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L A Levy

Publications and source records attributed to L A Levy.

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A new approach to the synthesis of APTRA indicators.

We have devised a general synthesis of Mg(2+) indicators which is based on the aminophenol triacetic acid (APTRA) structure. The key step is a palladium-catalyzed coupling reaction of a precursor of the APTRA ligand with a fluorescent group. This strategy resulted in new ratioable fluorescent APTRA indicators and the finding that the fluorescence response of these indicators is different for Mg(2+) and Ca(2+) in some cases. We believe that this represents a generally useful approach for combining fluorophore and chelator functionalities.

Acetates↗
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4-oxo-4H-quinolizine-3-carboxylic acids as Mg2+ selective, fluorescent indicators.

In this paper, we present the synthesis of a new series of substituted 4-oxo-4H-quinolizine-3-carboxylic acids and the evaluation of their fluorescent response upon complexation with Mg2+ and Ca2+. This has led to the development of the first Mg2+-selective, ratioable fluorescent indicators. We found that 4-oxo-4H-quinolizine-3-carboxylates are excellent fluorophores which show a strong fluorescent response to Mg2+ but not to Ca2; the latter metal ion often causing interference during Mg2+ measurements with previously described indicators. The dissociation constants of the studied fluorophores-around 1.0 mM-are of the same order of magnitude as is usually observed for intracellular Mg2+.

Calcium↗
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Fluorinated o-aminophenol derivatives for measurement of intracellular pH.

The simple 2-aminophenol group which serves as a building block for many cationic indicators has been modified to yield a series of pH sensitive probes. This approach is based on the replacement of one of the N-acetate groups of the chelator APTRA (o-aminophenol N,N,O-triacetate) by an N-ethyl group. The resulting series of (N-ethylamino)phenol (NEAP) compounds exhibit pK values in the physiological range and negligible affinity for physiological levels of other ions. Three fluorinated analogs have been prepared: N-ethyl-5-fluoro-2-aminophenol N,O-diacetate (5F NEAP), N-ethyl-2-((2-fluoro-4-carboxybenzyl)oxy)-4-fluoroaniline-N- acetic acid (5F NEAP-2), and 1-(2-(N-ethylamino)-5-fluorophenoxy)-2-(2-fluoro-4- aminophenoxy)ethane-N,N',N'-triacetic acid (5F NEAP-3). These derivatives exhibit total titration shifts of approximately 11 ppm. NEAP-2 and NEAP-3 contain an additional fluorine to serve as an internal chemical shift reference, and NEAP-3, the most highly charged analog prepared, was designed in order to minimize leakage.

Aminophenols↗