Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds
ABSTRACT: The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy phenyl moities in their structure. Thereby, the libraries o...
- Autores:
-
Tangarife Castaño, Verónica
Betancur Galvis, Liliana Amparo
Roa Linares, Vicky Constanza
Brand Miranda, Yaneth de Jesú
Kouznetsov, Vladimir
Puerto Galvis, sCarlos Eduardo
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2020
- Institución:
- Universidad de Antioquia
- Repositorio:
- Repositorio UdeA
- Idioma:
- eng
- OAI Identifier:
- oai:bibliotecadigital.udea.edu.co:10495/40306
- Acceso en línea:
- https://hdl.handle.net/10495/40306
- Palabra clave:
- Antifungal Agents
Antifúngicos
Antiviral Agents
Antivirales
Cytotoxins
Citotoxinas
https://id.nlm.nih.gov/mesh/D000935
https://id.nlm.nih.gov/mesh/D000998
https://id.nlm.nih.gov/mesh/D003603
- Rights
- openAccess
- License
- https://creativecommons.org/licenses/by/4.0/
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| dc.title.spa.fl_str_mv |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| title |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| spellingShingle |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds Antifungal Agents Antifúngicos Antiviral Agents Antivirales Cytotoxins Citotoxinas https://id.nlm.nih.gov/mesh/D000935 https://id.nlm.nih.gov/mesh/D000998 https://id.nlm.nih.gov/mesh/D003603 |
| title_short |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| title_full |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| title_fullStr |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| title_full_unstemmed |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| title_sort |
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds |
| dc.creator.fl_str_mv |
Tangarife Castaño, Verónica Betancur Galvis, Liliana Amparo Roa Linares, Vicky Constanza Brand Miranda, Yaneth de Jesú Kouznetsov, Vladimir Puerto Galvis, sCarlos Eduardo |
| dc.contributor.author.none.fl_str_mv |
Tangarife Castaño, Verónica Betancur Galvis, Liliana Amparo Roa Linares, Vicky Constanza Brand Miranda, Yaneth de Jesú Kouznetsov, Vladimir Puerto Galvis, sCarlos Eduardo |
| dc.contributor.researchgroup.spa.fl_str_mv |
GRID - Grupo de Investigación Dermatológica |
| dc.subject.decs.none.fl_str_mv |
Antifungal Agents Antifúngicos Antiviral Agents Antivirales Cytotoxins Citotoxinas |
| topic |
Antifungal Agents Antifúngicos Antiviral Agents Antivirales Cytotoxins Citotoxinas https://id.nlm.nih.gov/mesh/D000935 https://id.nlm.nih.gov/mesh/D000998 https://id.nlm.nih.gov/mesh/D003603 |
| dc.subject.meshuri.none.fl_str_mv |
https://id.nlm.nih.gov/mesh/D000935 https://id.nlm.nih.gov/mesh/D000998 https://id.nlm.nih.gov/mesh/D003603 |
| description |
ABSTRACT: The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy phenyl moities in their structure. Thereby, the libraries of β-nitrostyrenes 10a-10c, spiroisatin-dihydroquinolines 14a-14c, spiroisatinthiazolidinones 17a-17c and spiroisatin-nitropyrrolizidines 20a-20k were evaluated for their in vitro cytotoxic, anti-proliferative, antifungal and antiviral activities. Biological results revealed that among these compounds, β-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatindihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c molecules were active against human herpesviruses serotypes 1 and 2 (HHV-1 and HHV-2), but only 14a and 14b were effective against dengue virus serotype 2 (DENV-2). The spiroisatin-nitropyrrolizidine 20c exhibited moderate anti-herpetic activity, while 17c spiroisatin-thiazolidinone derivative also reduced the infection of HHV-1 and DENV-2. Finally, the molecular docking showed that these kind of molecules interact with the subunit α/β-tubulin. |
| publishDate |
2020 |
| dc.date.issued.none.fl_str_mv |
2020 |
| dc.date.accessioned.none.fl_str_mv |
2024-06-26T15:52:16Z |
| dc.date.available.none.fl_str_mv |
2024-06-26T15:52:16Z |
| dc.type.spa.fl_str_mv |
Artículo de investigación |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
| dc.type.redcol.spa.fl_str_mv |
https://purl.org/redcol/resource_type/ART |
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http://purl.org/coar/version/c_970fb48d4fbd8a85 |
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info:eu-repo/semantics/article |
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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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Brand, Yaneth, et al. “Combretastatin A-4: The antitubulin agent that inspired the design and synthesis of styrene and spiroisatin hybrids as promising cytotoxic, antifungal and antiviral compounds”. Journal of the Brazilian Chemical Society, 2020, doi:10.21577/0103-5053.20190265. |
| dc.identifier.issn.none.fl_str_mv |
0103-5053 |
| dc.identifier.uri.none.fl_str_mv |
https://hdl.handle.net/10495/40306 |
| dc.identifier.doi.none.fl_str_mv |
10.21577/0103-5053.20190265 |
| dc.identifier.eissn.none.fl_str_mv |
1678-4790 |
| identifier_str_mv |
Brand, Yaneth, et al. “Combretastatin A-4: The antitubulin agent that inspired the design and synthesis of styrene and spiroisatin hybrids as promising cytotoxic, antifungal and antiviral compounds”. Journal of the Brazilian Chemical Society, 2020, doi:10.21577/0103-5053.20190265. 0103-5053 10.21577/0103-5053.20190265 1678-4790 |
| url |
https://hdl.handle.net/10495/40306 |
| dc.language.iso.spa.fl_str_mv |
eng |
| language |
eng |
| dc.relation.ispartofjournalabbrev.spa.fl_str_mv |
J. Bra. Chem. Soc. |
| dc.relation.citationendpage.spa.fl_str_mv |
1010 |
| dc.relation.citationissue.spa.fl_str_mv |
5 |
| dc.relation.citationstartpage.spa.fl_str_mv |
999 |
| dc.relation.citationvolume.spa.fl_str_mv |
31 |
| dc.relation.ispartofjournal.spa.fl_str_mv |
Journal of the Brazilian Chemical Society |
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https://creativecommons.org/licenses/by/4.0/ |
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http://creativecommons.org/licenses/by/2.5/co/ |
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info:eu-repo/semantics/openAccess |
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openAccess |
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11 páginas |
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application/pdf |
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Sociedade Brasileira de Química |
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São Paulo, Brasil |
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Universidad de Antioquia |
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Tangarife Castaño, VerónicaBetancur Galvis, Liliana AmparoRoa Linares, Vicky ConstanzaBrand Miranda, Yaneth de JesúKouznetsov, VladimirPuerto Galvis, sCarlos EduardoGRID - Grupo de Investigación Dermatológica2024-06-26T15:52:16Z2024-06-26T15:52:16Z2020Brand, Yaneth, et al. “Combretastatin A-4: The antitubulin agent that inspired the design and synthesis of styrene and spiroisatin hybrids as promising cytotoxic, antifungal and antiviral compounds”. Journal of the Brazilian Chemical Society, 2020, doi:10.21577/0103-5053.20190265.0103-5053https://hdl.handle.net/10495/4030610.21577/0103-5053.201902651678-4790ABSTRACT: The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy phenyl moities in their structure. Thereby, the libraries of β-nitrostyrenes 10a-10c, spiroisatin-dihydroquinolines 14a-14c, spiroisatinthiazolidinones 17a-17c and spiroisatin-nitropyrrolizidines 20a-20k were evaluated for their in vitro cytotoxic, anti-proliferative, antifungal and antiviral activities. Biological results revealed that among these compounds, β-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatindihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c molecules were active against human herpesviruses serotypes 1 and 2 (HHV-1 and HHV-2), but only 14a and 14b were effective against dengue virus serotype 2 (DENV-2). The spiroisatin-nitropyrrolizidine 20c exhibited moderate anti-herpetic activity, while 17c spiroisatin-thiazolidinone derivative also reduced the infection of HHV-1 and DENV-2. Finally, the molecular docking showed that these kind of molecules interact with the subunit α/β-tubulin.Universidad de Antioquia. Vicerrectoría de investigación. Comité para el Desarrollo de la Investigación - CODIColombia. Ministerio de Ciencia, Tecnología e Innovación - MinicienciasBanco de la República ColombiaCOL005083911 páginasapplication/pdfengSociedade Brasileira de QuímicaSão Paulo, Brasilhttps://creativecommons.org/licenses/by/4.0/http://creativecommons.org/licenses/by/2.5/co/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral CompoundsArtículo de investigaciónhttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARThttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionAntifungal AgentsAntifúngicosAntiviral AgentsAntiviralesCytotoxinsCitotoxinashttps://id.nlm.nih.gov/mesh/D000935https://id.nlm.nih.gov/mesh/D000998https://id.nlm.nih.gov/mesh/D003603J. Bra. Chem. 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