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Imidazol-1-ylalkanoic acids as extrinsic 1H NMR probes for the determination of intracellular pH, extracellular pH and cell volume

AuthorsGil, M. Soledad; Zaderenko, Paula; Cruz, Fátima; Cerdán, Sebastián ; Ballesteros, Paloma
Issue Date1994
CitationBioorganic and Medicinal Chemistry 2(5): 305-314 (1994)
AbstractThe synthesis and biological evaluation of a novel series of extrinsic probes for intracellular pH (pHi), extracellular pH (pHo) and cell volume determination by 1H NMR is described. Imidazol-1-ylacetate, malonate, 3-glutarate and 2-succinate esters were synthesized by reaction of imidazole with α-bromo esters or with α,β-unsaturated esters. The corresponding acids were prepared by hydrolysis. Rat erythrocytes were readily permeable to methyl imidazol-1-ylacetate, moderately permeable to diethyl 2-imidazol-1-ylsuccinate and impermeable to diethyl 3-imidazol-1-yl-glutarate esters. Imidazol-1-ylacetic acid was the only acid derivative which penetrated the erythrocyte interior when added directly to the incubation medium. Transport of the permeable compounds to the erythrocyte interior was non-saturable up to 200 mM added compound. Addition of methyl imidazol-1-ylacetate or diethyl 2-imidazol-1-ylsuccinate esters to erythrocyte suspensions, resulted in hydrolysis to imidazol-1-ylacetic acid and 2-imidazol-1-ylsuccinic acid mono-ethyl ester in the intracellular and extracellular spaces, respectively. pHi and pHo were determined from the different chemical shifts of the H-2 proton of the acid derivatives in the intracellular (H-2i) and extracellular (H-2o) compartments. In addition, the relative intracellular and extracellular volumes could be calculated from the areas of the intracellular and extracellular H-2 resonances. © 1994.
Identifiersdoi: 10.1016/S0960-894X(00)80463-1
issn: 0968-0896
e-issn: 1464-3391
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