New route to macrocyclic-based phosphonate acetoxymethyl(AM)-esters

Synthesis, cell loading, and 31P NMR

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

Research output: Chapter in Book/Report/Conference proceedingChapter

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. 31P 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 Ca 2+ and Mg 2+ specific ligands for analytical, noninvasive measurement of these ions by 31P NMR.

Original languageEnglish (US)
Title of host publicationProceedings of SPIE - The International Society for Optical Engineering
PublisherSociety of Photo-Optical Instrumentation Engineers
Pages99-106
Number of pages8
Volume3600
StatePublished - 1999
EventProceedings of the 1999 Biomedical Imaging: Reporters, Dyes, and Instrumentation - San Jose, CA, USA
Duration: Jan 26 1999Jan 28 1999

Other

OtherProceedings of the 1999 Biomedical Imaging: Reporters, Dyes, and Instrumentation
CitySan Jose, CA, USA
Period1/26/991/28/99

Fingerprint

esters
Esters
Ligands
routes
Nuclear magnetic resonance
nuclear magnetic resonance
ligands
Cell membranes
synthesis
cells
attachment
membranes
Derivatives
Membranes
acids
Acids
rings
Ions
ions
Esterases

ASJC Scopus subject areas

  • Electrical and Electronic Engineering
  • Condensed Matter Physics

Cite this

Chavez, M. R., Kovacs, Z., & Sherry, A. D. (1999). New route to macrocyclic-based phosphonate acetoxymethyl(AM)-esters: Synthesis, cell loading, and 31P NMR. In Proceedings of SPIE - The International Society for Optical Engineering (Vol. 3600, pp. 99-106). Society of Photo-Optical Instrumentation Engineers.

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

Proceedings of SPIE - The International Society for Optical Engineering. Vol. 3600 Society of Photo-Optical Instrumentation Engineers, 1999. p. 99-106.

Research output: Chapter in Book/Report/Conference proceedingChapter

Chavez, MR, Kovacs, Z & Sherry, AD 1999, New route to macrocyclic-based phosphonate acetoxymethyl(AM)-esters: Synthesis, cell loading, and 31P NMR. in Proceedings of SPIE - The International Society for Optical Engineering. vol. 3600, Society of Photo-Optical Instrumentation Engineers, pp. 99-106, Proceedings of the 1999 Biomedical Imaging: Reporters, Dyes, and Instrumentation, San Jose, CA, USA, 1/26/99.
Chavez MR, Kovacs Z, Sherry AD. New route to macrocyclic-based phosphonate acetoxymethyl(AM)-esters: Synthesis, cell loading, and 31P NMR. In Proceedings of SPIE - The International Society for Optical Engineering. Vol. 3600. Society of Photo-Optical Instrumentation Engineers. 1999. p. 99-106
Chavez, Medardo R. ; Kovacs, Zoltan ; Sherry, A. Dean. / New route to macrocyclic-based phosphonate acetoxymethyl(AM)-esters : Synthesis, cell loading, and 31P NMR. Proceedings of SPIE - The International Society for Optical Engineering. Vol. 3600 Society of Photo-Optical Instrumentation Engineers, 1999. pp. 99-106
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