2-((E)-2-((E)-2-chloro-3-((E)-2-(3,3-dimethyl-1-propylindol-2-ylidene)ethylidene)cyclohex-1-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-lium

• 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: 2-((E)-2-((E)-2-chloro-3-((E)-2-(3,3-dimethyl-1-propylindol-2-ylidene)ethylidene)cyclohex-1-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-lium
• 英文别名: IR-780；(2E)-2-[(2Z)-2-[2-chloro-3-[(E)-2-(3,3-dimethyl-1-propylindol-1-ium-2-yl)ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-3,3-dimethyl-1-propylindole
• 化学式: C₃₆H₄₄ClN₂
• 分子量: 540.212
• InChiKey: MMSREVPDKSWDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-((E)-2-((E)-2-chloro-3-((E)-2-(3,3-dimethyl-1-propylindol-2-ylidene)ethylidene)cyclohex-1-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-lium 在 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,6-bis(2-(3,3-dimethyl-1-propyl-1,3-dihydro-2H-indolin-2-ylidene)ethylidene)cyclohexanone
  参考文献：
  名称：

  一种近红外花菁类比色荧光探针及其制备方法和应用

  摘要：

  本发明公开了一种近红外花菁类比色荧光探针及其制备方法和应用，该探针的结构式如式(I)所示。该荧光探针在无水乙醇和PBS缓冲液的混合溶液中，利用荧光和紫外可见吸收光谱可识别检测N2H4。该探针对N2H4的识别具有高选择性和灵敏度，抗干扰能力强，而且具有非常低的检测限；所述荧光探针可以应用于环境污染或生物体外以及生物体内抗结核药物代谢物N2H4的检测。

  公开号：

  CN113234068B
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 sodium acetate 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 2-((E)-2-((E)-2-chloro-3-((E)-2-(3,3-dimethyl-1-propylindol-2-ylidene)ethylidene)cyclohex-1-yl)vinyl)-3,3-dimethyl-1-propyl-3H-indol-1-lium
  参考文献：
  名称：

  Elucidating the cellular uptake mechanisms of heptamethine cyanine dye analogues for their use as an anticancer drug‐carrier molecule for the treatment of glioblastoma

  摘要：

  AbstractThe development of chemotherapies for glioblastoma is hindered by their limited bioavailability and toxicity on normal brain function. To overcome these limitations, we investigated the structure‐dependent activity of heptamethine cyanine dyes (HMCD), a group of tumour‐specific and BBB permeable near‐infrared fluorescent dyes, in both commercial (U87MG) and patient‐derived GBM cell lines. HMCD analogues with strongly ionisable sulphonic acid groups were not taken up by patient‐derived GBM cells, but were taken up by the U87MG cell line. HMCD uptake relies on a combination of transporter uptake through organic anion‐transporting polypeptides (OATPs) and endocytosis into GBM cells. The uptake of HMCDs was not affected by p‐glycoprotein efflux in GBM cells. Finally, we demonstrate structure‐dependent cytotoxic activity at high concentrations (EC50: 1–100 μM), likely due to mitochondrial damage‐induced apoptosis. An in vivo orthotopic glioblastoma model highlights tumour‐specific accumulation of our lead HMCD, MHI‐148, for up to 7 days following a single intraperitoneal injection. These studies suggest that strongly ionisable groups like sulphonic acids hamper the cellular uptake of HMCDs in patient‐derived GBM cell lines, highlighting cell line‐specific differences in HMCD uptake. We envisage these findings will help in the design and structural modifications of HMCDs for drug‐delivery applications for glioblastoma.

  DOI：

  10.1111/cbdd.14171

文献信息

• NEAR-IR GLUCOSE SENSORS
  申请人：Profusa, Inc.

  公开号：US20180179233A1

  公开（公告）日：2018-06-28

  Glucose-sensing luminescent dyes, polymers, and sensors are provided. Additionally, systems including the sensors and methods of using these sensors and systems are provided.

  提供了葡萄糖感应荧光染料、聚合物和传感器。此外，还提供了包括传感器的系统以及使用这些传感器和系统的方法。
• PEI-NIR Heptamethine Cyanine Nanotheranostics for Tumor Targeted Gene Delivery
  作者：Eduardo De los Reyes-Berbel、Rafael Salto-Gonzalez、Mariano Ortega-Muñoz、Francisco Jose Reche-Perez、Ana Belen Jodar-Reyes、Fernando Hernandez-Mateo、Maria Dolores Giron-Gonzalez、Francisco Santoyo-Gonzalez

  DOI：10.1021/acs.bioconjchem.8b00262

  日期：2018.8.15

  diagnosis in the fast-growing field of nanomedicine. A straightforward preparation of novel engineered PEI-based nanotheranostics incorporating NIR fluorescence heptamethine cyanine dyes (NIRF-HC) to enable them with tumor targeted gene delivery capabilities is reported. Branched PEI-2 kDa (b2kPEI) is conjugated with IR-780 and IR-783 dyes by both covalent and noncovalent simple preparative methodologies

  基于聚合物的纳米热力学是快速发展的纳米医学领域中用于癌症治疗和诊断的有吸引力的工具。报道了一种新的，基于工程学的，基于PEI的纳米热学的直接制备方法，该方法结合了NIR荧光七甲基亚甲基花青染料（NIRF-HC），使其具有靶向肿瘤的基因传递能力。通过改变化学计量比的共价和非共价简单制备方法，将支链PEI-2 kDa（b2kPEI）与IR-780和IR-783染料偶联。在体外和体内测定已制备的PEI-NIR-HC纳米载体评估其基因转染效率，细胞摄取，细胞毒性，内在化和运输机制，亚细胞分布以及肿瘤特异性基因传递。结果显示了该方法的有效性，特别是对于一种共价的IR783-b2kPEI缀合物，该缀合物显示出增强的肿瘤吸收（可能是由有机阴离子转运肽介导的），并且有利于细胞内转运至细胞核。该化合物在带有黑素瘤G361 Xenographs的NSG小鼠中起着有效的纳米热转染剂的作用，在目标肿瘤中伴随有成像
• COMPOUND BASED ON CYANINE SCAFFOLD FOR DIAGNOSIS SEPSIS BY SELECTIVELY DETECT GLUTATHIONE
  申请人：EWHA UNIVERSITY - INDUSTRY COLLABORATION FOUNDATION

  公开号：US20160083344A1

  公开（公告）日：2016-03-24

  The present invention relates to a compound based on cyanine scaffold for diagnosing sepsis by selectively detecting glutathione. The compound based on cyanine scaffold according to the present invention has the advantages of maintaining its structure in intracellular environment and of reacting selectively to glutathione only among many amino acids containing thiol group (R—SH) such as cysteine, homocysteine, and glutathione, to produce changes in absorption or fluorescence spectrum, making the compound useful for the detection of in vivo glutathione in biosamples and also for the diagnosis of sepsis characteristically displaying the changes of glutathione concentration.

  本发明涉及一种基于青蛉酮骨架的化合物，用于通过选择性检测谷胱甘肽诊断败血症。根据本发明的基于青蛉酮骨架的化合物具有在细胞内环境中保持其结构的优点，并且在众多含硫醇基团（R—SH）的氨基酸中只对谷胱甘肽选择性地发生反应，如半胱氨酸、同型半胱氨酸和谷胱甘肽，从而产生吸收或荧光光谱的变化，使得该化合物在生物样本中检测体内谷胱甘肽以及诊断表现为谷胱甘肽浓度变化的败血症具有用途。
• [EN] COPPER-CONTAINING COMPLEX AND USES THEREOF<br/>[FR] COMPLEXE CONTENANT DU CUIVRE ET UTILISATIONS DE CELUI-CI
  申请人：UNIV BAR ILAN

  公开号：WO2019092721A1

  公开（公告）日：2019-05-16

  Complexes comprising a coordinated Cu(II) ion are described herein, which are capable of binding to an extracellular portion of Ctr1 such that the complex with the Cu(II) ion is transported through the Ctr1. The complexes may comprise a Cu(II) ion coordinated to a ligand and to a peptide, wherein the peptide is released upon contact of the complex with an extracellular portion of Ctr1, thereby forming a second complex comprising the ligand, the copper ion and the extracellular portion of Ctr1. Further described herein are uses and methods utilizing the complex, in imaging, in radiation therapy, and for determining a redox state of cells.

  本文描述了包含一个配位的Cu(II)离子的复合物，这些复合物能够结合到Ctr1的细胞外部分，使含有Cu(II)离子的复合物通过Ctr1进行运输。这些复合物可能包括一个配位到配体和肽的Cu(II)离子，其中肽在复合物与Ctr1的细胞外部分接触时释放，从而形成包含配体、铜离子和Ctr1细胞外部分的第二个复合物。本文还描述了利用该复合物进行成像、放射治疗以及确定细胞氧化还原状态的用途和方法。
• FLUORESCENT MRI PROBE
  申请人：Nagano Tetsuo

  公开号：US20120065384A1

  公开（公告）日：2012-03-15

  A fluorescent gadolinium complex compound comprising a residue of gadolinium.1,4,7,10-tetraazacyclododecane-N,N′,N″,N′″-tetraacetic acid or a residue of gadolinium.diethylenetriaminepentaacetic acid bound covalently with a group represented by the following general formula (I) (R 1 represents hydrogen atom or a substituent R 2 , R 4 , R 5 and R 7 represent hydrogen atom, a halogen atom or a C 1-6 alkyl group, and R 3 and R 6 represent hydrogen atom, a halogen atom or a C 1-6 alkyl group), which is easily taken up into cells and useful as a probe observable by the fluorescence method and MRI.

  一种荧光钆配合物化合物，包括钆残基。1,4,7,10-四氮杂环十二烷-N,N′,N″,N′″-四乙酸或钆残基。乙二胺五乙酸与以下一般式（I）所代表的基团共价结合（其中R1代表氢原子或取代基R2，R4，R5和R7代表氢原子，卤原子或C1-6烷基，R3和R6代表氢原子，卤原子或C1-6烷基），该化合物易被细胞吸收，并且可作为荧光方法和MRI观察的探针。