1-[[2-(13,15-Dioxa-14-boradispiro[5.0.57.36]pentadecan-14-yl)phenyl]methyl]-1,4,7,10-tetrazacyclododecane | 1345693-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[[2-(13,15-Dioxa-14-boradispiro[5.0.57.36]pentadecan-14-yl)phenyl]methyl]-1,4,7,10-tetrazacyclododecane
• 英文别名: 1-[[2-(13,15-dioxa-14-boradispiro[5.0.57.36]pentadecan-14-yl)phenyl]methyl]-1,4,7,10-tetrazacyclododecane
• CAS: 1345693-26-6
• 化学式: C₂₇H₄₅BN₄O₂
• 分子量: 468.491
• InChiKey: ZQKFCJRAMWMBPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  57.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[(2-boronophenyl)methyl]-4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane 在 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-[[2-(13,15-Dioxa-14-boradispiro[5.0.57.36]pentadecan-14-yl)phenyl]methyl]-1,4,7,10-tetrazacyclododecane
  参考文献：
  名称：

  用于硼中子俘获疗法的含硼大环多胺及其锌 (II) 配合物的设计、合成和生物学评价

  摘要：

  硼中子俘获疗法 (BNCT) 是一种基于结合使用含硼 10 ( 10 B)的癌症特异性药物和热中子辐射的癌症治疗的二元治疗方法。对于成功的 BNCT，需要在癌细胞中特异性地积累10个含 B 分子，因为产生的重粒子的破坏作用基本上仅限于含硼细胞。在此，我们报告了用 9、12 和 15 元大环多胺及其 Zn 2+功能化的硼化合物的设计和合成复合体。还报道了它们的细胞毒性、癌细胞和正常细胞的细胞内摄取活性以及 BNCT 效应。实验数据表明，单质子和/或双质子化形式的无金属 [12]aneN 4 - 和 [15]aneN 5 - 型配体被癌细胞吸收，它们与细胞内金属如 Zn 2+的复合物会诱导热中子辐照后的细胞死亡，可能是通过与 DNA 的相互作用。

  DOI：

  10.1021/acs.jmedchem.1c00445

文献信息

• ¹¹B NMR Sensing of d-Block Metal Ions in Vitro and in Cells Based on the Carbon–Boron Bond Cleavage of Phenylboronic Acid-Pendant Cyclen (Cyclen = 1,4,7,10-Tetraazacyclododecane)
  作者：Masanori Kitamura、Toshihiro Suzuki、Ryo Abe、Takeru Ueno、Shin Aoki

  DOI：10.1021/ic201507q

  日期：2011.11.21

  Noninvasive magnetic resonance imaging (MRI) including the "chemical shift imaging (CSI)" technique based on H-1 NMR signals is a powerful method for the in vivo imaging of intracellular molecules and for monitoring various biological events. However, it has the drawback of low resolution because of background signals from intrinsic water protons. On the other hand, it is assumed that the B-11 NMR signals which can be applied to a CSI technique have certain advantages, since boron is an ultratrace element in animal cells and tissues. In this manuscript, we report on the sensing of biologically indispensable d-block metal cations such as zinc, copper, iron, cobalt, manganese, and nickel based on B-11 NMR signals of simple phenylboronic acid-pendant cyclen (cyclen = 1,4,7,10-tetraazacyclododecane), L-6 and L-7, in aqueous solution at physiological pH. The results indicate that the carbon-boron bond of L-6 is cleaved upon the addition of Zn2+ and the broad B-11 NMR signal of L-6 at 31 ppm is shifted upfield to 19 ppm, which corresponds to the signal of B(OH)(3). H-1 NMR, X-ray single crystal structure analysis, and UV absorption spectra also provide support for the carbon-boron bond cleavage of ZnL6. Because the cellular uptake of L-6 was very small, a more cell-membrane permeable ligand containing the boronic acid ester L-7 was synthesized and investigated for the sensing of d-block metal ions using B-11 NMR. Data on B-11 NMR sensing of Zn2+ in Jurkat T cells using L-7 is also presented.
• Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy
  作者：Hiroki Ueda、Minoru Suzuki、Reiko Kuroda、Tomohiro Tanaka、Shin Aoki

  DOI：10.1021/acs.jmedchem.1c00445

  日期：2021.6.24

  Boron neutron capture therapy (BNCT) is a binary therapeutic method for cancer treatment based on the use of a combination of a cancer-specific drug containing boron-10 (10B) and thermal neutron irradiation. For successful BNCT, 10B-containing molecules need to accumulate specifically in cancer cells, because destructive effect of the generated heavy particles is limited basically to boron-containing

  硼中子俘获疗法 (BNCT) 是一种基于结合使用含硼 10 ( 10 B)的癌症特异性药物和热中子辐射的癌症治疗的二元治疗方法。对于成功的 BNCT，需要在癌细胞中特异性地积累10个含 B 分子，因为产生的重粒子的破坏作用基本上仅限于含硼细胞。在此，我们报告了用 9、12 和 15 元大环多胺及其 Zn 2+功能化的硼化合物的设计和合成复合体。还报道了它们的细胞毒性、癌细胞和正常细胞的细胞内摄取活性以及 BNCT 效应。实验数据表明，单质子和/或双质子化形式的无金属 [12]aneN 4 - 和 [15]aneN 5 - 型配体被癌细胞吸收，它们与细胞内金属如 Zn 2+的复合物会诱导热中子辐照后的细胞死亡，可能是通过与 DNA 的相互作用。