Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers
| Main Author: | |
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| Publication Date: | 2017 |
| Other Authors: | , , , , , , , , , |
| Format: | Article |
| Language: | eng |
| Source: | Repositório Institucional da FIOCRUZ (ARCA) |
| Download full: | https://www.arca.fiocruz.br/handle/icict/34435 |
Summary: | Universidade Estadual de Londrina. Departamento de Química. Londrina, PR, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil. |
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Bispo, Marcelle L. F.Lima, Camilo H. S.Cardoso, Laura N. F.Candéa, André L. P.Bezerra, Flávio A. F. M.Lourenço, Maria C. S.Henriques, Maria G. M. O.Alencastro, Ricardo B.Kaiser, Carlos R.Souza, Marcus V. N.Albuquerque, Magaly G.2019-07-26T12:04:36Z2019-07-26T12:04:36Z2017BISPO, Marcelle L. F. et al. Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino–imino tautomers. Pharmaceuticals, v. 10, n. 52, p. 1-16, 2017.1424-8247https://www.arca.fiocruz.br/handle/icict/3443510.3390/ph100200521424-8247engMDPIAnti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomersinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Estadual de Londrina. Departamento de Química. Londrina, PR, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil.Universidade Federal Fluminense. Ciências Aplicadas a Produtos para Saúde. Niterói, RJ, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisas Clínicas Evandro Chagas. Rio de Janeiro. RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Pesquisas Clínicas Evandro Chagas. Rio de Janeiro. RJ, Brasil.Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil.Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil.In an ongoing research program for the development of new anti-tuberculosis drugs, we synthesized three series (A, B, and C) of 7-chloro-4-aminoquinolines, which were evaluated in vitro against Mycobacterium tuberculosis (MTB). Now, we report the anti-MTB and cytotoxicity evaluations of a new series, D (D01-D21). Considering the active compounds of series A (A01-A13), B (B01-B13), C (C01-C07), and D (D01-D09), we compose a data set of 42 compounds and carried out hologram quantitative structure-activity relationship (HQSAR) analysis. The amino-imino tautomerism of the 4-aminoquinoline moiety was considered using both amino (I) and imino (II) forms as independent datasets. The best HQSAR model from each dataset was internally validated and both models showed significant statistical indexes. Tautomer I model: leave-one-out (LOO) cross-validated correlation coefficient (q²) = 0.80, squared correlation coefficient (r²) = 0.97, standard error (SE) = 0.12, cross-validated standard error (SEcv) = 0.32. Tautomer II model: q² = 0.77, r² = 0.98, SE = 0.10, SEcv = 0.35. Both models were externally validated by predicting the activity values of the corresponding test set, and the tautomer II model, which showed the best external prediction performance, was used to predict the biological activity responses of the compounds that were not evaluated in the anti-MTB trials due to poor solubility, pointing out D21 for further solubility studies to attempt to determine its actual biological activity.Mycobacterium tuberculosis4-aminoquinolineAmino–imino tautomerismMolecular modelingHQSARDrug designAnti-mycobacterial activityCytotoxicityinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; 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| dc.title.pt_BR.fl_str_mv |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| title |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| spellingShingle |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers Bispo, Marcelle L. F. Mycobacterium tuberculosis 4-aminoquinoline Amino–imino tautomerism Molecular modeling HQSAR Drug design Anti-mycobacterial activity Cytotoxicity |
| title_short |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| title_full |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| title_fullStr |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| title_full_unstemmed |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| title_sort |
Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino-imino tautomers |
| author |
Bispo, Marcelle L. F. |
| author_facet |
Bispo, Marcelle L. F. Lima, Camilo H. S. Cardoso, Laura N. F. Candéa, André L. P. Bezerra, Flávio A. F. M. Lourenço, Maria C. S. Henriques, Maria G. M. O. Alencastro, Ricardo B. Kaiser, Carlos R. Souza, Marcus V. N. Albuquerque, Magaly G. |
| author_role |
author |
| author2 |
Lima, Camilo H. S. Cardoso, Laura N. F. Candéa, André L. P. Bezerra, Flávio A. F. M. Lourenço, Maria C. S. Henriques, Maria G. M. O. Alencastro, Ricardo B. Kaiser, Carlos R. Souza, Marcus V. N. Albuquerque, Magaly G. |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Bispo, Marcelle L. F. Lima, Camilo H. S. Cardoso, Laura N. F. Candéa, André L. P. Bezerra, Flávio A. F. M. Lourenço, Maria C. S. Henriques, Maria G. M. O. Alencastro, Ricardo B. Kaiser, Carlos R. Souza, Marcus V. N. Albuquerque, Magaly G. |
| dc.subject.en.pt_BR.fl_str_mv |
Mycobacterium tuberculosis 4-aminoquinoline Amino–imino tautomerism Molecular modeling HQSAR Drug design Anti-mycobacterial activity Cytotoxicity |
| topic |
Mycobacterium tuberculosis 4-aminoquinoline Amino–imino tautomerism Molecular modeling HQSAR Drug design Anti-mycobacterial activity Cytotoxicity |
| description |
Universidade Estadual de Londrina. Departamento de Química. Londrina, PR, Brasil / Universidade Federal do Rio de Janeiro. Instituto de Química. Programa de Pós-Graduação em Química. Rio de Janeiro, RJ, Brasil / Fundação Oswaldo Cruz. Instituto de Tecnologia em Fármacos. Rio de Janeiro. RJ, Brasil. |
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2017 |
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2017 |
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2019-07-26T12:04:36Z |
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2019-07-26T12:04:36Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
| dc.identifier.citation.fl_str_mv |
BISPO, Marcelle L. F. et al. Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino–imino tautomers. Pharmaceuticals, v. 10, n. 52, p. 1-16, 2017. |
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https://www.arca.fiocruz.br/handle/icict/34435 |
| dc.identifier.issn.pt_BR.fl_str_mv |
1424-8247 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/ph10020052 |
| dc.identifier.eissn.none.fl_str_mv |
1424-8247 |
| identifier_str_mv |
BISPO, Marcelle L. F. et al. Anti-mycobacterial evaluation of 7-chloro-4-aminoquinolines and hologram quantitative structure-activity relationship (HQSAR) modeling of amino–imino tautomers. Pharmaceuticals, v. 10, n. 52, p. 1-16, 2017. 1424-8247 10.3390/ph10020052 |
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https://www.arca.fiocruz.br/handle/icict/34435 |
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eng |
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eng |
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openAccess |
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MDPI |
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MDPI |
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