Delehedde, Caroline published the artcileNovel Sterically Crowded and Conformationally Constrained α-Aminophosphonates with a Near-Neutral pKa as Highly Accurate 31P NMR pH Probes. Application to Subtle pH Gradients Determination in Dictyostelium discoideum Cells, Computed Properties of 23783-42-8, the main research area is Dictyostelium discoideum cell aminophosphonate neutral pKa NMR pH probe; 31P NMR; Dictyostelium discoideum cells; X-ray crystallography; pH probes; phophorus pyramidalization angle; trans-sarcolemmal pH gradients; α-aminophosphonates.
In order to discover new 31P NMR markers for probing subtle pH changes (<0.2 pH unit) in biol. environments, fifteen new conformationally constrained or sterically hindered α-aminophosphonates derived from diethyl(2-methylpyrrolidin-2-yl)phosphonate were synthesized and tested for their pH reporting and cytotoxic properties in vitro. All compounds showed near-neutral pKas (ranging 6.28-6.97), chem. shifts not overlapping those of phosphorus metabolites, and spectroscopic sensitivities (i.e., chem. shifts variation Δδab between the acidic and basic forms) ranging from 9.2-10.7 ppm, being fourfold larger than conventional endogenous markers such as inorganic phosphate. X-ray crystallog. studies combined with predictive empirical relationships and ab initio calculations addressed the inductive and stereochem. effects of substituents linked to the protonated amine function. Satisfactory correlations were established between pKas and both the 2D structure and pyramidalization at phosphorus, showing that steric crowding around the phosphorus is crucial for modulating Δδab. Finally, the hit 31P NMR pH probe 1b bearing an unsubstituted 1,3,2-dioxaphosphorinane ring, which is moderately lipophilic, nontoxic on A549 and NHLF cells, and showing pKa = 6.45 with Δδab = 10.64 ppm, allowed the first clear-cut evidence of trans-sarcolemmal pH gradients in normoxic Dictyostelium discoideum cells with an accuracy of <0.05 pH units. Molecules published new progress about Biomarkers. 23783-42-8 belongs to class ethers-buliding-blocks, name is 2,5,8,11-Tetraoxatridecan-13-ol, and the molecular formula is C9H20O5, Computed Properties of 23783-42-8.
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem