title: Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA.
abstract: To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA. A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, A(T) shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that A(T) only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that A(T) shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.
authors.affiliation: Department of Chemical and Biological Engineering/Physical Chemistry, Chalmers University of Technology, University of Gothenburg, S-41296 Gothenburg, Sweden.
authors.forename: Anke
authors.initials: A
authors.lastname: Dierckx
authors.forename: Peter
authors.initials: P
authors.lastname: Dinér
authors.forename: Afaf H
authors.initials: AH
authors.lastname: El-Sagheer
authors.forename: Joshi Dhruval
authors.initials: JD
authors.lastname: Kumar
authors.forename: Tom
authors.initials: T
authors.lastname: Brown
authors.forename: Morten
authors.initials: M
authors.lastname: Grøtli
authors.forename: L Marcus
authors.initials: LM
authors.lastname: Wilhelmsson
mesh_terms: D020029:Base Pairing; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D004277:DNA, Single-Stranded / Q000737:chemistry; D003839:Deoxyadenosines / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D009691:Nucleic Acid Denaturation; D009943:Organophosphorus Compounds / Q000138:chemical synthesis; D013050:Spectrometry, Fluorescence; D014230:Triazoles / Q000737:chemistry*
chemical_list: C560092:8-(1-pentyl-1H-1,2,3-triazole-4-yl)-2'-deoxyadenosine; D004277:DNA, Single-Stranded; D003839:Deoxyadenosines; D005456:Fluorescent Dyes; D009943:Organophosphorus Compounds; D014230:Triazoles; C434331:phosphoramidite; D004247:DNA