Late-stage deuteration of 13C-enriched substrates for: T 1 prolongation in hyperpolarized 13C MRI

Céline Taglang; David E. Korenchan; Cornelius Von Morze; Justin Yu; Chloé Najac; Sinan Wang; Joseph E. Blecha; Sukumar Subramaniam; Robert Bok; Henry F. Vanbrocklin; Daniel B. Vigneron; Sabrina M. Ronen; Renuka Sriram; John Kurhanewicz; David M. Wilson; Robert R. Flavell

doi:10.1039/c8cc02246a

Late-stage deuteration of ¹³C-enriched substrates for: T ₁ prolongation in hyperpolarized ¹³C MRI

Céline Taglang, David E. Korenchan, Cornelius Von Morze, Justin Yu, Chloé Najac, Sinan Wang, Joseph E. Blecha, Sukumar Subramaniam, Robert Bok, Henry F. Vanbrocklin, Daniel B. Vigneron, Sabrina M. Ronen, Renuka Sriram, John Kurhanewicz, David M. Wilson, Robert R. Flavell

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Abstract

A robust and selective late-stage deuteration methodology was applied to ¹³C-enriched amino and alpha hydroxy acids to increase spin-lattice relaxation constant T₁ for hyperpolarized ¹³C magnetic resonance imaging. For the five substrates with ¹³C-labeling on the C1-position ([1-¹³C]alanine, [1-¹³C]serine, [1-¹³C]lactate, [1-¹³C]glycine, and [1-¹³C]valine), significant increase of their T₁ was observed at 3 T with deuterium labeling (+26%, 22%, +16%, +25% and +29%, respectively). Remarkably, in the case of [2-¹³C]alanine, [2-¹³C]serine and [2-¹³C]lactate, deuterium labeling led to a greater than four fold increase in T₁. [1-¹³C,2-²H]alanine, produced using this method, was applied to in vitro enzyme assays with alanine aminotransferase, demonstrating a kinetic isotope effect.

Original language	English
Pages (from-to)	5233-5236
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	41
DOIs	https://doi.org/10.1039/c8cc02246a
State	Published - 2018

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Taglang, C., Korenchan, D. E., Von Morze, C., Yu, J., Najac, C., Wang, S., Blecha, J. E., Subramaniam, S., Bok, R., Vanbrocklin, H. F., Vigneron, D. B., Ronen, S. M., Sriram, R., Kurhanewicz, J., Wilson, D. M., & Flavell, R. R. (2018). Late-stage deuteration of ¹³C-enriched substrates for: T ₁ prolongation in hyperpolarized ¹³C MRI. Chemical Communications, 54(41), 5233-5236. https://doi.org/10.1039/c8cc02246a

@article{415885643ae441f1adc023523ce6b198,

title = "Late-stage deuteration of 13C-enriched substrates for: T 1 prolongation in hyperpolarized 13C MRI",

abstract = "A robust and selective late-stage deuteration methodology was applied to 13C-enriched amino and alpha hydroxy acids to increase spin-lattice relaxation constant T1 for hyperpolarized 13C magnetic resonance imaging. For the five substrates with 13C-labeling on the C1-position ([1-13C]alanine, [1-13C]serine, [1-13C]lactate, [1-13C]glycine, and [1-13C]valine), significant increase of their T1 was observed at 3 T with deuterium labeling (+26%, 22%, +16%, +25% and +29%, respectively). Remarkably, in the case of [2-13C]alanine, [2-13C]serine and [2-13C]lactate, deuterium labeling led to a greater than four fold increase in T1. [1-13C,2-2H]alanine, produced using this method, was applied to in vitro enzyme assays with alanine aminotransferase, demonstrating a kinetic isotope effect.",

author = "C{\'e}line Taglang and Korenchan, {David E.} and {Von Morze}, Cornelius and Justin Yu and Chlo{\'e} Najac and Sinan Wang and Blecha, {Joseph E.} and Sukumar Subramaniam and Robert Bok and Vanbrocklin, {Henry F.} and Vigneron, {Daniel B.} and Ronen, {Sabrina M.} and Renuka Sriram and John Kurhanewicz and Wilson, {David M.} and Flavell, {Robert R.}",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc02246a",

language = "English",

volume = "54",

pages = "5233--5236",

journal = "Chemical Communications",

issn = "1359-7345",

number = "41",

}

Taglang, C, Korenchan, DE, Von Morze, C, Yu, J, Najac, C, Wang, S, Blecha, JE, Subramaniam, S, Bok, R, Vanbrocklin, HF, Vigneron, DB, Ronen, SM, Sriram, R, Kurhanewicz, J, Wilson, DM & Flavell, RR 2018, 'Late-stage deuteration of ¹³C-enriched substrates for: T ₁ prolongation in hyperpolarized ¹³C MRI', Chemical Communications, vol. 54, no. 41, pp. 5233-5236. https://doi.org/10.1039/c8cc02246a

TY - JOUR

T1 - Late-stage deuteration of 13C-enriched substrates for

T2 - T 1 prolongation in hyperpolarized 13C MRI

AU - Taglang, Céline

AU - Korenchan, David E.

AU - Von Morze, Cornelius

AU - Yu, Justin

AU - Najac, Chloé

AU - Wang, Sinan

AU - Blecha, Joseph E.

AU - Subramaniam, Sukumar

AU - Bok, Robert

AU - Vanbrocklin, Henry F.

AU - Vigneron, Daniel B.

AU - Ronen, Sabrina M.

AU - Sriram, Renuka

AU - Kurhanewicz, John

AU - Wilson, David M.

AU - Flavell, Robert R.

PY - 2018

Y1 - 2018

N2 - A robust and selective late-stage deuteration methodology was applied to 13C-enriched amino and alpha hydroxy acids to increase spin-lattice relaxation constant T1 for hyperpolarized 13C magnetic resonance imaging. For the five substrates with 13C-labeling on the C1-position ([1-13C]alanine, [1-13C]serine, [1-13C]lactate, [1-13C]glycine, and [1-13C]valine), significant increase of their T1 was observed at 3 T with deuterium labeling (+26%, 22%, +16%, +25% and +29%, respectively). Remarkably, in the case of [2-13C]alanine, [2-13C]serine and [2-13C]lactate, deuterium labeling led to a greater than four fold increase in T1. [1-13C,2-2H]alanine, produced using this method, was applied to in vitro enzyme assays with alanine aminotransferase, demonstrating a kinetic isotope effect.

AB - A robust and selective late-stage deuteration methodology was applied to 13C-enriched amino and alpha hydroxy acids to increase spin-lattice relaxation constant T1 for hyperpolarized 13C magnetic resonance imaging. For the five substrates with 13C-labeling on the C1-position ([1-13C]alanine, [1-13C]serine, [1-13C]lactate, [1-13C]glycine, and [1-13C]valine), significant increase of their T1 was observed at 3 T with deuterium labeling (+26%, 22%, +16%, +25% and +29%, respectively). Remarkably, in the case of [2-13C]alanine, [2-13C]serine and [2-13C]lactate, deuterium labeling led to a greater than four fold increase in T1. [1-13C,2-2H]alanine, produced using this method, was applied to in vitro enzyme assays with alanine aminotransferase, demonstrating a kinetic isotope effect.

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U2 - 10.1039/c8cc02246a

DO - 10.1039/c8cc02246a

M3 - Article

C2 - 29726563

AN - SCOPUS:85047275501

SN - 1359-7345

VL - 54

SP - 5233

EP - 5236

JO - Chemical Communications

JF - Chemical Communications

IS - 41

ER -

Late-stage deuteration of ¹³C-enriched substrates for: T ₁ prolongation in hyperpolarized ¹³C MRI

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