Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Self-Assembly of Perylenediimide–Single-Strand-DNA Conjugates: Employing Hydrophobic Interactions and DNA Base-Pairing To Create a Diverse Structural Space

Self-Assembly of Perylenediimide–Single-Strand-DNA Conjugates: Employing Hydrophobic Interactions and DNA Base-Pairing To Create a Diverse Structural Space
Frederick D. Lewis, Ashutosh Kumar Mishra, Elisha Krieg, Haim Weissman, Martin McCullagh, Boris Rybtchinski, Kevin A. Votaw
The self-assembly behavior of DNA conjugates possessing a perylenediimide (PDI) head group and an N-oligonucleotide tail has been investigated using a combination of optical spectroscopy and cryogenic transmission electron microscopy (cryo-TEM) imaging. To obtain insight into the interplay between PDI hydrophobic interactions and DNA base-pairing we employed systematic variation in the length and composition of the oligo tails. Conjugates with short (TA)n or (CG)n oligo tails (n≤3) form helical or nonhelical fibers constructed from π-stacked PDI head groups with pendent oligo tails in aqueous solution. Conjugates with longer (TA)n oligo tails also form stacks of PDI head groups, which are further aggregated by base-pairing between their oligo tails, leading to fiber bundling and formation of bilayers. The longer (CG)n conjugates form PDI end-capped duplexes, which further assemble into PDI-stacked arrays of duplexes leading to large scale ordered assemblies. Cryo-TEM imaging reveals that (CG)3 gives rise to both fibers and large assemblies, whereas (CG)5 assembles preferentially into large ordered structures. Heads or Tails? Assembly of PDI–single-strand-DNA conjugates (PDI=perylenediimide) can be directed to different structural space by the interplay between π-stacking and base-pairing. When the oligo tails are short, stacking of the PDI heads to form fibers wins. When (AT)n tails are long, cross-linking of the fibers occurs. When (GC)n tails are long, base-pairing dominates leading to formation of bilayers and ordered arrays.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700752

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