Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates
<b>Background/Objectives:</b> Breast cancer is a disease with a high mortality rate worldwide; consequently, urgent achievements are required to design new greener drugs, leaving natural products and their derivatives as good options. A constant antineoplastic effect has been observed wh...
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2024-11-01
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| author | Edgar Daniel Moyers-Montoya María Jazmín Castañeda-Muñoz Daniel Márquez-Olivas René Miranda-Ruvalcaba Carlos Alberto Martínez-Pérez Perla E. García-Casillas Wilber Montejo-López María Inés Nicolás-Vázquez René Gerardo Escobedo-González |
| author_facet | Edgar Daniel Moyers-Montoya María Jazmín Castañeda-Muñoz Daniel Márquez-Olivas René Miranda-Ruvalcaba Carlos Alberto Martínez-Pérez Perla E. García-Casillas Wilber Montejo-López María Inés Nicolás-Vázquez René Gerardo Escobedo-González |
| author_sort | Edgar Daniel Moyers-Montoya |
| collection | DOAJ |
| description | <b>Background/Objectives:</b> Breast cancer is a disease with a high mortality rate worldwide; consequently, urgent achievements are required to design new greener drugs, leaving natural products and their derivatives as good options. A constant antineoplastic effect has been observed when the phytoproduct contains an indole fragment. <b>Methods:</b> Therefore, the objective of this work was to carry out a thoughtful computational study to perform an appropriate evaluation of four novel molecules of the class of the 3-indolylquinones as phytodrug candidates for antineoplastic activity: thymoquinone (TQ), 2,6-dimethoxy-1,4-benzoquinone (DMQ), 2,3-dimethoxy-5-methyl-1,4-benzoquinone (DMMQ), and 2,5-dihydroxy-1,4-benzoquinone (DHQ). It is important to highlight that the obtained computational results of the target compounds were compared-correlated with the theoretical and experimental literature data previously reported of several indolylquinones: indolylperezone, indolylisoperezone, indolylmenadione, and indolylplumbagin (IE-IH, respectively). Results: The results revealed that the studied structures possibly presented antineoplastic activity, in addition to the fact that the reactivity parameters showed that two of the evaluated compounds have the option to present IC<sub>50</sub> values lower than or similar to 25 mg/mL, activity like that of indolylisoperezone; moreover, they show molecular coupling to PARP-1. Finally, the prediction of the calculated physicochemical parameters coincides with the Lipinski and Veber rules, indicating that the adsorption, metabolism, and toxicity parameters are acceptable for the studied compounds, obtaining high drug score values. <b>Conclusions:</b> Finally, a comparison between the proposed molecules and others previously synthesized was appropriately performed, establishing that the synthesis of the studied compounds and the determination of their pharmacological properties in an experimental manner are of interest. |
| format | Article |
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| issn | 1424-8247 |
| language | English |
| publishDate | 2024-11-01 |
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| spelling | doaj-art-d7a7b5e6a5674cb5a1783b04a5f1d4cf2025-08-20T02:01:11ZengMDPI AGPharmaceuticals1424-82472024-11-011712159510.3390/ph17121595Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer CandidatesEdgar Daniel Moyers-Montoya0María Jazmín Castañeda-Muñoz1Daniel Márquez-Olivas2René Miranda-Ruvalcaba3Carlos Alberto Martínez-Pérez4Perla E. García-Casillas5Wilber Montejo-López6María Inés Nicolás-Vázquez7René Gerardo Escobedo-González8Instituto de Ingeniería y Tecnología, Universidad Autónoma de Ciudad Juárez, Ave. Del Charro 450 Norte, Ciudad Juárez 32310, Chihuahua, MexicoCentro Médico de Especialidades, Av. De las Américas #201 Nte. Col. Margaritas, Ciudad Juárez 32300, Chihuahua, MexicoDepartamento de Mantenimiento Industrial y Nanotecnología, Universidad Tecnológica de Ciudad Juárez, Maestría en Ingeniería Industrial Sustentable, Av. Universidad Tecnológica No. 3051, Col. Lote Bravo II, Ciudad Juárez 32695, Chihuahua, MexicoDepartamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Avenida 1° de Mayo s/n, Colonia Santa María las Torres, Cuautitlán Izcalli 54740, Estado de México, MexicoInstituto de Ingeniería y Tecnología, Universidad Autónoma de Ciudad Juárez, Ave. Del Charro 450 Norte, Ciudad Juárez 32310, Chihuahua, MexicoCentro de Investigación en Química Aplicada, Blvd. Enrique Reyna Hermosillo No. 140, Saltillo 25294, Coahuila, MexicoEscuela de Ciencias Químicas, Universidad Autónoma de Chiapas, Ocozocoautla de Espinosa 29140, Chiapas, MexicoDepartamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Avenida 1° de Mayo s/n, Colonia Santa María las Torres, Cuautitlán Izcalli 54740, Estado de México, MexicoDepartamento de Mantenimiento Industrial y Nanotecnología, Universidad Tecnológica de Ciudad Juárez, Maestría en Ingeniería Industrial Sustentable, Av. Universidad Tecnológica No. 3051, Col. Lote Bravo II, Ciudad Juárez 32695, Chihuahua, Mexico<b>Background/Objectives:</b> Breast cancer is a disease with a high mortality rate worldwide; consequently, urgent achievements are required to design new greener drugs, leaving natural products and their derivatives as good options. A constant antineoplastic effect has been observed when the phytoproduct contains an indole fragment. <b>Methods:</b> Therefore, the objective of this work was to carry out a thoughtful computational study to perform an appropriate evaluation of four novel molecules of the class of the 3-indolylquinones as phytodrug candidates for antineoplastic activity: thymoquinone (TQ), 2,6-dimethoxy-1,4-benzoquinone (DMQ), 2,3-dimethoxy-5-methyl-1,4-benzoquinone (DMMQ), and 2,5-dihydroxy-1,4-benzoquinone (DHQ). It is important to highlight that the obtained computational results of the target compounds were compared-correlated with the theoretical and experimental literature data previously reported of several indolylquinones: indolylperezone, indolylisoperezone, indolylmenadione, and indolylplumbagin (IE-IH, respectively). Results: The results revealed that the studied structures possibly presented antineoplastic activity, in addition to the fact that the reactivity parameters showed that two of the evaluated compounds have the option to present IC<sub>50</sub> values lower than or similar to 25 mg/mL, activity like that of indolylisoperezone; moreover, they show molecular coupling to PARP-1. Finally, the prediction of the calculated physicochemical parameters coincides with the Lipinski and Veber rules, indicating that the adsorption, metabolism, and toxicity parameters are acceptable for the studied compounds, obtaining high drug score values. <b>Conclusions:</b> Finally, a comparison between the proposed molecules and others previously synthesized was appropriately performed, establishing that the synthesis of the studied compounds and the determination of their pharmacological properties in an experimental manner are of interest.https://www.mdpi.com/1424-8247/17/12/1595indolylquinonesin silico studyDFTmolecular dockingchemoinformatic tools |
| spellingShingle | Edgar Daniel Moyers-Montoya María Jazmín Castañeda-Muñoz Daniel Márquez-Olivas René Miranda-Ruvalcaba Carlos Alberto Martínez-Pérez Perla E. García-Casillas Wilber Montejo-López María Inés Nicolás-Vázquez René Gerardo Escobedo-González Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates Pharmaceuticals indolylquinones in silico study DFT molecular docking chemoinformatic tools |
| title | Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates |
| title_full | Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates |
| title_fullStr | Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates |
| title_full_unstemmed | Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates |
| title_short | Theoretical–Cheminformatic Study of Four Indolylphytoquinones, Prospective Anticancer Candidates |
| title_sort | theoretical cheminformatic study of four indolylphytoquinones prospective anticancer candidates |
| topic | indolylquinones in silico study DFT molecular docking chemoinformatic tools |
| url | https://www.mdpi.com/1424-8247/17/12/1595 |
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