title: Second-generation fluorescent quadracyclic adenine analogues: environment-responsive probes with enhanced brightness.
abstract: Fluorescent base analogues comprise a group of increasingly important molecules for the investigation of nucleic acid structure, dynamics, and interactions with other molecules. Herein, we report on the quantum chemical calculation aided design, synthesis, and characterization of four new putative quadracyclic adenine analogues. The compounds were efficiently synthesized from a common intermediate through a two-step pathway with the Suzuki-Miyaura coupling as the key step. Two of the compounds, qAN1 and qAN4, display brightnesses (εΦF) of 1700 and 2300, respectively, in water and behave as wavelength-ratiometric pH probes under acidic conditions. The other two, qAN2 and qAN3, display lower brightnesses but exhibit polarity-sensitive dual-band emissions that could prove useful to investigate DNA structural changes induced by DNA-protein or -drug interactions. The four qANs are very promising microenvironment-sensitive fluorescent adenine analogues that display considerable brightness for such compounds.
authors: Department of Chemical and Chemical Engineering/, Chemistry and Biochemistry, Chalmers University of Technology, 41296 Gothenburg (Sweden).
authors: Blaise
authors: B
authors: Dumat
authors: Mattias
authors: M
authors: Bood
authors: Moa S
authors: MS
authors: Wranne
authors: Christopher P
authors: CP
authors: Lawson
authors: Anders Foller
authors: AF
authors: Larsen
authors: Søren
authors: S
authors: Preus
authors: Jens
authors: J
authors: Streling
authors: Henrik
authors: H
authors: Gradén
authors: Eric
authors: E
authors: Wellner
authors: Morten
authors: M
authors: Grøtli
authors: L Marcus
authors: LM
authors: Wilhelmsson
mesh_terms: D000225:Adenine / Q000737:chemistry*; D020029:Base Pairing; D004396:Coloring Agents / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D009696:Nucleic Acids / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D004396:Coloring Agents; D005456:Fluorescent Dyes; D009696:Nucleic Acids; D000225:Adenine
keywords: CC coupling; aromatic substitution; fluorescent probes; nucleic acids; nucleobases