Characterization of 2‐Fluoro‐2'‐deoxyadenosine in Duplex, G‐Quadruplex and i‐Motif. (9th May 2022)

• Record Type: Journal Article
• Authors: Hirashima, Shingo; Sugiyama, Hiroshi; Park, Soyoung
• Is Part Of: Chembiochem. Volume 23:Number 12(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-05-09
• Subjects: fluorinated nucleosides -- adenosine analogues -- 2-fluoroadenine -- 2-fluoro-2'-deoxyadenosine -- nucleic acids; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.202200222
• Languages: English
• ISSNs: 1439-4227

Abstract

Abstract: Among various kinds of fluorine‐substituted biomolecules, 2‐fluoroadenine (2FA) and its derivatives have been actively investigated as therapeutic reagents, radio‐sensitizers, and 19 F NMR probes. In spite of their excellent properties, DNA containing 2FA has not been studied well. For fundamental understanding and future applications to the development of functional nucleic acids, we characterized 2FA‐containing oligonucleotides for canonical right‐handed DNA duplex, G‐quadruplex, and i‐motif structures. Properties of 2FA were similar to native adenine due to the small size of the fluorine atom, but it showed unique features caused by high electronegativity. This work provides useful information for future application of 2FA‐modified DNA. Abstract : A small, but effective modification : Canonical and non‐canonical DNA structures containing 2‐fluoroadenosine (2FA) were characterized by thermal stability and CD spectroscopy. The results show interesting features such as high thermal stability of the 2FA‐C base pair and different structural influences on G‐quadruplexes in the presence of sodium ions. Incorporation of 2FA into the i‐motif induced small increases in pKa .