Hyperpolarized Amino Acid Derivatives as Multivalent Magnetic Resonance pH Sensor Molecules

Sensors
Christian HundshammerFranz Schilling

Abstract

pH is a tightly regulated physiological parameter that is often altered in diseased states like cancer. The development of biosensors that can be used to non-invasively image pH with hyperpolarized (HP) magnetic resonance spectroscopic imaging has therefore recently gained tremendous interest. However, most of the known HP-sensors have only individually and not comprehensively been analyzed for their biocompatibility, their pH sensitivity under physiological conditions, and the effects of chemical derivatization on their logarithmic acid dissociation constant (pKa). Proteinogenic amino acids are biocompatible, can be hyperpolarized and have at least two pH sensitive moieties. However, they do not exhibit a pH sensitivity in the physiologically relevant pH range. Here, we developed a systematic approach to tailor the pKaof molecules using modifications of carbon chain length and derivatization rendering these molecules interesting for pH biosensing. Notably, we identified several derivatives such as [1-13C]serine amide and [1-13C]-2,3-diaminopropionic acid as novel pH sensors. They bear several spin-1/2 nuclei (13C,15N,31P) with high sensitivity up to 4.8 ppm/pH and we show that13C spins can be hyperpolarized with dissolution dy...Continue Reading

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Citations

Jan 29, 2019·Chemistry : a European Journal·Andrey N Pravdivtsev, Jan-Bernd Hövener
Feb 23, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Christian HundshammerFranz Schilling
May 3, 2019·Magnetic Resonance in Medicine : Official Journal of the Society of Magnetic Resonance in Medicine·David E KorenchanRobert R Flavell
Nov 28, 2020·Frontiers in Cardiovascular Medicine·Nikolaj BøghChristoffer Laustsen
Jan 9, 2021·Molecular Imaging and Biology : MIB : the Official Publication of the Academy of Molecular Imaging·Changhua MuRobert R Flavell
Feb 27, 2021·Angewandte Chemie·Andrey N PravdivtsevJan-Bernd Hövener
Mar 21, 2019·ACS Chemical Biology·Andrew ChoKayvan R Keshari

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Methods Mentioned

BETA
NMR
biosensors
amidation

Software Mentioned

SABRE
Matlab

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