N-dansyl-8-aminooctanoic acid | 64750-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-dansyl-8-aminooctanoic acid
• 英文别名: 8-{[5-(Dimethylamino)naphthalene-1-sulfonyl]amino}octanoic acid；8-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]octanoic acid
• CAS: 64750-21-6
• 化学式: C₂₀H₂₈N₂O₄S
• 分子量: 392.519
• InChiKey: GEHCYSZDOXPSJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁶-(4-aminobutyl)-5'-ethylamino-5'-oxo-5'-deoxyadenosine 、 N-dansyl-8-aminooctanoic acid 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ABEA-AO-dansyl
  参考文献：
  名称：

  Influence of fluorophore and linker composition on the pharmacology of fluorescent adenosine A1 receptor ligands

  摘要：

  Background and purpose:  The introduction of fluorescence‐based techniques, and in particular the development of fluorescent ligands, has allowed the study of G protein‐coupled receptor pharmacology at the single cell and single molecule level. This study evaluated how the physicochemical nature of the linker and the fluorophore affected the pharmacological properties of fluorescent agonists and antagonists.Experimental approach:  Chinese hamster ovary cells stably expressing the human adenosine A1 receptor and a cyclic 3′,5′ adenosine monophosphate response element‐secreted placental alkaline phosphatase (CRE‐SPAP) reporter gene, together with whole cell [3H]‐8‐cyclopentyl‐1,3‐dipropylxanthine (DPCPX) radioligand binding, were used to evaluate the pharmacological properties of a range of fluorescent ligands based on the antagonist xanthine amine congener (XAC) and the agonist 5′ (N‐ethylcarboxamido) adenosine (NECA).Key results:  Derivatives of NECA and XAC with different fluorophores, but equivalent linker length, showed significant differences in their binding properties to the adenosine A1 receptor. The BODIPY 630/650 derivatives had the highest affinity. Linker length also affected the pharmacological properties, depending on the fluorophore used. Particularly in fluorescent agonists, higher agonist potency could be achieved with large or small linkers for dansyl and BODIPY 630/650 derivatives, respectively.Conclusions and implications:  The pharmacology of a fluorescent ligand was critically influenced by both the fluorophore and the associated linker. Furthermore, our data strongly suggest that the physicochemical properties of the fluorophore/linker pairing determine where in the environment of the target receptor the fluorophore is placed, and this, together with the environmental sensitivity of the resulting fluorescence, may finally decide its utility as a fluorescent probe.This article is part of a themed section on Imaging in Pharmacology. To view the editorial for this themed section visit http://dx.doi.org/10.1111/j.1476‐5381.2010.00685.x

  DOI：

  10.1111/j.1476-5381.2009.00488.x
• 作为产物：
  描述：

  碳酸氢钠 、 丹酰氯 、 8-氨基辛酸 、 三乙胺 以 丙酮 、 水 为溶剂， 反应 2.0h， 生成 N-dansyl-8-aminooctanoic acid
  参考文献：
  名称：

  Fluorescence-Labelled Fatty Acids and Uses Thereof

  摘要：

  本发明涉及一种组合物，包括（i）一种荧光标记的脂肪酸和（ii）一种脂肪酸结合化合物，其中（a）荧光标记的脂肪酸的脂肪酸成分结合脂肪酸结合化合物，（b）荧光标记的脂肪酸的荧光成分和脂肪酸结合化合物相互作用，以引发FRET（Förster共振能量转移）效应。此外，本发明还涉及一种方法，通过在允许结合和FRET（Förster共振能量转移）效应的条件下，将荧光标记的脂肪酸与脂肪酸结合化合物接触，然后将荧光标记的脂肪酸与感兴趣的化合物结合，并测定荧光的变化来识别和/或表征感兴趣的化合物。此外，本发明还涉及相应的部件套件和组合物和方法的用途。

  公开号：

  US20150285812A1

文献信息

• [EN] FLUORESCENCE-LABELLED FATTY ACIDS AND USES THEREOF<br/>[FR] ACIDES GRAS MARQUÉS PAR FLUORESCENCE ET LEURS UTILISATIONS
  申请人：SANOFI SA

  公开号：WO2014037394A1

  公开（公告）日：2014-03-13

  The present invention relates to a composition comprising (i) a fluorescent-labelled fatty acid and (ii) a fatty acid binding compound, wherein (a) the fatty acid component of the fluorescent- labelled fatty acid binds the fatty acid binding compound and (b) the fluorescent component of the fluorescent-labelled fatty acid and the fatty acid binding compound interact to elicit FRET (Förster resonance energy transfer) effects. Moreover, the invention is directed to a method for identifying and/or characterizing a compound of interest by contacting a fluorescent-labelled fatty acid with a fatty acid binding compound under conditions that allow for binding and for FRET (Förster resonance energy transfer) effects, and then contacting the fluorescent-labelled fatty acid bound to the fatty acid binding compound with a compound of interest and determining the change in fluorescence. In addition, the invention pertains to corresponding kits of parts and uses of the compositions and methods.
• Influence of fluorophore and linker composition on the pharmacology of fluorescent adenosine A1 receptor ligands
  作者：Jillian G Baker、Richard Middleton、Luke Adams、Lauren T May、Stephen J Briddon、Barrie Kellam、Stephen J Hill

  DOI：10.1111/j.1476-5381.2009.00488.x

  日期：2010.2

  Background and purpose:  The introduction of fluorescence‐based techniques, and in particular the development of fluorescent ligands, has allowed the study of G protein‐coupled receptor pharmacology at the single cell and single molecule level. This study evaluated how the physicochemical nature of the linker and the fluorophore affected the pharmacological properties of fluorescent agonists and antagonists.Experimental approach:  Chinese hamster ovary cells stably expressing the human adenosine A1 receptor and a cyclic 3′,5′ adenosine monophosphate response element‐secreted placental alkaline phosphatase (CRE‐SPAP) reporter gene, together with whole cell [3H]‐8‐cyclopentyl‐1,3‐dipropylxanthine (DPCPX) radioligand binding, were used to evaluate the pharmacological properties of a range of fluorescent ligands based on the antagonist xanthine amine congener (XAC) and the agonist 5′ (N‐ethylcarboxamido) adenosine (NECA).Key results:  Derivatives of NECA and XAC with different fluorophores, but equivalent linker length, showed significant differences in their binding properties to the adenosine A1 receptor. The BODIPY 630/650 derivatives had the highest affinity. Linker length also affected the pharmacological properties, depending on the fluorophore used. Particularly in fluorescent agonists, higher agonist potency could be achieved with large or small linkers for dansyl and BODIPY 630/650 derivatives, respectively.Conclusions and implications:  The pharmacology of a fluorescent ligand was critically influenced by both the fluorophore and the associated linker. Furthermore, our data strongly suggest that the physicochemical properties of the fluorophore/linker pairing determine where in the environment of the target receptor the fluorophore is placed, and this, together with the environmental sensitivity of the resulting fluorescence, may finally decide its utility as a fluorescent probe.This article is part of a themed section on Imaging in Pharmacology. To view the editorial for this themed section visit http://dx.doi.org/10.1111/j.1476‐5381.2010.00685.x
• Fluorescence-Labelled Fatty Acids and Uses Thereof
  申请人：SANOFI

  公开号：US20150285812A1

  公开（公告）日：2015-10-08

  The present invention relates to a composition comprising (i) a fluorescent-labelled fatty acid and (ii) a fatty acid binding compound, wherein (a) the fatty acid component of the fluorescent-labelled fatty acid binds the fatty acid binding compound and (b) the fluorescent component of the fluorescent-labelled fatty acid and the fatty acid binding compound interact to elicit FRET (Förster resonance energy transfer) effects. Moreover, the invention is directed to a method for identifying and/or characterizing a compound of interest by contacting a fluorescent-labelled fatty acid with a fatty acid binding compound under conditions that allow for binding and for FRET (Förster resonance energy transfer) effects, and then contacting the fluorescent-labelled fatty acid bound to the fatty acid binding compound with a compound of interest and determining the change in fluorescence. In addition, the invention pertains to corresponding kits of parts and uses of the compositions and methods.

  本发明涉及一种组合物，包括（i）一种荧光标记的脂肪酸和（ii）一种脂肪酸结合化合物，其中（a）荧光标记的脂肪酸的脂肪酸成分结合脂肪酸结合化合物，（b）荧光标记的脂肪酸的荧光成分和脂肪酸结合化合物相互作用，以引发FRET（Förster共振能量转移）效应。此外，本发明还涉及一种方法，通过在允许结合和FRET（Förster共振能量转移）效应的条件下，将荧光标记的脂肪酸与脂肪酸结合化合物接触，然后将荧光标记的脂肪酸与感兴趣的化合物结合，并测定荧光的变化来识别和/或表征感兴趣的化合物。此外，本发明还涉及相应的部件套件和组合物和方法的用途。