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Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues
Analogues of the anticancer natural product oximidine II were prepared and evaluated for cytotoxicity. One analogue of oximidine II that carries a C15 allylic amide side chain as well as two analogues with C15 vinyl sulfone side chains were found to lack cytotoxicity against the cancer cell line SK‐...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4987132/ https://www.ncbi.nlm.nih.gov/pubmed/27240557 http://dx.doi.org/10.1002/cmdc.201600024 |
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author | Schneider, Christopher M. Li, Wei Khownium, Kriangsak Lushington, Gerald H. Georg, Gunda I. |
author_facet | Schneider, Christopher M. Li, Wei Khownium, Kriangsak Lushington, Gerald H. Georg, Gunda I. |
author_sort | Schneider, Christopher M. |
collection | PubMed |
description | Analogues of the anticancer natural product oximidine II were prepared and evaluated for cytotoxicity. One analogue of oximidine II that carries a C15 allylic amide side chain as well as two analogues with C15 vinyl sulfone side chains were found to lack cytotoxicity against the cancer cell line SK‐Mel‐5, thereby confirming the necessity of the C15 enamide side chain of oximidine II for cytotoxicity. Four analogues, designed by comparative molecular similarity index analysis (CoMSIA), that feature a less complex macrolactone scaffold were prepared and tested. The two analogues carrying a C15 vinyl sulfone group and the two analogues with a C15 oximidine II enamide side chain showed weak cytotoxicity against the SK‐Mel‐5 cell line and other cell lines, indicating that the designed simplified macrocycles cannot replace the oximidine II macrocycle. |
format | Online Article Text |
id | pubmed-4987132 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-49871322017-08-05 Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues Schneider, Christopher M. Li, Wei Khownium, Kriangsak Lushington, Gerald H. Georg, Gunda I. ChemMedChem Full Papers Analogues of the anticancer natural product oximidine II were prepared and evaluated for cytotoxicity. One analogue of oximidine II that carries a C15 allylic amide side chain as well as two analogues with C15 vinyl sulfone side chains were found to lack cytotoxicity against the cancer cell line SK‐Mel‐5, thereby confirming the necessity of the C15 enamide side chain of oximidine II for cytotoxicity. Four analogues, designed by comparative molecular similarity index analysis (CoMSIA), that feature a less complex macrolactone scaffold were prepared and tested. The two analogues carrying a C15 vinyl sulfone group and the two analogues with a C15 oximidine II enamide side chain showed weak cytotoxicity against the SK‐Mel‐5 cell line and other cell lines, indicating that the designed simplified macrocycles cannot replace the oximidine II macrocycle. John Wiley and Sons Inc. 2016-05-31 2016-08-05 /pmc/articles/PMC4987132/ /pubmed/27240557 http://dx.doi.org/10.1002/cmdc.201600024 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Full Papers Schneider, Christopher M. Li, Wei Khownium, Kriangsak Lushington, Gerald H. Georg, Gunda I. Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues |
title | Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues |
title_full | Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues |
title_fullStr | Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues |
title_full_unstemmed | Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues |
title_short | Enantiospecific Synthesis and Cytotoxicity Evaluation of Oximidine II Analogues |
title_sort | enantiospecific synthesis and cytotoxicity evaluation of oximidine ii analogues |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4987132/ https://www.ncbi.nlm.nih.gov/pubmed/27240557 http://dx.doi.org/10.1002/cmdc.201600024 |
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