Cargando…
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...
Autores principales: | , , , , , |
---|---|
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 |
_version_ | 1783339484624977920 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6044501 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT mayakrishnansivakalai ruiicatalyzedregiospecificchohoxidativeannulationtoaccessisochromeno81abphenazinesfarredfluorescenceandlivecancercellimaging AT arunyuvaraj ruiicatalyzedregiospecificchohoxidativeannulationtoaccessisochromeno81abphenazinesfarredfluorescenceandlivecancercellimaging AT balachandranchandrasekar ruiicatalyzedregiospecificchohoxidativeannulationtoaccessisochromeno81abphenazinesfarredfluorescenceandlivecancercellimaging AT awalesuresh ruiicatalyzedregiospecificchohoxidativeannulationtoaccessisochromeno81abphenazinesfarredfluorescenceandlivecancercellimaging AT maheswarinarayananuma ruiicatalyzedregiospecificchohoxidativeannulationtoaccessisochromeno81abphenazinesfarredfluorescenceandlivecancercellimaging AT perumalparamasivanthirumalai ruiicatalyzedregiospecificchohoxidativeannulationtoaccessisochromeno81abphenazinesfarredfluorescenceandlivecancercellimaging |