Facile synthesis of carbon-11-labeled cholesterol-based cationic lipids as new potential PET probes for imaging of gene delivery in cancer

Mingzhang Gao, Min Wang, Kathy D. Miller, George W. Sledge, Gary D. Hutchins, Qi Huang Zheng

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Gene therapy based on gene delivery is a promising strategy for the treatment of various human diseases such as cancer. Cationic lipids represent one of the important synthetic gene delivery systems. There is a great interest in imaging of gene therapy using the biomedical imaging technique positron emission tomography (PET). Carbon-11-labeled cholesterol-based cationic lipids were first designed and synthesized as new potential PET probes for imaging of gene delivery in cancer. The [11C-methyl]quaternary amine target tracers, N-[11C]methyl-N-[4-(cholest-5-en-3β-yloxycarbonyl) butyl]pyrrolidinium iodide ([11C]4a), N-[11C]methyl- N′-[4-(cholest-5-en-3β-yloxycarbonyl)butyl]imidazolium iodide ([ 11C]4b), N-[11C]methyl-N-[4-(cholest-5-en-3β- yloxycarbonyl)butyl]piperidinium iodide ([11C]4c), N-[ 11C]methyl-N-[4-(cholest-5-en-3β-yloxycarbonyl)butyl] -4-methylpiperidinium iodide ([11C]4d), and N-[11C]methyl- N-[4-(cholest-5-en-3β-yloxycarbonyl)butyl]morpholinium iodide ([ 11C]4e), were prepared from their corresponding tertiary amine precursors with [11C]methyl iodide ([11C]CH3I) through N-[11C]methylation and isolated by a simplified solid-phase extraction (SPE) method using a Silica Sep-Pak cartridge in 5060% radiochemical yields decay corrected to end-of-bombardment (EOB), based on [ 11C]CO2, and 111185 GBq/μmol specific activity at the end of synthesis (EOS).

Original languageEnglish (US)
Pages (from-to)715-720
Number of pages6
JournalSteroids
Volume75
Issue number10
DOIs
StatePublished - Oct 1 2010

    Fingerprint

Keywords

  • Cancer imaging
  • Cholesterol-based cationic lipids
  • Gene delivery
  • Gene therapy
  • Positron emission tomography
  • Probes

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology
  • Medicine(all)

Cite this