Triplexes with 8-Aza-2 `-Deoxyisoguanosine Replacing Protonated dC: Probing Third Strand Stability with a Fluorescent Nucleobase Targeting Duplex DNA

DC FieldValueLanguage
dc.contributor.authorSeela, Frank
dc.contributor.authorJiang, Dawei
dc.contributor.authorBudow, Simone
dc.date.accessioned2021-12-23T16:06:18Z-
dc.date.available2021-12-23T16:06:18Z-
dc.date.issued2010
dc.identifier.issn14394227
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7348-
dc.description.abstractThe fluorescent 8-aza-2'-deoxyisoguanosine (4) as well as the parent 2'-deoxyisoguanosine (1) were used as protonated dCH(+) surrogates in the third strand of oligonucleotide triplexes. Stable triplexes were formed by Hoogsteen base pairing. In contrast to dC, triplexes containing nucleoside 1 or 4 in place of dCH(+) are already formed under neutral conditions or even at alkaline pH values. Triplex melting can be monitored separately from duplex dissociation in cases in which the third strand contains the fluorescent nucleoside 4. Third-strand binding of oligonucleotides with 4, opposite to dG, was selective as demonstrated by hybridisation experiments studying mismatch discrimination. Third-strand binding is more efficient when the stability of the DNA duplex is reduced by mismatches, giving third-strand binding more flexibility.
dc.description.sponsorshipRoche Diagnostics GmbH; Penzberg and ChemBiotech, Munster, Germany; China Scholarship (CSC), Beijing; We thank Dr. Peter Leonard for supplying us with the phosphoramidite of 1. We thank Nhat Q. Tran for the oligonucleotide synthesis and Dr. Roland Thiele from Roche Diagnostics, Penzberg for the measurement of the MALDI spectra and appreciate critical reading of the manuscript by Suresh S. Pujari. Financial support by Roche Diagnostics GmbH, Penzberg and ChemBiotech, Munster, Germany, and a China Scholarship (CSC), Beijing are gratefully acknowledged.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMBIOCHEM
dc.subjectANALOG
dc.subjectBASE-PAIRS
dc.subjectBiochemistry & Molecular Biology
dc.subjectChemistry, Medicinal
dc.subjectDNA
dc.subjectDOUBLE-HELICAL DNA
dc.subjectETHIDIUM-BROMIDE
dc.subjectfluorescent probes
dc.subjectFORMING-OLIGONUCLEOTIDES
dc.subjectISOGUANINE
dc.subjectmismatch discrimination
dc.subjectmodified oligonucleotides
dc.subjectOLIGODEOXYNUCLEOTIDES
dc.subjectPH-INDEPENDENT RECOGNITION
dc.subjectPharmacology & Pharmacy
dc.subjectPHYSIOLOGICAL PH
dc.subjectSELECTIVITY
dc.subjecttriplex DNA
dc.titleTriplexes with 8-Aza-2 `-Deoxyisoguanosine Replacing Protonated dC: Probing Third Strand Stability with a Fluorescent Nucleobase Targeting Duplex DNA
dc.typejournal article
dc.identifier.doi10.1002/cbic.201000162
dc.identifier.isiISI:000280787400019
dc.description.volume11
dc.description.issue10
dc.description.startpage1443
dc.description.endpage1450
dc.identifier.eissn14397633
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationChemBioChem
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