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dc.contributor.authorTsotsoros, SD
dc.contributor.authorLutz, PB
dc.contributor.authorDaniel, AG
dc.contributor.authorPeterson, EJ
dc.contributor.authorde Paiva, REF
dc.contributor.authorRivera, E
dc.contributor.authorQu, Y
dc.contributor.authorBayse, CA
dc.contributor.authorFarrell, NP
dc.date.accessioned2023-06-09T00:17:45Z
dc.date.available2023-06-09T00:17:45Z
dc.date.issued2017
dc.identifier.issn2041-6520en_US
dc.identifier.doi10.1039/c6sc03445den_US
dc.identifier.urihttp://hdl.handle.net/10072/407726
dc.description.abstractPhysicochemical properties of coordination compounds can be exploited for molecular recognition of biomolecules. The inherent π-π stacking properties of [Pt(chelate)(N-donor)]2+ ([PtN4]) complexes were modulated by systematic variation of the chelate (diethylenetriamine and substituted derivatives) and N-donor (nucleobase or nucleoside) in the formally substitution-inert PtN4 coordination sphere. Approaches to target the HIV nucleocapsid protein HIVNCp7 are summarized building on (i) assessment of stacking interactions with simple tryptophan or tryptophan derivatives to (ii) the tryptophan-containing C-terminal zinc finger and (iii) to the full two-zinc finger peptide and its interactions with RNA and DNA. The xanthosine nucleoside was identified as having significantly enhanced stacking capability over guanosine. Correlation of the LUMO energies of the modified nucleobases with the DFT π-stacking energies shows that frontier orbital energies of the individual monomers can be used as a first estimate of the π-stacking strength to Trp. Cellular accumulation studies showed no significant correlation with lipophilicity of the compounds, but all compounds had very low cytotoxicity suggesting the potential for antiviral selectivity. The conceptual similarities between nucleobase alkylation and platination validates the design of formally substitution-inert coordination complexes as weak Lewis acid electrophiles for selective peptide targeting.en_US
dc.description.peerreviewedYesen_US
dc.languageengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.relation.ispartofpagefrom1269en_US
dc.relation.ispartofpageto1281en_US
dc.relation.ispartofissue2en_US
dc.relation.ispartofjournalChemical Scienceen_US
dc.relation.ispartofvolume8en_US
dc.subject.fieldofresearchChemical sciencesen_US
dc.subject.fieldofresearchcode34en_US
dc.titleEnhancement of the physicochemical properties of [Pt(dien)(nucleobase)]2+ for HIVNCp7 targetingen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Articlesen_US
dcterms.bibliographicCitationTsotsoros, SD; Lutz, PB; Daniel, AG; Peterson, EJ; de Paiva, REF; Rivera, E; Qu, Y; Bayse, CA; Farrell, NP, Enhancement of the physicochemical properties of [Pt(dien)(nucleobase)]2+ for HIVNCp7 targeting, Chemical Science, 2017, 8 (2), pp. 1269-1281en_US
dcterms.dateAccepted2016-10-06
dcterms.licensehttp://creativecommons.org/licenses/by-nc/3.0/en_US
dc.date.updated2021-09-07T06:35:25Z
dc.description.versionVersion of Record (VoR)en_US
gro.rights.copyright© The Authors 2016. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.en_US
gro.hasfulltextFull Text
gro.griffith.authorFarrell, Nicholas


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