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We have synthesized and studied a supramolecular system comprising a 39-mer DNA with porphyrin-modified thymidine nucleosides anchored to the surface of large unilamellar vesicles (liposomes). Liposome porphyrin binding characteristics, such as orientation, strength, homogeneity, and binding site size, was determined, suggesting that the porphyrin is well suited as a photophysical and redox-active lipid anchor, in comparison to the inert cholesterol anchor commonly used today. Furthermore, the binding characteristics and hybridization capabilities were studied as a function of anchor size and number of anchoring points, properties that are of importance for our future plans to use the addressability of these redox-active nodes in larger DNA-based nanoconstructs. Electron transfer from photoexcited porphyrin to a lipophilic benzoquinone residing in the lipid membrane was characterized by steady-state and time-resolved fluorescence and verified by femtosecond transient absorption.

Original publication

DOI

10.1021/nn100667b

Type

Journal article

Journal

ACS Nano

Publication Date

28/09/2010

Volume

4

Pages

5037 - 5046

Keywords

Alkynes, Base Pairing, Benzoquinones, Cell Membrane, DNA Adducts, Electron Transport, Ethers, Hydrophobic and Hydrophilic Interactions, Liposomes, Models, Molecular, Nanotechnology, Nucleic Acid Hybridization, Porphyrins, Surface Properties