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A Photoreactive G‐Quadruplex Ligand Triggered by Green Light
Author(s) -
Nadai Matteo,
Doria Filippo,
Germani Luca,
Richter Sara N.,
Freccero Mauro
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405215
Subject(s) - g quadruplex , nucleic acid , thymine , chemistry , covalent bond , dna , flash photolysis , combinatorial chemistry , biophysics , stereochemistry , photochemistry , biochemistry , biology , organic chemistry , kinetics , physics , quantum mechanics , reaction rate constant
A photoreactive molecular dye targeting the G‐quadruplex nucleic acid (G4) of the human telomeric sequence Tel22, and several mutated analogues, was activated by green light ( λ =532 nm). Highly selective covalent modification of G4 versus single‐stranded and double‐stranded DNA was achieved with efficiency up to 64 %. The phenoxyl radical was generated and detected by laser‐flash photolysis as a reactive intermediate that targeted loop thymine residues. These insights may suggest a non‐invasive tool for selective nucleic acid tagging and “pull‐down” cellular applications.