ABEA-AO-dansyl | 1224605-06-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: ABEA-AO-dansyl
• 英文别名: (2S,3S,4R,5R)-5-[6-[4-[8-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]octanoylamino]butylamino]purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• CAS: 1224605-06-4
• 化学式: C₃₆H₅₁N₉O₇S
• 分子量: 753.923
• InChiKey: XZLDNVKPYYZKOK-BSYZOHBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  221
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  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

文献信息

• 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