BODIPY-NHS | 1266617-61-1

• 英文名称: BODIPY-NHS
• 英文别名: 2,5-dioxopyrrolidin-1-yl 4-(4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-4-bora-s-indacen-8-yl)benzoate
• CAS: 1266617-61-1
• 化学式: C₂₄H₂₂BF₂N₃O₄
• 分子量: 465.264
• InChiKey: WYOFWPWVYRDJJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  BODIPY-NHS 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 4-(2,2-difluoro-5,11-diiodo-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-N-[4-[4-[6-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazol-2-yl]phenoxy]butyl]benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of bi-modal BODIPY-conjugated Hoechst applicable for Auger-electron and photodynamic cancer therapy

  摘要：

  DOI：

  10.1016/j.bmcl.2023.129534
• 作为产物：
  描述：

  8-(4-(甲氧羰基)苯基)-1,3,5,7-四甲基BODIPY 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 生成 BODIPY-NHS
  参考文献：
  名称：

  An efficient synthesis of a 6″-BODIPY-α-Galactosylceramide probe for monitoring α-Galactosylceramide uptake by cells

  摘要：

  Herein, an efficient synthesis of BODIPY-α-Galactosylceramide 3, which can be used to study the cellular uptake of the potent immunostimulatory parent compound α-Galactosylceramide, is reported. Key in our synthetic strategy is the six-step synthesis of the core BODIPY scaffold (64% yield overall) and its quantitative conversion to an N-hydroxysuccinimidyl ester to facilitate conjugation and purification of the target glycolipid. For the preparation of the core of the glycolipid, the solubility of the lipid acceptor proved to be critical. The ability of BODIPY-αGalCer 3 to activate invariant natural killer cells was then demonstrated in vitro.

  DOI：

  10.1016/j.carres.2019.107840

文献信息

• A design strategy for small molecule-based targeted MRI contrast agents: their application for detection of atherosclerotic plaques
  作者：Shimpei Iwaki、Kazuya Hokamura、Mikako Ogawa、Yasuo Takehara、Yasuaki Muramatsu、Takehiro Yamane、Kazuhisa Hirabayashi、Yuji Morimoto、Kohsuke Hagisawa、Kazuhide Nakahara、Tomoko Mineno、Takuya Terai、Toru Komatsu、Tasuku Ueno、Keita Tamura、Yusuke Adachi、Yasunobu Hirata、Makoto Arita、Hiroyuki Arai、Kazuo Umemura、Tetsuo Nagano、Kenjiro Hanaoka

  DOI：10.1039/c4ob01270d

  日期：——

  as contrast agents in magnetic resonance imaging (MRI), and many attempts have been made to couple them to sensor moieties in order to visualize biological phenomena of interest inside the body. However, the low sensitivity of MRI has made it difficult to develop practical MRI contrast agents for in vivo imaging. We hypothesized that practical MRI contrast agents could be designed by targeting a specific

  钆（III）离子（GD 3+）络合物被广泛用作在磁共振成像中的造影剂（MRI），并且许多已尝试以耦合他们到传感器部分，以可视化的身体内部的兴趣的生物现象。然而，MRI的低灵敏度使得难以开发用于体内成像的实用的MRI造影剂。我们假设可以通过针对特定的生物环境而非特定的蛋白质（例如受体）来设计实用的MRI造影剂。为了验证这一想法，我们设计并合成了基于Gd 3+的MRI造影剂2BDP3Gd，用于通过连接Gd 3+来可视化动脉粥样硬化斑块-与亲脂性荧光团BODIPY配合使用，可对富含脂质的环境进行染色。我们发现2BDP3Gd在细胞水平上选择性地积累到脂肪细胞的脂滴中。在体内静脉内注射2BDP3Gd后，在T 1加权MR图像中清楚地看到了渡边可遗传性高脂血症（WHHL）兔主动脉中的动脉粥样硬化斑块。
• Rational Design and Development of Near-Infrared-Emitting Firefly Luciferins Available In Vivo
  作者：Ryosuke Kojima、Hideo Takakura、Takeaki Ozawa、Yukio Tada、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1002/anie.201205151

  日期：2013.1.21

  Shine on: A new rational design strategy for near‐infrared‐emitting firefly luciferins that are available in vivo has been developed using intramolecular bioluminescence resonance energy transfer (BRET). The emission wavelength could be freely tuned by the choice of BRET acceptor, and NIR bioluminescence could be detected in living cells and mice without the need for luciferase manipulation.

  发光：利用分子内生物发光共振能量转移（BRET）为体内可用的近红外发射萤火虫荧光素开发了一种新的合理设计策略。可以通过选择BRET受体自由调节发射波长，并且可以在不需要荧光素酶操作的情况下在活细胞和小鼠中检测NIR生物发光。
• Broadband Light-Harvesting Molecular Triads with High FRET Efficiency Based on the Coumarin-Rhodamine-BODIPY Platform
  作者：Longwei He、Sasa Zhu、Yong Liu、Yinan Xie、Qiuyan Xu、Haipeng Wei、Weiying Lin

  DOI：10.1002/chem.201501375

  日期：2015.8.17

  Broadband capturing and FRET‐based light‐harvesting molecular triads, CRBs, based on the coumarin–rhodamine–BODIPY platform were rationally designed and synthesized. The absorption band of CRBs starts from blue–green to yellow–orange regions (330–610 nm), covering the strong radiation scope of sunlight. The peripheral coumarin and BODIPY chromophore energy could transfer to the central acceptor rhodamine

  合理设计和合成了基于香豆素-若丹明-BODIPY平台的宽带捕获和基于FRET的光捕获分子三联体CRB。CRB的吸收带从蓝绿色到黄橙色区域（330-610 nm）开始，覆盖了强烈的阳光辐射范围。外周香豆素和BODIPY发色团能量可以通过一步直接的方式转移到中央受体若丹明。香豆素部分的能量也可以转移到BODIPY单元，然后通过两步顺序的方式转移到罗丹明核心。通过两种不同的方法确定，香豆素部分和BODIPY单元对CRB中若丹明核心的效率都很高。
• Construction of a FRET-based ratiometric fluorescent thiol probe
  作者：Lingliang Long、Weiying Lin、Bingbing Chen、Wensha Gao、Lin Yuan

  DOI：10.1039/c0cc03806g

  日期：——

  We have rationally constructed a novel FRET-based ratiometric thiol probe suitable for ratiometric imaging in living cells based on the native chemical ligation reaction.

  我们理性地构建了一种新的基于FRET的比率型硫醇探针，适用于活细胞中的比率成像，基于源生化配接反应。
• Design of a binuclear Ni(II)–iminodiacetic acid (IDA) complex for selective recognition and covalent labeling of His-tag fused proteins
  作者：Ikuko Takahira、Hirokazu Fuchida、Shigekazu Tabata、Naoya Shindo、Shohei Uchinomiya、Itaru Hamachi、Akio Ojida

  DOI：10.1016/j.bmcl.2014.04.096

  日期：2014.7

  Selective protein labeling with a small molecular probe is a versatile method for elucidating protein functions under live-cell conditions. In this Letter, we report the design of the binuclear Ni(II)–iminodiacetic acid (IDA) complex for selective recognition and covalent labeling of His-tag-fused proteins. We found that the Ni(II)–IDA complex 1-2Ni(II) binds to the His6-tag (HHHHHH) with a strong

  用小分子探针进行选择性蛋白质标记是阐明活细胞条件下蛋白质功能的通用方法。在这封信中，我们报告了双核Ni（II）-亚氨基二乙酸（IDA）复合物的设计，该复合物用于选择性识别和共价标记His-tag融合蛋白。我们发现，Ni（II）–IDA配合物1 -2Ni（II）以很强的结合亲和力（K d  = 24 nM）与His6-tag（HHHHHH）结合，其值比H（-）高16倍。常规Ni（II）–NTA络合物（K d = 390 nM）。Ni（II）-IDA复合物的强结合亲和力已成功用于位于活细胞表面的His-tag融合GPCR（G蛋白偶联受体）的共价标记和荧光生物成像。