Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach

The World Health Organization has reported about 214 million new cases of malaria with about 438,000 deaths worldwide in 2015. An example of antimalarial compounds isolated from plants, and is currently in use, may be mentioned quinine and artemisinin. However, one of the major problems that have ar...

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Autores:
Flores, Maryury C
Marquez Brazon, Edgar Alexander
Mora, Jose R
Tipo de recurso:
Article of journal
Fecha de publicación:
2018
Institución:
Corporación Universidad de la Costa
Repositorio:
REDICUC - Repositorio CUC
Idioma:
eng
OAI Identifier:
oai:repositorio.cuc.edu.co:11323/1596
Acceso en línea:
https://hdl.handle.net/11323/1596
https://repositorio.cuc.edu.co/
Palabra clave:
Antimalarial
Computational Study
DFT
HOMO
Nitrogen Compounds
QSAR
Rights
openAccess
License
Atribución – No comercial – Compartir igual
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dc.title.eng.fl_str_mv Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
title Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
spellingShingle Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
Antimalarial
Computational Study
DFT
HOMO
Nitrogen Compounds
QSAR
title_short Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
title_full Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
title_fullStr Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
title_full_unstemmed Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
title_sort Molecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT Approach
dc.creator.fl_str_mv Flores, Maryury C
Marquez Brazon, Edgar Alexander
Mora, Jose R
dc.contributor.author.spa.fl_str_mv Flores, Maryury C
Marquez Brazon, Edgar Alexander
Mora, Jose R
dc.subject.eng.fl_str_mv Antimalarial
Computational Study
DFT
HOMO
Nitrogen Compounds
QSAR
topic Antimalarial
Computational Study
DFT
HOMO
Nitrogen Compounds
QSAR
description The World Health Organization has reported about 214 million new cases of malaria with about 438,000 deaths worldwide in 2015. An example of antimalarial compounds isolated from plants, and is currently in use, may be mentioned quinine and artemisinin. However, one of the major problems that have arisen in recent years is the resistance of parasites against existing antimalarial drugs. Thus, there is a strong need to find new agents to control and to eradicate the disease. In this regard, marine organisms constitute a universally recognized source of potentially bioactive molecules, which have been enzymatically engineered and biologically validated. In this study, a quantitative structure–activity relationship (QSAR) analysis has been performed on data set of 14 bromopyrrole alkaloids (sponge metabolites) for antimalarial activity. Using density functional theory (DFT) several types of descriptors, including thermodynamics and electronic, have been calculated, in order to derive a quantitative relationship between antimalarial activity and structural properties. Simple and multiple regressions were used to generate the model. The best model (r2 = 0.97, Q2 = 0.86, F = 41.85) was obtained with descriptors as entropy, dipole momentum, molecular polarizability, HOMO energy softness, and electrophilic Index. The robustness of the QSAR models was verified by the leave-one-out cross-validation and external validation methods. The model obtained in this study should aid further study and could suggest some characteristics of novel potent bromopyrrole alkaloids against malaria.
publishDate 2018
dc.date.accessioned.none.fl_str_mv 2018-11-21T01:28:54Z
dc.date.available.none.fl_str_mv 2018-11-21T01:28:54Z
dc.date.issued.none.fl_str_mv 2018-03-01
dc.type.spa.fl_str_mv Artículo de revista
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dc.type.content.spa.fl_str_mv Text
dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/article
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status_str acceptedVersion
dc.identifier.issn.spa.fl_str_mv 10542523
dc.identifier.uri.spa.fl_str_mv https://hdl.handle.net/11323/1596
dc.identifier.doi.spa.fl_str_mv DOI: 10.1007/s00044-017-2107-3
dc.identifier.instname.spa.fl_str_mv Corporación Universidad de la Costa
dc.identifier.reponame.spa.fl_str_mv REDICUC - Repositorio CUC
dc.identifier.repourl.spa.fl_str_mv https://repositorio.cuc.edu.co/
identifier_str_mv 10542523
DOI: 10.1007/s00044-017-2107-3
Corporación Universidad de la Costa
REDICUC - Repositorio CUC
url https://hdl.handle.net/11323/1596
https://repositorio.cuc.edu.co/
dc.language.iso.none.fl_str_mv eng
language eng
dc.rights.spa.fl_str_mv Atribución – No comercial – Compartir igual
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rights_invalid_str_mv Atribución – No comercial – Compartir igual
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.publisher.spa.fl_str_mv Medicinal Chemistry Research
institution Corporación Universidad de la Costa
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spelling Flores, Maryury CMarquez Brazon, Edgar AlexanderMora, Jose R2018-11-21T01:28:54Z2018-11-21T01:28:54Z2018-03-0110542523https://hdl.handle.net/11323/1596DOI: 10.1007/s00044-017-2107-3Corporación Universidad de la CostaREDICUC - Repositorio CUChttps://repositorio.cuc.edu.co/The World Health Organization has reported about 214 million new cases of malaria with about 438,000 deaths worldwide in 2015. An example of antimalarial compounds isolated from plants, and is currently in use, may be mentioned quinine and artemisinin. However, one of the major problems that have arisen in recent years is the resistance of parasites against existing antimalarial drugs. Thus, there is a strong need to find new agents to control and to eradicate the disease. In this regard, marine organisms constitute a universally recognized source of potentially bioactive molecules, which have been enzymatically engineered and biologically validated. In this study, a quantitative structure–activity relationship (QSAR) analysis has been performed on data set of 14 bromopyrrole alkaloids (sponge metabolites) for antimalarial activity. Using density functional theory (DFT) several types of descriptors, including thermodynamics and electronic, have been calculated, in order to derive a quantitative relationship between antimalarial activity and structural properties. Simple and multiple regressions were used to generate the model. The best model (r2 = 0.97, Q2 = 0.86, F = 41.85) was obtained with descriptors as entropy, dipole momentum, molecular polarizability, HOMO energy softness, and electrophilic Index. The robustness of the QSAR models was verified by the leave-one-out cross-validation and external validation methods. The model obtained in this study should aid further study and could suggest some characteristics of novel potent bromopyrrole alkaloids against malaria.Flores, Maryury C-234aec38-39bf-4f5e-90b6-75ba2e37b2fa-0Marquez Brazon, Edgar Alexander-6efca75f-b74b-4b64-8eaf-052d0dd77642-0Mora, Jose R-cd44a0d3-3300-4246-b77f-c8c937f8c40d-0engMedicinal Chemistry ResearchAtribución – No comercial – Compartir igualinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2AntimalarialComputational StudyDFTHOMONitrogen CompoundsQSARMolecular Modeling Studies Of Bromopyrrole Alkaloids As Potential Antimalarial Compounds: A DFT ApproachArtículo de revistahttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1Textinfo:eu-repo/semantics/articlehttp://purl.org/redcol/resource_type/ARTinfo:eu-repo/semantics/acceptedVersionPublicationORIGINALMolecular Modeling Studies Of Bromopyrrole.pdfMolecular Modeling Studies Of Bromopyrrole.pdfapplication/pdf284381https://repositorio.cuc.edu.co/bitstreams/1054eb8a-3865-43f7-b5fc-46e5db1f019c/download21174f4db0560b1448801d581f0f7bd0MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://repositorio.cuc.edu.co/bitstreams/a87494fa-eaac-4f86-a815-fe104afa1d42/download8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILMolecular Modeling Studies Of Bromopyrrole.pdf.jpgMolecular Modeling Studies Of Bromopyrrole.pdf.jpgimage/jpeg44799https://repositorio.cuc.edu.co/bitstreams/3b9a51f2-01b5-4d4e-8629-d7135383eb2b/download875292377701890c1ffb928b955f4070MD54TEXTMolecular Modeling Studies Of Bromopyrrole.pdf.txtMolecular Modeling Studies Of Bromopyrrole.pdf.txttext/plain1895https://repositorio.cuc.edu.co/bitstreams/149a0d7e-1501-4d76-ac18-61fa4e2fee1c/download880ef369ecc910fe5a9622caf1e26484MD5511323/1596oai:repositorio.cuc.edu.co:11323/15962024-09-17 14:15:04.145open.accesshttps://repositorio.cuc.edu.coRepositorio de la Universidad de la Costa CUCrepdigital@cuc.edu.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