CY7-N-羟基琥珀酰胺酯 | 477908-53-5

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 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
• 中文名称: CY7-N-羟基琥珀酰胺酯
• 英文名称: Cy7 NHS ester
• 英文别名: (2Z)-2-[(2Z,4E,6E)-7-[1-[6-(2,5-dioxopyrrolidin-1-yl)oxy-6-oxohexyl]-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]hepta-2,4,6-trienylidene]-1-ethyl-3,3-dimethylindole-5-sulfonate
• CAS: 477908-53-5
• 化学式: C₃₉H₄₅N₃O₁₀S₂
• 分子量: 779.932
• InChiKey: ROGODJHHEBREAB-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  54
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  11

安全信息

• 海关编码：
  32049010
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H317

制备方法与用途

生物活性

CY7-SE（Sulfo-Cyanine7 Succinimidyl Ester）是一种荧光标记试剂，其激发光谱范围为700-770 nm，发射光谱为790 nm。Cyanine染料广泛用于标记蛋白质、抗体、肽以及寡聚核苷酸等生物分子。

反应信息

• 作为反应物：
  描述：

  CY7-N-羟基琥珀酰胺酯 、 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成
  参考文献：
  名称：

  Red Light-Initiated Cross-Linking of NIR Probes to Cytoplasmic RNA: An Innovative Strategy for Prolonged Imaging and Unexpected Tumor Suppression

  摘要：

  Improving the enrichment of drugs or theranostic agents within tumors is very vital to achieve effective cancer diagnosis and therapy while greatly reducing the dosage and damage to normal tissues. Herein, as a proof of concept, we for the first time report a red light-initiated probe-RNA cross-linking (RLIPRC) strategy that can not only robustly promote the accumulation and retention of the probe in the tumor for prolonged imaging but also significantly inhibits the tumor growth. A near-infrared (NIR) fluorescent probe f-CR consisting of a NIR dye (Cyanine 7) as a signal reporter, a cyclic-(arginine-glycine-aspartic acid) (cRGD) peptide for tumor targeting, and a singlet oxygen (¹O₂)-sensitive furan moiety for RNA cross-linking was rationally designed and synthesized. This probe possessed both passive and active tumor targeting abilities and emitted intense NIR/photoacoustic (PA) signals, allowing for specific and sensitive dual-modality imaging of tumors in vivo. Notably, probe f-CR could be specifically and covalently cross-linked to cytoplasmic RNAs via the cycloaddition reaction between furan and adenine, cytosine, or guanine under the oxidation of ¹O₂ generated in situ by irradiation of methylene blue (MB) with 660 nm laser light, which effectively blocks the exocytosis of the probes resulting in enhanced tumor accumulation and retention. More excitingly, for the first time, we revealed that the covalent cross-linking of probe f-CR to cytoplasmic RNAs could induce severe apoptosis of cancer cells leading to remarkable tumor suppression. This study thus represents the first red light-initiated RNA cross-linking system with high potential to improve the diagnostic and therapeutic outcomes of tumors in vivo.

  DOI：

  10.1021/jacs.0c10755

文献信息

• Synthesis and fluorescence characteristics of ATP-based FRET probes
  作者：Norman Hardt、Stephan M. Hacker、Andreas Marx

  DOI：10.1039/c3ob41751d

  日期：——

  Adenosine triphosphate (ATP) analogues labelled with two dyes suitable for undergoing Förster Resonance Energy Transfer (FRET) have the potential to be valuable tools to continuously study the enzymatic activity of ATP consuming enzymes. Here, we present a synthesis strategy that allows obtaining these ATP analogues in a straight-forward manner. Earlier studies indicate that modifying ATP at the O2′-

  用两种染料标记的三磷酸腺苷（ATP）类似物适合进行福斯特共振能量转移（FRET），具有成为继续研究消耗ATP的酶的酶活性的有价值的工具的潜力。在这里，我们提出了一种合成策略，可以直接获得这些ATP类似物。较早的研究表明，在O处修饰ATP2'和γ位置是设计这些探针的非常有前途的起点。我们合成了探针，该探针用附着在这些位置的五种不同的染料组合修饰，并研究了未切割状态以及酶水解后的荧光特性。所有提供的探针在切割后都会大大改变其荧光特性。它们包括比例FRET探针以及暗淬灭的类似物。对于典型的体外应用，磺化聚次甲基染料Sulfo-Cy3和Sulfo-Cy5的组合似乎是最有前途的，因为它们在水性缓冲液中的出色溶解性和裂解后的荧光特性发生了很大的变化。对于这种染料组合，我们还合成了在γ-和C处修饰的类似物分别是2或O 3'位置，因为这些连接位点也被某些消耗ATP的酶很好地接受。这些类似物显示出相当大的荧
• Synthesis and Biological Evaluation of Low Molecular Weight Fluorescent Imaging Agents for the Prostate-Specific Membrane Antigen
  作者：Ying Chen、Mrudula Pullambhatla、Sangeeta R. Banerjee.、Youngjoo Byun、Marigo Stathis、Camilo Rojas、Barbara S. Slusher、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1021/bc3003919

  日期：2012.12.19

  Targeted near-infrared (MR) optical imaging can be used in vivo to detect specific tissues, including malignant cells. A series of NIR fluorescent ligands targeting the prostate-specific membrane antigen (PSMA) was synthesized and each compound was tested for its ability to image PSMA+ tissues in experimental models of prostate cancer. The agents were prepared by conjugating commercially available active esters of NIR dyes, including IRDye800CW, IRDye800RS, Cy5.5, Cy7, or a derivative of indocyanine green (ICG) to the terminal amine group of (S)-2-(3-((S)-5-amino-1-carboxypentyl)ureido)pentanedioic acid 1, (14S,18S)-1-amino-8,16-dioxo-3,6-dioxa-9,15,17-triazaicosane-14,18,20-tricarboxylic acid 2 and (3S,7S)-26-amino-5,13,20-trioxo-4,6,12,21-tetraaza-hexacosane-1,3,7,22-tetracarboxylic acid 3. The K-i values for the dye-inhibitor conjugates ranged from 1 to 700 pM. All compounds proved capable of imaging PSMA+ tumors selectively to varying degrees depending on the choice of fluorophore and linker. The highest tumor uptake was observed with IRDye800CW employing a poly(ethylene glycol) or lysine suberate linker, as in 800CW-2 and 800CW-3, while the highest tumor to nontarget tissue ratios were obtained for Cy7 with these same linkers, as in Cy7-2 and Cy7-3. Compounds 2 and 3 provide useful scaffolds for targeting of PSMA+ tissues in vivo and should be useful for preparing NIR dye conjugates designed specifically for clinical intraoperative optical imaging devices.
• Toward preparation of antibody-based imaging probe libraries for dual-modality positron emission tomography and fluorescence imaging
  作者：Heng Xu、Peter K. Eck、Kwamena E. Baidoo、Peter L. Choyke、Martin W. Brechbiel

  DOI：10.1016/j.bmc.2009.05.048

  日期：2009.7

  Two novel imaging agents trastuzumab-Cy5.5-CHX-A '' 1 and cetuximab-Cy7-CHX-A '' 2, bearing both a chelating moiety (CHX-A '') for sequestering metallic radionuclides (Y-86 or In-111) and the near infrared dye Cy5.5/Cy7, were prepared by a novel modular synthetic strategy as examples of dual-labeled, anti-body-based imaging probe library. Fluorescent microscopy illustrated that 1 and 2 strongly bind to HER2-expressing cancer cells (e.g., NIH3T3-HER2(+), SKOV-3) and to EGFR-expressing cancer cells (e. g., A431), respectively, thereby demonstrating that the functionality of the targeting moiety is conserved. Hence, the described novel synthesis strategy can be applied to engineer other tumor-targeted monoclonal antibody based probes for multimodality imaging. Published by Elsevier Ltd.
• Red Light-Initiated Cross-Linking of NIR Probes to Cytoplasmic RNA: An Innovative Strategy for Prolonged Imaging and Unexpected Tumor Suppression
  作者：Shuyue Ye、Chaoxiang Cui、Xiaju Cheng、Meng Zhao、Qiulian Mao、Yuqi Zhang、Anna Wang、Jing Fang、Yan Zhao、Haibin Shi

  DOI：10.1021/jacs.0c10755

  日期：2020.12.23

  Improving the enrichment of drugs or theranostic agents within tumors is very vital to achieve effective cancer diagnosis and therapy while greatly reducing the dosage and damage to normal tissues. Herein, as a proof of concept, we for the first time report a red light-initiated probe-RNA cross-linking (RLIPRC) strategy that can not only robustly promote the accumulation and retention of the probe in the tumor for prolonged imaging but also significantly inhibits the tumor growth. A near-infrared (NIR) fluorescent probe f-CR consisting of a NIR dye (Cyanine 7) as a signal reporter, a cyclic-(arginine-glycine-aspartic acid) (cRGD) peptide for tumor targeting, and a singlet oxygen (¹O₂)-sensitive furan moiety for RNA cross-linking was rationally designed and synthesized. This probe possessed both passive and active tumor targeting abilities and emitted intense NIR/photoacoustic (PA) signals, allowing for specific and sensitive dual-modality imaging of tumors in vivo. Notably, probe f-CR could be specifically and covalently cross-linked to cytoplasmic RNAs via the cycloaddition reaction between furan and adenine, cytosine, or guanine under the oxidation of ¹O₂ generated in situ by irradiation of methylene blue (MB) with 660 nm laser light, which effectively blocks the exocytosis of the probes resulting in enhanced tumor accumulation and retention. More excitingly, for the first time, we revealed that the covalent cross-linking of probe f-CR to cytoplasmic RNAs could induce severe apoptosis of cancer cells leading to remarkable tumor suppression. This study thus represents the first red light-initiated RNA cross-linking system with high potential to improve the diagnostic and therapeutic outcomes of tumors in vivo.