3-(5-carboxyl)pentyl-1,1,2-trimethylbenzo[e]indolium

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(5-carboxyl)pentyl-1,1,2-trimethylbenzo[e]indolium
• 英文别名: 3-(5-carboxypentyl)-1,1,2-trimethyl-1H-benzo[e]indole-3-onium；3-(5-carboxypentyl)-1,1,2-trimethyl-1H-benzo[e]indole；6-(1,1,2-Trimethylbenzo[e]indol-3-ium-3-yl)hexanoic acid
• 化学式: C₂₁H₂₆NO₂
• 分子量: 324.443
• InChiKey: PPPYIABAZASBHI-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-carboxyl)pentyl-1,1,2-trimethylbenzo[e]indolium 在 吡啶 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  基于4-氨基-2-巯基嘧啶-5-羧酸乙酯的花菁探针及其制备方法和应用

  摘要：

  本发明属于生物检测领域，具体涉及一种基于4‑氨基‑2‑巯基嘧啶‑5‑羧酸乙酯的花菁探针及其制备方法和应用。首先制备CY5.5染料，然后将CY5.5染料与N‑羟基丁二酰亚胺(NHS)反应形成活性酯，最后与4‑氨基‑2‑巯基嘧啶‑5‑羧酸乙酯在碱性条件下反应，所得粗品通过薄层色谱法分离，得到最终产物CY5.5O。本发明制备得到的花菁探针具有优良的光学性能并且可以通过荧光变化的方式选择性识别溶菌酶。

  公开号：

  CN115028622A
• 作为产物：
  描述：

  2-萘肼 在 溶剂黄146 作用下， 反应 96.0h， 生成 3-(5-carboxyl)pentyl-1,1,2-trimethylbenzo[e]indolium
  参考文献：
  名称：

  Evaluation of asymmetric orthogonal cyanine fluorophores

  摘要：

  Pentamethine cyanine (Cy5) fluomphores have proven to be versatile imaging agents (i.e., tracers) for a range of micro- and macroscopic imaging applications, including image-guided surgery. In this study the relationship between the structure of asymmetric Cy5 fluorophores and their photophysical properties was studied. To this end, seven Cy5 analogues, bearing orthogonal N-indole substituents (H, SC3-, or benzene), were synthesised and evaluated. In-depth analysis revealed that introduction of sulfonates enhanced the fluorescence brightness and photostability, while reducing the lipophilicity, serum binding and stacking tendency. The addition of benzene moieties induced a bathochromic shift of 10-20 nm, increased the lipophilicity (LogP = -1.56-1.23) and serum binding (67.3-93.8% bound), as well as negatively impacted the brightness (0.74-42.9 . 10(3) M-1 cm(-1)), photostability (24.4-90.6% remaining), and stacking tendency. Chemical stability was uninfluenced by the substitution pattern. Additionally, the generation of a c[RGDyK]-based hybrid tracer based on one of these fluomphores in combination with a diethylenetriaminepentaacetic acid (DTPA) chelate and an In-111-isotope was reported. This compound was evaluated in vitro using alpha(v)beta(3)-overexpressing Ge beta 3 cells and in vivo using a 4T1 mouse tumour model. Overall, the presented results imply that alterations of the asymmetrical orthogonal Cy5 fluomphore structure have impact on the (photo)physical properties. Furthermore, the orthogonal Cy5 fluorophore framework can readily be applied in tracer development.

  DOI：

  10.1016/j.dyepig.2020.108712

文献信息

• Synthetic probes for in vitro purification and in vivo tracking of hepatocytes derived from human pluripotent stem cells
  作者：Ji Young Park、Jiyou Han、Hyo Sung Jung、Gyunggyu Lee、Hyo Jin Kim、Gun-Sik Cho、Han-Jin Park、Choongseong Han、Jong Seung Kim、Jong-Hoon Kim

  DOI：10.1016/j.biomaterials.2019.119431

  日期：2019.11

  Hepatocytes derived from human pluripotent stem cells (hPSCs) are promising candidates for cell therapy and drug discovery. However, it remains challenging to efficiently purify hepatocytes from undesired cell types after differentiation and to accurately monitor grafted cells after transplantation. Indocyanine Green (ICG), an FDA-approved, near-infrared (NIR) dye, has been used for various clinical

  源自人类多能干细胞（hPSC）的肝细胞有望用于细胞治疗和药物开发。然而，在分化后从不期望的细胞类型中有效纯化肝细胞以及在移植后准确地监测移植的细胞仍然具有挑战性。吲哚菁绿（ICG）是FDA批准的近红外（NIR）染料，已用于各种临床目的，并且仅被肝细胞吸收。但是，ICG的发射波长长（λem  > 800 nm），超出了荧光激活细胞分选（FACS）系统的检测范围。此外，它很容易从肝细胞中清除，从而阻碍了其在近红外成像中的应用。在这里，我们根据ICG的特性设计和合成了两种不同的探针。1）肝细胞净化剂（HPA， λ EM  = 562纳米），用于体外排序和2）肝细胞成像剂（HIA， λ EM  = 817 nm）的为高效的体内NIR成像。我们使用基于HPA探针的FACS纯化从各种hPSC系中获得了高度富集的hPSC衍生肝细胞（hPSC-Heps）群体。此外，通过HIA标记和NIR成像，可以直接观察
• BENZINDOCYANINE COMPOUND FOR LABELING SUBSTANCE, INTERMEDIATE THEREOF, AND METHOD FOR PREPARING THE SAME
  申请人：Park Jin Woo

  公开号：US20130102752A1

  公开（公告）日：2013-04-25

  The present disclosure relates to a novel benzindocyanine compound for labeling biomolecules and a method for preparing the same.

  本公开涉及一种用于标记生物分子的新型苯并二氰染料化合物以及其制备方法。
• AZACYANINE DYES AND USE THEREOF
  申请人：Ecole Polytechnique Fédérale de Lausanne (EPFL)

  公开号：US20180079906A1

  公开（公告）日：2018-03-22

  The application provides fluorescent dyes, which are cyanine dyes that incorporate additional aza moieties in the indolenium heterocycles and/or in the methine chains connecting them. Symmetrical and unsymmetrical chemically reactive azacyanine dyes are described for conjugation, as well as their bioconjugates for in-vitro and in-vivo assays and fluorescence imaging.

  该应用程序提供荧光染料，这些染料是氰染料，它们在吲哚啉环中和/或连接它们的亚甲链中包含额外的氮杂基。描述了用于共轭的对称和非对称化学反应性氮杂氰染料，以及它们的生物共轭物用于体外和体内分析和荧光成像。
• Conjugation of Dasatinib with MHI‐148 Has a Significant Advantageous Effect in Viability Assays for Glioblastoma Cells
  作者：Syed Muhammad Usama、Zhengyang Jiang、Kathryn Pflug、Raquel Sitcheran、Kevin Burgess

  DOI：10.1002/cmdc.201900356

  日期：2019.9.4

  We hypothesized that conjugation of the near-infrared dye MHI-148 with the anti-leukemia drug dasatinib might produce a potential theranostic for glioblastoma. In fact, the conjugate was found to bind the kinases Src and Lyn, and to inhibit the viability of a glioblastoma cell line with significantly greater potency than dasatinib alone, MHI-148 alone, or a mixture of dasatinib and MHI-148 at the same

  我们假设近红外染料MHI-148与抗白血病药物dasatinib的结合可能会产生胶质母细胞瘤的潜在治疗治疗作用。实际上，发现缀合物结合激酶Src和Lyn，并抑制胶质母细胞瘤细胞系的活力，其效力明显高于单独的达沙替尼，单独的MHI-148或同时达沙替尼和MHI-148的混合物专注。它也被用来在体内成功地成像皮下成胶质细胞瘤肿瘤。
• Tumor-targeted optical contrast agents
  申请人：MALLINCKRODT INC.

  公开号：US20040141920A1

  公开（公告）日：2004-07-22

  Cyanine dye bioconjugates useful for diagnostic imaging and therapy are disclosed. The conjugates include several cyanine dyes with a variety of bis- and tetrakis (carboxylic acid) homologs. The compounds may be conjugated to bioactive peptides, carbohydrates, hormones, drugs, or other bioactive agents. The small size of the compounds allows more favorable delivery to tumor cells as compared to larger molecular weight imaging agents. The various dyes are useful over the range of 350 to 1300 nm, the exact range being dependent upon the particular dye. The use of dimethylsulfoxide helps to maintain the fluorescence of the compounds. The inventive compounds are useful for diagnostic imaging and therapy, in endoscopic applications for the detection of tumors and other abnormalities, for localized therapy, for photoacoustic tumor imaging, detection and therapy, and for sonofluoresence tumor imaging, detection and therapy.

  揭示了用于诊断成像和治疗的青菁染料生物共轭物。这些共轭物包括几种青菁染料，具有各种双和四(羧酸)同系物。这些化合物可以与生物活性肽、碳水化合物、激素、药物或其他生物活性剂结合。与分子量较大的成像试剂相比，这些化合物的小尺寸使其更有利于输送到肿瘤细胞。各种染料在350到1300纳米范围内是有用的，确切范围取决于特定的染料。二甲基亚砜的使用有助于保持化合物的荧光。这些创新的化合物在诊断成像和治疗中很有用，用于内窥镜应用以检测肿瘤和其他异常，用于局部治疗，用于光声肿瘤成像、检测和治疗，以及用于声荧光肿瘤成像、检测和治疗。