Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities
ABSTRACT: Six derivatives of the known biopesticide rotenone were prepared by several chemical transformations. Rotenone and its derivatives showed differential in vitro antiparasitic activity and selective cytotoxicity. In general, compounds were more active against Plasmodium falciparum than Leish...
- Autores:
-
Upegui Zapata, Yulieth Alexandra
Gil Romero, Juan Fernando
Quiñones Fletcher, Winston
Torres, Fernando
Escobar Peláez, Gustavo
Robledo Restrepo, Sara María
Echeverri López, Luis Fernando
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2014
- Institución:
- Universidad de Antioquia
- Repositorio:
- Repositorio UdeA
- Idioma:
- eng
- OAI Identifier:
- oai:bibliotecadigital.udea.edu.co:10495/23682
- Acceso en línea:
- http://hdl.handle.net/10495/23682
- Palabra clave:
- Rotenone
Rotenona
Cytotoxicity
Cytotoxicidad
Chemical transformations
Antiparasite
Differential activity
http://aims.fao.org/aos/agrovoc/c_6665
http://aims.fao.org/aos/agrovoc/c_34251
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by/2.5/co/
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| dc.title.spa.fl_str_mv |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| title |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| spellingShingle |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities Rotenone Rotenona Cytotoxicity Cytotoxicidad Chemical transformations Antiparasite Differential activity http://aims.fao.org/aos/agrovoc/c_6665 http://aims.fao.org/aos/agrovoc/c_34251 |
| title_short |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| title_full |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| title_fullStr |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| title_full_unstemmed |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| title_sort |
Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities |
| dc.creator.fl_str_mv |
Upegui Zapata, Yulieth Alexandra Gil Romero, Juan Fernando Quiñones Fletcher, Winston Torres, Fernando Escobar Peláez, Gustavo Robledo Restrepo, Sara María Echeverri López, Luis Fernando |
| dc.contributor.author.none.fl_str_mv |
Upegui Zapata, Yulieth Alexandra Gil Romero, Juan Fernando Quiñones Fletcher, Winston Torres, Fernando Escobar Peláez, Gustavo Robledo Restrepo, Sara María Echeverri López, Luis Fernando |
| dc.subject.agrovoc.none.fl_str_mv |
Rotenone Rotenona Cytotoxicity Cytotoxicidad |
| topic |
Rotenone Rotenona Cytotoxicity Cytotoxicidad Chemical transformations Antiparasite Differential activity http://aims.fao.org/aos/agrovoc/c_6665 http://aims.fao.org/aos/agrovoc/c_34251 |
| dc.subject.proposal.spa.fl_str_mv |
Chemical transformations Antiparasite Differential activity |
| dc.subject.agrovocuri.none.fl_str_mv |
http://aims.fao.org/aos/agrovoc/c_6665 http://aims.fao.org/aos/agrovoc/c_34251 |
| description |
ABSTRACT: Six derivatives of the known biopesticide rotenone were prepared by several chemical transformations. Rotenone and its derivatives showed differential in vitro antiparasitic activity and selective cytotoxicity. In general, compounds were more active against Plasmodium falciparum than Leishmania panamensis. Rotenone had an EC50 of 19.0 µM against P. falciparum, and 127.2 µM against L. panamensis. Although chemical transformation does not improve its biological profile against P. falciparum, three of its derivatives showed a significant level of action within an adequate range of activity with EC50 values < 50.0 µM. This antiplasmodial activity was not due to red blood cell hemolysis, since LC50 was >>400 µM. On the other hand, all derivatives displayed a non-specific cytotoxicity on several cell lines and primary human cell cultures. |
| publishDate |
2014 |
| dc.date.issued.none.fl_str_mv |
2014 |
| dc.date.accessioned.none.fl_str_mv |
2021-11-02T13:24:53Z |
| dc.date.available.none.fl_str_mv |
2021-11-02T13:24:53Z |
| dc.type.spa.fl_str_mv |
info:eu-repo/semantics/article |
| dc.type.coarversion.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
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info:eu-repo/semantics/publishedVersion |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
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https://purl.org/redcol/resource_type/ART |
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Artículo de investigación |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
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publishedVersion |
| dc.identifier.citation.spa.fl_str_mv |
Upegui, Y., Gil, J., Quiñones, W., Torres, F., Escobar, G., Robledo, S., & Echeverri, F. (2014). Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities. Molecules, 19(11), 18911–18922. Retrieved from http://dx.doi.org/10.3390/molecules191118911 |
| dc.identifier.issn.none.fl_str_mv |
1420-3049 |
| dc.identifier.uri.none.fl_str_mv |
http://hdl.handle.net/10495/23682 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/molecules191118911 |
| identifier_str_mv |
Upegui, Y., Gil, J., Quiñones, W., Torres, F., Escobar, G., Robledo, S., & Echeverri, F. (2014). Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities. Molecules, 19(11), 18911–18922. Retrieved from http://dx.doi.org/10.3390/molecules191118911 1420-3049 10.3390/molecules191118911 |
| url |
http://hdl.handle.net/10495/23682 |
| dc.language.iso.spa.fl_str_mv |
eng |
| language |
eng |
| dc.relation.ispartofjournalabbrev.spa.fl_str_mv |
Molecules |
| dc.rights.spa.fl_str_mv |
info:eu-repo/semantics/openAccess |
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http://creativecommons.org/licenses/by/2.5/co/ |
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http://purl.org/coar/access_right/c_abf2 |
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https://creativecommons.org/licenses/by/4.0/ |
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openAccess |
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http://creativecommons.org/licenses/by/2.5/co/ http://purl.org/coar/access_right/c_abf2 https://creativecommons.org/licenses/by/4.0/ |
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12 |
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application/pdf |
| dc.publisher.spa.fl_str_mv |
MDPI |
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Programa de Estudio y Control de Enfermedades Tropicales (PECET) Química Orgánica de Productos Naturales |
| dc.publisher.place.spa.fl_str_mv |
Basilea, Suiza |
| institution |
Universidad de Antioquia |
| bitstream.url.fl_str_mv |
http://bibliotecadigital.udea.edu.co/bitstream/10495/23682/1/UpeguiYulieth_2014_PreparationRotenoneAntimalarial.pdf http://bibliotecadigital.udea.edu.co/bitstream/10495/23682/2/license_rdf http://bibliotecadigital.udea.edu.co/bitstream/10495/23682/3/license.txt |
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Repositorio Institucional Universidad de Antioquia |
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andres.perez@udea.edu.co |
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1812173161301540864 |
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Upegui Zapata, Yulieth AlexandraGil Romero, Juan FernandoQuiñones Fletcher, WinstonTorres, FernandoEscobar Peláez, GustavoRobledo Restrepo, Sara MaríaEcheverri López, Luis Fernando2021-11-02T13:24:53Z2021-11-02T13:24:53Z2014Upegui, Y., Gil, J., Quiñones, W., Torres, F., Escobar, G., Robledo, S., & Echeverri, F. (2014). Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic Activities. Molecules, 19(11), 18911–18922. Retrieved from http://dx.doi.org/10.3390/molecules1911189111420-3049http://hdl.handle.net/10495/2368210.3390/molecules191118911ABSTRACT: Six derivatives of the known biopesticide rotenone were prepared by several chemical transformations. Rotenone and its derivatives showed differential in vitro antiparasitic activity and selective cytotoxicity. In general, compounds were more active against Plasmodium falciparum than Leishmania panamensis. Rotenone had an EC50 of 19.0 µM against P. falciparum, and 127.2 µM against L. panamensis. Although chemical transformation does not improve its biological profile against P. falciparum, three of its derivatives showed a significant level of action within an adequate range of activity with EC50 values < 50.0 µM. This antiplasmodial activity was not due to red blood cell hemolysis, since LC50 was >>400 µM. On the other hand, all derivatives displayed a non-specific cytotoxicity on several cell lines and primary human cell cultures.COL0015339COL001509912application/pdfengMDPIPrograma de Estudio y Control de Enfermedades Tropicales (PECET)Química Orgánica de Productos NaturalesBasilea, Suizainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARTArtículo de investigaciónhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/co/http://purl.org/coar/access_right/c_abf2https://creativecommons.org/licenses/by/4.0/Preparation of Rotenone Derivatives and in Vitro Analysis of Their Antimalarial, Antileishmanial and Selective Cytotoxic ActivitiesRotenoneRotenonaCytotoxicityCytotoxicidadChemical transformationsAntiparasiteDifferential activityhttp://aims.fao.org/aos/agrovoc/c_6665http://aims.fao.org/aos/agrovoc/c_34251MoleculesMolecules18911189221911ORIGINALUpeguiYulieth_2014_PreparationRotenoneAntimalarial.pdfUpeguiYulieth_2014_PreparationRotenoneAntimalarial.pdfArtículo de investigaciónapplication/pdf267077http://bibliotecadigital.udea.edu.co/bitstream/10495/23682/1/UpeguiYulieth_2014_PreparationRotenoneAntimalarial.pdf8a9e84170f2df2cfa67a2bf2d4facf5bMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8927http://bibliotecadigital.udea.edu.co/bitstream/10495/23682/2/license_rdf1646d1f6b96dbbbc38035efc9239ac9cMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://bibliotecadigital.udea.edu.co/bitstream/10495/23682/3/license.txt8a4605be74aa9ea9d79846c1fba20a33MD5310495/23682oai:bibliotecadigital.udea.edu.co:10495/236822021-11-02 08:24:53.65Repositorio Institucional Universidad de Antioquiaandres.perez@udea.edu.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 |