QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora
Abstract Background Aphis craccivora has many plant hosts, though it seemingly forechoice to groups of bean family. Other plants it hosts are families of Solanaceae, Rosaceae, Malvaceae, Chenopodiaceae, Caryophyllaceae, Ranunculaceae, Cucurbitaceae, Brassicaceae, and Asteraceae. Result A computation...
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| Format: | Article |
| Language: | English |
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SpringerOpen
2020-03-01
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| Series: | Bulletin of the National Research Centre |
| Subjects: | |
| Online Access: | http://link.springer.com/article/10.1186/s42269-020-00297-w |
| _version_ | 1818775763810254848 |
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| author | Yusuf Isyaku Adamu Uzairu Sani Uba Muhammad Tukur Ibrahim Abdullahi Bello Umar |
| author_facet | Yusuf Isyaku Adamu Uzairu Sani Uba Muhammad Tukur Ibrahim Abdullahi Bello Umar |
| author_sort | Yusuf Isyaku |
| collection | DOAJ |
| description | Abstract Background Aphis craccivora has many plant hosts, though it seemingly forechoice to groups of bean family. Other plants it hosts are families of Solanaceae, Rosaceae, Malvaceae, Chenopodiaceae, Caryophyllaceae, Ranunculaceae, Cucurbitaceae, Brassicaceae, and Asteraceae. Result A computational study was carried out on a series of twenty compounds of novel 4-(N,N-diarylmethylamines) furan-2(5H)-one derivatives against Aphis craccivora insect. Optimization of the compounds was performed with the aid of Spartan 14 software using DFT/B3LYP/6-31G** quantum mechanical method. Using PaDel descriptor software to calculate the descriptors, Generic Function Approximation (GFA) was employed to generate the model. Model 1 found to be the optimal out of four models generated which has the following statistical parameters; R 2 = 0.871489, R 2 adj = 0.83644, cross-validated R 2 = 0.790821, and external R 2 = 0.550768. Molecular docking study occurred between the compounds and the complex crystal structure of the acetylcholine (protein AChBP) (PDB CODE 2zju) in which compound 13 was identified to have the highest binding energy of − 8.4 kcalmol−1. Statistical analyses, such as variance inflation factor, mean effect, and the applicability domain, were conducted on the model. This compound has a strong affinity with the macromolecular target point of the A. craccivora (2zju) producing H-bond and as well the hydrophobic interaction at the target point of amino acid residue. Molecular docking gave an insight into the structure-based design of the new compounds with better activity against A. craccivora in which three compounds A, B, and C were designed and discovered to be of high quality and have greater binding affinity compared to the one obtained from the literature. Conclusion The QSAR model was generated by the employment of Genetic Function Approximation (GFA). The model was found to be robust and possessed a good statistical parameter. Furthermore, a molecular docking study was performed to get an idea for structure-based design in which three (3) compounds A, B, and C were designed and were found to be more active than the template (compound 13, i.e., the one with highest docking score). QSAR model was developed to give an insight into the ligand/template-based design of computer-aided drug design. |
| first_indexed | 2024-12-18T11:02:13Z |
| format | Article |
| id | doaj.art-102410112fc54ac49e12ca9e459e9b27 |
| institution | Directory Open Access Journal |
| issn | 2522-8307 |
| language | English |
| last_indexed | 2024-12-18T11:02:13Z |
| publishDate | 2020-03-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Bulletin of the National Research Centre |
| spelling | doaj.art-102410112fc54ac49e12ca9e459e9b272022-12-21T21:10:11ZengSpringerOpenBulletin of the National Research Centre2522-83072020-03-0144111110.1186/s42269-020-00297-wQSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivoraYusuf Isyaku0Adamu Uzairu1Sani Uba2Muhammad Tukur Ibrahim3Abdullahi Bello Umar4Department of Chemistry, Ahamadu Bello UniversityDepartment of Chemistry, Ahamadu Bello UniversityDepartment of Chemistry, Ahamadu Bello UniversityDepartment of Chemistry, Ahamadu Bello UniversityDepartment of Chemistry, Ahamadu Bello UniversityAbstract Background Aphis craccivora has many plant hosts, though it seemingly forechoice to groups of bean family. Other plants it hosts are families of Solanaceae, Rosaceae, Malvaceae, Chenopodiaceae, Caryophyllaceae, Ranunculaceae, Cucurbitaceae, Brassicaceae, and Asteraceae. Result A computational study was carried out on a series of twenty compounds of novel 4-(N,N-diarylmethylamines) furan-2(5H)-one derivatives against Aphis craccivora insect. Optimization of the compounds was performed with the aid of Spartan 14 software using DFT/B3LYP/6-31G** quantum mechanical method. Using PaDel descriptor software to calculate the descriptors, Generic Function Approximation (GFA) was employed to generate the model. Model 1 found to be the optimal out of four models generated which has the following statistical parameters; R 2 = 0.871489, R 2 adj = 0.83644, cross-validated R 2 = 0.790821, and external R 2 = 0.550768. Molecular docking study occurred between the compounds and the complex crystal structure of the acetylcholine (protein AChBP) (PDB CODE 2zju) in which compound 13 was identified to have the highest binding energy of − 8.4 kcalmol−1. Statistical analyses, such as variance inflation factor, mean effect, and the applicability domain, were conducted on the model. This compound has a strong affinity with the macromolecular target point of the A. craccivora (2zju) producing H-bond and as well the hydrophobic interaction at the target point of amino acid residue. Molecular docking gave an insight into the structure-based design of the new compounds with better activity against A. craccivora in which three compounds A, B, and C were designed and discovered to be of high quality and have greater binding affinity compared to the one obtained from the literature. Conclusion The QSAR model was generated by the employment of Genetic Function Approximation (GFA). The model was found to be robust and possessed a good statistical parameter. Furthermore, a molecular docking study was performed to get an idea for structure-based design in which three (3) compounds A, B, and C were designed and were found to be more active than the template (compound 13, i.e., the one with highest docking score). QSAR model was developed to give an insight into the ligand/template-based design of computer-aided drug design.http://link.springer.com/article/10.1186/s42269-020-00297-wQSARMolecular dockingDesignInsecticides |
| spellingShingle | Yusuf Isyaku Adamu Uzairu Sani Uba Muhammad Tukur Ibrahim Abdullahi Bello Umar QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora Bulletin of the National Research Centre QSAR Molecular docking Design Insecticides |
| title | QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora |
| title_full | QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora |
| title_fullStr | QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora |
| title_full_unstemmed | QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora |
| title_short | QSAR, molecular docking, and design of novel 4-(N,N-diarylmethyl amines) Furan-2(5H)-one derivatives as insecticides against Aphis craccivora |
| title_sort | qsar molecular docking and design of novel 4 n n diarylmethyl amines furan 2 5h one derivatives as insecticides against aphis craccivora |
| topic | QSAR Molecular docking Design Insecticides |
| url | http://link.springer.com/article/10.1186/s42269-020-00297-w |
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