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dc.contributor.authorWu, Runzhi
dc.contributor.authorSmidansky, Eric D.
dc.contributor.authorOh, Hyung Suk
dc.contributor.authorTakhampunya, Ratree
dc.contributor.authorPadmanabhan, Radhakrishnan
dc.contributor.authorCameron, Craig E.
dc.contributor.authorPeterson, Blake R.
dc.date.accessioned2017-04-12T15:58:50Z
dc.date.available2017-04-12T15:58:50Z
dc.date.issued2010-11-25
dc.identifier.citationWu, R., Smidansky, E. D., Oh, H. S., Takhampunya, R., Padmanabhan, R., Cameron, C. E., & Peterson, B. R. (2010). Synthesis of a 6-Methyl-7-Deaza Analogue of Adenosine that Potently Inhibits Replication of Polio and Dengue Viruses. Journal of Medicinal Chemistry, 53(22), 7958–7966. http://doi.org/10.1021/jm100593sen_US
dc.identifier.urihttp://hdl.handle.net/1808/23631
dc.description.abstractBioisosteric deaza analogues of 6-methyl-9-β-D-ribofuranosylpurine, a hydrophobic analogue of adenosine, were synthesized and evaluated for antiviral activity. Whereas the 1-deaza and 3-deaza analogues were essentially inactive in plaque assays of infectivity, a novel 7-deaza-6-methyl-9-β-D-ribofuranosylpurine analogue, structurally related to the natural product tubercidin, potently inhibited replication of poliovirus (PV) in HeLa cells (IC50 = 11 nM) and dengue virus (DENV) in Vero cells (IC50 = 62 nM). Selectivity against PV over cytotoxic effects to HeLa cells was >100-fold after incubation for 7 h. Mechanistic studies of the 5'-triphosphate of 7-deaza-6-methyl-9-β-D-ribofuranosylpurine revealed that this compound is an efficient substrate of PV RNA-dependent RNA polymerase (RdRP) and is incorporated into RNA mimicking both ATP and GTP.en_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Medicinal Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jm100593s.en_US
dc.titleSynthesis of a 6-Methyl-7-Deaza Analogue of Adenosine that Potently Inhibits Replication of Polio and Dengue Virusesen_US
dc.typeArticleen_US
kusw.kuauthorWu, Runzhi
kusw.kuauthorPeterson, Blake R.
kusw.kudepartmentMedicinal Chemistryen_US
dc.identifier.doi10.1021/jm100593sen_US
kusw.oaversionScholarly/refereed, author accepted manuscripten_US
kusw.oapolicyThis item meets KU Open Access policy criteria.en_US
dc.rights.accessrightsopenAccess


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