Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study
<i>Aedes aegypti</i> is a vector for the arbovirus responsible for yellow fever, Zika and Chikungunya virus. Essential oils and their constituents are known for their larvicidal properties and are strong candidates for mosquito control. This work aimed to develop a quantitative structure...
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| Format: | Article |
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MDPI AG
2023-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/6/2454 |
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| author | Adrián Ulises Cruz-Castillo Luz María Rodríguez-Valdez José Correa-Basurto Benjamín Nogueda-Torres Sergio Andrade-Ochoa Guadalupe Virginia Nevárez-Moorillón |
| author_facet | Adrián Ulises Cruz-Castillo Luz María Rodríguez-Valdez José Correa-Basurto Benjamín Nogueda-Torres Sergio Andrade-Ochoa Guadalupe Virginia Nevárez-Moorillón |
| author_sort | Adrián Ulises Cruz-Castillo |
| collection | DOAJ |
| description | <i>Aedes aegypti</i> is a vector for the arbovirus responsible for yellow fever, Zika and Chikungunya virus. Essential oils and their constituents are known for their larvicidal properties and are strong candidates for mosquito control. This work aimed to develop a quantitative structure–activity study and molecular screening for the search and design of new larvicidal agents. Twenty-five monoterpenes with previously evaluated larvicidal activity were built and optimized using computational tools. QSAR models were constructed through genetic algorithms from the larvicidal activity and the calculation of theoretical descriptors for each molecule. Docking studies on acetylcholinesterase (AChE) and sterol carrier protein (SCP-2) were also carried out. Results demonstrate that the epoxide groups in the structure of terpenes hinder larvicidal activity, while lipophilicity plays an important role in enhancing biological activity. Larvicidal activity correlates with the interaction of the sterol-carrier protein. Of the 25 compounds evaluated, carvacrol showed the highest larvicidal activity with an LC<sub>50</sub> of 8.8 µg/mL. The information included in this work contributes to describing the molecular, topological, and quantum mechanical properties related to the larvicidal activity of monoterpenes and their derivatives. |
| first_indexed | 2024-03-11T06:08:49Z |
| format | Article |
| id | doaj.art-ec797ac319ce40d5973a311045cb1d9b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T06:08:49Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ec797ac319ce40d5973a311045cb1d9b2023-11-17T12:50:34ZengMDPI AGMolecules1420-30492023-03-01286245410.3390/molecules28062454Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular StudyAdrián Ulises Cruz-Castillo0Luz María Rodríguez-Valdez1José Correa-Basurto2Benjamín Nogueda-Torres3Sergio Andrade-Ochoa4Guadalupe Virginia Nevárez-Moorillón5Campus Coyoacán, Universidad del Valle de México, Calzada De Tlalpan No. 3016 y 3058, Ex Hacienda Coapa, Delegación Coyoacán, Ciudad de México 04910, MexicoFacultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario S/N Campus Universitario II, Chihuahua 31125, MexicoEscuela Superior de Medicina, Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón S/N Col. Santo Tomas, Ciudad de México 11340, MexicoEscuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N Col. Santo Tomas, Ciudad de México 11340, MexicoCampus Coyoacán, Universidad del Valle de México, Calzada De Tlalpan No. 3016 y 3058, Ex Hacienda Coapa, Delegación Coyoacán, Ciudad de México 04910, MexicoFacultad de Ciencias Químicas, Universidad Autónoma de Chihuahua, Circuito Universitario S/N Campus Universitario II, Chihuahua 31125, Mexico<i>Aedes aegypti</i> is a vector for the arbovirus responsible for yellow fever, Zika and Chikungunya virus. Essential oils and their constituents are known for their larvicidal properties and are strong candidates for mosquito control. This work aimed to develop a quantitative structure–activity study and molecular screening for the search and design of new larvicidal agents. Twenty-five monoterpenes with previously evaluated larvicidal activity were built and optimized using computational tools. QSAR models were constructed through genetic algorithms from the larvicidal activity and the calculation of theoretical descriptors for each molecule. Docking studies on acetylcholinesterase (AChE) and sterol carrier protein (SCP-2) were also carried out. Results demonstrate that the epoxide groups in the structure of terpenes hinder larvicidal activity, while lipophilicity plays an important role in enhancing biological activity. Larvicidal activity correlates with the interaction of the sterol-carrier protein. Of the 25 compounds evaluated, carvacrol showed the highest larvicidal activity with an LC<sub>50</sub> of 8.8 µg/mL. The information included in this work contributes to describing the molecular, topological, and quantum mechanical properties related to the larvicidal activity of monoterpenes and their derivatives.https://www.mdpi.com/1420-3049/28/6/2454larvicidal activityterpenic compounds<i>Aedes aegypti</i>molecular modeling |
| spellingShingle | Adrián Ulises Cruz-Castillo Luz María Rodríguez-Valdez José Correa-Basurto Benjamín Nogueda-Torres Sergio Andrade-Ochoa Guadalupe Virginia Nevárez-Moorillón Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study Molecules larvicidal activity terpenic compounds <i>Aedes aegypti</i> molecular modeling |
| title | Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study |
| title_full | Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study |
| title_fullStr | Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study |
| title_full_unstemmed | Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study |
| title_short | Terpenic Constituents of Essential Oils with Larvicidal Activity against <i>Aedes Aegypti</i>: A QSAR and Docking Molecular Study |
| title_sort | terpenic constituents of essential oils with larvicidal activity against i aedes aegypti i a qsar and docking molecular study |
| topic | larvicidal activity terpenic compounds <i>Aedes aegypti</i> molecular modeling |
| url | https://www.mdpi.com/1420-3049/28/6/2454 |
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