4-[1-(5-carboxypentyl)-2,3-dimethyl-5-sulfo-3H-3-indoliumyl]-1-butanesulfonate | 851528-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[1-(5-carboxypentyl)-2,3-dimethyl-5-sulfo-3H-3-indoliumyl]-1-butanesulfonate
• 英文别名: 1-(5-carboxypentyl)-2,3-dimethyl-3-(4-sulphobutyl)-3H-indolium-5-sulphonate；4-[1-(5-Carboxypentyl)-2,3-dimethyl-5-sulfoindol-1-ium-3-yl]butane-1-sulfonate；4-[1-(5-carboxypentyl)-2,3-dimethyl-5-sulfoindol-1-ium-3-yl]butane-1-sulfonate
• CAS: 851528-23-9
• 化学式: C₂₀H₂₉NO₈S₂
• 分子量: 475.584
• InChiKey: ZXFJYBCUJLCDIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  169
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[1-(5-carboxypentyl)-2,3-dimethyl-5-sulfo-3H-3-indoliumyl]-1-butanesulfonate 、 三乙胺 以 甲醇 、 水 为溶剂， 生成 1-(5-carboxypentyl)-2,3-dimethyl-3-(4-sulphobutyl)-3H-indolium-5-sulphonate triethylammonium salt
  参考文献：
  名称：

  [EN] CYANINE DYE LABELLING REAGENTS
  [FR] REACTIFS DE MARQUAGE A COLORANTS DE CYANINE

  摘要：

  揭示了一种对生物和其他材料进行标记和检测有用的青菁染料。该染料具有以下结构式（I），其中基团R3和R4连接到Z1环结构，基团R5和R6连接到Z2环结构，n = 1、2或3；Z1和Z2独立表示完成一个环或两个融合环芳香系统所需的碳原子；基团R1、R2、R3、R4、R5、R6和R7中至少有一个是基团-E-F，其中E是一个单键或一个间隔基团，F是一个目标结合基团；基团R11、R12、R13和R14中的一个或多个是独立选择自羟基-(CH2)k-W的群，其中W是磺酸或膦酸，k是1到10之间的整数。这些染料可用于荧光标记应用，其中将至少一个且最好是多个水溶性基团连接到吲哚啉环的3位，可以减少染料间的相互作用，从而减少染料间的猝灭，特别是当多个染料分子连接到核酸、寡核苷酸、蛋白质和抗体等组分时。

  公开号：

  WO2005044923A1
• 作为产物：
  描述：

  disodium 2,3-dimethyl-3-(4-sulphonatobutyl)-3H-indole-5-sulphonate 、 6-溴己酸 在 环丁砜 作用下， 反应 38.0h， 生成 4-[1-(5-carboxypentyl)-2,3-dimethyl-5-sulfo-3H-3-indoliumyl]-1-butanesulfonate
  参考文献：
  名称：

  [EN] CYANINE DYE LABELLING REAGENTS
  [FR] REACTIFS DE MARQUAGE A COLORANTS DE CYANINE

  摘要：

  揭示了一种对生物和其他材料进行标记和检测有用的青菁染料。该染料具有以下结构式（I），其中基团R3和R4连接到Z1环结构，基团R5和R6连接到Z2环结构，n = 1、2或3；Z1和Z2独立表示完成一个环或两个融合环芳香系统所需的碳原子；基团R1、R2、R3、R4、R5、R6和R7中至少有一个是基团-E-F，其中E是一个单键或一个间隔基团，F是一个目标结合基团；基团R11、R12、R13和R14中的一个或多个是独立选择自羟基-(CH2)k-W的群，其中W是磺酸或膦酸，k是1到10之间的整数。这些染料可用于荧光标记应用，其中将至少一个且最好是多个水溶性基团连接到吲哚啉环的3位，可以减少染料间的相互作用，从而减少染料间的猝灭，特别是当多个染料分子连接到核酸、寡核苷酸、蛋白质和抗体等组分时。

  公开号：

  WO2005044923A1

文献信息

• HALOGENATED COMPOUNDS FOR PHOTODYNAMIC THERAPY
  申请人：Jones Gary W.

  公开号：US20130231604A1

  公开（公告）日：2013-09-05

  Halo-organic heterocyclic compounds are described, in which at least two halogen atoms are bound to a nitrogen-containing heterocyclic terminal moiety of the compound, with at least one of such halogen atoms being iodine or bromine. Also described are polymethine dyes based on these heterocyclic compounds, and dendrimeric compounds and conjugates of such polymethine dyes. The polymethine dyes are characterized by enhanced properties, e.g., brightness, photostability, sensitivity and/or selective affinity that make them useful to target cancer cells, pathogenic microorganisms, and/or other biological materials, in applications such as photodynamic therapy, photodynamic antimicrobial chemotherapy (PACT), cancer treatment, selective removal or attachment of biological materials, antimicrobial coating materials, and other diagnostic, theranostic, spectrum shifting, deposition/growth, and analytic applications.

  描述了卤素有机杂环化合物，其中至少有两个卤素原子与化合物的含氮杂环末端基团结合，其中至少一个卤素原子为碘或溴。还描述了基于这些杂环化合物的聚甲烯染料，以及这些聚甲烯染料的树枝状化合物和共轭物。这些聚甲烯染料具有增强的性能，例如亮度、光稳定性、灵敏度和/或选择性亲和力，使它们在靶向癌细胞、病原微生物和/或其他生物材料的应用中具有用途，例如光动力疗法、光动力抗微生物化疗（PACT）、癌症治疗、选择性去除或附着生物材料、抗微生物涂层材料以及其他诊断、治疗学、光谱转移、沉积/生长和分析应用。
• Halogenated compounds for photodynamic therapy
  申请人：Jones Gary W.

  公开号：US08748446B2

  公开（公告）日：2014-06-10

  Halo-organic heterocyclic compounds are described, which have the formulas Ring A is an aromatic ring bound to at least two halogen atoms, at least one of which is iodine or bromine. Also described are polymethine dyes based on these heterocyclic compounds, and dendrimeric compounds and conjugates of such polymethine dyes. The polymethine dyes are characterized by enhanced properties, e.g., brightness, photostability, sensitivity and/or selective affinity that make them useful to target cancer cells, pathogenic microorganisms, and/or other biological materials, in applications such as photodynamic therapy, photodynamic antimicrobial chemotherapy (PACT), cancer treatment, selective removal or attachment of biological materials, antimicrobial coating materials, and other diagnostic, theranostic, spectrum shifting, deposition/growth, and analytic applications.

  描述了一种有机卤代杂环化合物，其化学式为环A是芳香环，与至少两个卤原子结合，其中至少一个是碘或溴。还描述了基于这些杂环化合物的聚甲烯染料，以及这些聚甲烯染料的树枝状化合物和共轭物。这些聚甲烯染料具有增强的性能，例如亮度、光稳定性、灵敏度和/或选择性亲和力，使它们在靶向癌细胞、病原微生物和/或其他生物材料方面具有用途，应用包括光动力疗法、光动力抗微生物化疗（PACT）、癌症治疗、选择性去除或附着生物材料、抗微生物涂层材料以及其他诊断、治疗学、光谱转移、沉积/生长和分析应用。
• Cyanine Dye Labelling Reagents
  申请人：West M. Richard

  公开号：US20070203343A1

  公开（公告）日：2007-08-30

  Disclosed are cyanine dyes that are useful for labeling and detecting biological and other materials. The dyes are of formula (I) in which groups R 3 and R 4 are attached to the Z 1 ring structure and groups R 5 and R 6 are attached to the Z 2 ring structure, and n=1, 2 or 3; Z 1 and Z 2 independently represent the carbon atoms necessary to complete a one ring, or two-fused ring aromatic system; at least one of groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is the group -E-F where E is a single bond or a spacer group and F is a target bonding group; one or more of groups R 11 , R 12 , R 13 and R 14 are independently selected from the group —(CH 2 ) k —W, where W is sulphonic acid or phosphonic acid and k is an integer from 1 to 10. The dyes may be used in fluorescence labeling applications, where the presence of one and preferably multiple water solubilising groups attached to the 3-position of the indolinium ring reduces dye-dye interactions, and hence dye-dye quenching, particularly where multiple dye molecules are attached to components such as nucleic acids, oligonucleotides, proteins and antibodies.

  本发明涉及一种靛烯染料，可用于标记和检测生物和其他材料。该染料的化学式为（I），其中基团R3和R4连接到Z1环结构上，基团R5和R6连接到Z2环结构上，n = 1、2或3；Z1和Z2独立地表示完成一个环或两个融合环芳香系统所需的碳原子；基团R1、R2、R3、R4、R5、R6和R7中至少有一个是-E-F基团，其中E是单键或间隔基团，F是目标结合基团；基团R11、R12、R13和R14中的一个或多个独立地选自组-（CH2）k-W，其中W为磺酸或膦酸，k为1至10的整数。该染料可用于荧光标记应用中，在该应用中，附加到靛烯环的3位的一个或多个水溶性基团降低了染料-染料相互作用，从而减少了染料-染料淬灭，特别是当多个染料分子附加到核酸、寡核苷酸、蛋白质和抗体等组分时。
• Cyanine dye labelling reagents
  申请人：GE Healthcare U.K. Limited

  公开号：US07750163B2

  公开（公告）日：2010-07-06

  Disclosed are cyanine dyes that are useful for labeling and detecting biological and other materials. The dyes are of formula (I) in which groups R3 and R4 are attached to the Z1 ring structure and groups R5 and R6 are attached to the Z2 ring structure, and n=1, 2 or 3; Z1 and Z2 independently represent the carbon atoms necessary to complete a one ring, or two-fused ring aromatic system; at least one of groups R1, R2, R3, R4, R5, R6 and R7 is the group -E-F where E is a single bond or a spacer group and F is a target bonding group; one or more of groups R11, R12, R13 and R14 are independently selected from the group —(CH2)k—W, where W is sulphonic acid or phosphonic acid and k is an integer from 1 to 10. The dyes may be used in fluorescence labeling applications, where the presence of one and preferably multiple water solubilising groups attached to the 3-position of the indolinium ring reduces dye-dye interactions, and hence dye-dye quenching, particularly where multiple dye molecules are attached to components such as nucleic acids, oligonucleotides, proteins and antibodies.

  本发明涉及一种靛烯染料，可用于标记和检测生物和其他材料。该染料的化学式为(I)，其中基团R3和R4连接到Z1环结构上，基团R5和R6连接到Z2环结构上，n = 1、2或3；Z1和Z2独立地表示完成一个环或两个融合环芳香系统所需的碳原子；R1、R2、R3、R4、R5、R6和R7中至少一个是-E-F基团，其中E是单键或间隔基团，F是目标结合基团；R11、R12、R13和R14中的一个或多个独立地选择自羟基烷基（CH2）k-W群，其中W是磺酸或膦酸，k是1至10的整数。该染料可用于荧光标记应用，其中连接到靛烯环的3位置的一个或多个水溶性基团减少了染料-染料相互作用，从而减少了染料-染料猝灭，特别是当多个染料分子连接到核酸、寡核苷酸、蛋白质和抗体等组分时。
• Fluorescently-labelled target components
  申请人：GE Healthcare Limited

  公开号：EP2360211A1

  公开（公告）日：2011-08-24

  Disclosed are cyanine dyes that are useful for labelling and detecting biological and other materials. The dyes are of formula (I): in which groups R3 and R4 are attached to the Z1 ring structure and groups R5 and R6 are attached to the Z2 ring structure, and n = 1, 2 or 3; Z1 and Z2 independently represent the carbon atoms necessary to complete a one ring, or two-fused ring aromatic system; at least one of groups R1, R2, R3, R4, R5, R6 and R7 is the group -E-F where E is a single bond or a spacer group and F is a target bonding group; one or more of groups R11, R12, R13 and R14 are independently selected from the group -(CH2)k-W, where W is sulphonic acid or phosphonic acid and k is an integer from 1 to 10. The dyes may be used in fluorescence labelling applications, where the presence of one and preferably multiple water solubilising groups attached to the 3-position of the indolinium ring reduces dye-dye interactions, and hence dye-dye quenching, particularly where multiple dye molecules are attached to components such as nucleic acids, oligonucleotides, proteins and antibodies.

  所公开的氰基染料可用于标记和检测生物材料和其他材料。这些染料为式 (I)： 其中基团 R3 和 R4 连接到 Z1 环结构上，基团 R5 和 R6 连接到 Z2 环结构上，n = 1、2 或 3；Z1 和 Z2 独立地代表完成一个环或两个融合环芳香系统所需的碳原子；基团 R1、R2、R3、R4、R5、R6 和 R7 中至少有一个是基团-E-F，其中 E 是单键或间隔基，F 是目标键基；基团 R11、R12、R13 和 R14 中的一个或多个独立地选自基团-(CH2)k-W，其中 W 是磺酸或膦酸，k 是 1 到 10 的整数。这些染料可用于荧光标记应用，其中，连接到吲哚啉鎓环 3 位上的一个、最好是多个水溶性基团的存在可减少染料-染料相互作用，从而减少染料-染料淬灭，特别是在多个染料分子连接到核酸、寡核苷酸、蛋白质和抗体等成分上时。