Small molecule recognition of homopurine nucleic acid structures

dc.contributor.advisor Hud, Nicholas V.
dc.contributor.author Persil Cetinkol, Ozgul en_US
dc.contributor.committeeMember Doyle, Donald
dc.contributor.committeeMember Lobachev, Kirill
dc.contributor.committeeMember Oyelere, Adegboyega
dc.contributor.committeeMember Wartell, Roger
dc.contributor.department Chemistry and Biochemistry en_US
dc.date.accessioned 2009-08-26T18:15:24Z
dc.date.available 2009-08-26T18:15:24Z
dc.date.issued 2008-07-08 en_US
dc.description.abstract The thesis topic entitled above involves the use of small molecules as a general means to drive nucleic acid assembly and structural transitions. We have shown that coralyne, a crescent-shaped small molecule, can assemble homo-adenine DNA and RNA sequences into anti-parallel duplexes at neutral pH, a structure containing putative purine-purine (A*A) base pairs that is otherwise unstable. The importance of the structure of the small molecule in the recognition and stabilization of A*A base pairing has been established by experimental evidence. We further provide structural evidence for the putative A*A base pairing that is stabilized by coralyne and molecules of similar size and shape. Our hypothesis that planar molecules that are slightly too large to intercalate Watson-Crick base pairs might intercalate the larger purine-purine base pairs has led to the design of a new class of small molecules that tightly bind purine-purine duplexes with excellent selectively. We have demonstrated that azacyanines can exhibit strong and selective association with a human telomeric sequence that forms a unimolecular G-quadruplex in solution. The synthetic accessibility of azacyanines makes this class of molecules amenable to library preparation for high-throughput screening. Together, the findings reported in this thesis provide further evidence for the robust and versatile nature of selective small molecule recognition of nucleic acids, especially purine-purine duplexes. en_US
dc.description.degree Ph.D. en_US
dc.identifier.uri http://hdl.handle.net/1853/29739
dc.publisher Georgia Institute of Technology en_US
dc.subject Physical characterization en_US
dc.subject Nucleic acids en_US
dc.subject Small molecule binding en_US
dc.subject Assembly en_US
dc.subject Intercalation en_US
dc.subject.lcsh Biomolecules
dc.subject.lcsh Nucleic acids
dc.subject.lcsh Supramolecular chemistry
dc.subject.lcsh Purines
dc.title Small molecule recognition of homopurine nucleic acid structures en_US
dc.type Text
dc.type.genre Dissertation
dspace.entity.type Publication
local.contributor.advisor Hud, Nicholas V.
local.contributor.corporatename School of Chemistry and Biochemistry
local.contributor.corporatename College of Sciences
relation.isAdvisorOfPublication 32914b8e-b40c-41d2-872d-04991293374e
relation.isOrgUnitOfPublication f1725b93-3ab8-4c47-a4c3-3596c03d6f1e
relation.isOrgUnitOfPublication 85042be6-2d68-4e07-b384-e1f908fae48a
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