Rotaxane-mediated suppression and activation of cucurbit[6]uril for molecular detection by 129 Xe hyperCEST NMR

Finbloom, Joel A.; Slack, Clancy C.; Bruns, Carson J.; Jeong, Keunhong; Wemmer, David E.; Pines, Alexander; Francis, Matthew B.

doi:10.1039/c5cc10410f

Rotaxane-mediated suppression and activation of cucurbit[6]uril for molecular detection by ¹²⁹ Xe hyperCEST NMR

Journal Article · Fri Jan 15 04:00:00 EST 2016 · ChemComm

DOI:https://doi.org/10.1039/c5cc10410f· OSTI ID:1378760

Finbloom, Joel A. ^[1]; Slack, Clancy C. ^[2]; Bruns, Carson J. ^[1]; Jeong, Keunhong ^[2]; Wemmer, David E. ^[3]; Pines, Alexander ^[2]; Francis, Matthew B. ^[2]

Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Science Division
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Physical Biosciences Division

Here, we report a method for blocking interactions between ¹²⁹Xe and cucurbit[6]uril (CB6) until activation by a specific chemical event. We then synthesized a CB6-rotaxane that allowed no ¹²⁹Xe interaction with the CB6 macrocycle component until a cleavage event released the CB6, which then produced a ¹²⁹ Xe@CB6 NMR signal. This contrast-upon-activation ¹²⁹Xe NMR platform allows for modular synthesis and can be expanded to applications in detection and disease imaging.

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

DOE Contract Number:: AC02-05CH11231

OSTI ID:: 1378760

Journal Information:: ChemComm, Journal Name: ChemComm Journal Issue: 15 Vol. 52; ISSN CHCOFS; ISSN 1359-7345

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (30)

Molecular Imaging of Cancer Cells Using a Bacteriophage-Based ¹²⁹ Xe NMR Biosensor Palaniappan, Krishnan K.; Ramirez, R. Matthew; Bajaj, Vikram S. Angewandte Chemie International Edition, Vol. 52, Issue 18 https://doi.org/10.1002/anie.201300170	journal	March 2013
Cryptophane-Folate Biosensor for ¹²⁹Xe NMR Khan, Najat S.; Riggle, Brittany A.; Seward, Garry K. Bioconjugate Chemistry, Vol. 26, Issue 1 https://doi.org/10.1021/bc5005526	journal	December 2014
Water soluble cucurbit[6]uril derivative as a potential Xe carrier for 129Xe NMR-based biosensors Kim, Byoung Soo; Ko, Young Ho; Kim, Youngkook Chemical Communications, Issue 24 https://doi.org/10.1039/b805724a	journal	January 2008
Design and characterization of a new irreversible responsive PARACEST MRI contrast agent that detects nitric oxide Liu, Guanshu; Li, Yuguo; Pagel, Mark D. Magnetic Resonance in Medicine, Vol. 58, Issue 6 https://doi.org/10.1002/mrm.21428	journal	November 2007
Supramolecular Assays for Mapping Enzyme Activity by Displacement-Triggered Change in Hyperpolarized ¹²⁹ Xe Magnetization Transfer NMR Spectroscopy Schnurr, Matthias; Sloniec-Myszk, Jagoda; Döpfert, Jörg Angewandte Chemie International Edition, Vol. 54, Issue 45 https://doi.org/10.1002/anie.201507002	journal	October 2015
Comprehensive Synthesis of Monohydroxy–Cucurbit[n]urils (n = 5, 6, 7, 8): High Purity and High Conversions Ayhan, Mehmet M.; Karoui, Hakim; Hardy, Micaël Journal of the American Chemical Society, Vol. 137, Issue 32 https://doi.org/10.1021/jacs.5b04553	journal	August 2015
Optimization of Xenon Biosensors for Detection of Protein Interactions Lowery, Thomas J.; Garcia, Sandra; Chavez, Lana ChemBioChem, Vol. 7, Issue 1 https://doi.org/10.1002/cbic.200500327	journal	December 2005
Cucurbituril chemistry: a tale of supramolecular success Masson, Eric; Ling, Xiaoxi; Joseph, Roymon RSC Adv., Vol. 2, Issue 4 https://doi.org/10.1039/C1RA00768H	journal	January 2012
Genetically encoded reporters for hyperpolarized xenon magnetic resonance imaging Shapiro, Mikhail G.; Ramirez, R. Matthew; Sperling, Lindsay J. Nature Chemistry, Vol. 6, Issue 7 https://doi.org/10.1038/nchem.1934	journal	April 2014
A cell-permeable gadolinium contrast agent for magnetic resonance imaging of copper in a Menkes disease model Que, Emily L.; New, Elizabeth J.; Chang, Christopher J. Chemical Science, Vol. 3, Issue 6 https://doi.org/10.1039/c2sc20273e	journal	January 2012
Tunable solid-state fluorescent materials for supramolecular encryption Hou, Xisen; Ke, Chenfeng; Bruns, Carson J. Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms7884	journal	April 2015
Catalysis by cucurbituril. The significance of bound-substrate destabilization for induced triazole formation Mock, William L.; Irra, Ted A.; Wepsiec, James P. The Journal of Organic Chemistry, Vol. 54, Issue 22 https://doi.org/10.1021/jo00283a024	journal	October 1989
Promising strategies for Gd-based responsive magnetic resonance imaging contrast agents Shen, Clara; New, Elizabeth J. Current Opinion in Chemical Biology, Vol. 17, Issue 2 https://doi.org/10.1016/j.cbpa.2012.10.031	journal	April 2013
Cucurbit[6]uril is an ultrasensitive ¹²⁹ Xe NMR contrast agent Wang, Yanfei; Dmochowski, Ivan J. Chemical Communications, Vol. 51, Issue 43 https://doi.org/10.1039/C5CC01826A	journal	January 2015
Redox-responsive branched-bottlebrush polymers for in vivo MRI and fluorescence imaging Sowers, Molly A.; McCombs, Jessica R.; Wang, Ying Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6460	journal	November 2014
Molecular Imaging Using a Targeted Magnetic Resonance Hyperpolarized Biosensor Schroder, L.; Lowery, T. J.; Hilty, C. Science, Vol. 314, Issue 5798 https://doi.org/10.1126/science.1131847	journal	October 2006
Mechanism of Host−Guest Complexation by Cucurbituril Márquez, César; Hudgins, Robert R.; Nau, Werner M. Journal of the American Chemical Society, Vol. 126, Issue 18 https://doi.org/10.1021/ja0319846	journal	April 2004
A Hydrogen Peroxide-Responsive Hyperpolarized ¹³ C MRI Contrast Agent Lippert, Alexander R.; Keshari, Kayvan R.; Kurhanewicz, John Journal of the American Chemical Society, Vol. 133, Issue 11 https://doi.org/10.1021/ja111589a	journal	March 2011
Designing ¹²⁹ Xe NMR Biosensors for Matrix Metalloproteinase Detection Wei, Qian; Seward, Garry K.; Hill, P. Aru Journal of the American Chemical Society, Vol. 128, Issue 40 https://doi.org/10.1021/ja0640501	journal	October 2006
The synthesis of [2], [3] and [4]rotaxanes and semirotaxanes Tuncel, Dönüs; Steinke, Joachim H. G. Chemical Communications, Issue 5 https://doi.org/10.1039/b109256c	journal	January 2002
Bioresponsive, Cell-Penetrating, and Multimeric MR Contrast Agents Major, Jody L.; Meade, Thomas J. Accounts of Chemical Research, Vol. 42, Issue 7 https://doi.org/10.1021/ar800245h	journal	July 2009
Live-cell MRI with Xenon Hyper-CEST Biosensors Targeted to Metabolically Labeled Cell-Surface Glycans Witte, Christopher; Martos, Vera; Rose, Honor May Angewandte Chemie International Edition, Vol. 54, Issue 9 https://doi.org/10.1002/anie.201410573	journal	February 2015
Hyperpolarized xenon in NMR and MRI Oros, Ana-Maria; Shah, N. Jon Physics in Medicine and Biology, Vol. 49, Issue 20 https://doi.org/10.1088/0031-9155/49/20/R01	journal	September 2004
Hyperpolarized Xenon-Based Molecular Sensors for Label-Free Detection of analytes Garimella, Praveena D.; Meldrum, Tyler; Witus, Leah S. Journal of the American Chemical Society, Vol. 136, Issue 1 https://doi.org/10.1021/ja406760r	journal	December 2013
Functionalized xenon as a biosensor Spence, M. M.; Rubin, S. M.; Dimitrov, I. E. Proceedings of the National Academy of Sciences, Vol. 98, Issue 19 https://doi.org/10.1073/pnas.191368398	journal	September 2001
Development of an antibody-based, modular biosensor for ¹²⁹ Xe NMR molecular imaging of cells at nanomolar concentrations Rose, Honor M.; Witte, Christopher; Rossella, Federica Proceedings of the National Academy of Sciences, Vol. 111, Issue 32 https://doi.org/10.1073/pnas.1406797111	journal	July 2014
Identification, classification, and signal amplification capabilities of high-turnover gas binding hosts in ultra-sensitive NMR Kunth, Martin; Witte, Christopher; Hennig, Andreas Chemical Science, Vol. 6, Issue 11 https://doi.org/10.1039/C5SC01400J	journal	January 2015
Biological magnetic resonance imaging using laser-polarized 129Xe Albert, M. S.; Cates, G. D.; Driehuys, B. Nature, Vol. 370, Issue 6486 https://doi.org/10.1038/370199a0	journal	July 1994
pH-Responsive Supramolecular Nanovalves Based on Cucurbit[6]uril Pseudorotaxanes Angelos, Sarah; Yang, Ying-Wei; Patel, Kaushik Angewandte Chemie International Edition, Vol. 47, Issue 12 https://doi.org/10.1002/anie.200705211	journal	March 2008
Quantitative Emergence of Hetero[4]rotaxanes by Template-Directed Click Chemistry Ke, Chenfeng; Smaldone, Ronald A.; Kikuchi, Takashi Angewandte Chemie International Edition, Vol. 52, Issue 1 https://doi.org/10.1002/anie.201205087	journal	September 2012

Similar Records

Rotaxane probes for protease detection by ¹²⁹Xe hyperCEST NMR

Journal Article · Wed Dec 14 23:00:00 EST 2016 · ChemComm · OSTI ID:1437955

Programming A Molecular Relay for Ultrasensitive Biodetection through ¹²⁹ Xe NMR

Journal Article · Sun Dec 20 19:00:00 EST 2015 · Angewandte Chemie (International Edition) · OSTI ID:1260842

Rotaxane Probes for the Detection of Hydrogen Peroxide by ¹²⁹Xe HyperCEST NMR Spectroscopy

Journal Article · Thu Apr 18 20:00:00 EDT 2019 · Angewandte Chemie (International Edition) · OSTI ID:1604689

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Rotaxane-mediated suppression and activation of cucurbit[6]uril for molecular detection by 129 Xe hyperCEST NMR

Citation Formats

References (30)

Similar Records

Related Subjects

Rotaxane-mediated suppression and activation of cucurbit[6]uril for molecular detection by ¹²⁹ Xe hyperCEST NMR