NDLI: Base pairing involving artificial bases <i>in vitro</i> and <i>in vivo</i>

Content Provider	Royal Society of Chemistry (RSC)
Author	Jang, Miyeon Schepers, Guy Herdewijn, Piet Braddick, Darren Lescrinier, Eveline Marlière, Philippe Agnello, Stefano Pezo, Valérie Rozenski, Jef Bande, Omprakash
Copyright Year	2016
Abstract	Herein we report the synthesis of N8-glycosylated 8-aza-deoxyguanosine (N8-8-aza-dG) and 8-aza-9-deaza-deoxyguanosine (N8-8-aza-9-deaza-dG) nucleotides and their base pairing properties with 5-methyl-isocytosine (d-isoCMe), 8-amino-deoxyinosine (8-NH2-dI), 1-N-methyl-8-amino-deoxyinosine (1-Me-8-NH2-dI), 7,8-dihydro-8-oxo-deoxyinosine (8-Oxo-dI), 7,8-dihydro-8-oxo-deoxyadenosine (8-Oxo-dA), and 7,8-dihydro-8-oxo-deoxyguanosine (8-Oxo-dG), in comparison with the d-isoCMe:d-isoG artificial genetic system. As demonstrated by Tm measurements, the N8-8-aza-dG:d-isoCMe base pair formed less stable duplexes as the C:G and d-isoCMe:d-isoG pairs. Incorporation of 8-NH2-dI versus the N8-8-aza-dG nucleoside resulted in a greater reduction in Tm stability, compared to d-isoCMe:d-isoG. Insertion of the methyl group at the N1 position of 8-NH2-dI did not affect duplex stability with N8-8-aza-dG, thus suggesting that the base paring takes place through Hoogsteen base pairing. The cellular interpretation of the nucleosides was studied, whereby a lack of recognition or mispairing of the incorporated nucleotides with the canonical DNA bases indicated the extent of orthogonality in vivo. The most biologically orthogonal nucleosides identified included the 8-amino-deoxyinosines (1-Me-8-NH2-dI and 8-NH2-dI) and N8-8-aza-9-deaza-dG. The 8-oxo modifications mimic oxidative damage ahead of cancer development, and the impact of the MutM mediated recognition of these 8-oxo-deoxynucleosides was studied, finding no significant impact in their in vivo assay.
Starting Page	995
Ending Page	1010
Page Count	16
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	2
Journal	Chemical Science
DOI	10.1039/c5sc03474d
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Methyl group DNA Hoogsteen base pair Nucleoside Glycosylation Orthogonality Hoogsteen 8-Oxo-2'-deoxyguanosine Base pair Cancer
Content Type	Text
Resource Type	Article
Subject	Chemistry

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2′-Deoxyimmunosine: stereoselective synthesis, base pairing and duplex stability of oligonucleotides containing 8-oxo-7-thiaguanine

An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson–Crick versus Hoogsteen base pairing

Correction: Base pairing involving artificial bases in vitro and in vivo

Cellular level of 8-oxo-2'-deoxyguanosine in DNA does not correlate with urinary excretion of the modified base/nucleoside.

Incorporation and replication of 8-oxo-deoxyguanosine by the human mitochondrial DNA polymerase.

QUARTERLY Communication Cellular level of 8-oxo-2�-deoxyguanosine in DNA does not correlate with urinary excretion of the modified base/nucleoside �

Cadmium(II), unlike nickel(II), inhibits 8-oxo-dGTPase activity and increases 8-oxo-dG level in DNA of the rat testis, a target organ for cadmium(II) carcinogenesis

“Action-at-a-Distance” Mutagenesis 8-OXO-7,8-DIHYDRO-2′-DEOXYGUANOSINE CAUSES BASE SUBSTITUTION ERRORS AT NEIGHBORING TEMPLATE SITES WHEN COPIED BY DNA POLYMERASE β

Effect of Watson−Crick and Hoogsteen Base Pairing on the Conformational Stability of C8-Phenoxyl-2′-deoxyguanosine Adducts

Base pairing involving artificial bases in vitro and in vivo

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Correction: Base pairing involving artificial bases in vitro and in vivo

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