N-(+)-biotinylpiperazine | 216655-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N-(+)-biotinylpiperazine
• 英文别名: piperazine biotinamide；(3aS,4S,6aR)-4-(5-oxo-5-piperazin-1-ylpentyl)-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
• CAS: 216655-94-6
• 化学式: C₁₄H₂₄N₄O₂S
• 分子量: 312.436
• InChiKey: CFRIWYIYQFMZQA-GVXVVHGQSA-N

物化性质

• 沸点：
  622.6±55.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  98.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-O-desacetyl-11-O-(hex-5-ynoyl)wortmannin 、 N-(+)-biotinylpiperazine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到
  参考文献：
  名称：

  Intracellular effects of prodrug-like wortmannin probes

  摘要：

  Wortmannin, a known inhibitor of phosphoinositide 3-kinases (PI3Ks), their low selectivity and high toxicity is still problematic and less is known about their effects on PI3Ks in cellular systems. Hence, we have synthesized a series of multifunctional wortmannin probes with the ability to self-activate, by installing a clickable handle at C11 site, and secondary amine and cancer-targeting moiety at C20 site, respectively. MTT assay first confirmed that self-activating probes have better inhibition potency and biotin enhanced their cancer cell uptake. Further experiments showed most of probes can target P13K Akt/mTOR pathway with prolonged turn-over time. Protein profiling and pull-down results were observed that the derivatives not only labelled four PI3Ks with selectivity, but also engaged in covalent interactions with numerous cellular proteins which could be the major reason of their high toxicity. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2018.05.030
• 作为产物：
  描述：

  哌嗪 、 D-生物素 在 氯化亚砜 、 吡啶 作用下， 反应 0.08h， 生成 N-(+)-biotinylpiperazine
  参考文献：
  名称：

  [EN] SUBSTITUTED ARYL-FLUOROBORATES AS IMAGING AGENTS
  [FR] ARYL-FLUOROBORATES SUBSTITUÉS EN TANT QU'AGENTS D'IMAGERIE

  摘要：

  含有至少一个18F原子的取代芳基硼化合物，如公式(I)所示，其中Y1或Y2中至少有一个是18F，A1为取代芳香环，其中G1-5独立地为C或N，芳香环或多环基团（除硼外）的取代基包括至少一个电子吸引基（EWG），前提是当至少一个EWG位于B的正交位置时，芳香环或多环基团的所有取代基的总σ（σ total）约为0.06或更高，或当没有EWG位于B的正交位置时，约为0.2或更高。该化合物包括中性（N = 1）和离子硼酸酯（N = 2）实施例。该化合物可用作正电子发射断层扫描（PET）成像剂。

  公开号：

  WO2009012596A1

文献信息

• A biotin-guided hydrogen sulfide fluorescent probe and its application in living cell imaging
  作者：Chen Zhang、Jiewen Zhang、Zhiqiang Xu、Kun Zang、Feng Liu、Jun Yin、Ying Tan、Yuyang Jiang

  DOI：10.1039/d0ra06524b

  日期：——

  Hydrogen sulfide (H2S), a well-known signaling molecule, exerts significant regulatory effects on the cardiovascular and nervous systems. Therefore, monitoring the metabolism of H2S offers a potential mechanism to detect various diseases. In addition, biotin is significantly used as a targeting group to detect cancer cells exclusively. In this work, a biotin-guided benzoxadizole-based fluorescent probe

  硫化氢（H 2 S）是一种众所周知的信号分子，对心血管和神经系统具有显着的调节作用。因此，监测H 2 S的代谢为检测各种疾病提供了潜在的机制。此外，生物素还被广泛用作专门检测癌细胞的靶向基团。在这项工作中，开发了一种生物素引导的基于苯并恶二唑的荧光探针 NP-生物素，用于 H 2 S 检测，并在正常肝细胞 (LO2) 和肝癌细胞 (HepG2) 系中进行评估。结果表明，NP-生物素可以高灵敏度和选择性地检测细胞H 2 S。而且，在生物素组的指导下，NP-生物素已被证实具有靶向癌细胞的能力。
• Toward [¹⁸F]-Labeled Aryltrifluoroborate Radiotracers: In Vivo Positron Emission Tomography Imaging of Stable Aryltrifluoroborate Clearance in Mice
  作者：Richard Ting、Curtis Harwig、Ulrich auf dem Keller、Siobhan McCormick、Pamela Austin、Christopher M. Overall、Michael J. Adam、Thomas J. Ruth、David M. Perrin

  DOI：10.1021/ja802734t

  日期：2008.9.10

  The use of a boronic ester as a captor of aqueous [(18)F]-fluoride has been previously suggested as a means of labeling biomolecules in one step for positron emission tomography (PET) imaging. For this approach to be seriously considered, the [(18)F]-labeled trifluoroborate should be humorally stable such that it neither leaches free [(18)F]-fluoride to the bone nor accumulates therein. Herein, we

  以前曾建议使用硼酸酯作为 [(18) F]-氟化物水溶液的捕获剂，作为在正电子发射断层扫描 (PET) 成像的一个步骤中标记生物分子的一种手段。为了认真考虑这种方法，[(18)F]-标记的三氟硼酸盐应该是体液稳定的，这样它既不会将游离的 [(18)F]-氟化物浸出到骨骼中，也不会在其中积聚。在此，我们合成了一种生物素化硼酸酯，该酯在 [(18) F] 氟化物水溶液的存在下转化为相应的三氟硼酸盐。与其在 pH 7.5 下的体外水性动力学稳定性保持一致，三氟硼酸盐似乎在体内以稳定的三氟硼酸盐的形式迅速清除到膀胱，而没有可检测到的游离 [(18)F]-氟化物浸出到骨骼中。当这种标记的生物素与抗生物素蛋白预孵育时，所得复合物的药代动力学清除率明显改变。这项工作证实了最初的说法，即硼酸酯可能用作 [(18) F]-PET 试剂的易于标记的前体。
• Substituted Aryl-Fluoroborates as Imaging Agents
  申请人：Perrin David

  公开号：US20100254903A1

  公开（公告）日：2010-10-07

  Substituted aryl-boron compounds comprising at least one 18 F atom, as illustrated by the formula (I), where at least one of Y 1 or Y 2 is 18 F and A 1 is a substituted aromatic ring, with G 1-5 being, independently, C or N, and where the substitutents of the aromatic ring or polycyclic moiety (other than boron) comprise at least one electron-withdrawing group (EWG), providing that sigma total (σ total ) for all substituents on the aromatic ring or polycyclic moiety except B is about 0.06 or more when said at least one EWG is positioned ortho to B, or about 0.2 or more when no EWG is positioned ortho to B. The compounds include neutral (N=1) and ionic borate (N=2) embodiments. The compounds are useful as positron emission tomography (PET) imaging agents.

  含有至少一个18F原子的取代芳基硼化合物，其由公式（I）所示，其中Y1或Y2中至少有一个为18F，A1为取代芳香环，G1-5分别为C或N，且芳香环或多环基团（除硼外）的取代基至少包括一个电子吸引基团（EWG），前提是当至少一个EWG位于B的正交位置时，芳香环或多环基团上所有取代基的总σ（σtotal）约为0.06或更高，或当没有EWG位于B的正交位置时，σtotal约为0.2或更高。该化合物包括中性（N=1）和离子硼酸盐（N=2）的实施例。该化合物可用作正电子发射断层扫描（PET）成像剂。
• A triazene-based new photolabile linker in solid phase chemistry
  作者：Dieter Enders、Christiaan Rijksen、Elke Bremus-Köbberling、Arnold Gillner、Johannes Köbberling

  DOI：10.1016/j.tetlet.2004.02.002

  日期：2004.3

  An extension of the T2 linker methodology by showing its applicability as a photocleavable linker is reported. Photocleavage was carried out with 355 nm UV laser irradiation (3omega Nd-YAG) in methanol/diethyl ether and is suitable for protected amino acid derivatives, as well as simple small organic molecules including resin-bound biotin. The linker is stable under a wide range of conditions with the exception of strongly acidic media. (C) 2004 Elsevier Ltd. All rights reserved.
• US8574546B2
  申请人：——

  公开号：US8574546B2

  公开（公告）日：2013-11-05