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Sensors, Vol. 18, Pages 600: Hyperpolarized Amino Acid Derivatives as Multivalent Magnetic Resonance pH Sensor Molecules

Sensors, Vol. 18, Pages 600: Hyperpolarized Amino Acid Derivatives as Multivalent Magnetic Resonance pH Sensor Molecules

Sensors doi: 10.3390/s18020600

Authors: Christian Hundshammer Stephan Düwel David Ruseckas Geoffrey Topping Piotr Dzien Christoph Müller Benedikt Feuerecker Jan B. Hövener Axel Haase Markus Schwaiger Steffen J. Glaser Franz Schilling

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 pKa of 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 that 13C spins can be hyperpolarized with dissolution dynamic polarization (DNP). Our findings elucidate the molecular mechanisms of chemical shift pH sensors that might help to design tailored probes for specific pH in vivo imaging applications.

Authors:   Hundshammer, Christian ; Düwel, Stephan ; Ruseckas, David ; Topping, Geoffrey ; Dzien, Piotr ; Müller, Christoph ; Feuerecker, Benedikt ; Hövener, Jan B.; Haase, Axel ; Schwaiger, Markus ; Glaser, Steffen J.; Schilling, Franz
Journal:   Sensors
Volume:   18
edition:   2
Year:   2018
Pages:   600
DOI:   10.3390/s18020600
Publication date:   15-Feb-2018
Facts, background information, dossiers
  • derivatization
  • spin
  • amino acid derivatives
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