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- Title
Second-Generation Fluorescent Quadracyclic Adenine Analogues: Environment-Responsive Probes with Enhanced Brightness.
- Authors
Dumat, Blaise; Bood, Mattias; Wranne, Moa S.; Lawson, Christopher P.; Larsen, Anders Foller; Preus, Søren; Streling, Jens; Gradén, Henrik; Wellner, Eric; Grøtli, Morten; Wilhelmsson, L. Marcus
- 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-ratio-metric 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.
- Subjects
ADENINE; MOLECULAR probes; DRUG-DNA interactions; RADIANCE; SUZUKI reaction; POLARITY (Chemistry); DNA-protein interactions
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 10, p4039
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201405759