2-(4-((E)-4-azido-2,3,5,6-tetrafluorostyryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile | 1193501-26-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(4-((E)-4-azido-2,3,5,6-tetrafluorostyryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile
• 英文别名: 2-{4-[2-(4-azido-2,3,5,6-tetrafluoro-phenyl)-vinyl]-3-cyano-5,5-dimethyl-5H-furan-2-ylidene}-malononitrile；(E)-2-{4-[2-(4-azido-2,3,5,6-tetrafluoro-phenyl)-vinyl]-3-cyano-5,5-dimethyl-2(5H)-furan-2-ylidene}-malononitrile；2-[4-[(E)-2-(4-azido-2,3,5,6-tetrafluorophenyl)ethenyl]-3-cyano-5,5-dimethylfuran-2-ylidene]propanedinitrile
• CAS: 1193501-26-6
• 化学式: C₁₈H₈F₄N₆O
• 分子量: 400.295
• InChiKey: KKHKQKKYKCRKPW-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(4-((E)-4-azido-2,3,5,6-tetrafluorostyryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile 以 乙醇 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels

  摘要：

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)

  DOI：

  10.1021/jp907080r
• 作为产物：
  描述：

  五氟苯甲醛 在 吡啶 、 sodium azide 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 70.0h， 生成 2-(4-((E)-4-azido-2,3,5,6-tetrafluorostyryl)-3-cyano-5,5-dimethylfuran-2(5H)-ylidene)malononitrile
  参考文献：
  名称：

  Azido Push−Pull Fluorogens Photoactivate to Produce Bright Fluorescent Labels

  摘要：

  Dark azido push-pull chromophores have the ability to be photoactivated to produce bright fluorescent labels suitable for single-molecule imaging Upon illumination, the aryl azide functionality in the fluorogens participates in a photochemical conversion to an aryl amine thus restoring charge-transfer absorption and fluorescence Previously we reported that one compound DCDHF-V-P-azide was photoactivatable Here we demonstrate that the azide-to amine photoactivation process is generally applicable to a variety of push-pull chromophores, and we characterize the photophysical parameters including photoconversion quantum yield photostability and turn-on ratio Azido push-pull fluorogens provide a new class of photoactivatable single molecule probes for flourescent labeling and super-resolution microscopy Lastly we demonstrate that photoactivated push-pull dyes can insert into bonds of nearby biomolecules, simultaneously forming a covalent bond and becoming fluorescent (fluorogenic photoaffinity labeling)

  DOI：

  10.1021/jp907080r

文献信息

• Fluorogenic compounds converted to fluorophores by photochemical or chemical means and their use in biological systems
  申请人：Tweg Robert J.

  公开号：US20100029952A1

  公开（公告）日：2010-02-04

  Fluorophores derived from photoactivatable azide-pi-acceptor fluorogens or from a thermal reaction of an azide-pi-acceptor fluorogen with an alkene or alkyne are disclosed. Fluorophores derived from a thermal reaction of an alkyne-pi-acceptor fluorogen with an azide are also disclosed. The fluorophores can readily be activated by light and can be used to label a biomolecule and imaged on a single-molecule level in living cells.

  从可光活化的叠氮-π-受体荧光发色团或从叠氮-π-受体荧光发色团与烯烃或炔烃的热反应中衍生的荧光色团被披露。还披露了从炔烃-π-受体荧光发色团与叠氮的热反应中衍生的荧光色团。这些荧光色团可以很容易地被光激活，并可用于标记生物分子，并在活细胞中以单分子水平进行成像。
• FLUOROGENIC COMPOUNDS CONVERTED TO FLUOROPHORES BY PHOTOCHEMICAL OR CHEMICAL MEANS AND THEIR USE IN BIOLOGICAL SYSTEMS
  申请人：TWIEG ROBERT J.

  公开号：US20120190098A1

  公开（公告）日：2012-07-26

  Fluorophores derived from photoactivatable azide-pi-acceptor fluorogens or from a thermal reaction of an azide-pi-acceptor fluorogen with an alkene or alkyne are disclosed. Fluorophores derived from a thermal reaction of an alkyne-pi-acceptor fluorogen with an azide are also disclosed. The fluorophores can readily be activated by light and can be used to label a biomolecule and imaged on a single-molecule level in living cells.

  本发明揭示了从光活化偶氮-π-受体荧光原子或从偶氮-π-受体荧光原子与烯烃或炔烃进行热反应中得到的荧光原子。还揭示了从炔基-π-受体荧光原子与偶氮进行热反应中得到的荧光原子。这些荧光原子可以轻松地被光激活，并可用于标记生物分子，并在单分子水平上在活细胞中成像。
• THREE-DIMENSIONAL SINGLE-MOLECULE FLUORESCENCE IMAGING BEYOND THE DIFFRACTION LIMIT USING A DOUBLE-HELIX POINT SPREAD FUNCTION
  申请人：Piestun Rafael

  公开号：US20100278400A1

  公开（公告）日：2010-11-04

  Embodiments of the present invention can resolve molecules beyond the optical diffraction limit in three dimensions. A double-helix point spread function can be used to in conjunction with a microscope to provide dual-lobed images of a molecule. Based on the rotation of the dual-lobed image, the axial position of the molecule can be estimated or determined. In some embodiments, the angular rotation of the dual-lobed imaged can be determined using a centroid fit calculation or by finding the midpoints of the centers of the two lobes. Regardless of the technique, the correspondence between the rotation and axial position can be utilized. A double-helix point spread function can also be used to determine the lateral positions of molecules and hence their three-dimensional location.
• US8153446B2
  申请人：——

  公开号：US8153446B2

  公开（公告）日：2012-04-10
• US8772048B2
  申请人：——

  公开号：US8772048B2

  公开（公告）日：2014-07-08