biotinoylaminopropyltriethoxysilane | 863118-16-5

• 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: biotinoylaminopropyltriethoxysilane
• 英文别名: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(3-triethoxysilylpropyl)pentanamide
• CAS: 863118-16-5
• 化学式: C₁₉H₃₇N₃O₅SSi
• 分子量: 447.671
• InChiKey: QCONGHIIFTWTGG-BQFCYCMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  biotinoylaminopropyltriethoxysilane 在 [¹⁸F]fluoride 、 potassium hydride 作用下， 反应 0.83h， 生成
  参考文献：
  名称：

  Arylfluoroborates and Alkylfluorosilicates as Potential PET Imaging Agents:  High-Yielding Aqueous Biomolecular ¹⁸F-Labeling

  摘要：

  Organometalloid compositions of silicon and boron permit rapid, high-yielding, one-step radiolabeling of a covalently linked protein ligand (biotin) under aqueous conditions to give the corresponding alkyltetrafluorosilicates and aryltrifluoroborate salts. Biotin was chosen as a test ligand for protein targeting because of its quantitative interaction with avidin, which in turn allowed us to calculate fluoridation yields that approach 80-100%. The silicate was found to be moderately stable to hydrolysis, whereas the borate appears to be so stable that its hydrolytic decomposition was not readily measured. With the stability of both compounds ascertained, this work describes a novel and robust radiolabeling method that may find use in the development of positron emission tomography radiopharmaceuticals.

  DOI：

  10.1021/ja053293a
• 作为产物：
  描述：

  D-生物素 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 biotinoylaminopropyltriethoxysilane
  参考文献：
  名称：

  Arylfluoroborates and Alkylfluorosilicates as Potential PET Imaging Agents:  High-Yielding Aqueous Biomolecular ¹⁸F-Labeling

  摘要：

  Organometalloid compositions of silicon and boron permit rapid, high-yielding, one-step radiolabeling of a covalently linked protein ligand (biotin) under aqueous conditions to give the corresponding alkyltetrafluorosilicates and aryltrifluoroborate salts. Biotin was chosen as a test ligand for protein targeting because of its quantitative interaction with avidin, which in turn allowed us to calculate fluoridation yields that approach 80-100%. The silicate was found to be moderately stable to hydrolysis, whereas the borate appears to be so stable that its hydrolytic decomposition was not readily measured. With the stability of both compounds ascertained, this work describes a novel and robust radiolabeling method that may find use in the development of positron emission tomography radiopharmaceuticals.

  DOI：

  10.1021/ja053293a

文献信息

• Environmentally Responsive Dual-Targeting Nanoparticles: Improving Drug Accumulation in Cancer Cells as a Way of Preventing Anticancer Drug Efflux
  作者：Cenk Daglioglu

  DOI：10.1016/j.xphs.2017.10.029

  日期：2018.3

  Drug targeting and stimuli-responsive drug release are 2 active areas of cancer research and hold tremendous potential in the management of cancer drug resistance. In this study, I addressed this issue and focused on the synthesis and characterization of pH-responsive Fe3O4@SiO2(FITC)-BTN/folic acid/DOX multifunctional nanoparticles aiming to increase drug accumulation in malignancies with both dual active targeting and endosomal drug release properties. Dye-doped silica magnetic-fluorescent composite was constructed by a simple coprecipitation of Fe+2/Fe+3 salts followed by sol-gel formation and dual-targeting function was obtained by conjugating folate and biotin moieties on the silica surface of nanoparticles via an esterification reaction. Doxorubicin was then successfully attached on the amine-functionalized nanoparticles using a pH-sensitive Schiff-base formation. The physicochemical characterization of the structure was performed by dynamic light scattering, zeta potential measurement, X-ray diffraction, Fourier transform infrared spectroscopy, electron microscopy techniques, and an in vitro pH-dependent release study. Cellular uptake and cytotoxicity experiments demonstrated an enhanced intracellular delivery and reduction of cancer cell viability in the cervical carcinoma HeLa cell line. Furthermore, proapoptotic studies showed that the nanoparticles increased the apoptotic rates within the same cancer cells. The preliminary cell tests confirm the potential of these multifunctional nanoparticles against the development of drug resistance in cancer cells. (c) 2018 American Pharmacists Association (R). Published by Elsevier Inc. All rights reserved.
• Arylfluoroborates and Alkylfluorosilicates as Potential PET Imaging Agents:  High-Yielding Aqueous Biomolecular ¹⁸F-Labeling
  作者：Richard Ting、Michael J. Adam、Thomas J. Ruth、David M. Perrin

  DOI：10.1021/ja053293a

  日期：2005.9.28

  Organometalloid compositions of silicon and boron permit rapid, high-yielding, one-step radiolabeling of a covalently linked protein ligand (biotin) under aqueous conditions to give the corresponding alkyltetrafluorosilicates and aryltrifluoroborate salts. Biotin was chosen as a test ligand for protein targeting because of its quantitative interaction with avidin, which in turn allowed us to calculate fluoridation yields that approach 80-100%. The silicate was found to be moderately stable to hydrolysis, whereas the borate appears to be so stable that its hydrolytic decomposition was not readily measured. With the stability of both compounds ascertained, this work describes a novel and robust radiolabeling method that may find use in the development of positron emission tomography radiopharmaceuticals.