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. 2018 Feb 2;13(3):280-283.
doi: 10.1002/asia.201701652. Epub 2018 Jan 16.

Rational Design of [13 C,D14 ]Tert-butylbenzene as a Scaffold Structure for Designing Long-lived Hyperpolarized 13 C Probes

Yuki Imakura  1 , Hiroshi Nonaka  1 , Yoichi Takakusagi  2 , Kazuhiro Ichikawa  2   3 , Nesmine R Maptue  4 , Alexander M Funk  4 , Chalermchai Khemtong  4   5 , Shinsuke Sando  1
Affiliations

Rational Design of [13 C,D14 ]Tert-butylbenzene as a Scaffold Structure for Designing Long-lived Hyperpolarized 13 C Probes

Yuki Imakura et al. Chem Asian J. .

Abstract

Dynamic nuclear polarization (DNP) is a technique to polarize the nuclear spin population. As a result of the hyperpolarization, the NMR sensitivity of the nuclei in molecules can be dramatically enhanced. Recent application of the hyperpolarization technique has led to advances in biochemical and molecular studies. A major problem is the short lifetime of the polarized nuclear spin state. Generally, in solution, the polarized nuclear spin state decays to a thermal spin equilibrium, resulting in loss of the enhanced NMR signal. This decay is correlated directly with the spin-lattice relaxation time T1 . Here we report [13 C,D14 ]tert-butylbenzene as a new scaffold structure for designing hyperpolarized 13 C probes. Thanks to the minimized spin-lattice relaxation (T1 ) pathways, its water-soluble derivative showed a remarkably long 13 C T1 value and long retention of the hyperpolarized spin state.

Keywords: chemical probe; dynamic nuclear polarization; hyperpolarization; nuclear magnetic resonance; spin-lattice relaxation time.

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Conflict of interest statement

Conflicts of interest

There are no conflicts to declare.

Figures

Figure 1.
Figure 1.
Schematic illustration of 15N and 13C scaffold structures reported in previous and this study, respectively.
Figure 2.
Figure 2.
T1 of tert-butanol and tert-butylbenzene (1 and 1D). 13C T1 were determined by using inversion recovery method (9.4 T, 25 °C, CD3OD, tert-butanol = 1.0 M, [D9]tert-butanol = 1.5 M, 1 = 0.05 M, 1D = 0.05 M)
Figure 3.
Figure 3.
Stacked bar graph of 1/T1 X of 1 and 1D (50 mM, toluene-d8, 25 °C, 9.4 T). 1/T1 X values were determined experimentally (see, supporting information).
Figure 4.
Figure 4.
(a) Molecular design of S1D. T1s in D2O and 90% H2O were determined by inversion recovery method at 50 mM S1D, 37 °C, 9.4 T. (b) 13C NMR spectra of the hyperpolarized probe S1D (2 mM in H2O), stacked from 0 to 15 min (every 2 s, pulse angle 5°).
Scheme 1.
Scheme 1.
Synthesis of [13C,D14]tert-butylbenzene (1D).
See this image and copyright information in PMC

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References

    1. Lee JH, Okuno Y, Cavagnero S, J. Magn. Reson 2014, 241, 18–31. - PMC - PubMed
    1. Nikolaou P, Goodson BM, Chekmenev EY, Chem. Eur. J 2015, 21, 3156–3166. - PMC - PubMed
    1. Ardenkjær Larsen JH, Fridlund B, Gram A, Hansson G, Hansson L, Lerche MH, Servin R, Thaning M, Golman K, Proc. Natl. Acad. Sci. U.S.A 2003, 100, 10158–10163. - PMC - PubMed
    1. Keshari KR, Wilson DM, Chem. Soc. Rev 2014, 43, 1627–1659. - PMC - PubMed
    1. Kurhanewicz J, Vigneron DB, Brindle K, Chekmenev EY, Comment A, Cunningham CH, Deberardinis RJ, Green GG, Leach MO, Rajan SS, Rizi RR, Ross BD, Warren WS, Malloy CR, Neoplasia 2011, 13, 81–97. - PMC - PubMed

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