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Proceedings Paper

New route to macrocyclic-based phosphonate acetoxymethyl (AM)-esters: synthesis, cell loading, and 31P NMR
Author(s): Medardo R. Chavez; Zoltan Kovacs; A. Dean Sherry
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Paper 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.

Paper Details

Date Published: 2 July 1999
PDF: 8 pages
Proc. SPIE 3600, Biomedical Imaging: Reporters, Dyes, and Instrumentation, (2 July 1999); doi: 10.1117/12.351017
Show Author Affiliations
Medardo R. Chavez, Univ. of Texas/Dallas (United States)
Zoltan Kovacs, Univ. of Texas/Dallas (Germany)
A. Dean Sherry, Univ. of Texas/Dallas and Univ. of Texas Southwestern Medical Ctr. (United States)

Published in SPIE Proceedings Vol. 3600:
Biomedical Imaging: Reporters, Dyes, and Instrumentation
Eva Marie Sevick-Muraca; Darryl J. Bornhop; Christopher H. Contag; Eva Marie Sevick-Muraca, Editor(s)

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