Beilstein J. Org. Chem.2012,8, 2072–2084, doi:10.3762/bjoc.8.233
.8.233 Abstract Phallotoxins inhibit the dynamics of microfilaments in cells and lead to apoptosis. Due to poor cellular uptake these effects cannot be studied in live cells, even at millimolar toxin concentrations, nor can phalloidin be used for the elimination of tumor cells. Uptake is greatly enhanced
by conjugation of phallotoxins to either lipophilic or polycationic moieties, such as oleic acid, polylysine, or Tat-peptide. These conjugates were lethally toxic for cells, e.g., mouse fibroblasts or Jurkat leukemia cells, in the micromolar range. Uptake into cells starts with the attachment of the
weight methoxy-polyethyleneglycol, two compounds unknown so far for their uptake-mediating activity. Conjugation to carriers as investigated in this work will allow the use of phallotoxins in experimental cell biology and possibly in tumor therapy. The findings obtained with phallotoxins could be applied
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Graphical Abstract
Figure 1:
Chemical structure of phalloidin with the attachment site (R) used for conjugation to uptake-mediat...