4-(2-((1E,3E,5E,7E)-7-(3-(2-carboxyethyl)-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)hepta-1,3,5-trienyl)-1,1-dimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonic acid | 161239-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-((1E,3E,5E,7E)-7-(3-(2-carboxyethyl)-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)hepta-1,3,5-trienyl)-1,1-dimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonic acid
• 英文别名: 4-[2-[(1E,3E,5E,7E)-7-[3-(2-carboxyethyl)-1,1-dimethylbenzo[e]indol-2-ylidene]hepta-1,3,5-trienyl]-1,1-dimethylbenzo[e]indol-3-ium-3-yl]butane-1-sulfonate
• CAS: 161239-16-3
• 化学式: C₄₂H₄₄N₂O₅S
• 分子量: 688.888
• InChiKey: JPVWSOSHJAYWGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-((1E,3E,5E,7E)-7-(3-(2-carboxyethyl)-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)hepta-1,3,5-trienyl)-1,1-dimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonic acid 、 dioleoylphosphatidylethanolamine 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 3.0h， 以0.37 g的产率得到2-[(1E,3E,5E)-7-[(2E)-3-[2-({2-[({2,3-bis[octadec-9-enoyloxy]propoxy}(hydroxy)phosphoryl)oxy]ethyl}carbamoyl)ethyl]-1,1-dimethyl-1H,2H,3H-benzo[e]indol-2-ylidene]hepta-1,3,5-trien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)-1H-benzo[e]indol-3-ium
  参考文献：
  名称：

  Preparation and characterization of phospholipid-conjugated indocyanine green as a near-infrared probe

  摘要：

  We have rationally designed and synthesized a novel near-infrared (NIR) photoactivating probe, designated by iDOPE, in which an indocyanine green (ICG) fluorophore is covalently conjugated with a phospholipid moiety, 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), to incorporate into liposome bilayers. NIR irradiation showed that iDOPE retained the optical and fluorescence properties of ICG and demonstrated photoactivator characteristics: fluorescence emission at around 820 nm in a solvent, singlet oxygen production, and concentration-dependent heat generation. Additionally, iDOPE was incorporated into liposome bilayers and maintained stable liposomally formulated iDOPE (LP-iDOPE) over 1 week under physiological conditions. We also observed the tumor-specific biodistribution of LP-iDOPE of in vivo xenografts. These findings suggest that LP-iDOPE might be a promising tool for NIR optical imaging, photodynamic therapy, and photothermal therapy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.044
• 作为产物：
  描述：

  1,1,2-三甲基苯-1H-苯并[e]吲哚 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 16.75h， 生成 4-(2-((1E,3E,5E,7E)-7-(3-(2-carboxyethyl)-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)hepta-1,3,5-trienyl)-1,1-dimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonic acid
  参考文献：
  名称：

  EP2764861

  摘要：

  公开号：

文献信息

• Fluorescent Probe for Imaging Lymph Nodes
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20160222211A1

  公开（公告）日：2016-08-04

  Disclosed is a near-infrared fluorescent imaging agent comprising an indocyanine-based fluorescent dye and a liposome. The near-infrared fluorescent imaging agent of the present invention demonstrates high fluorescence intensity and a long anchoring time in sentinel lymph nodes, thereby making it useful for detecting sentinel lymph nodes in sentinel lymph node navigation surgery. Also disclosed is an indocyanine green derivative that is particularly suitable for use in the near-infrared fluorescent imaging agent of the present invention.

  本发明公开了一种近红外荧光成像剂，包括吲哚菁绿类荧光染料和脂质体。本发明的近红外荧光成像剂在哨兵淋巴结中表现出高荧光强度和长时间的锚定，因此适用于在哨兵淋巴结导航手术中检测哨兵淋巴结。本发明还公开了一种吲哚菁绿衍生物，特别适用于本发明的近红外荧光成像剂中使用。
• [EN] EPSILON-POLY-L-LYSINE-BASED DRUG CONJUGATE, INTERMEDIATE THEREOF, AND APPLICATION THEREOF<br/>[FR] CONJUGUÉ DE MÉDICAMENT À BASE D'EPSILON-POLY-L-LYSINE, INTERMÉDIAIRE DE CELUI-CI, ET SON APPLICATION<br/>[ZH] 一种基于ε-聚-L-赖氨酸的药物偶联物、其中间体及其应用
  申请人：[en]SHANGHAI BEST-LINK BIOSCIENCE, LLC;[zh]上海弼领生物技术有限公司

  公开号：WO2023078464A1

  公开（公告）日：2023-05-11

  本发明公开了一种基于ε-聚-L-赖氨酸的药物偶联物、其中间体及其应用。本发明提供了一种如式(I)所示的具有基团偶联数量可控和基团偶联位点可控的ε-聚-L-赖氨酸衍生物-药物偶联物。本发明的药物偶联物具有肾脏清除率低、肝脾清除率低、血浆半衰期长、快速在病灶蓄积有效药物浓度和治疗效果更好的效果优势中的一个或多个。
• US9872833B2
  申请人：——

  公开号：US9872833B2

  公开（公告）日：2018-01-23
• EP2764861
  申请人：——

  公开号：——

  公开（公告）日：——
• Preparation and characterization of phospholipid-conjugated indocyanine green as a near-infrared probe
  作者：Akiko Suganami、Taro Toyota、Shigetoshi Okazaki、Kengo Saito、Katsuhiko Miyamoto、Yasunori Akutsu、Hiroshi Kawahira、Akira Aoki、Yutaka Muraki、Tomoyuki Madono、Hideki Hayashi、Hisahiro Matsubara、Takashige Omatsu、Hiroshi Shirasawa、Yutaka Tamura

  DOI：10.1016/j.bmcl.2012.10.044

  日期：2012.12

  We have rationally designed and synthesized a novel near-infrared (NIR) photoactivating probe, designated by iDOPE, in which an indocyanine green (ICG) fluorophore is covalently conjugated with a phospholipid moiety, 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), to incorporate into liposome bilayers. NIR irradiation showed that iDOPE retained the optical and fluorescence properties of ICG and demonstrated photoactivator characteristics: fluorescence emission at around 820 nm in a solvent, singlet oxygen production, and concentration-dependent heat generation. Additionally, iDOPE was incorporated into liposome bilayers and maintained stable liposomally formulated iDOPE (LP-iDOPE) over 1 week under physiological conditions. We also observed the tumor-specific biodistribution of LP-iDOPE of in vivo xenografts. These findings suggest that LP-iDOPE might be a promising tool for NIR optical imaging, photodynamic therapy, and photothermal therapy. (C) 2012 Elsevier Ltd. All rights reserved.