Journal article
Synthesis and activity of fluorescent isoprenoid pyrophosphate analogues
Journal of organic chemistry, Vol.69(24), pp.8186-8193
11/26/2004
DOI: 10.1021/jo049101w
PMID: 15549786
Abstract
New fluorescent analogues of farnesol and geranylgeraniol have been prepared and then converted to the corresponding pyrophosphates. These analogues incorporate anthranylate or dansyl-like groups anchored to the terpenoid skeleton through amine bonds that would be expected to be relatively stable to metabolism. After addition of the alcohols or the pyrophosphates to the culture medium, their fluorescence is readily observed inside a human-derived leukemia cell line. Enzyme assays have revealed that the farnesyl pyrophosphate analogue is an inhibitor of FTase, while the corresponding alcohol is not. These results, together with Western blot analyses of cell lysates, indicate that the farnesyl pyrophosphate analogue penetrates the cells as an intact pyrophosphate and that it does so at a biologically relevant concentration.
Details
- Title: Subtitle
- Synthesis and activity of fluorescent isoprenoid pyrophosphate analogues
- Creators
- MeeKyoung Kim - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USATroy S KleckleyAndrew J WiemerSarah A HolsteinRaymond J HohlDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.69(24), pp.8186-8193
- DOI
- 10.1021/jo049101w
- PMID
- 15549786
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- United States
- Language
- English
- Date published
- 11/26/2004
- Academic Unit
- Neuroscience and Pharmacology; Chemistry; Internal Medicine
- Record Identifier
- 9983985945802771
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