[3-propargyloxy-4-(2-iodoethoxy)phenyl]methanol | 914095-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [3-propargyloxy-4-(2-iodoethoxy)phenyl]methanol
• 英文别名: [4-(2-iodoethoxy)-3-prop-2-ynoxyphenyl]methanol
• CAS: 914095-36-6
• 化学式: C₁₂H₁₃IO₃
• 分子量: 332.138
• InChiKey: HFFHMHQYNDZNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-propargyloxy-4-(2-iodoethoxy)phenyl]methanol 在 高氯酸 、 caesium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成 tripropargyl cryptophane-A
  参考文献：
  名称：

  Thermodynamics of Xenon Binding to Cryptophane in Water and Human Plasma

  摘要：

  Xenon-129 biosensors offer an attractive alternative to conventional MRI contrast agents due to the chemical shift sensitivity and large nuclear magnetic resonance signal of hyperpolarized Xe-129. Here we report the use of fluorescence spectroscopy and isothermal titration calorimetry (ITC) to determine xenon binding affinity and thermodynamics with a water-soluble triacid-cryptophane-A (1). 1 was synthesized in 10 steps with a 4% overall yield. Fluorescence spectroscopy measured an association constant of (1.7 +/- 0.2) x 10(4) M-1 in phosphate buffer at 293 K. ITC measurements at 293 and 310 K yielded association constants of (1.73 +/- 0.17) x 10(4) and (3.01 +/- 0.26) x 10(4) M-1 and indicated a large entropic contribution to xenon binding in water. On the basis of these data, cryptophane 1 showed roughly 2-fold higher affinity for xenon than any previously measured compound. Remarkably, ITC measurements in human plasma at 310 K gave a similar binding constant, K-A = (2.19 +/- 0.22) x 10(4) M-1, which supports the development of Xe-129 NMR biosensors for biological applications.

  DOI：

  10.1021/ja072965p
• 作为产物：
  描述：

  4-hydroxy-3-(prop-2-yn-1-yloxy)benzaldehyde 在 sodium tetrahydroborate 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.17h， 生成 [3-propargyloxy-4-(2-iodoethoxy)phenyl]methanol
  参考文献：
  名称：

  WO2008/27162

  摘要：

  公开号：

文献信息

• “Clickable” Hydrosoluble PEGylated Cryptophane as a Universal Platform for¹²⁹Xe Magnetic Resonance Imaging Biosensors
  作者：Léa Delacour、Naoko Kotera、Ténin Traoré、Sébastien Garcia-Argote、Céline Puente、François Leteurtre、Edmond Gravel、Nawal Tassali、Céline Boutin、Estelle Léonce、Yves Boulard、Patrick Berthault、Bernard Rousseau

  DOI：10.1002/chem.201204218

  日期：2013.5.3

  We describe the synthesis of a highly water‐soluble cryptophane 1 that can be seen as a universal platform for the construction of 129Xe magnetic resonance imaging (MRI)‐based biosensors. Compound 1 is easily functionalized by Huisgen cycloaddition and exhibits excellent xenon‐encapsulation properties. In addition, 1 is nontoxic at the concentrations typically used for hyperpolarized 129Xe MRI.

  我们描述了高度水溶性隐身蛋白1的合成，该蛋白可被视为构建基于129 Xe磁共振成像（MRI）的生物传感器的通用平台。化合物1易于通过Huisgen环加成功能化，并具有出色的氙气封装性能。此外，1在超极化129 Xe MRI通常使用的浓度下是无毒的。
• 129Xe BIOSENSORS AND THEIR USE
  申请人：Dmochowski Ivan

  公开号：US20110104075A1

  公开（公告）日：2011-05-05

  This invention relates to enzyme-sensitive biosensors and methods and kits using the same. Specifically, the invention relates to methods, systems and kits for the detection of enzymes using the chemical shift observed in an isotope complexed to the biosensor resulting from a change in the biosensor as the result of the enzyme's activity.

  本发明涉及酶敏感生物传感器及其使用的方法和试剂盒。具体而言，本发明涉及使用同位素与生物传感器相结合所观察到的化学位移来检测酶的方法、系统和试剂盒，该化学位移是由于酶的活性导致生物传感器发生变化所致。
• 129Xe biosensors and their use
  申请人：Dmochowski Ivan

  公开号：US08470587B2

  公开（公告）日：2013-06-25

  This invention relates to enzyme-sensitive biosensors and methods and kits using the same. Specifically, the invention relates to methods, systems and kits for the detection of enzymes using the chemical shift observed in an isotope complexed to the biosensor resulting from a change in the biosensor as the result of the enzyme's activity.

  本发明涉及酶敏感生物传感器，以及使用其的方法和试剂盒。具体而言，本发明涉及使用同位素与生物传感器结合所观察到的化学位移，来检测酶的方法、系统和试剂盒。该化学位移是由于酶的活性导致生物传感器发生变化所引起的。
• Designing ¹²⁹Xe NMR Biosensors for Matrix Metalloproteinase Detection
  作者：Qian Wei、Garry K. Seward、P. Aru Hill、Brian Patton、Ivan E. Dimitrov、Nicholas N. Kuzma、Ivan J. Dmochowski

  DOI：10.1021/ja0640501

  日期：2006.10.1

  Xenon-129 biosensors offer an attractive alternative to conventional MRI contrast agents due to the chemical shift sensitivity and large nuclear magnetic signal of hyperpolarized Xe-129. Here, we report the first enzyme-responsive Xe-129 NMR biosensor. This compound was synthesized in 13 steps by attaching the consensus peptide substrate for matrix metalloproteinase-7 (MMP-7), an enzyme that is upregulated in many cancers, to the xenon-binding organic cage, cryptophane-A. The final coupling step was achieved on solid support in 80-92% yield via a copper (I)-catalyzed [3+2] cycloaddition. In vitro enzymatic cleavage assays were monitored by HPLC and fluorescence spectroscopy. The biosensor was determined to be an excellent substrate for MMP-7 (K-M = 43 mu M, V-max = 1.3 x 10(-8) M s(-1), k(cat)/K-M = 7200 M-1 s(-1)). Enzymatic cleavage of the tryptophan-containing peptide led to a dramatic decrease in Trp fluorescence, lambda(max) = 358 nm. Stern-Volmer analysis gave an association constant of 9000 +/- 1000 M-1 at 298 K between the cage and Trp-containing hexapeptide under enzymatic assay conditions. Most promisingly, Xe-129 NMR spectroscopy distinguished between the intact and cleaved biosensors with a 0.5 ppm difference in chemical shift. This difference most likely reflected a change in the electrostatic environment of Xe-129, caused by the cleavage of three positively charged residues from the C-terminus. This work provides guidelines for the design and application of new enzyme-responsive Xe-129 NMR biosensors.
• US8470587B2
  申请人：——

  公开号：US8470587B2

  公开（公告）日：2013-06-25