Irreversible catalyst activation enables hyperpolarization and water solubility for NMR signal amplification by reversible exchange

Journal of Physical Chemistry B

Volumn 118, Issue 48, 2014, Pages 13882-13889

  Truong, Milton L ^a   Shi, Fan ^f   He, Ping ^f   Yuan, Bingxin ^f   Plunkett, Kyle N ^f   Coffey, Aaron M ^a,b   Shchepin, Roman V ^a   Barskiy, Danila A ^d,e   Kovtunov, Kirill V ^d,e   Koptyug, Igor V ^d,e   Waddell, Kevin W ^a   Goodson, Boyd M ^f   Chekmenev, Eduard Y ^a,b,c  

^a VANDERBILT UNIVERSITY   (United States)

^b VANDERBILT UNIVERSITY   (United States)

^c VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d INTERNATIONAL TOMOGRAPHY CENTER   (Russian Federation)

^e NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^f SOUTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; HYDRIDES; IRIDIUM; MEDICAL APPLICATIONS; NUCLEAR MAGNETIC RESONANCE; SIGNAL PROCESSING; SOLUBILITY;

ACTIVATION PROCESS; BIOMEDICAL APPLICATIONS; CATALYST ACTIVATION; CATALYST MOLECULE; HYPERPOLARIZATION; SIGNAL AMPLIFICATIONS; SUBSTRATE POLARIZATION; WATER SOLUBILITIES;

CATALYST DEACTIVATION;

COORDINATION COMPOUND; HYDROGEN; IRIDIUM; NICOTINAMIDE; PYRIDINE; PYRIDINE DERIVATIVE; WATER;

CATALYSIS; CHEMISTRY; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY;

CATALYSIS; COORDINATION COMPLEXES; HYDROGEN; HYDROGENATION; IRIDIUM; MAGNETIC RESONANCE SPECTROSCOPY; NIACINAMIDE; PYRIDINES; SOLUBILITY; WATER;

EID: 84915746647     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp510825b     Document Type: Article

References (49)

1. Ardenkjaer-Larsen, J. H.; Fridlund, B.; Gram, A.; Hansson, G.; Hansson, L.; Lerche, M. H.; Servin, R.; Thaning, M.; Golman, K. Increase in Signal-to-Noise Ratio of > 10,000 Times in Liquid-State NMR Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 10158-10163
2. 129Xe Spin Exchange Optical Pumping Anal. Chem. 2014, 86, 8206-8212
3. Kurhanewicz, J.; Vigneron, D. B.; Brindle, K.; Chekmenev, E. Y.; Comment, A.; Cunningham, C. H.; DeBerardinis, R. J.; Green, G. G.; Leach, M. O.; Rajan, S. S. Analysis of Cancer Metabolism by Imaging Hyperpolarized Nuclei: Prospects for Translation to Clinical Research Neoplasia 2011, 13, 81-97
4. Goodson, B. M. Nuclear Magnetic Resonance of Laser-Polarized Noble Gases in Molecules, Materials, and Organisms J. Magn. Reson. 2002, 155, 157-216
5. Schroder, L. Xenon for NMR Biosensing-Inert but Alert Phys. Med. 2013, 29, 3-16
6. Eisenschmid, T. C.; Kirss, R. U.; Deutsch, P. P.; Hommeltoft, S. I.; Eisenberg, R.; Bargon, J.; Lawler, R. G.; Balch, A. L. Para Hydrogen Induced Polarization in Hydrogenation Reactions J. Am. Chem. Soc. 1987, 109, 8089-8091
7. Bowers, C. R.; Weitekamp, D. P. Transformation of Symmetrization Order to Nuclear-Spin Magnetization by Chemical-Reaction and Nuclear-Magnetic-Resonance Phys. Rev. Lett. 1986, 57, 2645-2648
8. Goldman, M.; Johannesson, H. Conversion of a Proton Pair Para Order into C-13 Polarization by Rf Irradiation, for Use in MRI C. R. Phys. 2005, 6, 575-581
9. Cai, C.; Coffey, A. M.; Shchepin, R. V.; Chekmenev, E. Y.; Waddell, K. W. Efficient Transformation of Parahydrogen Spin Order into Heteronuclear Magnetization J. Phys. Chem. B 2013, 117, 1219-1224
10. Chekmenev, E. Y.; Hovener, J.; Norton, V. A.; Harris, K.; Batchelder, L. S.; Bhattacharya, P.; Ross, B. D.; Weitekamp, D. P. PASADENA Hyperpolarization of Succinic Acid for MRI and NMR Spectroscopy J. Am. Chem. Soc. 2008, 130, 4212-4213
11. 13C-Phospholactate-D2 for Biomedical Imaging with >30,000,000-Fold NMR Signal Enhancement in Water Anal. Chem. 2014, 86, 5601-5605
12. 13C-Succinate Imaging of Brain Cancer J. Magn. Reson. 2007, 186, 150-155
13. 13C Imaging of Atheroma in Mice NMR Biomed. 2011, 24, 1023-1028
14. Zacharias, N. M.; Chan, H. R.; Sailasuta, N.; Ross, B. D.; Bhattacharya, P. Real-Time Molecular Imaging of Tricarboxylic Acid Cycle Metabolism in Vivo by Hyperpolarized 1-C-13 Diethyl Succinate J. Am. Chem. Soc. 2012, 134, 934-943
15. Adams, R. W.; Aguilar, J. A.; Atkinson, K. D.; Cowley, M. J.; Elliott, P. I. P.; Duckett, S. B.; Green, G. G. R.; Khazal, I. G.; Lopez-Serrano, J.; Williamson, D. C. Reversible Interactions with Para-Hydrogen Enhance NMR Sensitivity by Polarization Transfer Science 2009, 323, 1708-1711
16. Atkinson, K. D.; Cowley, M. J.; Elliott, P. I. P.; Duckett, S. B.; Green, G. G. R.; Lopez-Serrano, J.; Whitwood, A. C. Spontaneous Transfer of Parahydrogen Derived Spin Order to Pyridine at Low Magnetic Field J. Am. Chem. Soc. 2009, 131, 13362-13368
17. Gloggler, S.; Muller, R.; Colell, J.; Emondts, M.; Dabrowski, M.; Blumich, B.; Appelt, S. Para-Hydrogen Induced Polarization of Amino Acids, Peptides and Deuterium-Hydrogen Gas Phys. Chem. Chem. Phys. 2011, 13, 13759-13764
18. Zeng, H.; Xu, J.; Gillen, J.; McMahon, M. T.; Artemov, D.; Tyburn, J.-M.; Lohman, J. A. B.; Mewis, R. E.; Atkinson, K. D.; Green, G. G. R. Optimization of SABRE for Polarization of the Tuberculosis Drugs Pyrazinamide and Isoniazid J. Magn. Reson. 2013, 237, 73-78
19. Hövener, J.-B.; Schwaderlapp, N.; Borowiak, R.; Lickert, T.; Duckett, S. B.; Mewis, R. E.; Adams, R. W.; Burns, M. J.; Highton, L. A. R.; Green, G. G. R. Toward Biocompatible Nuclear Hyperpolarization Using Signal Amplification by Reversible Exchange: Quantitative in Situ Spectroscopy and High-Field Imaging Anal. Chem. 2014, 86, 1767-1774
20. Shi, F.; Coffey, A. M.; Waddell, K. W.; Chekmenev, E. Y.; Goodson, B. M. Heterogeneous Solution NMR Signal Amplification by Reversible Exchange Angew. Chem., Int. Ed. 2014, 53, 7495-7498
21. He, P.; Best, Q. A.; Groome, K. A.; Coffey, A. M.; Truong, M. L.; Waddell, K. W.; Chekmenev, E. Y.; Goodson, B. M. A Water-Soluble SABRE Catalyst for NMR/MRI Enhancement. Presented at the 55th ENC Conference, March 23-28, Boston, MA, 2014.
22. Zeng, H.; Xu, J.; McMahon, M. T.; Lohman, J. A. B.; van Zijl, P. C. M. Achieving 1% NMR Polarization in Water in Less Than 1 min Using SABRE J. Magn. Reson. 2014, 246, 119-121
23. Dechent, J. F.; Highton, L. A. R.; Green, G. G. R.; Duckett, S. B.; Spiess, H. W.; Schreiber, L. M.; Münnemann, K. Continuous Proton Hyperpolarization Via SABRE and Hollow Fibre Membranes Proc. Int. Soc. Mag. Reson. Med. 2013, 1937
24. Mewis, R. E.; Atkinson, K. D.; Cowley, M. J.; Duckett, S. B.; Green, G. G. R.; Green, R. A.; Highton, L. A. R.; Kilgour, D.; Lloyd, L. S.; Lohman, J. A. B. Probing Signal Amplification by Reversible Exchange Using an NMR Flow System Magn. Reson. Chem. 2014, 52, 358-369
25. 129Xe MRI of the Human Lung J. Magn. Reson. Imaging 2013, 37, 313-331
26. Nelson, S. J.; Kurhanewicz, J.; Vigneron, D. B.; Larson, P. E. Z.; Harzstark, A. L.; Ferrone, M.; van Criekinge, M.; Chang, J. W.; Bok, R.; Park, I. Metabolic Imaging of Patients with Prostate Cancer Using Hyperpolarized 1-C-13 Pyruvate Sci. Transl. Med. 2013, 5, 198ra108
27. Nikolaou, P.; Goodson, B. M.; Chekmenev, E. Y. NMR Hyperpolarization Techniques for Biomedicine Chem.-Eur. J. 2014, 10.1002/chem.201405253
28. Barskiy, D. A.; Kovtunov, K. V.; Koptyug, I. V.; He, P.; Groome, K. A.; Best, Q. A.; Shi, F.; Goodson, B. M.; Shchepin, R. V.; Coffey, A. M. The Feasibility of Formation and Kinetics of NMR Signal Amplification by Reversible Exchange (SABRE) at High Magnetic Field (9.4 T) J. Am. Chem. Soc. 2014, 136, 3322-3325
29. Cowley, M. J.; Adams, R. W.; Atkinson, K. D.; Cockett, M. C. R.; Duckett, S. B.; Green, G. G. R.; Lohman, J. A. B.; Kerssebaum, R.; Kilgour, D.; Mewis, R. E. Iridium N-Heterocyclic Carbene Complexes as Efficient Catalysts for Magnetization Transfer from Para-Hydrogen J. Am. Chem. Soc. 2011, 133, 6134-6137
30. Vazquez-Serrano, L. D.; Owens, B. T.; Buriak, J. M. The Search for New Hydrogenation Catalyst Motifs Based on N-Heterocyclic Carbene Ligands Inorg. Chim. Acta 2006, 359, 2786-2797
31. Torres, O.; Martin, M.; Sola, E. Labile N-Heterocyclic Carbene Complexes of Iridium Organometallics 2009, 28, 863-870
32. Feng, B.; Coffey, A. M.; Colon, R. D.; Chekmenev, E. Y.; Waddell, K. W. A Pulsed Injection Parahydrogen Generator and Techniques for Quantifying Enrichment J. Magn. Reson. 2012, 214, 258-262
33. Bowers, C. R.; Weitekamp, D. P. Para-Hydrogen and Synthesis Allow Dramatically Enhanced Nuclear Alignment J. Am. Chem. Soc. 1987, 109, 5541-5542
34. Green, R. A.; Adams, R. W.; Duckett, S. B.; Mewis, R. E.; Williamson, D. C.; Green, G. G. R. The Theory and Practice of Hyperpolarization in Magnetic Resonance Using Parahydrogen Prog. Nucl. Magn. Res. Spectrosc. 2012, 67, 1-48
35. Theis, T.; Truong, M.; Coffey, A. M.; Chekmenev, E. Y.; Warren, W. S. LIGHT-SABRE Enables Efficient in-Magnet Catalytic Hyperpolarization J. Magn. Reson. 2014, 248, 23-26
36. Pravdivtsev, A. N.; Yurkovskaya, A. V.; Vieth, H.-M.; Ivanov, K. L. Spin Mixing at Level Anti-Crossings in the Rotating Frame Makes High-Field SABRE Feasible Phys. Chem. Chem. Phys. 2014, 10.1039/C4CP03765K
37. Crabtree, R. Iridium Compounds in Catalysis Acc. Chem. Res. 1979, 12, 331-338
38. Tang, C. Y.; Lednik, J.; Vidovic, D.; Thompson, A. L.; Aldridge, S. Responses to Unsaturation in Iridium Mono(N-Heterocyclic Carbene) Complexes: Synthesis and Oligomerization of LIr(H)(2)Cl and LIr(H)(2) (+) Chem. Commun. 2011, 47, 2523-2525
39. Permin, A. B.; Eisenberg, R. One-Hydrogen Polarization in Hydroformylation Promoted by Platinum-Tin and Iridium Carbonyl Complexes: A New Type of Parahydrogen-Induced Effect J. Am. Chem. Soc. 2002, 124, 12406-12407
40. van Weerdenburg, B. J. A.; Gloggler, S.; Eshuis, N.; Engwerda, A. H. J.; Smits, J. M. M.; de Gelder, R.; Appelt, S.; Wymenga, S. S.; Tessari, M.; Feiters, M. C. Ligand Effects of NHC-Iridium Catalysts for Signal Amplification by Reversible Exchange (SABRE) Chem. Commun. 2013, 49, 7388-7390
41. Song, Y. Q. Spin Polarization-Induced Nuclear Overhauser Effect: An Application of Spin-Polarized Xenon and Helium Concept Magn. Reson. 2000, 12, 6-20
42. Navon, G.; Song, Y. Q.; Room, T.; Appelt, S.; Taylor, R. E.; Pines, A. Enhancement of Solution NMR and MRI with Laser-Polarized Xenon Science 1996, 271, 1848-1851
43. Herskowitz, M.; Wisniak, J.; Skladman, L. Hydrogen Solubility in Organic Liquids J. Chem. Eng. Data 1983, 28, 164-166
44. Brunner, E. Solubility of Hydrogen in 10 Organic-Solvents at 298.15-K, 323.15-K, and 373.15-K J. Chem. Eng. Data 1985, 30, 269-273
45. Purwanto; Deshpande, R. M.; Chaudhari, R. V.; Delmas, H. Solubility of Hydrogen, Carbon Monoxide, and 1-Octene in Various Solvents and Solvent Mixtures J. Chem. Eng. Data 1996, 41, 1414-1417
46. Adams, R. W.; Duckett, S. B.; Green, R. A.; Williamson, D. C.; Green, G. G. R. A Theoretical Basis for Spontaneous Polarization Transfer in Non-Hydrogenative Parahydrogen-Induced Polarization J. Chem. Phys. 2009, 131, 194505
47. 13C Biomolecules: Equipment Design and Installation Magn. Reson. Mater. Phys. 2009, 22, 111-121
48. Waddell, K. W.; Coffey, A. M.; Chekmenev, E. Y. In Situ Detection of PHIP at 48 mT: Demonstration Using a Centrally Controlled Polarizer J. Am. Chem. Soc. 2011, 133, 97-101
49. Roth, M.; Kindervater, P.; Raich, H.-P.; Bargon, J.; Spiess, H. W.; Muennemann, K. Continuous H-1 and C-13 Signal Enhancement in NMR Spectroscopy and MRI Using Parahydrogen and Hollow-Fiber Membranes Angew. Chem., Int. Ed. 2010, 49, 8358-8362