Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids
ABSTRACT: Viral infections affect several million patients annually. Although hundreds of viruses are known to be pathogenic, only a few can be treated in the clinic with available antiviral drugs. Naturally based pharmacotherapy may be a proper alternative for treating viral diseases. Several natur...
- Autores:
-
González Cardenete, Miguel Ángel
Hamulić, Damir
Miquel Leal, Francisco
González Zapata, Natalia
Jiménez Jarava, Orlando José
Miranda Brand, Yaneth
Restrepo Mendez, Laura
Martínez Gutiérrez, Marlen
Betancur Galvis, Liliana Amparo
Marín, María
- Tipo de recurso:
- Article of investigation
- Fecha de publicación:
- 2022
- Institución:
- Universidad de Antioquia
- Repositorio:
- Repositorio UdeA
- Idioma:
- eng
- OAI Identifier:
- oai:bibliotecadigital.udea.edu.co:10495/43338
- Acceso en línea:
- https://hdl.handle.net/10495/43338
- Palabra clave:
- Abietanos
Abietanes
Antivirales
Antiviral Agents
Virus Chikungunya
Chikungunya virus
Replicación Viral
Virus Replication
Virus
Viruses
Infección por el Virus Zika
Zika Virus Infection
https://id.nlm.nih.gov/mesh/D045784
https://id.nlm.nih.gov/mesh/D000998
https://id.nlm.nih.gov/mesh/D002646
https://id.nlm.nih.gov/mesh/D014779
https://id.nlm.nih.gov/mesh/D014780
https://id.nlm.nih.gov/mesh/D000071243
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by/2.5/co/
| id |
UDEA2_ed0d30e4f4eb61fa741482f6bf68c2c7 |
|---|---|
| oai_identifier_str |
oai:bibliotecadigital.udea.edu.co:10495/43338 |
| network_acronym_str |
UDEA2 |
| network_name_str |
Repositorio UdeA |
| repository_id_str |
|
| dc.title.spa.fl_str_mv |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| title |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| spellingShingle |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids Abietanos Abietanes Antivirales Antiviral Agents Virus Chikungunya Chikungunya virus Replicación Viral Virus Replication Virus Viruses Infección por el Virus Zika Zika Virus Infection https://id.nlm.nih.gov/mesh/D045784 https://id.nlm.nih.gov/mesh/D000998 https://id.nlm.nih.gov/mesh/D002646 https://id.nlm.nih.gov/mesh/D014779 https://id.nlm.nih.gov/mesh/D014780 https://id.nlm.nih.gov/mesh/D000071243 |
| title_short |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| title_full |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| title_fullStr |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| title_full_unstemmed |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| title_sort |
Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids |
| dc.creator.fl_str_mv |
González Cardenete, Miguel Ángel Hamulić, Damir Miquel Leal, Francisco González Zapata, Natalia Jiménez Jarava, Orlando José Miranda Brand, Yaneth Restrepo Mendez, Laura Martínez Gutiérrez, Marlen Betancur Galvis, Liliana Amparo Marín, María |
| dc.contributor.author.none.fl_str_mv |
González Cardenete, Miguel Ángel Hamulić, Damir Miquel Leal, Francisco González Zapata, Natalia Jiménez Jarava, Orlando José Miranda Brand, Yaneth Restrepo Mendez, Laura Martínez Gutiérrez, Marlen Betancur Galvis, Liliana Amparo Marín, María |
| dc.contributor.researchgroup.spa.fl_str_mv |
GRID - Grupo de Investigación Dermatológica Grupo de Investigación en Microbiología Básica y Aplicada-Microba |
| dc.subject.decs.none.fl_str_mv |
Abietanos Abietanes Antivirales Antiviral Agents Virus Chikungunya Chikungunya virus Replicación Viral Virus Replication Virus Viruses Infección por el Virus Zika Zika Virus Infection |
| topic |
Abietanos Abietanes Antivirales Antiviral Agents Virus Chikungunya Chikungunya virus Replicación Viral Virus Replication Virus Viruses Infección por el Virus Zika Zika Virus Infection https://id.nlm.nih.gov/mesh/D045784 https://id.nlm.nih.gov/mesh/D000998 https://id.nlm.nih.gov/mesh/D002646 https://id.nlm.nih.gov/mesh/D014779 https://id.nlm.nih.gov/mesh/D014780 https://id.nlm.nih.gov/mesh/D000071243 |
| dc.subject.meshuri.none.fl_str_mv |
https://id.nlm.nih.gov/mesh/D045784 https://id.nlm.nih.gov/mesh/D000998 https://id.nlm.nih.gov/mesh/D002646 https://id.nlm.nih.gov/mesh/D014779 https://id.nlm.nih.gov/mesh/D014780 https://id.nlm.nih.gov/mesh/D000071243 |
| description |
ABSTRACT: Viral infections affect several million patients annually. Although hundreds of viruses are known to be pathogenic, only a few can be treated in the clinic with available antiviral drugs. Naturally based pharmacotherapy may be a proper alternative for treating viral diseases. Several natural and semisynthetic abietane-type diterpenoids have shown important antiviral activities. In this study, a biological evaluation of a number of either C-18- or C-19-functionalized known semisynthetic abietanes against Zika virus, Dengue virus, Herpes virus simplex type 1, and Chikungunya virus are reported. Semisynthetic abietane ferruginol and its analogue 18-(phthalimid-2-yl)ferruginol displayed broad-spectrum antiviral properties. The scale-up synthesis of this analogue has been optimized for further studies and development. This molecule displayed an EC50 between 5.0 and 10.0 μM against Colombian Zika virus strains and EC50 = 9.8 μM against Chikungunya virus. Knowing that this ferruginol analogue is also active against Dengue virus type 2 (EC50 = 1.4 μM, DENV-2), we can conclude that this compound is a promising broad-spectrum antiviral agent paving the way for the development of novel antivirals. |
| publishDate |
2022 |
| dc.date.issued.none.fl_str_mv |
2022 |
| dc.date.accessioned.none.fl_str_mv |
2024-11-10T16:45:05Z |
| dc.date.available.none.fl_str_mv |
2024-11-10T16:45:05Z |
| dc.type.spa.fl_str_mv |
Artículo de investigación |
| dc.type.coar.spa.fl_str_mv |
http://purl.org/coar/resource_type/c_2df8fbb1 |
| dc.type.redcol.spa.fl_str_mv |
https://purl.org/redcol/resource_type/ART |
| dc.type.coarversion.spa.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| dc.type.driver.spa.fl_str_mv |
info:eu-repo/semantics/article |
| dc.type.version.spa.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
| format |
http://purl.org/coar/resource_type/c_2df8fbb1 |
| status_str |
publishedVersion |
| dc.identifier.citation.spa.fl_str_mv |
González-Cardenete MA, Hamulić D, Miquel-Leal FJ, González-Zapata N, Jimenez-Jarava OJ, Brand YM, Restrepo-Mendez LC, Martinez-Gutierrez M, Betancur-Galvis LA, Marín ML. Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids. J Nat Prod. 2022 Aug 26;85(8):2044-2051. doi: 10.1021/acs.jnatprod.2c00464. |
| dc.identifier.issn.none.fl_str_mv |
0163-3864 |
| dc.identifier.uri.none.fl_str_mv |
https://hdl.handle.net/10495/43338 |
| dc.identifier.doi.none.fl_str_mv |
10.1021/acs.jnatprod.2c00464 |
| dc.identifier.eissn.none.fl_str_mv |
1520-6025 |
| identifier_str_mv |
González-Cardenete MA, Hamulić D, Miquel-Leal FJ, González-Zapata N, Jimenez-Jarava OJ, Brand YM, Restrepo-Mendez LC, Martinez-Gutierrez M, Betancur-Galvis LA, Marín ML. Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids. J Nat Prod. 2022 Aug 26;85(8):2044-2051. doi: 10.1021/acs.jnatprod.2c00464. 0163-3864 10.1021/acs.jnatprod.2c00464 1520-6025 |
| url |
https://hdl.handle.net/10495/43338 |
| dc.language.iso.spa.fl_str_mv |
eng |
| language |
eng |
| dc.relation.ispartofjournalabbrev.spa.fl_str_mv |
J. Nat. Prod. |
| dc.relation.citationendpage.spa.fl_str_mv |
2051 |
| dc.relation.citationissue.spa.fl_str_mv |
8 |
| dc.relation.citationstartpage.spa.fl_str_mv |
2044 |
| dc.relation.citationvolume.spa.fl_str_mv |
85 |
| dc.relation.ispartofjournal.spa.fl_str_mv |
Journal of Natural Products |
| dc.rights.uri.*.fl_str_mv |
http://creativecommons.org/licenses/by/2.5/co/ |
| dc.rights.uri.spa.fl_str_mv |
https://creativecommons.org/licenses/by/4.0/ |
| dc.rights.accessrights.spa.fl_str_mv |
info:eu-repo/semantics/openAccess |
| dc.rights.coar.spa.fl_str_mv |
http://purl.org/coar/access_right/c_abf2 |
| rights_invalid_str_mv |
http://creativecommons.org/licenses/by/2.5/co/ https://creativecommons.org/licenses/by/4.0/ http://purl.org/coar/access_right/c_abf2 |
| eu_rights_str_mv |
openAccess |
| dc.format.extent.spa.fl_str_mv |
8 páginas |
| dc.format.mimetype.spa.fl_str_mv |
application/pdf |
| dc.publisher.spa.fl_str_mv |
American Chemical Society |
| dc.publisher.place.spa.fl_str_mv |
Cincinnati, Estados Unidos |
| institution |
Universidad de Antioquia |
| bitstream.url.fl_str_mv |
https://bibliotecadigital.udea.edu.co/bitstreams/4ab55b64-1ad0-4217-8abc-f00698d443b0/download https://bibliotecadigital.udea.edu.co/bitstreams/8ec0c4f8-c8f9-4f72-a93c-50bdb1cf2c0d/download https://bibliotecadigital.udea.edu.co/bitstreams/4c904c06-4c07-4e8a-bb3d-f7e1c8f1358c/download https://bibliotecadigital.udea.edu.co/bitstreams/1c13a53c-525f-4aed-a9af-c2b5a4bacd3e/download https://bibliotecadigital.udea.edu.co/bitstreams/ea3422d1-8981-4831-9175-57121efe63dc/download |
| bitstream.checksum.fl_str_mv |
70a59d536fe99ce3eeaac0abb676d63a 1646d1f6b96dbbbc38035efc9239ac9c 8a4605be74aa9ea9d79846c1fba20a33 5c868244eb3cd5b444adc762087c6ffb f5b6bf59909b9692f896d8b740cf77ae |
| bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
| repository.name.fl_str_mv |
Repositorio Institucional de la Universidad de Antioquia |
| repository.mail.fl_str_mv |
aplicacionbibliotecadigitalbiblioteca@udea.edu.co |
| _version_ |
1851052255583666176 |
| spelling |
González Cardenete, Miguel ÁngelHamulić, DamirMiquel Leal, FranciscoGonzález Zapata, NataliaJiménez Jarava, Orlando JoséMiranda Brand, YanethRestrepo Mendez, LauraMartínez Gutiérrez, MarlenBetancur Galvis, Liliana AmparoMarín, MaríaGRID - Grupo de Investigación DermatológicaGrupo de Investigación en Microbiología Básica y Aplicada-Microba2024-11-10T16:45:05Z2024-11-10T16:45:05Z2022González-Cardenete MA, Hamulić D, Miquel-Leal FJ, González-Zapata N, Jimenez-Jarava OJ, Brand YM, Restrepo-Mendez LC, Martinez-Gutierrez M, Betancur-Galvis LA, Marín ML. Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane Diterpenoids. J Nat Prod. 2022 Aug 26;85(8):2044-2051. doi: 10.1021/acs.jnatprod.2c00464.0163-3864https://hdl.handle.net/10495/4333810.1021/acs.jnatprod.2c004641520-6025ABSTRACT: Viral infections affect several million patients annually. Although hundreds of viruses are known to be pathogenic, only a few can be treated in the clinic with available antiviral drugs. Naturally based pharmacotherapy may be a proper alternative for treating viral diseases. Several natural and semisynthetic abietane-type diterpenoids have shown important antiviral activities. In this study, a biological evaluation of a number of either C-18- or C-19-functionalized known semisynthetic abietanes against Zika virus, Dengue virus, Herpes virus simplex type 1, and Chikungunya virus are reported. Semisynthetic abietane ferruginol and its analogue 18-(phthalimid-2-yl)ferruginol displayed broad-spectrum antiviral properties. The scale-up synthesis of this analogue has been optimized for further studies and development. This molecule displayed an EC50 between 5.0 and 10.0 μM against Colombian Zika virus strains and EC50 = 9.8 μM against Chikungunya virus. Knowing that this ferruginol analogue is also active against Dengue virus type 2 (EC50 = 1.4 μM, DENV-2), we can conclude that this compound is a promising broad-spectrum antiviral agent paving the way for the development of novel antivirals.Universidad de Antioquia. Vicerrectoría de investigación. Comité para el Desarrollo de la Investigación - CODIColombia. Ministerio de Ciencia, Tecnología e Innovación - MinCienciasCOL0126131COL00508398 páginasapplication/pdfengAmerican Chemical SocietyCincinnati, Estados Unidoshttp://creativecommons.org/licenses/by/2.5/co/https://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Antiviral Profiling of C-18- or C-19-Functionalized Semisynthetic Abietane DiterpenoidsArtículo 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/publishedVersionAbietanosAbietanesAntiviralesAntiviral AgentsVirus ChikungunyaChikungunya virusReplicación ViralVirus ReplicationVirusVirusesInfección por el Virus ZikaZika Virus Infectionhttps://id.nlm.nih.gov/mesh/D045784https://id.nlm.nih.gov/mesh/D000998https://id.nlm.nih.gov/mesh/D002646https://id.nlm.nih.gov/mesh/D014779https://id.nlm.nih.gov/mesh/D014780https://id.nlm.nih.gov/mesh/D000071243J. Nat. Prod.20518204485Journal of Natural ProductsMinCiencias 111574455595MinCiencias 141577757439RoR:03bp5hc83RoR:03fd5ne08PublicationORIGINALJimenezOrlando_2022_Antiviral_Profiling_C-18-C-19-.pdfJimenezOrlando_2022_Antiviral_Profiling_C-18-C-19-.pdfArtículo de investigaciónapplication/pdf3768152https://bibliotecadigital.udea.edu.co/bitstreams/4ab55b64-1ad0-4217-8abc-f00698d443b0/download70a59d536fe99ce3eeaac0abb676d63aMD51trueAnonymousREADCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8927https://bibliotecadigital.udea.edu.co/bitstreams/8ec0c4f8-c8f9-4f72-a93c-50bdb1cf2c0d/download1646d1f6b96dbbbc38035efc9239ac9cMD52falseAnonymousREADLICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://bibliotecadigital.udea.edu.co/bitstreams/4c904c06-4c07-4e8a-bb3d-f7e1c8f1358c/download8a4605be74aa9ea9d79846c1fba20a33MD53falseAnonymousREADTEXTJimenezOrlando_2022_Antiviral_Profiling_C-18-C-19-.pdf.txtJimenezOrlando_2022_Antiviral_Profiling_C-18-C-19-.pdf.txtExtracted texttext/plain72933https://bibliotecadigital.udea.edu.co/bitstreams/1c13a53c-525f-4aed-a9af-c2b5a4bacd3e/download5c868244eb3cd5b444adc762087c6ffbMD54falseAnonymousREADTHUMBNAILJimenezOrlando_2022_Antiviral_Profiling_C-18-C-19-.pdf.jpgJimenezOrlando_2022_Antiviral_Profiling_C-18-C-19-.pdf.jpgGenerated Thumbnailimage/jpeg18596https://bibliotecadigital.udea.edu.co/bitstreams/ea3422d1-8981-4831-9175-57121efe63dc/downloadf5b6bf59909b9692f896d8b740cf77aeMD55falseAnonymousREAD10495/43338oai:bibliotecadigital.udea.edu.co:10495/433382025-03-26 19:26:06.435http://creativecommons.org/licenses/by/2.5/co/open.accesshttps://bibliotecadigital.udea.edu.coRepositorio Institucional de la Universidad de Antioquiaaplicacionbibliotecadigitalbiblioteca@udea.edu.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 |