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Fatty acylation enhances cellular localization of dansylated phenylalanines

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Abstract

Two series of fluorescent molecules were synthesized by acylation of dansyl ethylenediamine and phenylalanine dansyl ethylenediamine with one of either acetyl (C2), hexanyl (C6), cyclohexanecarbonyl (C7), myristyl (C14), or palmityl (C16) groups and examined for entry and localization in Chinese Hamster Ovary (CHO) cells in tissue culture. Gross total fluorescence retention and cellular microscopic fluorescence patterns were analyzed. In both series, molecules with myristyl or palmityl groups entered cells. Only in the phenylalanine series did hexyl and cyclohexanecarbonyl modification enable entry. Consistent with a mechanism of passive diffusion, entry of compounds into cells was neither energy dependent nor endocytosis linked. Acylated molecules were observed to localize in cytoplasm and not enter nuclei or associate with lipophilic plasma membranes.

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Acknowledgment

We would like to thank Dr. Scott Molitor (Department of Bioengineering, University of Toledo) for assistance with microscopy and image acquisition.

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, College of Pharmacy, The University of Findlay, 1000 North Main Street, Findlay, OH, 45840, USA

    Richard W. Dudley

  2. Department of Medicinal and Biological Chemistry, College of Pharmacy, The University of Toledo, 2801 West Bancroft Street, Toledo, OH, 43606, USA

    Brandon D. Slotterbeck, Marcia F. McInerney & Steven M. Peseckis

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  1. Richard W. Dudley
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  2. Brandon D. Slotterbeck
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  3. Marcia F. McInerney
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  4. Steven M. Peseckis
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Correspondence to Steven M. Peseckis.

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Dudley, R.W., Slotterbeck, B.D., McInerney, M.F. et al. Fatty acylation enhances cellular localization of dansylated phenylalanines. Mol Cell Biochem 346, 81–87 (2011). https://doi.org/10.1007/s11010-010-0593-4

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  • DOI: https://doi.org/10.1007/s11010-010-0593-4

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