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DNA‐Targeted NO Release Photoregulated by Green Light
Author(s) -
Parisi Cristina,
Fraix Aurore,
Guglielmo Stefano,
Spyrakis Francesca,
Rolando Barbara,
Lazzarato Loretta,
Fruttero Roberta,
Gasco Alberto,
Sortino Salvatore
Publication year - 2020
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.202001538
Subject(s) - moiety , dna , chemistry , intramolecular force , molecule , covalent bond , fluorescence , biophysics , photochemistry , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , optics , biology , physics
A novel molecular hybrid has been designed and synthesized in which acridine orange (AO) is covalently linked to an N ‐nitrosoaniline derivative through an alkyl spacer. Photoexcitation of the AO antenna with the highly biocompatible green light results in intense fluorescence emission and triggers NO detachment from the N ‐nitroso appendage via an intramolecular electron transfer. The presence of the AO moiety encourages the binding with DNA through both external and partially intercalative fashions, depending on the DNA:molecular hybrid molar ratio. Importantly, this dual‐mode binding interaction with the biopolymer does not preclude the NO photoreleasing performances of the molecular hybrid, permitting NO to be photogenerated nearby DNA with an efficiency similar to that of the free molecule. These properties make the presented compound an intriguing candidate for fundamental and potential applicative research studies where NO delivery in the DNA proximity precisely regulated by harmless green light is required.