PMID- 32453464
OWN - NLM
STAT- MEDLINE
DCOM- 20210226
LR  - 20210226
IS  - 1521-3765 (Electronic)
IS  - 0947-6539 (Linking)
VI  - 26
IP  - 60
DP  - 2020 Oct 27
TI  - DNA-Targeted NO Release Photoregulated by Green Light.
PG  - 13627-13633
LID - 10.1002/chem.202001538 [doi]
AB  - 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.
CI  - (c) 2020 Wiley-VCH GmbH.
FAU - Parisi, Cristina
AU  - Parisi C
AD  - PhotoChemLab, Department of Drug Sciences, University of Catania, 95125, Catania, 
      Italy.
FAU - Fraix, Aurore
AU  - Fraix A
AD  - PhotoChemLab, Department of Drug Sciences, University of Catania, 95125, Catania, 
      Italy.
FAU - Guglielmo, Stefano
AU  - Guglielmo S
AD  - Department of Science and Drug Technology, University of Torino, Via Pietro 
      Giuria 9, 10125, Torino, Italy.
FAU - Spyrakis, Francesca
AU  - Spyrakis F
AD  - Department of Science and Drug Technology, University of Torino, Via Pietro 
      Giuria 9, 10125, Torino, Italy.
FAU - Rolando, Barbara
AU  - Rolando B
AD  - Department of Science and Drug Technology, University of Torino, Via Pietro 
      Giuria 9, 10125, Torino, Italy.
FAU - Lazzarato, Loretta
AU  - Lazzarato L
AD  - Department of Science and Drug Technology, University of Torino, Via Pietro 
      Giuria 9, 10125, Torino, Italy.
FAU - Fruttero, Roberta
AU  - Fruttero R
AD  - Department of Science and Drug Technology, University of Torino, Via Pietro 
      Giuria 9, 10125, Torino, Italy.
FAU - Gasco, Alberto
AU  - Gasco A
AD  - Department of Science and Drug Technology, University of Torino, Via Pietro 
      Giuria 9, 10125, Torino, Italy.
FAU - Sortino, Salvatore
AU  - Sortino S
AUID- ORCID: 0000-0002-2086-1276
AD  - PhotoChemLab, Department of Drug Sciences, University of Catania, 95125, Catania, 
      Italy.
LA  - eng
GR  - IG-19859/Associazione Italiana per la Ricerca sul Cancro/
PT  - Journal Article
DEP - 20200928
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
RN  - 0 (Fluorescent Dyes)
RN  - 0 (Nitrosamines)
RN  - 31C4KY9ESH (Nitric Oxide)
RN  - 9007-49-2 (DNA)
RN  - F30N4O6XVV (Acridine Orange)
SB  - IM
MH  - *Acridine Orange
MH  - *DNA
MH  - Fluorescent Dyes
MH  - Light
MH  - *Nitric Oxide
MH  - Nitrosamines
MH  - Photochemical Processes
MH  - Spectrometry, Fluorescence
OTO - NOTNLM
OT  - DNA
OT  - fluorescence
OT  - light
OT  - nitric oxide
OT  - photochemistry
EDAT- 2020/05/27 06:00
MHDA- 2021/02/27 06:00
CRDT- 2020/05/27 06:00
PHST- 2020/03/30 00:00 [received]
PHST- 2020/05/20 00:00 [revised]
PHST- 2020/05/27 06:00 [pubmed]
PHST- 2021/02/27 06:00 [medline]
PHST- 2020/05/27 06:00 [entrez]
AID - 10.1002/chem.202001538 [doi]
PST - ppublish
SO  - Chemistry. 2020 Oct 27;26(60):13627-13633. doi: 10.1002/chem.202001538. Epub 2020 
      Sep 28.