Acetophenyl‐thienyl‐aniline‐Linked Nucleotide for Construction of Solvatochromic Fluorescence Light‐Up DNA Probes Sensing Protein‐DNA Interactions
Pedro Güixens‐Gallardo, Michal Hocek
Abstract
The synthesis of 2'-deoxycytidine and its 5'-O-triphosphate bearing solvatochromic acetophenyl-thienyl-aniline fluorophore was developed using the Sonogashira cross-coupling reaction as the key step. The triphosphate was used for polymerase synthesis of labelled DNA. The labelled nucleotide or DNA exerted weak red fluorescence when excited at 405 nm, but a significant colour change (to yellow or green) and light-up (up to 20 times) was observed when the DNA probes interacted with proteins or lipids.
Topics & Concepts
SolvatochromismFluorophoreSonogashira couplingNucleotideDNAFluorescenceChemistryAnilinePhotochemistryBiophysicsBiochemistryBiologyOrganic chemistrySolventQuantum mechanicsCatalysisGenePalladiumPhysicsDNA and Nucleic Acid ChemistryAdvanced biosensing and bioanalysis techniquesPhotochromic and Fluorescence Chemistry