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Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

[Image: see text] A facile ruthenium(II)-catalyzed regiospecific C–H/O–H oxidative annulation methodology was developed to construct isochromeno[8,1-ab]phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability...

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Autores principales: Mayakrishnan, Sivakalai, Arun, Yuvaraj, Balachandran, Chandrasekar, Awale, Suresh, Maheswari, Narayanan Uma, Perumal, Paramasivan Thirumalai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044501/
https://www.ncbi.nlm.nih.gov/pubmed/30023674
http://dx.doi.org/10.1021/acsomega.7b00335
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author Mayakrishnan, Sivakalai
Arun, Yuvaraj
Balachandran, Chandrasekar
Awale, Suresh
Maheswari, Narayanan Uma
Perumal, Paramasivan Thirumalai
author_facet Mayakrishnan, Sivakalai
Arun, Yuvaraj
Balachandran, Chandrasekar
Awale, Suresh
Maheswari, Narayanan Uma
Perumal, Paramasivan Thirumalai
author_sort Mayakrishnan, Sivakalai
collection PubMed
description [Image: see text] A facile ruthenium(II)-catalyzed regiospecific C–H/O–H oxidative annulation methodology was developed to construct isochromeno[8,1-ab]phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging. The synthesized compounds displayed notable fluorescence properties in solution and thin-film. Their application in live cancer cell imaging was investigated using various cancer cell lines. The synthesized compound showed prominent FR fluorescence, with high quantum yield, and exhibited better cell-imaging properties, with excellent biocompatibility.
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spelling pubmed-60445012018-07-16 Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging Mayakrishnan, Sivakalai Arun, Yuvaraj Balachandran, Chandrasekar Awale, Suresh Maheswari, Narayanan Uma Perumal, Paramasivan Thirumalai ACS Omega [Image: see text] A facile ruthenium(II)-catalyzed regiospecific C–H/O–H oxidative annulation methodology was developed to construct isochromeno[8,1-ab]phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging. The synthesized compounds displayed notable fluorescence properties in solution and thin-film. Their application in live cancer cell imaging was investigated using various cancer cell lines. The synthesized compound showed prominent FR fluorescence, with high quantum yield, and exhibited better cell-imaging properties, with excellent biocompatibility. American Chemical Society 2017-06-17 /pmc/articles/PMC6044501/ /pubmed/30023674 http://dx.doi.org/10.1021/acsomega.7b00335 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Mayakrishnan, Sivakalai
Arun, Yuvaraj
Balachandran, Chandrasekar
Awale, Suresh
Maheswari, Narayanan Uma
Perumal, Paramasivan Thirumalai
Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging
title Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging
title_full Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging
title_fullStr Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging
title_full_unstemmed Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging
title_short Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-ab]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging
title_sort ru(ii)-catalyzed regiospecific c–h/o–h oxidative annulation to access isochromeno[8,1-ab]phenazines: far-red fluorescence and live cancer cell imaging
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6044501/
https://www.ncbi.nlm.nih.gov/pubmed/30023674
http://dx.doi.org/10.1021/acsomega.7b00335
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