6-Trifluoromethylpyridoxine: novel (19)F NMR pH indicator for in vivo detection

J Med Chem. 2012 Aug 9;55(15):6814-21. doi: 10.1021/jm300520q. Epub 2012 Jul 27.

Abstract

pH plays an important role in tumor proliferation, angiogenesis, metabolic control, and the efficacy of cytotoxic therapy, and accurate noninvasive assessment of tumor pH promises to provide insight into developmental processes and prognostic information. In this paper, we report the design, synthesis, and characterization of two novel pH indicators 6-trifluoromethylpyridoxine 8 and α(4),α(5)-di-O-[3'-O-(β-d-glucopyranosyl)propyl]-6-trifluoromethylpyridoxine 17 and demonstrate 8 as an extracellular (19)F NMR pH probe to assess pH(e) of various tumors in vivo.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Extracellular Space / chemistry
  • Female
  • Fluorine
  • Hydrogen-Ion Concentration
  • Indicators and Reagents / chemical synthesis*
  • Indicators and Reagents / chemistry
  • Magnetic Resonance Spectroscopy / methods
  • Male
  • Myocardium / chemistry
  • Neoplasms, Experimental / chemistry
  • Pyridoxine / analogs & derivatives*
  • Pyridoxine / chemical synthesis
  • Pyridoxine / chemistry
  • Rats
  • Rats, Inbred F344
  • Tumor Microenvironment

Substances

  • 6-trifluoromethylpyridoxine
  • Indicators and Reagents
  • Fluorine
  • Pyridoxine