title: Self-assembling oligothiophene-bolaamphiphiles for loading and controlled release of doxorubicin into living cells.
abstract: 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.
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany. sylvia.schmid@uni-ulm.de.
authors.forename: S
authors.initials: S
authors.lastname: Schmid
authors.affiliation: Institute of Organic Chemistry III/Macromolecular Chemistry, University of Ulm, Albert Einstein Allee 11, 89081 Ulm, Germany.
authors.forename: D Y W
authors.initials: DY
authors.lastname: Ng
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany. sylvia.schmid@uni-ulm.de.
authors.forename: E
authors.initials: E
authors.lastname: Mena-Osteritz
authors.affiliation: Institute of Organic Chemistry III/Macromolecular Chemistry, University of Ulm, Albert Einstein Allee 11, 89081 Ulm, Germany.
authors.forename: Y
authors.initials: Y
authors.lastname: Wu
authors.affiliation: Institute of Organic Chemistry III/Macromolecular Chemistry, University of Ulm, Albert Einstein Allee 11, 89081 Ulm, Germany.
authors.forename: T
authors.initials: T
authors.lastname: Weil
authors.affiliation: Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany. sylvia.schmid@uni-ulm.de.
authors.forename: P
authors.initials: P
authors.lastname: Bäuerle
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000008:administration & dosage*; D003692:Delayed-Action Preparations; D004317:Doxorubicin / Q000008:administration & dosage*; D018625:Microscopy, Atomic Force; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D000903:Antibiotics, Antineoplastic; D003692:Delayed-Action Preparations; D013876:Thiophenes; D004317:Doxorubicin