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Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies

[Image: see text] An iodine-catalyzed, environmentally benign one-pot methodology has been developed for the synthesis of diverse substituted imidazoles. This transition-metal-free, aerobic, water-mediated cyclization reaction is operationally simple and works well with different amines or aldehydes...

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Autores principales: Adhikary, Saswati, Majumder, Leena, Pakrashy, Sourav, Srinath, Ravuri, Mukherjee, Kaustuv, Mandal, Chitra, Banerji, Biswadip
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7315425/
https://www.ncbi.nlm.nih.gov/pubmed/32596577
http://dx.doi.org/10.1021/acsomega.0c00934
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author Adhikary, Saswati
Majumder, Leena
Pakrashy, Sourav
Srinath, Ravuri
Mukherjee, Kaustuv
Mandal, Chitra
Banerji, Biswadip
author_facet Adhikary, Saswati
Majumder, Leena
Pakrashy, Sourav
Srinath, Ravuri
Mukherjee, Kaustuv
Mandal, Chitra
Banerji, Biswadip
author_sort Adhikary, Saswati
collection PubMed
description [Image: see text] An iodine-catalyzed, environmentally benign one-pot methodology has been developed for the synthesis of diverse substituted imidazoles. This transition-metal-free, aerobic, water-mediated cyclization reaction is operationally simple and works well with different amines or aldehydes by multiple C–N bond formations with satisfactory yield. The methodology is regioselective as well as scalable. These imidazole derivatives show excellent fluorescence properties both in the solid and solution phase, which is further extended to live-cell imaging. Due to the suitable fluorescence properties of these scaffolds, lysosome-directing groups are incorporated in two of these derivatized imidazoles to track intracellular lysosomes. Successfully, those molecules show bright blue fluorescence while detecting lysosomes in human or murine cells and can be considered to be rapid lysosome-staining probes.
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spelling pubmed-73154252020-06-26 Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies Adhikary, Saswati Majumder, Leena Pakrashy, Sourav Srinath, Ravuri Mukherjee, Kaustuv Mandal, Chitra Banerji, Biswadip ACS Omega [Image: see text] An iodine-catalyzed, environmentally benign one-pot methodology has been developed for the synthesis of diverse substituted imidazoles. This transition-metal-free, aerobic, water-mediated cyclization reaction is operationally simple and works well with different amines or aldehydes by multiple C–N bond formations with satisfactory yield. The methodology is regioselective as well as scalable. These imidazole derivatives show excellent fluorescence properties both in the solid and solution phase, which is further extended to live-cell imaging. Due to the suitable fluorescence properties of these scaffolds, lysosome-directing groups are incorporated in two of these derivatized imidazoles to track intracellular lysosomes. Successfully, those molecules show bright blue fluorescence while detecting lysosomes in human or murine cells and can be considered to be rapid lysosome-staining probes. American Chemical Society 2020-06-11 /pmc/articles/PMC7315425/ /pubmed/32596577 http://dx.doi.org/10.1021/acsomega.0c00934 Text en Copyright © 2020 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 Adhikary, Saswati
Majumder, Leena
Pakrashy, Sourav
Srinath, Ravuri
Mukherjee, Kaustuv
Mandal, Chitra
Banerji, Biswadip
Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies
title Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies
title_full Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies
title_fullStr Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies
title_full_unstemmed Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies
title_short Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H(2)O and Cell-Imaging Studies
title_sort polysubstituted imidazoles as lysotracker molecules: their synthesis via iodine/h(2)o and cell-imaging studies
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7315425/
https://www.ncbi.nlm.nih.gov/pubmed/32596577
http://dx.doi.org/10.1021/acsomega.0c00934
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