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https://hdl.handle.net/2440/47991
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DC Field | Value | Language |
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dc.contributor.author | Van Vliet, L. | - |
dc.contributor.author | Ellis, T. | - |
dc.contributor.author | Foley, P. | - |
dc.contributor.author | Liu, L. | - |
dc.contributor.author | Pfeffer, F. | - |
dc.contributor.author | Russell, R. | - |
dc.contributor.author | Warrener, R. | - |
dc.contributor.author | Hollfelder, F. | - |
dc.contributor.author | Waring, M. | - |
dc.date.issued | 2007 | - |
dc.identifier.citation | Journal of Medicinal Chemistry, 2007; 50(10):2326-2340 | - |
dc.identifier.issn | 0022-2623 | - |
dc.identifier.issn | 1520-4804 | - |
dc.identifier.uri | http://hdl.handle.net/2440/47991 | - |
dc.description | Copyright © 2007 American Chemical Society | - |
dc.description.abstract | We have exploited the concept of multivalency in the context of DNA recognition, using novel chemistry to synthesize a new type of bis-intercalator with unusual sequence-selectivity. Bis-intercalation has been observed previously, but design principles for de novo construction of such molecules are not known. Our compounds feature two aromatic moieties projecting from a rigid, polynorbornane-based scaffold. The length and character of the backbone as well as the identity of the intercalators were varied, resulting in mono- or divalent recognition of the double helix with varying affinity. Our lead compound proved to be a moderately sequence-selective bis-intercalator with an unwinding angle of 27 degrees and a binding constant of about 8 microM. 9-aminoacridine rings were preferred over acridine carboxamides or naphthalimides, and a rigid [3]-polynorbornane scaffold was superior to a [5]-polynorbornane. The flexibility of the linker connecting the rings to the scaffold, although less influential, could affect the strength and character of the DNA binding. | - |
dc.description.statementofresponsibility | Liisa D. Van Vliet, Tom Ellis, Patrick J. Foley, Ligong Liu, Frederick M. Pfeffer, Richard A. Russell, Ronald N. Warrener, Florian Hollfelder, and Michael J. Waring | - |
dc.language.iso | en | - |
dc.publisher | Amer Chemical Soc | - |
dc.source.uri | http://pubs.acs.org/cgi-bin/abstract.cgi/jmcmar/2007/50/i10/abs/jm0613020.html | - |
dc.subject | Amides | - |
dc.subject | Norbornanes | - |
dc.subject | Acridines | - |
dc.subject | Aminoacridines | - |
dc.subject | Deoxyribonucleases | - |
dc.subject | DNA | - |
dc.subject | Intercalating Agents | - |
dc.subject | Dialysis | - |
dc.subject | Electrophoresis, Gel, Two-Dimensional | - |
dc.subject | Structure-Activity Relationship | - |
dc.subject | Naphthalimides | - |
dc.title | Molecular recognition of DNA by rigid [n]-polynorbornane-derived bifunctional intercalators: Synthesis and evaluation of their binding properties | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jm0613020 | - |
pubs.publication-status | Published | - |
Appears in Collections: | Adelaide Graduate Centre publications Aurora harvest |
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