Molecular-Level Helical Stack of a Nucleotide-Appended Oligo(p-phenylenevinylene) Directed by Supramolecular Self-Assembly with a Complementary Oligonucleotide as a Template

Citations Over TimeTop 10% of 2006 papers

Abstract

The nucleotide-appended oligo(p-phenylenevinylene), {bis[2,5-bis(2-methoxyethoxy)-1,4-phenylene]bis(2,1-ethenediyl-1,4-phenylenemethylene)}bis(2'-deoxy-3'-thymidylic acid) (8), has been synthesized, and self-assembly of the single-component 8 and binary self-assembly of 8 with a complementary single-stranded 20-meric oligodeoxyadenylic acid (9) have been examined in aqueous solutions. Atomic force microscopy (AFM), UV-visible (UV-vis), and circular dichroism (CD) measurements revealed that right-handed helical stacks with 6.4- and 5.1-nm diameters self-assemble from the binary components of 8 and 9 as a template depending on the residual stoichiometry of the two components (thymine (T):adenine (A) = 1:1 and T:A = 2:1, respectively). The concentration of 9 was found to strongly influence the CD spectra of 8 in aqueous solutions. Consequently, we concluded that the one side of the thymine moieties in the stacked assemblies of 8 complexes with a single chain of 9. Complementary T-A base pairs thus formed and induced helical stack of the oligo(p-phenylenevinylene)s in the binary self-assembly. In contrast, self-assembly of the single-component 8 and binary self-assembly of 8 with the noncomplementary 20-meric oligothymidylic acid (10) produced no remarkable formation of fibrous structures like helical stacks.

Related Papers

• → The use of circular dichroism spectroscopy for studying the chiral molecular self‐assembly: An overview(2007)224 cited
• → Induction of chirality from ligand to the supramolecular helical packing in Mo(VI)–Ln(III) heterobimetallic complexes: Synthesis, structure and photoluminescence properties(2015)5 cited
• → Synthesis and incorporation of an α-hexofuranosyl thymidine into oligodeoxynucleotides via its two exocyclic OH-groups(2004)3 cited
• → The synthesis and binding properties of oligonucleotide analogs containing diastereomerically pure conformationally restricted acetal linkages(1997)14 cited
• Changes in pyrimidine nucleotide clusters of DNA following in vitro x-irradiation(1977)