IR-820 | 162411-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: IR-820
• 英文别名: 4-[2-[(2E)-2-[2-chloro-3-[2-[1,1-dimethyl-3-(4-sulfobutyl)benzo[e]indol-3-ium-2-yl]ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,1-dimethylbenzo[e]indol-3-yl]butane-1-sulfonate
• CAS: 162411-28-1
• 化学式: C₄₆H₅₁ClN₂O₆S₂
• 分子量: 827.506
• InChiKey: AWZSJBDJHOOBGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  57
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-(di-n-hexylamino)phenol 、 IR-820 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以48%的产率得到sodium 4-(2-((E)-2-((E)-2-(4-(dihexyamino)phenoxy)-3-((E)-2-(1,1-dimethyl-3-(4-sulfonatobutyl)-1H-benzo[e]indol-2(3H)-ylidene)ethylidene)cyclohexenyl)vinyl)-1,1-dimethyl-1H-benzo[e]indolium-3-yl)butane-1-sulfonate
  参考文献：
  名称：

  Fluorescent Probe for Imaging Lymph Nodes

  摘要：

  本发明公开了一种近红外荧光成像剂，包括靛青基荧光染料和脂质体。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锚定，因此可用于检测哨兵淋巴结导航手术中的哨兵淋巴结。本发明还公开了一种靛青绿衍生物，特别适用于本发明的近红外荧光成像剂。

  公开号：

  US20130129631A1
• 作为产物：
  描述：

  1,1,2-三甲基苯-1H-苯并[e]吲哚 在 乙酸酐 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 IR-820
  参考文献：
  名称：

  Fluorescent Probe for Imaging Lymph Nodes

  摘要：

  本发明公开了一种近红外荧光成像剂，包括靛青基荧光染料和脂质体。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锚定，因此可用于检测哨兵淋巴结导航手术中的哨兵淋巴结。本发明还公开了一种靛青绿衍生物，特别适用于本发明的近红外荧光成像剂。

  公开号：

  US20130129631A1

文献信息

• Regioselective Synthesis and Photophysical and Electrochemical Studies of 20-Substituted Cyanine Dye-Purpurinimide Conjugates: Incorporation of Ni^IIinto the Conjugate Enhances its Tumor-Uptake and Fluorescence-Imaging Ability
  作者：Manivannan Ethirajan、Ping Chen、Tymish Y. Ohulchanskyy、Lalit N. Goswami、Anurag Gupta、Avinash Srivatsan、Mahabeer P. Dobhal、Joseph R. Missert、Paras N. Prasad、Karl M. Kadish、Ravindra K. Pandey

  DOI：10.1002/chem.201203867

  日期：2013.5.17

  approach to the synthesis of a variety of meso‐substituted purpurinimides. The reaction of meso‐substituted purpurinimide with N‐bromosuccinimide regioselectively introduced a bromo functionality at the 20‐position, which on further reaction with a variety of boronic acids under Suzuki reaction conditions yielded the corresponding meso‐substituted analogues. Interestingly, the free base and the metalated

  我们在这里报告了一种简单有效的方法来合成各种内消旋取代的紫嘌呤亚胺。的反应内消旋-取代紫红素与Ñ溴代琥珀酰亚胺区域选择性引入到20位，将其用各种Suzuki反应条件下，硼酸进一步反应得到相应的溴功能内消旋取代的类似物。有趣的是，游离碱和金属化类似物在光敏功效（PDT）和肿瘤成像能力方面显示出显着差异。例如，游离碱偶联物在体外具有显着的PDT功效，但在荷瘤小鼠中肿瘤亲和力有限，而相应的Ni II该衍生物不会产生任何细胞杀伤作用，但在注射后24、48和72 h，以0.3μmolkg -1的剂量显示出优异的肿瘤成像能力。Ni II类似物的PDT功效有限可能是由于其无法产生单线态氧，而单线态氧是PDT中杀死细胞所需的关键细胞毒剂。根据DMSO中的电化学和光谱电化学数据，游离碱和相应的Ni II的第一次单电子氧化（0.52 V vs. SCE）和第一次单电子还原（-0.57-0.67 V vs. S
• 一种七甲川苯并吲哚花菁染料的制备方法及其应用
  申请人：中国科学院宁波材料技术与工程研究所

  公开号：CN111662563A

  公开（公告）日：2020-09-15

  本申请公开了一种七甲川苯并吲哚花菁染料的制备方法及其应用，属于多甲川吲哚花菁染料及其制备领域。所述方法包括以下步骤：1)将含有2,3,3‑三甲基‑4,5‑苯并吲哚衍生物和亲核取代化合物的原料在真空条件下升温反应，得到有机铵盐；2)将含有步骤1)中得到的有机铵盐和环烯衍生物的溶液在封闭条件下升温反应。所述七甲川苯并吲哚花菁染料的结构式如式(I)所示：该染料具有近红外光吸收和荧光显影性能，可用于探针助剂。所述方法具有合成路线短、溶剂环境友好、工艺简单、避免贵金属催化、产率高以及纯度高等优点，且适用性强，可用于合成多种结构类型的产物。
• Effect of Metalation on Porphyrin-Based Bifunctional Agents in Tumor Imaging and Photodynamic Therapy
  作者：Nayan J. Patel、Yihui Chen、Penny Joshi、Paula Pera、Heinz Baumann、Joseph R. Missert、Kei Ohkubo、Shunichi Fukuzumi、Roger R. Nani、Martin J. Schnermann、Ping Chen、Jialiang Zhu、Karl M. Kadish、Ravindra K. Pandey

  DOI：10.1021/acs.bioconjchem.5b00656

  日期：2016.3.16

  Herein we report the syntheses and comparative photophysical, electrochemical, in vitro, and in vivo biological efficacy of 3-(1′-hexyloxy)ethyl-3-devinylpyropheophorbide-cyanine dye (HPPH-CD) and the corresponding indium (In), gallium (Ga), and palladium (Pd) conjugates. The insertion of a heavy metal in the HPPH moiety makes a significant difference in FRET (Förster resonance energy transfer) and electrochemical properties, which correlates with singlet oxygen production [a key cytotoxic agent for photodynamic therapy (PDT)] and long-term in vivo PDT efficacy. Among the metalated analogs, the In(III) HPPH-CD showed the best cancer imaging and PDT efficacy. Interestingly, in contrast to free base HPPH-CD, which requires a significantly higher therapeutic dose (2.5 μmol/kg) than imaging dose (0.3 μmol/kg), the corresponding In(III) HPPH-CD showed excellent imaging and therapeutic potential at a remarkably low dose (0.3 μmol/kg) in BALB/c mice bearing Colon26 tumors. A comparative study of metalated and corresponding nonmetalated conjugates further confirmed that STAT-3 dimerization can be used as a biomarker for determining the level of photoreaction and tumor response.

  在此，我们报告了 3-(1'-己氧基)乙基-3-脱乙烯基焦脱镁叶绿酸-花青染料 (HPPH-CD) 和相应的铟 (In)、镓的合成和比较光物理、电化学、体外和体内生物学功效。 (Ga) 和钯 (Pd) 缀合物。 HPPH 部分中插入重金属会导致 FRET（福斯特共振能量转移）和电化学特性产生显着差异，这与单线态氧的产生（光动力疗法 (PDT) 的关键细胞毒剂）和体内长期作用相关PDT疗效。在金属化类似物中，In(III) HPPH-CD 显示出最佳的癌症成像和 PDT 功效。有趣的是，与游离碱 HPPH-CD 需要的治疗剂量 (2.5 μmol/kg) 显着高于成像剂量 (0.3 μmol/kg) 相比，相应的 In(III) HPPH-CD 在在携带 Colon26 肿瘤的 BALB/c 小鼠中，剂量非常低（0.3 μmol/kg）。金属化和相应的非金属化缀合物的比较研究进一步证实STAT-3二聚化可以作为确定光反应和肿瘤反应水平的生物标志物。
• A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels
  作者：Narasimhachari Narayanan、Gabor Patonay

  DOI：10.1021/jo00113a018

  日期：1995.4

  A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.
• Impact of Substituents in Tumor Uptake and Fluorescence Imaging Ability of Near-Infrared Cyanine-like Dyes
  作者：Nayan J. Patel、Ethirajan Manivannan、Penny Joshi、Tymish J. Ohulchanskyy、Roger R. Nani、Martin J. Schnermann、Ravindra K. Pandey

  DOI：10.1111/php.12482

  日期：2015.9

  AbstractThis report presents a simple strategy to introduce various functionalities in a cyanine dye (bis‐indole‐N‐butylsulfonate‐polymethine bearing a fused cyclic chloro‐cyclohexene ring structure), and assess the impact of these substitutions in tumor uptake, retention and imaging. The results obtained from the structural activity relationship (SAR) study demonstrate that certain structural features introduced in the cyanine dye moiety make a remarkable difference in tumor avidity. Among the compounds investigated, the symmetrical CDs containing an amino‐phenyl thioether group attached to a cyclohexene ring system and the two N‐butyl linkers with terminal sulfonate groups in benzoindole moieties exhibited excellent tumor imaging ability in BALB/c mice bearing Colon26 tumors. Compared to indocyanine green (ICG), approved by FDA as a blood pooling agent, which has also been investigated for the use in tumor imaging, the modified CD selected on the basis of SAR study produced enhanced uptake and longer retention in tumor(s). A facile approach reported herein for introducing a variety of functionalities in tumor‐avid CD provides an opportunity to create multi‐imaging modality agent(s). Using a combination of mass spectrometry and absorbance techniques, the photobleaching of one of the CDs was analyzed and significant regioselective photooxidation was observed.