Schmid S, Ng D Y W, Mena-Osteritz E, Wu Y, Weil T, Bäuerle P
Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany.
Institute of Organic Chemistry III/Macromolecular Chemistry, University of Ulm, Albert Einstein Allee 11, 89081 Ulm, Germany.
Chem Commun (Camb). 2016 Feb 21;52(15):3235-8. doi: 10.1039/c5cc08483k.
Design and synthesis of symmetric mannose-functionalized oligothiophenes is reported. Self-organization of these bolaamphiphiles in solution and in the solid state was investigated by optical and AFM experiments. Fluorescence measurements revealed efficient loading and pH-dependent release of the anti-cancer drug doxorubicin. Delivery and release of the active drug into viable A549 cells as well as chirality-dependent cellular toxicity of the bolaamphiphilic transporter were evident from in vitro experiments.