(4-[18F]fluoro-3-iodobenzyl)guanidine, a potential MIBG analogue for positron emission tomography

J Med Chem. 1994 Oct 14;37(21):3655-62. doi: 10.1021/jm00047a022.

Abstract

The aims of this investigation were to develop a no-carrier-added (nca) synthesis of (4-[18F]-fluoro-3-iodobenzyl)guanidine ([18F]FIBG) and to evaluate its potential as an MIBG analogue useful for positron emission tomography. [18F]FIBG was prepared in four steps starting from 4-cyano-2-iodo-N,N,N-trimethylanilinium trifluoromethanesulfonate in 5% decay-corrected radiochemical yield in a total synthesis time of 130 min. The specific activity was more than 1500 Ci per mmol. In vitro binding studies showed that the percent binding of [18F]FIBG to SK-N-SH human neuroblastoma cells remained constant over a 3-log activity range and was similar to that of nca [131I]MIBG. Specific and high uptake of FIBG was also seen in mouse heart and adrenals. The in vitro and in vivo properties of [18F]FIBG suggest that this compound may be a useful positron-emitting analogue of MIBG.

Publication types

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

MeSH terms

  • 3-Iodobenzylguanidine
  • Adrenal Glands / metabolism
  • Animals
  • Contrast Media*
  • Fluorine Radioisotopes
  • Humans
  • Iodobenzenes* / chemical synthesis*
  • Iodobenzenes* / metabolism
  • Iodobenzenes* / pharmacokinetics
  • Lipid Metabolism
  • Mice
  • Mice, Inbred BALB C
  • Myocardium / metabolism
  • Neuroblastoma / metabolism
  • Tissue Distribution
  • Tomography, Emission-Computed*
  • Tumor Cells, Cultured

Substances

  • Contrast Media
  • Fluorine Radioisotopes
  • Iodobenzenes
  • (4-fluoro-3-iodobenzyl)guanidine
  • 3-Iodobenzylguanidine