6-(2-sulpho-9-oxo-9H-acridin-10-yl)hexanoic acid | 477865-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(2-sulpho-9-oxo-9H-acridin-10-yl)hexanoic acid
• 英文别名: 6-(2-Sulfo-9-oxo-9h-acridin-10-yl)-hexanoic acid；6-(9-oxo-2-sulfoacridin-10-yl)hexanoic acid
• CAS: 477865-94-4
• 化学式: C₁₉H₁₉NO₆S
• 分子量: 389.429
• InChiKey: GZWZJAMGURHWPP-UHFFFAOYSA-N

物化性质

• 熔点：
  269 °C (decomp)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-溴己酸乙酯 在 硫酸 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 20.5h， 生成 6-(2-sulpho-9-oxo-9H-acridin-10-yl)hexanoic acid
  参考文献：
  名称：

  用于直接监测泛素激活的荧光标记的ATP类似物。

  摘要：

  缺乏用于实时高效监测酶促ATP裂解的简单而强大的测定方法。为了解决这个缺点，我们开发了荧光标记的ATP三磷酸，四磷酸和五磷酸腺苷类似物。与早期报道相反，新型ATP类似物仅在末端磷酸基团上带有一种基于a啶酮的染料。染料的荧光被ATP类似物的腺嘌呤成分淬灭，并在磷酸链断裂和染料从腺苷部分解离后恢复。因此，可以实时地跟踪ATP切割酶的活性。我们证明了这种通过泛素激活酶UBA1和UBA6进行泛素激活的能力，这代表了导致泛素与底物蛋白共价结合的酶促级联反应的第一步。从酵母到人类都高度保守的过程。我们发现，用作UBA1 / UBA6辅助因子的效率在很大程度上取决于ATP类似物的磷酸酯链的长度：三磷酸酯的使用不佳，而五磷酸酯的加工效率最高。值得注意的是，具有五磷酸酯的新型ATP类似物取代了最近报道的双染料标记的类似物的功效，因此，在广泛的应用中是有希望的候选者。

  DOI：

  10.1002/chem.202001091

文献信息

• Acridone derivatives as labels for fluorescence detection of target materials
  申请人：——

  公开号：US20040191792A1

  公开（公告）日：2004-09-30

  Disclosed are new acridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the acridone dyes and use of the labelled materials in biological assays. The acridone derivatives have the following structure:in which Z 1 and Z 2 represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R 2 , R 3 , R 4 and R 5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C 1 -C 4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C 1 -C 6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C 1 -C 20 alkyl, aralkyl, sulphonate, sulphonic acid, quatemary ammonium, the group —E—F and the group —(CH 2 —) n Y; R 1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C 1 -C 20 alkyl, aralkyl, the group —E—F and the group —(CH 2 —) n Y; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent acridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis. 1

  本发明涉及具有特征性荧光寿命的新吖啶酮染料衍生物。还公开了利用吖啶酮染料标记目标生物材料的方法，并将标记的材料用于生物分析中。吖啶酮衍生物具有以下结构：其中Z1和Z2代表必要的原子，以完成一个环，两个融合环或三个融合环的芳香或杂芳系统，每个环由选自碳原子和最多两个选自氧、氮和硫的原子组成；R2、R3、R4和R5选自氢、卤素、酰胺、羟基、氰基、硝基、单取代或双硝基取代苄基、氨基、单取代或双C1-C4烷基取代的氨基、巯基、羰基、羧基、C1-C6烷氧基、丙烯酸酯、乙烯基、苯乙烯基、芳基、杂芳基、C1-C20烷基、芳基烷基、磺酸酯、磺酸、季铵盐、羟基基团—E—F和基团—(CH2—)nY；R1选自氢、单取代或双硝基取代苄基、C1-C20烷基、芳基烷基、基团—E—F和基团—(CH2—)nY；其中E是一个间隔基团，F是一个目标配位基团；Y选自磺酸酯、硫酸酯、膦酸酯、磷酸酯、季铵盐和羧基；n为1至6的整数。该发明还涉及一组不同荧光吖啶酮染料衍生物，每种染料具有不同的荧光寿命，该染料组特别适用于多参数分析。
• ACRIDONE DERIVATIVES AS LABELS FOR FLUORESCENCE DETECTION OF TARGET MATERIALS
  申请人：SMITH JOHN ANTHONY

  公开号：US20080139788A1

  公开（公告）日：2008-06-12

  Disclosed are new acridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the acridone dyes and use of the labelled materials in biological assays. The acridone derivatives have the following structure: in which Z 1 and Z 2 represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R 2 , R 3 , R 4 and R 5 are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C 1 -C 4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C 1 -C 6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C 1 -C 20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group -E-F and the group —(CH 2 —) n Y; R 1 is selected from hydrogen, mono- or di-nitro-substituted benzyl, C 1 -C 20 alkyl, aralkyl, the group -E-F and the group —(CH 2 —) n Y; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent acridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis.

  本发明涉及具有特征荧光寿命的新蒽醌染料衍生物。本发明还涉及使用蒽醌染料标记目标生物材料的方法以及标记材料在生物测定中的应用。蒽醌衍生物具有以下结构：其中Z1和Z2代表必要的原子以完成一个环，两个融合环或三个融合环的芳香或杂芳香系统，每个环具有从碳原子中选择的五个或六个原子以及最多从氧，氮和硫中选择的两个原子；R2，R3，R4和R5选择自氢，卤素，酰胺，羟基，氰基，硝基，单取代或双取代苯甲基，氨基，单取代或双取代C1-C4烷基取代的氨基，巯基，羰基，羧基，C1-C6烷氧基，丙烯酸酯，乙烯基，苯乙烯基，芳基，杂芳基，C1-C20烷基，芳基烷基，磺酸盐，磺酸，季铵盐，-E-F基团和-(CH2-)nY基团；R1选择自氢，单取代或双取代苯甲基，C1-C20烷基，芳基烷基，-E-F基团和-(CH2-)nY基团；其中E是一个间隔基团，F是一个目标键合基团；Y选择自磺酸盐，硫酸盐，膦酸盐，磷酸盐，季铵盐和羧基；n是1到6的整数。本发明还涉及一组不同荧光蒽醌染料衍生物，每种染料具有不同的荧光寿命，该染料组合特别适用于多参数分析。
• US8034558B2
  申请人：——

  公开号：US8034558B2

  公开（公告）日：2011-10-11
• [EN] ACRIDONE DERIVATIVES AS LABELS FOR FLUORESCENCE DETECTION OF TARGET MATERIALS<br/>[FR] DERIVES D'ACRIDONE UTILISES COMME ETIQUETTES DANS LA DETECTION PAR FLUORESCENCE DE MATERIAUX CIBLES
  申请人：AMERSHAM BIOSCIENCES UK LTD

  公开号：WO2002099424A2

  公开（公告）日：2002-12-12

  Disclosed are new acridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the acridone dyes and use of the labelled materials in biological assays. The acridone derivatives have the following structure:in which Z?1 and Z2¿ represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R?2, R3, R4 and R5¿ are selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C¿1?-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group -E-F and the group -(CH2-)nY; R?1¿ is selected from hydrogen, mono- or di-nitro-substituted benzyl, C¿1?-C20 alkyl, aralkyl, the group -E-F and the group -(CH2-)nY; where E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6.The invention also relates to a set of different fluorescent acridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis.
• Fluorescently Labelled ATP Analogues for Direct Monitoring of Ubiquitin Activation
  作者：Daniel Hammler、Katrin Stuber、Fabian Offensperger、Martin Scheffner、Andreas Zumbusch、Andreas Marx

  DOI：10.1002/chem.202001091

  日期：2020.5.15

  developed fluorescently labelled adenosine tri-, tetra- and pentaphosphate analogues of ATP. The novel ATP analogues bear - in contrast to earlier reports - only a single acridone-based dye at the terminal phosphate group. The dye's fluorescence is quenched by the adenine component of the ATP analogue and is restored upon cleavage of the phosphate chain and dissociation of the dye from the adenosine moiety

  缺乏用于实时高效监测酶促ATP裂解的简单而强大的测定方法。为了解决这个缺点，我们开发了荧光标记的ATP三磷酸，四磷酸和五磷酸腺苷类似物。与早期报道相反，新型ATP类似物仅在末端磷酸基团上带有一种基于a啶酮的染料。染料的荧光被ATP类似物的腺嘌呤成分淬灭，并在磷酸链断裂和染料从腺苷部分解离后恢复。因此，可以实时地跟踪ATP切割酶的活性。我们证明了这种通过泛素激活酶UBA1和UBA6进行泛素激活的能力，这代表了导致泛素与底物蛋白共价结合的酶促级联反应的第一步。从酵母到人类都高度保守的过程。我们发现，用作UBA1 / UBA6辅助因子的效率在很大程度上取决于ATP类似物的磷酸酯链的长度：三磷酸酯的使用不佳，而五磷酸酯的加工效率最高。值得注意的是，具有五磷酸酯的新型ATP类似物取代了最近报道的双染料标记的类似物的功效，因此，在广泛的应用中是有希望的候选者。