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Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines

Two new series of synthetic renieramycins including 22-O-amino ester and hydroquinone 5-O-amino ester derivatives of renieramycin M were semi-synthesized and evaluated for their cytotoxicity against the metastatic non-small-cell lung cancer H292 and H460 cell lines. Interestingly, the series of 22-O...

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Autores principales: Chamni, Supakarn, Sirimangkalakitti, Natchanun, Chanvorachote, Pithi, Suwanborirux, Khanit, Saito, Naoki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7460379/
https://www.ncbi.nlm.nih.gov/pubmed/32785022
http://dx.doi.org/10.3390/md18080418
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author Chamni, Supakarn
Sirimangkalakitti, Natchanun
Chanvorachote, Pithi
Suwanborirux, Khanit
Saito, Naoki
author_facet Chamni, Supakarn
Sirimangkalakitti, Natchanun
Chanvorachote, Pithi
Suwanborirux, Khanit
Saito, Naoki
author_sort Chamni, Supakarn
collection PubMed
description Two new series of synthetic renieramycins including 22-O-amino ester and hydroquinone 5-O-amino ester derivatives of renieramycin M were semi-synthesized and evaluated for their cytotoxicity against the metastatic non-small-cell lung cancer H292 and H460 cell lines. Interestingly, the series of 22-O-amino ester derivatives displayed a potent cytotoxic activity greater than the hydroquinone derivatives. The most cytotoxic derivative of the series was the 22-O-(N-Boc-l-glycine) ester of renieramycin M (5a: IC(50) 3.56 nM), which showed 7-fold higher potency than renieramycin M (IC(50) 24.56 nM) and 61-fold more than jorunnamycin A (IC(50) 217.43 nM) against H292 cells. In addition, 5a exhibited a significantly higher cytotoxic activity than doxorubicin (ca. 100 times). The new semi-synthetic renieramycin derivatives will be further studied and developed as potential cytotoxic agents for non-small-cell lung cancer treatment.
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spelling pubmed-74603792020-09-02 Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines Chamni, Supakarn Sirimangkalakitti, Natchanun Chanvorachote, Pithi Suwanborirux, Khanit Saito, Naoki Mar Drugs Article Two new series of synthetic renieramycins including 22-O-amino ester and hydroquinone 5-O-amino ester derivatives of renieramycin M were semi-synthesized and evaluated for their cytotoxicity against the metastatic non-small-cell lung cancer H292 and H460 cell lines. Interestingly, the series of 22-O-amino ester derivatives displayed a potent cytotoxic activity greater than the hydroquinone derivatives. The most cytotoxic derivative of the series was the 22-O-(N-Boc-l-glycine) ester of renieramycin M (5a: IC(50) 3.56 nM), which showed 7-fold higher potency than renieramycin M (IC(50) 24.56 nM) and 61-fold more than jorunnamycin A (IC(50) 217.43 nM) against H292 cells. In addition, 5a exhibited a significantly higher cytotoxic activity than doxorubicin (ca. 100 times). The new semi-synthetic renieramycin derivatives will be further studied and developed as potential cytotoxic agents for non-small-cell lung cancer treatment. MDPI 2020-08-10 /pmc/articles/PMC7460379/ /pubmed/32785022 http://dx.doi.org/10.3390/md18080418 Text en © 2020 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chamni, Supakarn
Sirimangkalakitti, Natchanun
Chanvorachote, Pithi
Suwanborirux, Khanit
Saito, Naoki
Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
title Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
title_full Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
title_fullStr Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
title_full_unstemmed Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
title_short Chemistry of Renieramycins. Part 19: Semi-Syntheses of 22-O-Amino Ester and Hydroquinone 5-O-Amino Ester Derivatives of Renieramycin M and Their Cytotoxicity against Non-Small-Cell Lung Cancer Cell Lines
title_sort chemistry of renieramycins. part 19: semi-syntheses of 22-o-amino ester and hydroquinone 5-o-amino ester derivatives of renieramycin m and their cytotoxicity against non-small-cell lung cancer cell lines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7460379/
https://www.ncbi.nlm.nih.gov/pubmed/32785022
http://dx.doi.org/10.3390/md18080418
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