New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides
A variety of spirostan saponins and related glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). A linear glycosylation strategy allowed for accessing a variety of functionalization patterns at both the spirostanic and the saccharide moieties, which provides new information regarding the structure-cytotoxicity relationship of this family of steroidal glycosides. Intriguing results were achieved with respect to hecogenyl and 5α-hydroxy-laxogenyl β-chacotriosides, turning out to be the former very cytotoxic and the latter no cytotoxic at all. Importantly, the partially pivaloylated β-d-glucosides of 5α-hydroxy-laxogenin were the most potent cytotoxic compounds among all tested glycosides. This comprises the first report on acylated spirostanyl glucosides displaying significant cytotoxicity, and therefore, it opens up new opportunities toward the development of saponin analogues as anticancer agents.
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Format: | artículo biblioteca |
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Elsevier
2012-04-15
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Subjects: | Steroids, Saponins, Structure–activity relationship, Cytotoxicity, HL-60 cell, |
Online Access: | http://hdl.handle.net/10261/199546 http://dx.doi.org/10.13039/501100003767 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 |
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dig-ipna-es-10261-1995462020-12-09T16:23:20Z New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides Pérez-Labrada, Karell Brouard, Ignacio Estévez, Sara Marrero, María Teresa Estévez, Francisco Bermejo, Jaime Rivera, Daniel G. Consejo Superior de Investigaciones Científicas (España) Ministerio de Ciencia e Innovación (España) European Commission Ministerio de Asuntos Exteriores y Cooperación (España) Steroids Saponins Structure–activity relationship Cytotoxicity HL-60 cell A variety of spirostan saponins and related glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). A linear glycosylation strategy allowed for accessing a variety of functionalization patterns at both the spirostanic and the saccharide moieties, which provides new information regarding the structure-cytotoxicity relationship of this family of steroidal glycosides. Intriguing results were achieved with respect to hecogenyl and 5α-hydroxy-laxogenyl β-chacotriosides, turning out to be the former very cytotoxic and the latter no cytotoxic at all. Importantly, the partially pivaloylated β-d-glucosides of 5α-hydroxy-laxogenin were the most potent cytotoxic compounds among all tested glycosides. This comprises the first report on acylated spirostanyl glucosides displaying significant cytotoxicity, and therefore, it opens up new opportunities toward the development of saponin analogues as anticancer agents. This work was partially supported by CSIC (Proyecto Intramural de Incorporación—2007022), the Ministry of Science and Innovation of Spain and the European Regional Development Fund (SAF2010–21380 to F.E.). K. Pérez-Labrada gratefully acknowledges to MAEC-AECID for a doctoral scholarship. 2020-02-03T15:44:40Z 2020-02-03T15:44:40Z 2012-04-15 2020-02-03T15:44:41Z artículo http://purl.org/coar/resource_type/c_6501 doi: 10.1016/j.bmc.2012.02.026 issn: 0968-0896 e-issn: 1464-3391 Bioorganic and Medicinal Chemistry 20(18): 2690-2700 (2012) http://hdl.handle.net/10261/199546 10.1016/j.bmc.2012.02.026 http://dx.doi.org/10.13039/501100003767 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 Postprint http://dx.doi.org/10.1016/j.bmc.2012.02.026 Sí none Elsevier |
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Steroids Saponins Structure–activity relationship Cytotoxicity HL-60 cell Steroids Saponins Structure–activity relationship Cytotoxicity HL-60 cell |
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Steroids Saponins Structure–activity relationship Cytotoxicity HL-60 cell Steroids Saponins Structure–activity relationship Cytotoxicity HL-60 cell Pérez-Labrada, Karell Brouard, Ignacio Estévez, Sara Marrero, María Teresa Estévez, Francisco Bermejo, Jaime Rivera, Daniel G. New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
description |
A variety of spirostan saponins and related glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). A linear glycosylation strategy allowed for accessing a variety of functionalization patterns at both the spirostanic and the saccharide moieties, which provides new information regarding the structure-cytotoxicity relationship of this family of steroidal glycosides. Intriguing results were achieved with respect to hecogenyl and 5α-hydroxy-laxogenyl β-chacotriosides, turning out to be the former very cytotoxic and the latter no cytotoxic at all. Importantly, the partially pivaloylated β-d-glucosides of 5α-hydroxy-laxogenin were the most potent cytotoxic compounds among all tested glycosides. This comprises the first report on acylated spirostanyl glucosides displaying significant cytotoxicity, and therefore, it opens up new opportunities toward the development of saponin analogues as anticancer agents. |
author2 |
Consejo Superior de Investigaciones Científicas (España) |
author_facet |
Consejo Superior de Investigaciones Científicas (España) Pérez-Labrada, Karell Brouard, Ignacio Estévez, Sara Marrero, María Teresa Estévez, Francisco Bermejo, Jaime Rivera, Daniel G. |
format |
artículo |
topic_facet |
Steroids Saponins Structure–activity relationship Cytotoxicity HL-60 cell |
author |
Pérez-Labrada, Karell Brouard, Ignacio Estévez, Sara Marrero, María Teresa Estévez, Francisco Bermejo, Jaime Rivera, Daniel G. |
author_sort |
Pérez-Labrada, Karell |
title |
New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
title_short |
New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
title_full |
New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
title_fullStr |
New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
title_full_unstemmed |
New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
title_sort |
new insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides |
publisher |
Elsevier |
publishDate |
2012-04-15 |
url |
http://hdl.handle.net/10261/199546 http://dx.doi.org/10.13039/501100003767 http://dx.doi.org/10.13039/501100003339 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 |
work_keys_str_mv |
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1777669830812368896 |