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 Miller, George W. Sledge, Gary Hutchins, Qi-Huang Zheng

Research output: Contribution to journalArticle

3 Citations (Scopus)

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

Fingerprint

Positron emission tomography
Iodides
Positron-Emission Tomography
Carbon
Genes
Cholesterol
Lipids
Imaging techniques
Gene therapy
Neoplasms
Genetic Therapy
Amines
Synthetic Genes
Gene Transfer Techniques
Methylation
Solid Phase Extraction
Silicon Dioxide

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

Facile synthesis of carbon-11-labeled cholesterol-based cationic lipids as new potential PET probes for imaging of gene delivery in cancer. / Gao, Mingzhang; Wang, Min; Miller, Kathy; Sledge, George W.; Hutchins, Gary; Zheng, Qi-Huang.

In: Steroids, Vol. 75, No. 10, 10.2010, p. 715-720.

Research output: Contribution to journalArticle

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