取代基对水溶性隐穴穴醚与氙结合亲和力及溶液行为的影响。
Substituent effects on xenon binding affinity and solution behavior of water-soluble cryptophanes.
机构信息
Department of Chemistry, Biotechnology Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
出版信息
J Am Chem Soc. 2009 Mar 4;131(8):3069-77. doi: 10.1021/ja8100566.
Abstract
A water-soluble triacetic acid cryptophane-A derivative (TAAC) was synthesized and determined by isothermal titration calorimetry and fluorescence quenching assay to have a xenon association constant of 33,000 M(-1) at 293 K, which is the largest value measured for any host molecule to date. Fluorescence lifetime measurements of TAAC in the presence of varying amounts of xenon indicated static quenching by the encapsulated xenon and the presence of a second non-xenon-binding conformer in solution. Acid-base titrations and aqueous NMR spectroscopy of TAAC and a previously synthesized tris(triazole propionic acid) cryptophane-A derivative (TTPC) showed how solvation of the carboxylate anions can affect the aqueous behavior of the large, nonpolar cryptophane. Specifically, whereas only the crown-crown conformer of TTPC was observed, a crown-saddle conformer of TAAC was also assigned in aqueous solution.
摘要
一种水溶性三乙酸 cryptophane-A 衍生物（TAAC）被合成，并通过等温热滴定法和荧光猝灭法测定，其在 293 K 时的 xenon 缔合常数为 33,000 M(-1)，这是迄今为止测量到的任何主体分子的最大值。在不同 xenon 浓度下的 TAAC 的荧光寿命测量表明，被包裹的 xenon 发生静态猝灭，并且在溶液中存在第二种非 xenon 结合构象。TAAC 和先前合成的三（三唑丙酸） cryptophane-A 衍生物（TTPC）的酸碱滴定和水相 NMR 光谱表明，羧酸根阴离子的溶剂化如何影响大的非极性 cryptophane 的水相行为。具体而言，尽管仅观察到 TTPC 的冠-冠构象，但在水溶液中还分配到了 TAAC 的冠-鞍构象。
相似文献
1
Substituent effects on xenon binding affinity and solution behavior of water-soluble cryptophanes.取代基对水溶性隐穴穴醚与氙结合亲和力及溶液行为的影响。
J Am Chem Soc. 2009 Mar 4;131(8):3069-77. doi: 10.1021/ja8100566.
2
Utilizing a water-soluble cryptophane with fast xenon exchange rates for picomolar sensitivity NMR measurements.利用具有快速氙气交换率的水溶性隐色 cryptophane 实现皮摩尔灵敏度的 NMR 测量。
Anal Chem. 2012 Nov 20;84(22):9935-41. doi: 10.1021/ac302347y. Epub 2012 Nov 6.
3
Measurement of radon and xenon binding to a cryptophane molecular host.测量氡和氙与笼形分子主体的结合。
Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):10969-73. doi: 10.1073/pnas.1105227108. Epub 2011 Jun 20.
4
Effect of pH and counterions on the encapsulation properties of xenon in water-soluble cryptophanes.pH 值和抗衡离子对水溶性隐穴醚包封氙的影响。
Chemistry. 2010 Nov 15;16(43):12941-6. doi: 10.1002/chem.201001170.
5
Monomeric Cryptophane with Record-High Xe Affinity Gives Insights into Aggregation-Dependent Sensing.具有创纪录高氙亲和力的单体隐藻素为聚集依赖性传感提供了见解。
Anal Chem. 2021 Jan 26;93(3):1507-1514. doi: 10.1021/acs.analchem.0c03776. Epub 2020 Dec 28.
6
Synthesis of Cryptophanes with Two Different Reaction Sites: Chemical Platforms for Xenon Biosensing.具有两个不同反应位点的穴番合成：用于氙生物传感的化学平台
J Org Chem. 2015 Jun 19;80(12):6143-51. doi: 10.1021/acs.joc.5b00653. Epub 2015 Jun 10.
7
Dendronized cryptophanes as water-soluble xenon hosts for (129)Xe magnetic resonance imaging.树枝状隐烷作为水溶性氙气主体用于（129）Xe 磁共振成像。
Org Lett. 2014 Sep 5;16(17):4436-9. doi: 10.1021/ol501951z. Epub 2014 Aug 25.
8
Water soluble cucurbit[6]uril derivative as a potential Xe carrier for 129Xe NMR-based biosensors.水溶性葫芦[6]脲衍生物作为基于129Xe核磁共振的生物传感器的潜在氙载体。
Chem Commun (Camb). 2008 Jun 28(24):2756-8. doi: 10.1039/b805724a. Epub 2008 May 19.
9
-Cryptophanes: macrocyclic compounds with optimized characteristics for the design of Xe NMR-based biosensors.隐色烷：具有优化特性的大环化合物，可用于设计基于 Xe NMR 的生物传感器。
Phys Chem Chem Phys. 2022 Oct 19;24(40):24793-24799. doi: 10.1039/d2cp03714a.
10
Scalable synthesis of cryptophane-1.1.1 and its functionalization.可扩展合成隐色烯-1.1.1 及其功能化。
Org Lett. 2010 Mar 5;12(5):960-2. doi: 10.1021/ol902952h.
引用本文的文献
1
Counteranions at Peripheral Sites Tune Guest Affinity for a Protonated Hemicryptophane.外围位置的抗衡离子调节质子化半穴醚客体的亲和性。
J Org Chem. 2022 Apr 15;87(8):5158-5165. doi: 10.1021/acs.joc.1c03128. Epub 2022 Mar 25.
2
Cryptophane-xenon complexes for Xe MRI applications.用于氙磁共振成像应用的隐窝素-氙配合物。
RSC Adv. 2021;11(13):7693-7703. doi: 10.1039/d0ra10765d. Epub 2021 Feb 17.
3
Mapping of Absolute Host Concentration and Exchange Kinetics of Xenon Hyper-CEST MRI Agents.氙气超极化化学交换饱和转移磁共振成像剂的绝对宿主浓度及交换动力学映射
Pharmaceuticals (Basel). 2021 Jan 21;14(2):79. doi: 10.3390/ph14020079.
4
Monomeric Cryptophane with Record-High Xe Affinity Gives Insights into Aggregation-Dependent Sensing.具有创纪录高氙亲和力的单体隐藻素为聚集依赖性传感提供了见解。
Anal Chem. 2021 Jan 26;93(3):1507-1514. doi: 10.1021/acs.analchem.0c03776. Epub 2020 Dec 28.
5
Decacationic Pillar[5]arene: A New Scaffold for the Development of Xe MRI Imaging Agents.十阳离子柱[5]芳烃：一种用于开发氙磁共振成像剂的新型支架。
ACS Omega. 2020 Oct 20;5(43):27783-27788. doi: 10.1021/acsomega.0c02565. eCollection 2020 Nov 3.
6
Molecular Sensing with Host Systems for Hyperpolarized Xe.基于宿主体系的超极化氙分子传感
Molecules. 2020 Oct 11;25(20):4627. doi: 10.3390/molecules25204627.
7
Ultrasound Responsive Noble Gas Microbubbles for Applications in Image-Guided Gas Delivery.用于图像引导气体输送的超声响应性稀有气体微泡
Adv Healthc Mater. 2020 May;9(9):e1901721. doi: 10.1002/adhm.201901721. Epub 2020 Mar 24.
8
Xe affinities of water-soluble cryptophanes and the role of confined water.水溶性穴番的氙亲和力及受限水的作用
Chem Sci. 2015 Dec 1;6(12):7238-7248. doi: 10.1039/c5sc02401c. Epub 2015 Sep 22.
9
Cryptophane Nanoscale Assemblies Expand Xe NMR Biosensing.隐色烷纳米级组装体扩展 Xe NMR 生物传感。
Anal Chem. 2018 Jun 19;90(12):7730-7738. doi: 10.1021/acs.analchem.8b01630. Epub 2018 Jun 1.
10
A cryptophane-based "turn-on" Xe NMR biosensor for monitoring calmodulin.一种用于监测钙调蛋白的基于隐藻素的“开启型”氙核磁共振生物传感器。
Org Biomol Chem. 2017 Oct 31;15(42):8883-8887. doi: 10.1039/c7ob02391j.
本文引用的文献
1
Sensitivity and multiplexing capabilities of MRI based on polarized 129Xe biosensors.基于极化129Xe生物传感器的MRI的灵敏度和多重检测能力。
J Am Chem Soc. 2008 Dec 10;130(49):16456-7. doi: 10.1021/ja805274u.
2
Cryptophane xenon-129 nuclear magnetic resonance biosensors targeting human carbonic anhydrase.靶向人类碳酸酐酶的隐藻素-氙-129核磁共振生物传感器。
J Am Chem Soc. 2009 Jan 21;131(2):563-9. doi: 10.1021/ja806092w.
3
Cryptophanes and their complexes--present and future.隐窝素及其配合物——现状与未来。
Chem Rev. 2009 Jan;109(1):88-130. doi: 10.1021/cr0680437.
4
Cryptophane-xenon complexes in organic solvents observed through NMR spectroscopy.通过核磁共振光谱法观察到的有机溶剂中的隐窝蛋白 - 氙配合物。
J Phys Chem A. 2008 Nov 13;112(45):11363-72. doi: 10.1021/jp807425t. Epub 2008 Oct 17.
5
Water soluble cucurbit[6]uril derivative as a potential Xe carrier for 129Xe NMR-based biosensors.水溶性葫芦[6]脲衍生物作为基于129Xe核磁共振的生物传感器的潜在氙载体。
Chem Commun (Camb). 2008 Jun 28(24):2756-8. doi: 10.1039/b805724a. Epub 2008 May 19.
6
Structure of a 129Xe-cryptophane biosensor complexed with human carbonic anhydrase II.与人类碳酸酐酶II复合的129Xe-隐色团生物传感器的结构
J Am Chem Soc. 2008 Jun 4;130(22):6942-3. doi: 10.1021/ja802214x. Epub 2008 May 8.
7
A cryptophane core optimized for xenon encapsulation.一种针对氙气封装进行优化的穴状配体核心。
J Am Chem Soc. 2007 Aug 29;129(34):10332-3. doi: 10.1021/ja073771c. Epub 2007 Aug 3.
8
Thermodynamics of xenon binding to cryptophane in water and human plasma.氙在水和人体血浆中与穴醚结合的热力学
J Am Chem Soc. 2007 Aug 1;129(30):9262-3. doi: 10.1021/ja072965p. Epub 2007 Jul 7.
9
Gas hosting in enantiopure self-assembled oximes.对映体纯自组装肟中的气体容纳
Angew Chem Int Ed Engl. 2007;46(26):4972-5. doi: 10.1002/anie.200701123.
10
Hydrophobic encapsulation of hydrocarbon gases.烃类气体的疏水封装。
Org Lett. 2007 Apr 26;9(9):1753-5. doi: 10.1021/ol070465v. Epub 2007 Mar 30.
Zotero 插件