BODIPY-FL N-(2-aminoethyl)maleinimide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: BODIPY-FL N-(2-aminoethyl)maleinimide
• 英文别名: B-10250；BODIPY maleimide；BDP FL maleimide；3-(2,2-difluoro-10,12-dimethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-4-yl)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]propanamide
• 化学式: C₂₀H₂₁BF₂N₄O₃
• 分子量: 414.22
• InChiKey: OEMKXDGSMCHMJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  美登素 、 BODIPY-FL N-(2-aminoethyl)maleinimide 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Maytansinoid–BODIPY Conjugates: Application to Microscale Determination of Drug Extinction Coefficients and for Quantification of Maytansinoid Analytes

  摘要：

  Determining drug to antibody ratios (DAR) for antibody-drug conjugates (ADCs) in early research and development can be hampered by difficulties in accurate weighing of the effector payload and subsequent determination of its extinction coefficient. Two maytansinoids, DM1 and DM4, potent antimitotic agents used in clinical ADCs, were derivatized with the compact fluorophore BODIPY FL using two different linker designs. We identified DM1-mal-BODIPY as a conjugate with little through-space interaction between the maytansinoid and BODIPY chromophores. The 1:1 stoichiometry between the maytansinoid and BODIPY makes the molar concentration of both components equal and the extinction coefficient of the maytansinoid in proportion with the known BODIPY chromophore according to Beer's Law. By only derivatizing 50 mu g of unpurified DM1 and analyzing about 25 mu g of DM1-mal-BODIPY by UV-vis, we determined epsilon(DM1) (252 nm) and epsilon(DM1) (280 nm) as 26 355 +/- 360 and 5230 +/- 160 cm(-1) M-1, respectively. These values are nearly identical to those accepted for DM1 based on weighing >100 mg of pure sample. Surprisingly, some of the maytansinoid-BODIPY conjugates that were synthesized were partially or completely fluorescence-quenched. The green fluorescence of quenched DM4-acetamide-BODIPY could be fully restored in the presence of an antibody designed to tightly bind maytansine. We exploited this observation to develop a simple "mix and read" fluorogenic immunoassay for detection of nanogram quantities of maytansinoids.

  DOI：

  10.1021/mp500843r

文献信息

• PSMA BINDING LIGAND-LINKER CONJUGATES AND METHODS FOR USING
  申请人：Purdue Research Foundation

  公开号：US20160067341A1

  公开（公告）日：2016-03-10

  Described herein are prostate specific membrane antigen (PSMA) binding conjugates that are useful for delivering therapeutic, diagnostic and imaging agents. Also described herein are pharmaceutical composition containing them and methods of using the conjugates and compositions. Also described are processes for manufacture of the conjugates and the compositions containing them.

  本文描述了用于传递治疗、诊断和成像剂的前列腺特异性膜抗原（PSMA）结合共轭物。本文还描述了含有它们的药物组合物以及使用这些共轭物和组合物的方法。还描述了用于制造这些共轭物和含有它们的组合物的过程。
• Efficient Acid-Catalyzed¹⁸F/¹⁹F Fluoride Exchange of BODIPY Dyes
  作者：Edmund J. Keliher、Jenna A. Klubnick、Thomas Reiner、Ralph Mazitschek、Ralph Weissleder

  DOI：10.1002/cmdc.201300506

  日期：2014.7

  the 18F‐labeled BODIPY‐FL fluorophore has emerged as an important platform, but little is known about alternative 18F‐labeling strategies or labeling on red‐shifted fluorophores. In this study we explore acid‐catalyzed 18F/19F exchange on a range of commercially available N‐hydroxysuccinimidyl ester and maleimide BODIPY fluorophores. We show this method to be a simple and efficient 18F‐labeling strategy

  含氟荧光染料是正电子发射断层扫描成像化合物的重要验证剂，因为它们可以通过荧光成像在细胞中轻松验证。特别是18 F 标记的 BODIPY-FL 荧光团已成为一个重要的平台，但对替代18 F 标记策略或红移荧光团的标记知之甚少。在这项研究中，我们探索了一系列市售N-羟基琥珀酰亚胺酯和马来酰亚胺 BODIPY 荧光团的酸催化18 F/ 19 F 交换。我们证明这种方法是一种简单有效的18多种荧光化合物的 F 标记策略，包括 BODIPY 修饰的 PARP-1 抑制剂和胺和硫醇反应性 BODIPY 荧光团。
• Optimization of the cellular import of functionally active SH2-domain-interacting phosphopeptides
  作者：Á. Kertész、G. Váradi、G. K. Tóth、R. Fajka-Boja、É. Monostori、G. Sármay

  DOI：10.1007/s00018-006-6346-6

  日期：2006.11

  Phosphopeptides interacting with src homology 2 (SH2) domains can activate essential signaling enzymes in vitro. When delivered to cells, they may disrupt protein-protein interactions, thereby influencing intracellular signaling. We showed earlier that phosphopeptides corresponding to the inhibitory motif of Fc gamma receptor IIb and a motif of the Grb2-associated binder 1 adaptor protein activate SH2-containing tyrosine phosphatase 2 in vitro. To study the ex vivo effects of these peptides, we have now compared different methods for peptide delivery: (i) permeabilization of the target cells and (ii) the use of cell-permeable vectors, which are potentially able to transport biologically active compounds into B cells. We found octanoyl-Arg(8) to be an optimal carrier for the delivery of phosphopeptides to the cells. With this strategy, the function of cell-permeable SHP-2-binding phosphopeptides was analyzed. These peptides modulated the protein phosphorylation in B cells in a dose- and time-dependent manner.