in cells. This approach provides a strategy to access biosensors for many targets and to more practically harness the varied environmental sensitivities of synthetic dyes.

  DOI：

  10.1021/jacs.8b09841

文献信息

• [EN] IMPROVED ENVIRONMENT SENSING CYANINE AND MEROCYANINE DYES<br/>[FR] COLORANTS CYANINE ET MÉROCYANINE AMÉLIORÉS À TITRE DE CAPTEURS D'ENVIRONNEMENT
  申请人：UNIV NORTH CAROLINA

  公开号：WO2015103587A3

  公开（公告）日：2015-09-11
• Membrane-Permeant, Environment-Sensitive Dyes Generate Biosensors within Living Cells
  作者：Christopher J. MacNevin、Takashi Watanabe、Matthew Weitzman、Akash Gulyani、Sheryl Fuehrer、Nicholas K. Pinkin、Xu Tian、Feng Liu、Jian Jin、Klaus M. Hahn

  DOI：10.1021/jacs.8b09841

  日期：2019.5.8

  Dyes with environment-sensitive fluorescence have proven useful to study the spatiotemporal dynamics of protein activity in living cells. When attached to proteins, their fluorescence can reflect protein conformational changes, post-translational modifications, or protein interactions. However, the utility of such dye-protein conjugates has been limited because it is difficult to load them into cells. They usually must be introduced using techniques that perturb cell physiology, limit throughput, or generate fluorescent vesicles (e.g., electroporation, microinjection, or membrane transduction peptides). Here we circumvent these problems by modifying a proven, environment-sensitive biosensor fluorophore so that it can pass through cell membranes without staining intracellular compartments and can be attached to proteins within living cells using unnatural amino acid (UAA) mutagenesis. Reactive groups were incorporated for attachment to UAAs or small molecules (mero166, azide; mero167, alkyne; mero76, carboxylic acid). These dyes are bright and fluoresce at long wavelengths (reaching epsilon = 100 000 M-1 cm(-1), phi = 0.24, with excitation 565 nm and emission 594 nm). The utility of mero166 was demonstrated by in-cell labeling of a UAA to generate a biosensor for the small GTPase Cdc42. In addition, conjugation of mero166 to a small molecule produced a membrane-permeable probe that reported the localization of the DNA methyltransferase G9a in cells. This approach provides a strategy to access biosensors for many targets and to more practically harness the varied environmental sensitivities of synthetic dyes.