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Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics
A series of new chiral benzisoselenazol-3(2H)-ones and their corresponding diselenides bearing an o-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to th...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8950439/ https://www.ncbi.nlm.nih.gov/pubmed/35329523 http://dx.doi.org/10.3390/ma15062068 |
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author | Laskowska, Anna Pacuła-Miszewska, Agata Joanna Długosz-Pokorska, Angelika Janecka, Anna Wojtczak, Andrzej Ścianowski, Jacek |
author_facet | Laskowska, Anna Pacuła-Miszewska, Agata Joanna Długosz-Pokorska, Angelika Janecka, Anna Wojtczak, Andrzej Ścianowski, Jacek |
author_sort | Laskowska, Anna |
collection | PubMed |
description | A series of new chiral benzisoselenazol-3(2H)-ones and their corresponding diselenides bearing an o-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure–activity correlation. First, bensisoselenazol-3(2H)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se–N bond was cleaved by a reduction–oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2′-diselenobis[N-(1S,2S)-(-)-trans-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was N-[(1S,2R)-(-)-cis-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2H)-one. The structure–activity relationship of the obtained organoselenium derivatives was discussed. |
format | Online Article Text |
id | pubmed-8950439 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-89504392022-03-26 Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics Laskowska, Anna Pacuła-Miszewska, Agata Joanna Długosz-Pokorska, Angelika Janecka, Anna Wojtczak, Andrzej Ścianowski, Jacek Materials (Basel) Article A series of new chiral benzisoselenazol-3(2H)-ones and their corresponding diselenides bearing an o-amido function substituted on the nitrogen atom with various aliphatic and aromatic moieties were synthesized. All derivatives representing pairs of enantiomers or diastereoisomers were obtained to thoroughly evaluate the three-dimensional structure–activity correlation. First, bensisoselenazol-3(2H)-ones were synthesized by reacting 2-(chloroseleno)benzoyl chloride with an appropriate enantiomerically pure amine. Then, the Se–N bond was cleaved by a reduction–oxidation procedure using sodium borohydride and then air oxidation to obtain the corresponding diselenides. All derivatives were tested as antioxidants and anticancer agents. In general, the diselenides were more reactive peroxide scavengers, with the highest activity observed for 2,2′-diselenobis[N-(1S,2S)-(-)-trans-2-hydroksy-1-indanylbezamide]. The most cytotoxic derivative towards human promyelocytic leukemia HL-60 and breast cancer MCF-7 cell lines was N-[(1S,2R)-(-)-cis-2-hydroksy-1-indanyl]-1,2-benzizoselenazol-3(2H)-one. The structure–activity relationship of the obtained organoselenium derivatives was discussed. MDPI 2022-03-11 /pmc/articles/PMC8950439/ /pubmed/35329523 http://dx.doi.org/10.3390/ma15062068 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Laskowska, Anna Pacuła-Miszewska, Agata Joanna Długosz-Pokorska, Angelika Janecka, Anna Wojtczak, Andrzej Ścianowski, Jacek Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
title | Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
title_full | Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
title_fullStr | Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
title_full_unstemmed | Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
title_short | Attachment of Chiral Functional Groups to Modify the Activity of New GPx Mimetics |
title_sort | attachment of chiral functional groups to modify the activity of new gpx mimetics |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8950439/ https://www.ncbi.nlm.nih.gov/pubmed/35329523 http://dx.doi.org/10.3390/ma15062068 |
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