Recently, it has been shown that different complexes consisting of protein and fatty acids, which we call liprotides, have common functional and structural features. Liprotides can transfer their fatty acid content to membranes, highlighting the potential to incorporate other small molecules and help transfer them to membranes. In this study, this potential was explored with regard to the poorly water-soluble vitamin E compound α-tocopherol (Toc). Uptake into liprotides increased Toc solubility and chemical stability. The liprotide-Toc complexes retained the characteristic liprotide structure with a core of fatty acid surrounded by protein. Toc and fatty acid could be transferred to artificial vesicles upon being incorporated into the liprotide complex. Extending this work, we found that free tryptophan and the vitamin A precursor retinaldehyde could also be incorporated in the liprotides; however, other small molecules failed to be taken up, and we conclude that successful incorporation requires a hydrophobic terminal moiety that can be accommodated within the micelle interior of the liprotides. Nevertheless, our work suggests that liprotides are able to stabilize and transport a number of otherwise insoluble small molecules with significant potential health benefits.
