alexa DNA Binding Polyamides and the Importance of DNA Recognition in their use as Gene-Specific and Antiviral Agents
ISSN: 2161-0444

Medicinal Chemistry
Open Access

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Research Article

DNA Binding Polyamides and the Importance of DNA Recognition in their use as Gene-Specific and Antiviral Agents

Kevin J Koeller1, G Davis Harris1, Karl Aston1, Gaofei He1, Carlos H Castaneda1, Melissa A Thornton1, Terri G Edwards2, Shuo Wang3, Rupesh Nanjunda3, W David Wilson3*, Chris Fisher2* and James K Bashkin1,2*

1Department of Chemistry & Biochemistry, University of Missouri-St. Louis, St.Louis, MO 63121, USA

2NanoVir, LLC, Kalamazoo, MI 49008, USA

3Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA

*Corresponding Author:
James K Bashkin
Department of Chemistry & Biochemistry
University of Missouri- St. Louis, St. Louis, MO 63121, USA
Tel: +1(314)516-7352
Fax: +1(314)516-5432
E-mail: [email protected]
 
Chris Fisher
NanoVir, LLC, Kalamazoo, MI 49008, USA
Tel: +1(269)372-3261
Fax: +1(269)372-3397
E-mail: [email protected]
 
W. David Wilson
Department of Chemistry, Georgia State University
Atlanta, GA 30303, USA
Tel: +1(404)413-5503
Fax: +1(404)413-5505
E-mail: [email protected]

Received date: January 22, 2014; Accepted date: February 20, 2014; Published date: February 22, 2014

Citation: Koeller KJ, Davis Harris G, Aston K, He G, Castaneda CH, Thornton MA, et al. (2014) DNA Binding Polyamides and the Importance of DNA Recognition in their use as Gene-Specific and Antiviral Agents. Med chem 4:338-344. doi: 10.4172/2161-0444.1000162

Copyright: © 2014 Koeller KJ, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

Abstract

There is a long history for the bioorganic and biomedical use of N-methyl-pyrrole-derived polyamides (PAs) that are higher homologs of natural products such as distamycin A and netropsin. This work has been pursued by many groups, with the Dervan and Sugiyama groups responsible for many breakthroughs. We have studied PAs since about 1999, partly in industry and partly in academia. Early in this program, we reported methods to control cellular uptake of polyamides in cancer cell lines and other cells likely to have multidrug resistance efflux pumps induced. We went on to discover antiviral polyamides active against HPV31, where SAR showed that a minimum binding size of about 10 bp of DNA was necessary for activity. Subsequently we discovered polyamides active against two additional high-risk HPVs, HPV16 and 18, a subset of which showed broad spectrum activity against HPV16, 18 and 31. Aspects of our results presented here are incompatible with reported DNA recognition rules. For example, molecules with the same cognate DNA recognition properties varied from active to inactive against HPVs. We have since pursued the mechanism of action of antiviral polyamides, and polyamides in general, with collaborators at NanoVir, the University of Missouri-St. Louis, and Georgia State University. We describe dramatic consequences of β-alanine positioning even in relatively small, 8-ring polyamides; these results contrast sharply with prior reports. This paper was originally presented by JKB as a Keynote Lecture in the 2nd International Conference on Medicinal Chemistry and Computer Aided Drug Design Conference in Las Vegas, NV, October 2013.

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