4-[1-(5-carboxypentyl)-4,5,6,7-tetrafluoro-2,3-dimethyl-3H-indolium-3-yl]butane-1-sulfonate | 913198-61-5

• 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)-4,5,6,7-tetrafluoro-2,3-dimethyl-3H-indolium-3-yl]butane-1-sulfonate
• 英文别名: 1-(5-carboxypentyl)-2,3-dimethyl-3-(4-sulfobutyl)-4,5,6,7-tetrafluoro-3H-indolium；4-[1-(5-carboxypentyl)-4,5,6,7-tetrafluoro-2,3-dimethylindol-1-ium-3-yl]butane-1-sulfonate
• CAS: 913198-61-5
• 化学式: C₂₀H₂₅F₄NO₅S
• 分子量: 467.482
• InChiKey: DUYPCNSAXRBEFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[1-(5-carboxypentyl)-4,5,6,7-tetrafluoro-2,3-dimethyl-3H-indolium-3-yl]butane-1-sulfonate 、 丙二醛双苯亚胺单盐酸盐 在 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 1.83h， 生成 6-[(2E)-4,5,6,7-tetrafluoro-3-methyl-2-[(2E,4E)-4-(phenylimino)but-2-enylidene]-3-(4-sulfobutyl)-2,3-dihydro-1H-indol-1-yl]hexanoic acid
  参考文献：
  名称：

  WATER-SOLUBLE FLUORO-SUBSTITUTED CYANINE DYES AS REACTIVE FLUORESCENCE LABELLING REAGENTS

  摘要：

  揭示了一种对于标记和检测生物和其他材料有用的青霉素染料。该染料的化学式为（I）：其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13和R14中的至少一个是-L-M或-L-P，其中L是连接基团，M是目标键合基团，P是共轭组分，并且R3、R4、R5、R6、R7、R8、R9和R10中的至少一个包含氟。通过用氟取代并具有三个或更多磺酸基团的青霉素染料标记生物靶分子，得到的标记产品中减少了染料-染料聚集并提高了光稳定性，与没有这种取代的青霉素染料相比。本发明的染料在涉及荧光检测的分析中特别有用，其中需要连续或重复激发，例如在动力学研究中，或在微阵列分析中，微阵列玻片可能需要在数天内重新分析。

  公开号：

  US20060239922A1
• 作为产物：
  描述：

  2,3-dimethyl-3-(4-sulfonatobutyl)-4.5,6,7-tetrafluoro-3H-indole 、 6-溴己酸 反应 24.0h， 生成 4-[1-(5-carboxypentyl)-4,5,6,7-tetrafluoro-2,3-dimethyl-3H-indolium-3-yl]butane-1-sulfonate
  参考文献：
  名称：

  WO2008/15415

  摘要：

  公开号：

文献信息

• ASYMMETRIC FLUORO-SUBSTITUTED POLYMETHINE DYES
  申请人：Cooper Michael Edward

  公开号：US20090252687A1

  公开（公告）日：2009-10-08

  The present invention relates to improved conjugates of biological molecules with an improved class of water-soluble, green to near infra-red (NIR) cyanine labelling dyes. The dyes are asymmetric fluoro-substituted polymethines, and exhibit a high degree of photostability and reduced dye-dye quenching, as well as a high fluorescence quantum yield. The conjugates are useful for in vivo optical imaging, as well as fluorescence detection methods. Also disclosed are pharmaceutical compositions containing the conjugates, kits for the preparation of such compositions, and methods of in vivo imaging using the conjugates.

  本发明涉及改进的生物分子共轭物，使用改进的水溶性、绿色至近红外（NIR）青菁染料类。这些染料是不对称的含氟多亚甲基染料，具有高度的光稳定性和减少染料-染料淬灭，以及高荧光量子产率。这些共轭物可用于体内光学成像，以及荧光检测方法。本发明还公开了含有这些共轭物的药物组成物、制备这些组成物的工具包，以及使用这些共轭物进行体内成像的方法。
• FLUORO-SUBSTITUTED BENZOXAZOLE POLYMETHINE DYES
  申请人：Said Najeeb

  公开号：US20100015054A1

  公开（公告）日：2010-01-21

  Disclosed are reactive polyfluoro benzoxazole polymethine dyes that are useful for labelling and detecting biological and other materials. The dyes are of formula (I): in which X is selected from the group consisting of —O—, —S— and at least one of groups R 1 and R 2 is the group -L-R x or -L-R p , where L is a linking group, R x is a group suitable for covalent attachment of the dye to a component and R p is a component; and at least one of groups R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 comprises fluorine. The use of polymethine dyes substituted by fluorine and having additional substitution by sulphonic acid groups, for labelling biological target molecules results in a labelled product in which there is reduced dye-dye aggregation and improved photostability, compared with cyanine dyes having no such substitutions.

  本发明涉及一种反应性聚氟苯并噁唑聚甲烷染料，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X选自—O—、—S—和至少一个R1和R2中的基团是-L-Rx或-L-Rp，其中L是连接基团，Rxis适合于染料与组分的共价连接的基团，Rp是组分；且R3、R4、R5、R6、R7、R8、R9和R10中的至少一个含有氟。使用由含有氟的聚甲烷染料取代并具有额外的磺酸基团取代的方法，用于标记生物靶分子，结果是标记的产物中染料-染料聚集减少，光稳定性得到改善，与没有这种取代的青霉素染料相比。
• WO2008/40994
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] FLUORO-SUBSTITUTED BENZOXAZOLE POLYMETHINE DYES<br/>[FR] COLORANTS DE BENZOXAZOLE POLYMÉTHINE FLUORO-SUBSTITUÉE
  申请人：GE HEALTHCARE UK LTD

  公开号：WO2008040994A2

  公开（公告）日：2008-04-10

  [EN] Disclosed are reactive polyfluoro benzoxazole polymethine dyes that are useful for labelling and detecting biological and other materials. The dyes are of formula (I): in which X is selected from the group consisting of -O-, -S- and at least one of groups R¹ and R² is the group -L-R^x or -L-R^p, where L is a linking group, R^x is a group suitable for covalent attachment of the dye to a component and R^p is a component; and at least one of groups R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ comprises fluorine. The use of polymethine dyes substituted by fluorine and having additional substitution by sulphonic acid groups, for labelling biological target molecules results in a labelled product in which there is reduced dye-dye aggregation and improved photostability, compared with cyanine dyes having no such substitutions.
  [FR] L'invention concerne des colorants de benzoxazole polyméthine polyfluorée utiles dans le marquage et la détection de substances biologiques et autres. Ces colorants sont de formule (I): dans laquelle X est choisi par le groupe constitué de -O-, -S- et au moins l'un des groupes R¹ et R² est -L-R^x ou -L-R^p, L représentant un groupe de liaison, R^xreprésentant un groupe qui convient à la fixation covalente du colorant à un composant et R^p représente un composant, et au moins un des groupes R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ et R¹⁰ contient du fluor. L'utilisation de colorants de polyméthine substituée par des groupes acide sulfonique permet d'obtenir un produit destiné à marquer des résultats de molécules cibles biologiques dans un produit marqué dans lequel il y a une agrégation colorant-colorant réduite et une photostabilité améliorée, par rapport à des colorants à base de cyanine ne possédant pas de telles substitutions.
• WATER-SOLUBLE FLUORO-SUBSTITUTED CYANINE DYES AS REACTIVE FLUORESCENCE LABELLING REAGENTS
  申请人：COOPER EDWARD MICHAEL

  公开号：US20060239922A1

  公开（公告）日：2006-10-26

  Disclosed are cyanine dyes that are useful for labelling and detecting biological and other materials. The dyes are of formula (I): in which at least one of groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 R 11 , R 12 , R 13 and R 14 is -L-M or -L-P, where L is a linking group, M is a target bonding group and P is a conjugated component, and at least one of groups R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 comprises fluorine. The use of cyanine dyes substituted by fluorine and having additional substitution with three or more sulphonic acid groups for labelling biological target molecules results in a labelled product in which there is reduced dye-dye aggregation and improved photostability, compared with cyanine dyes having no such substitutions. The dyes of the present invention are particularly useful in assays involving fluorescence detection where continual or repeated excitation is a requirement, for example in kinetic studies, or in microarray analyses where microarray slides may need to be reanalysed over a period of days.

  揭示了一种对于标记和检测生物和其他材料有用的青霉素染料。该染料的化学式为（I）：其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13和R14中的至少一个是-L-M或-L-P，其中L是连接基团，M是目标键合基团，P是共轭组分，并且R3、R4、R5、R6、R7、R8、R9和R10中的至少一个包含氟。通过用氟取代并具有三个或更多磺酸基团的青霉素染料标记生物靶分子，得到的标记产品中减少了染料-染料聚集并提高了光稳定性，与没有这种取代的青霉素染料相比。本发明的染料在涉及荧光检测的分析中特别有用，其中需要连续或重复激发，例如在动力学研究中，或在微阵列分析中，微阵列玻片可能需要在数天内重新分析。