New route to macrocyclic-based phosphonate acetoxymethyl (AM)-esters: synthesis, cell loading, and 31P NMR

Medardo R. Chavez; Zoltan Kovacs; A. Dean Sherry

doi:10.1117/12.351017

2 July 1999 New route to macrocyclic-based phosphonate acetoxymethyl (AM)-esters: synthesis, cell loading, and ³¹P NMR

Medardo R. Chavez, Zoltan Kovacs, A. Dean Sherry

Proceedings Volume 3600, Biomedical Imaging: Reporters, Dyes, and Instrumentation; (1999) https://doi.org/10.1117/12.351017
Event: BiOS '99 International Biomedical Optics Symposium, 1999, San Jose, CA, United States

Abstract

The ligand, 1,4,7,10-tetraazacyclododecane-1,4,7,10- tetrakis(methylenephosphonic acid, ethyl ester) (DOTPME) was made membrane permeable by preparing its acetoxymethyl (AM) derivative (DOTPME-AM). The synthetic approach was to prepare the AM ester of the phosphonate side-chain prior to attachment to the macrocyclic ring. P NMR was used to demonstrate that DOTPME-AM can penetrate cell membranes, get hydrolyzed by cellular esterases to regenerate charged DOTPME, and hence become trapped inside cells. This technology offers the potential of designing Ca²⁺ and Mg²⁺ specific ligands for analytical, noninvasive measurement of these ions by ³¹P NMR.

Citation Download Citation

Medardo R. Chavez, Zoltan Kovacs, and A. Dean Sherry "New route to macrocyclic-based phosphonate acetoxymethyl (AM)-esters: synthesis, cell loading, and ³¹P NMR", Proc. SPIE 3600, Biomedical Imaging: Reporters, Dyes, and Instrumentation, (2 July 1999); https://doi.org/10.1117/12.351017

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