New highly sensitive pH probes for 31P NMR spectroscopy. Spin-lattice relaxation time measurements as a function of
molecular structure, temperature, pH, and biological medium.

Gosset Gaelle; Sophie Martel; Jean-Louis Clément; Bruno Blaive; Gilles Olive; Marcel Culcasi; Roselyne Rosas; André Thévand; Sylvia Pietri

doi:10.1016/j.crci.2007.08.016

Journal articles

New highly sensitive pH probes for 31P NMR spectroscopy. Spin-lattice relaxation time measurements as a function of molecular structure, temperature, pH, and biological medium.

Gosset Gaelle ¹ Sophie Martel ¹ Jean-Louis Clément ¹ Bruno Blaive ¹ Gilles Olive ^{1, 2} Marcel Culcasi ¹ Roselyne Rosas ³ André Thévand ³ Sylvia Pietri ¹

1 ICR - Institut de Chimie Radicalaire

2 EICVN - Ecole Industrielle et Commerciale de la Ville de Namur

3 AMU SPEC - Spectropôle - Aix Marseille Université

Abstract : New uncharged a-aminophosphonates derived from diethyl(2- methylpyrrolidin-2-yl) phosphonate were synthesized by nucleophilic addition of dialkylphosphites on 2-methyl-1-pyrroline. These compounds were intended as enhanced 31P-NMR pH probes in biological systems. Compared to standard pH markers such as inorganic phosphate or methylphosphonate, they demonstrated in vitro low acidic pKa values (6.6 < pKa < 7.0), resonance peaks ranging from 21 to 35 ppm, distinct from those of phosphorylated metabolites, and 3e4 times as sensitive (9.2 < Ddab < 9.9 ppm) as usual markers, such as inorganic phosphate or methylphosphonate. The detailed synthetic procedures for three representative new pH probes, which were non-toxic (in the mM range) in rat isolated heart preparations, was reported. In a larger series of 27 structurally related a-aminophosphonates, 1/T1 (31P) values were given in different conditions of milieu, temperature and pH. The data support unique features for these compounds to reveal acidic cellular compartments.

Keywords : alpha-Aminophosphonates pH probe 31P-NMR Spin-lattice relaxation Biological systems Acidic compartments

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Journal articles

Domain :

Chemical Sciences

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https://hal-amu.archives-ouvertes.fr/hal-01251547
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Submitted on : Wednesday, January 6, 2016 - 1:35:34 PM
Last modification on : Tuesday, January 30, 2018 - 12:28:02 PM

New highly sensitive pH probes for 31P NMR spectroscopy. Spin-lattice relaxation time measurements as a function of molecular structure, temperature, pH, and biological medium.

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New highly sensitive pH probes for 31P NMR spectroscopy. Spin-lattice relaxation time measurements as a function of molecular structure, temperature, pH, and biological medium.

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