2. Academic Validation
  3. Clickable Polyamine Derivatives as Chemical Probes for the Polyamine Transport System

Clickable Polyamine Derivatives as Chemical Probes for the Polyamine Transport System

  • Chembiochem. 2018 May 4;19(9):907-911. doi: 10.1002/cbic.201800043.
Roeland Vanhoutte 1,  Jan Pascal Kahler 1,  Shaun Martin 2,  Sarah van Veen 2,  Steven H L Verhelst 1 3
Affiliations

Affiliations

  • 1 Laboratory of Chemical Biology, Department of Cellular and Molecular Medicine, KU Leuven, Herestraat 49, Box 802, 3000, Leuven, Belgium.
  • 2 Laboratory of Cellular Transport Systems, Department of Cellular and Molecular Medicine, KU Leuven, Herestraat 49, Box 802, 3000, Leuven, Belgium.
  • 3 Leibniz Institute for Analytical Sciences ISAS, Otto-Hahn-Strasse 6b, 44227, Dortmund, Germany.
PMID: 29451723 DOI: 10.1002/cbic.201800043
Abstract

Polyamines are essential for cell growth and differentiation, but their trafficking by the polyamine transport system is not fully understood. Herein, the synthesis of several azido-derivatized polyamines for easy conjugation by Click Chemistry is described. Attachment of a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dye gave fluorescent polyamine probes, which were tested in Cell Culture. The linear probe series showed superior cellular uptake compared with that of probes in which the dye was attached to a branch on one of the central amines. Interestingly, the linear probes accumulated rapidly in Cancer cells (MCF-7), but not in nontumorigenic cells (MCF-10A). The fluorescent polyamine probes are therefore applicable to the study of polyamine trafficking, whereas the azido polyamines may be further utilized to transport cargo into Cancer cells by exploiting the polyamine transport system.

Keywords

bioorganic chemistry; click chemistry; fluorescent probes; imaging agents; polyamines.

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