Fluorine Atoms on C6H5-Corrole Affect the Interaction with Mpro and PLpro Proteases of SARS-CoV-2: Molecular Docking and 2D-QSAR Approaches

dc.creatorChaves, Otávio Augusto
dc.creatorSantos, Cláudio Eduardo Rodrigues
dc.creatorEchevarria, Áurea
dc.creatorSacramento, Carolina Q.
dc.creatorRodrigues, Natalia Fintelman
dc.creatorTemerozo, Jairo R.
dc.creatorFaria Neto, Hugo Caire Castro
dc.creatorSouza, Thiago Moreno Lopes e
dc.date2022-10-20T14:05:36Z
dc.date2022-10-20T14:05:36Z
dc.date2022
dc.date.accessioned2023-09-27T00:13:08Z
dc.date.available2023-09-27T00:13:08Z
dc.identifierCHAVES, Otávio Augusto et al. Fluorine Atoms on C6H5-Corrole Affect the Interaction with Mpro and PLpro Proteases of SARS-CoV-2: Molecular Docking and 2D-QSAR Approaches. International Journal of Molecular Sciences, v. 23, 10936, p. 1 - 20, Sept. 2022.
dc.identifier1422-0067
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/55207
dc.identifier10.3390/ijms231810936
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8898631
dc.descriptionThe chymotrypsin-like cysteine protease (3CLpro, also known as main protease—Mpro) and papain-like protease (PLpro) of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) have been used as the main targets for screening potential synthetic inhibitors for posterior in vitro evaluation of the most promising compounds. In this sense, the present work reports for the first time the evaluation of the interaction between Mpro/PLpro with a series of 17 porphyrin analoguescorrole (C1), meso-aryl-corrole (C2), and 15 fluorinated-meso-aryl-corrole derivatives (C3–C17) via molecular docking calculations. The impact of fluorine atoms on meso-aryl-corrole structure was also evaluated in terms of binding affinity and physical-chemical properties by two-dimensional quantitative structure–activity relationship (2D-QSAR). The presence of phenyl moieties increased the binding capacity of corrole for both proteases and depending on the position of fluorine atoms might impact positively or negatively the binding capacity. For Mpro the para-fluorine atoms might decrease drastically the binding capacity, while for PLpro there was a certain increase in the binding affinity of fluorinated-corroles with the increase of fluorine atoms into meso-aryl-corrole structure mainly from tri-fluorinated insertions. The 2D-QSAR models indicated two separated regions of higher and lower affinity for Mpro:C1–C17 based on dual electronic parameters ( I and R), as well as one model was obtained with a correlation between the docking score value of Mpro:C2–C17 and the corresponding 13C nuclear magnetic resonance (NMR) chemical shifts of the sp2 carbon atoms ( C-1 and C-2) of C2–C17. Overall, the fluorinated-meso-aryl-corrole derivatives showed favorable in silico parameters as potential synthetic compounds for future in vitro assays on the inhibition of SARS-CoV-2 replication.
dc.formatapplication/pdf
dc.languageeng
dc.publisherMDPI
dc.rightsopen access
dc.subjectSARS-CoV-2
dc.subjectAncoragem molecular
dc.subjectCorroles
dc.subjectSARS-CoV-2
dc.subjectMpro
dc.subjectPLpro
dc.subjectMolecular docking
dc.subject2D-QSAR
dc.titleFluorine Atoms on C6H5-Corrole Affect the Interaction with Mpro and PLpro Proteases of SARS-CoV-2: Molecular Docking and 2D-QSAR Approaches
dc.typeArticle


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