Synthesis and evaluation of novel enhanced gene reporter molecules: Detection of β-galactosidase activity using 19F NMR of trifluoromethylated aryl β-d-galactopyranosides

Jianxin Yu, Li Liu, Vikram D. Kodibagkar, Weina Cui, Ralph P. Mason

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Gene therapy has emerged as a promising strategy for treatment of various diseases, but there is a pressing need for the development of non-invasive reporter techniques based on appropriate molecules and imaging modalities to assay gene expression. We now report the design, synthesis, and evaluation of novel enhanced reporter molecules, which reveal lacZ gene expression: trifluoromethylated aryl β-d-galactopyranosides. A series of five molecular structures were screened in solution and with stably transfected lacZ expressing human MCF7 breast cancer cells in vitro. p-Trifluoromethyl-o- nitrophenyl β-d-galactopyranoside (PCF3ONPG) was found to exhibit valuable properties including a single 19F NMR signal, stability in aqueous solution and with wild type cells, but a chemical shift response to enzyme cleavage (Δδ = 1.14 ppm) in breast cancer cells transfected to stably express lacZ.

Original languageEnglish (US)
Pages (from-to)326-333
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number2
DOIs
StatePublished - Jan 15 2006

Keywords

  • F NMR
  • Reporter gene
  • lacZ
  • β-Galactosidase

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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