(2S)-3-[6-(dimethylamino)-1,3-dioxobenzo[de]isoquinolin-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S)-3-[6-(dimethylamino)-1,3-dioxobenzo[de]isoquinolin-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• 化学式: C₃₆H₆₀N₅O₁₀Pol
• 分子量: 549.6
• InChiKey: AUIZGANPFIRSKJ-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-3-[6-(dimethylamino)-1,3-dioxobenzo[de]isoquinolin-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid 在 4-甲基哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-α-Boc-(4-N,N-dimethylamino-1,8-naphthalimido)alanine
  参考文献：
  名称：

  A Versatile Amino Acid Analogue of the Solvatochromic Fluorophore 4-N,N-Dimethylamino-1,8-naphthalimide: A Powerful Tool for the Study of Dynamic Protein Interactions

  摘要：

  We have developed a new unnatural amino acid based on the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN) for application in the study of protein-protein interactions. The fluorescence quantum yield of this chromophore is highly sensitive to changes in the local solvent environment, demonstrating "switch-like" emission properties characteristic of the dimethylaminophthalimide family of fluorophores. In particular, this new species possesses a number of significant advantages over related fluorophores, including greater chemical stability under a wide range of conditions, a longer wavelength of excitation (408 nm), and improved synthetic accessibility. This amino acid has been prepared as an Fmoc-protected building block and may readily be incorporated into peptides via standard solid-phase peptide synthesis. A series of comparative studies are presented to demonstrate the advantageous properties of the 4-DMN amino acid relative to those of the previously reported 4-N,N-dimethylaminoph-thalimidoalanine and 6-N,N-dimethylamino-2,3-naphthalimidoalanine amino acids. Other commercially available solvatochromic fluorophores are also include in these studies. The potential of this new probe as a tool for the study of protein-protein interactions is demonstrated by introducing it into a peptide that is recognized by calcium-activated calmodulin. The binding interaction between these two components yields an increase in fluorescence emission greater than 900-fold.

  DOI：

  10.1021/ja804754y
• 作为产物：
  描述：

  在 4-甲基哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 (2S)-3-[6-(dimethylamino)-1,3-dioxobenzo[de]isoquinolin-2-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
  参考文献：
  名称：

  A Versatile Amino Acid Analogue of the Solvatochromic Fluorophore 4-N,N-Dimethylamino-1,8-naphthalimide: A Powerful Tool for the Study of Dynamic Protein Interactions

  摘要：

  We have developed a new unnatural amino acid based on the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN) for application in the study of protein-protein interactions. The fluorescence quantum yield of this chromophore is highly sensitive to changes in the local solvent environment, demonstrating "switch-like" emission properties characteristic of the dimethylaminophthalimide family of fluorophores. In particular, this new species possesses a number of significant advantages over related fluorophores, including greater chemical stability under a wide range of conditions, a longer wavelength of excitation (408 nm), and improved synthetic accessibility. This amino acid has been prepared as an Fmoc-protected building block and may readily be incorporated into peptides via standard solid-phase peptide synthesis. A series of comparative studies are presented to demonstrate the advantageous properties of the 4-DMN amino acid relative to those of the previously reported 4-N,N-dimethylaminoph-thalimidoalanine and 6-N,N-dimethylamino-2,3-naphthalimidoalanine amino acids. Other commercially available solvatochromic fluorophores are also include in these studies. The potential of this new probe as a tool for the study of protein-protein interactions is demonstrated by introducing it into a peptide that is recognized by calcium-activated calmodulin. The binding interaction between these two components yields an increase in fluorescence emission greater than 900-fold.

  DOI：

  10.1021/ja804754y

文献信息

• ENVIRONMENTALLY SENSITIVE FLUOROPHORES
  申请人：Imperiali Barbara

  公开号：US20100168428A1

  公开（公告）日：2010-07-01

  The present invention generally relates to environment-sensitive fluorophores, including environment-sensitive fluorophores for reporting protein/protein and peptide/protein interactions. In one aspect, the present invention is directed to compounds and salts thereof, compositions and methods useful in determining biological interactions. In some cases, the compounds of the present invention are environment-sensitive fluorophores that have spectroscopic behavior that may depend on factors such as the physicochemical properties of the surrounding environment. The compounds of the present invention can be used, in certain embodiments, to monitor ions, small molecules, and biological processes such as protein folding, protein-protein interactions and phosphorylation events.
• US8440835B2
  申请人：——

  公开号：US8440835B2

  公开（公告）日：2013-05-14
• [EN] ENVIRONMENTALLY SENSITIVE FLUOROPHORES<br/>[FR] FLUOROPHORES SENSIBLES À L'ENVIRONNEMENT
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2008106104A2

  公开（公告）日：2008-09-04

  [EN] The present invention generally relates to environment-sensitive fluorophores, including environment-sensitive fluorophores for reporting protein/protein and peptide/protein interactions. In one aspect, the present invention is directed to compounds and salts thereof, compositions and methods useful in determining biological interactions. In some cases, the compounds of the present invention are environment- sensitive fluorophores that have spectroscopic behavior that may depend on factors such as the physicochemical properties of the surrounding environment. The compounds of the present invention can be used, in certain embodiments, to monitor ions, small molecules, and biological processes such as protein folding, protein-protein interactions and phosphorylation events.
  [FR] L'invention concerne des fluorophores sensibles à l'environnement, y compris des fluorophores sensibles à l'environnement pour signaler des interactions protéine/protéine et peptide/protéine. Selon un aspect, la présente invention concerne des compositions et des sels de ceux-ci, des compositions et des procédés utiles pour déterminer des interactions biologiques. Dans certains cas, les composés de la présente invention sont des fluorophores sensibles à l'environnement qui ont un comportement spectroscopique qui peut dépendre de facteurs tels que les propriétés physico-chimiques de l'environnement environnant. Les composés de la présente invention peuvent être utilisés, selon certains modes de réalisation, pour surveiller des ions, de petites molécules, et des processus biologiques tels qu'un repliement de protéines, des interactions protéine/protéine et des événements de phosphorylation.
• A Versatile Amino Acid Analogue of the Solvatochromic Fluorophore 4-<i>N,N</i>-Dimethylamino-1,8-naphthalimide: A Powerful Tool for the Study of Dynamic Protein Interactions
  作者：Galen Loving、Barbara Imperiali

  DOI：10.1021/ja804754y

  日期：2008.10.15

  We have developed a new unnatural amino acid based on the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide (4-DMN) for application in the study of protein-protein interactions. The fluorescence quantum yield of this chromophore is highly sensitive to changes in the local solvent environment, demonstrating "switch-like" emission properties characteristic of the dimethylaminophthalimide family of fluorophores. In particular, this new species possesses a number of significant advantages over related fluorophores, including greater chemical stability under a wide range of conditions, a longer wavelength of excitation (408 nm), and improved synthetic accessibility. This amino acid has been prepared as an Fmoc-protected building block and may readily be incorporated into peptides via standard solid-phase peptide synthesis. A series of comparative studies are presented to demonstrate the advantageous properties of the 4-DMN amino acid relative to those of the previously reported 4-N,N-dimethylaminoph-thalimidoalanine and 6-N,N-dimethylamino-2,3-naphthalimidoalanine amino acids. Other commercially available solvatochromic fluorophores are also include in these studies. The potential of this new probe as a tool for the study of protein-protein interactions is demonstrated by introducing it into a peptide that is recognized by calcium-activated calmodulin. The binding interaction between these two components yields an increase in fluorescence emission greater than 900-fold.