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Real‐Time Interrogation of Aspirin Reactivity, Biochemistry, and Biodistribution by Hyperpolarized Magnetic Resonance Spectroscopy
Author(s) -
Zacharias Niki M.,
Ornelas Argentina,
Lee Jaehyuk,
Hu Jingzhe,
Davis Jennifer S.,
Uddin Nasir,
Pudakalakatti Shivanand,
Menter David G.,
Karam Jose A.,
Wood Christopher G.,
Hawk Ernest T.,
Kopetz Scott,
Vilar Eduardo,
Bhattacharya Pratip K.,
Millward Steven W.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812759
Subject(s) - biodistribution , chemistry , nuclear magnetic resonance spectroscopy , nuclear magnetic resonance , in vivo , spectroscopy , hyperpolarization (physics) , in vitro , organic chemistry , biochemistry , physics , microbiology and biotechnology , quantum mechanics , biology
Hyperpolarized magnetic resonance spectroscopy enables quantitative, non‐radioactive, real‐time measurement of imaging probe biodistribution and metabolism in vivo. Here, we investigate and report on the development and characterization of hyperpolarized acetylsalicylic acid (aspirin) and its use as a nuclear magnetic resonance (NMR) probe. Aspirin derivatives were synthesized with single‐ and double‐ 13 C labels and hyperpolarized by dynamic nuclear polarization with 4.7 % and 3 % polarization, respectively. The longitudinal relaxation constants ( T 1 ) for the labeled acetyl and carboxyl carbonyls were approximately 30 seconds, supporting in vivo imaging and spectroscopy applications. In vitro hydrolysis, transacetylation, and albumin binding of hyperpolarized aspirin were readily monitored in real time by 13 C‐NMR spectroscopy. Hyperpolarized, double‐labeled aspirin was well tolerated in mice and could be observed by both 13 C‐MR imaging and 13 C‐NMR spectroscopy in vivo.