Synthesis, molecular structure, spectroscopic, electronic properties, molecular docking, and molecular dynamics studies on novel 1,2,3-triazole-thiosemicarbazone: A potent breast cancer drug.
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| Titel: | Synthesis, molecular structure, spectroscopic, electronic properties, molecular docking, and molecular dynamics studies on novel 1,2,3-triazole-thiosemicarbazone: A potent breast cancer drug. |
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| Autoren: | Ait Elmachkouri Y; Laboratory of Organic and physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco. Electronic address: younesse.aitelmachkouri@edu.uiz.ac.ma., Rajesh R; Department of Physics, Vel Tech High Tech Dr.Rangarajan Dr.Sakunthala Engineering College, Avadi, Chennai, Tamil Nadu 600 062, India., Altharawi A; Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia., Frit A AP; Department of Physics, Vel Tech High Tech Dr.Rangarajan Dr.Sakunthala Engineering College, Avadi, Chennai, Tamil Nadu 600 062, India., Alossaimi MA; Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia., Riadi Y; Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia., Aldakhil T; Department of Pharmaceutical Chemistry, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj 11942, Saudi Arabia., Taha ML; Laboratory of Organic and physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco., Haggam RA; Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi Arabia; Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44519, Egypt. Electronic address: relhaggan@iu.edu.sa. |
| Quelle: | Computational biology and chemistry [Comput Biol Chem] 2025 Dec; Vol. 119, pp. 108580. Date of Electronic Publication: 2025 Jul 02. |
| Publikationsart: | Journal Article |
| Sprache: | English |
| Info zur Zeitschrift: | Publisher: Elsevier Country of Publication: England NLM ID: 101157394 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1476-928X (Electronic) Linking ISSN: 14769271 NLM ISO Abbreviation: Comput Biol Chem Subsets: MEDLINE |
| Imprint Name(s): | Publication: Oxford : Elsevier Original Publication: Oxford : Pergamon, c2003- |
| MeSH-Schlagworte: | Triazoles*/chemistry , Triazoles*/pharmacology , Triazoles*/chemical synthesis , Thiosemicarbazones*/chemistry , Thiosemicarbazones*/pharmacology , Thiosemicarbazones*/chemical synthesis , Molecular Dynamics Simulation* , Molecular Docking Simulation* , Antineoplastic Agents*/chemical synthesis , Antineoplastic Agents*/chemistry , Antineoplastic Agents*/pharmacology , Breast Neoplasms*/drug therapy , Breast Neoplasms*/metabolism, Molecular Structure ; Humans ; Density Functional Theory ; Female ; Electrons |
| Abstract: | Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. This paper reports a comprehensive multi-step synthesis, characterization using various analytical techniques, and theoretical analysis of a novel hybrid 1,2,3-Triazole-Thiosemicarbazones compound 5. The structure of the 1,2,3-triazole-thiosemicarbazone 5 was confirmed through detailed analyses such as NMR ( 1 H and 13 C), IR, and UV techniques. Also, a Density Functional theory (DFT) investigation was carried out on compound 5 to support experimental results by utilizing the B3LYP approach with the 6-311 + +G(d,p) basis set. The observed FT-IR NMR, and UV-Vis spectra match well with the simulated spectra. The electronic transition happened between n → π*. The stability of the compound is analyzed by NBO. Various chemical parameters were obtained using Frontier Molecular Orbital analysis and confirmed the presence of intermolecular charge transfer (ICT). The qualitative studies of reactive sites are obtained by Molecular Electrostatic Potential. Using DFT theory NLO studies carried out. The topological studies like ELF and LOL carried on the compound to know the electron density and binding nature around an atom. The weak interactions are identified by non-covalent interactions (NCI) and RDG. Furthermore, in-silico molecular docking and dynamics simulations were carried out, complemented by ADMET predictions to assess interactions between this derivative and the active sites of ESR1 (Estrogen Receptor Alpha) after a pharmacological network study. The findings demonstrated strong binding affinity of the synthesized 1,2,3-triazole-thiosemicarbazone hybrid with ESR1, displaying a binding energy score of -6.48 Kcal mol -1 , and also confirmed the notable stability of the complex through molecular dynamics studies. (Copyright © 2025 Elsevier Ltd. All rights reserved.) |
| Contributed Indexing: | Keywords: 1; 2; 3-Triazole; DFT calculations; Molecular docking; Molecular dynamics; Molecular structure; Synthesis; Thiosemicarbazone |
| Substance Nomenclature: | 0 (Triazoles) 0 (Thiosemicarbazones) 0 (Antineoplastic Agents) |
| Entry Date(s): | Date Created: 20250705 Date Completed: 20250903 Latest Revision: 20250908 |
| Update Code: | 20250908 |
| DOI: | 10.1016/j.compbiolchem.2025.108580 |
| PMID: | 40617050 |
| Datenbank: | MEDLINE |
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Nájsť tento článok vo Web of Science | Abstract: | Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br />This paper reports a comprehensive multi-step synthesis, characterization using various analytical techniques, and theoretical analysis of a novel hybrid 1,2,3-Triazole-Thiosemicarbazones compound 5. The structure of the 1,2,3-triazole-thiosemicarbazone 5 was confirmed through detailed analyses such as NMR ( <sup>1</sup> H and <sup>13</sup> C), IR, and UV techniques. Also, a Density Functional theory (DFT) investigation was carried out on compound 5 to support experimental results by utilizing the B3LYP approach with the 6-311 + +G(d,p) basis set. The observed FT-IR NMR, and UV-Vis spectra match well with the simulated spectra. The electronic transition happened between n → π*. The stability of the compound is analyzed by NBO. Various chemical parameters were obtained using Frontier Molecular Orbital analysis and confirmed the presence of intermolecular charge transfer (ICT). The qualitative studies of reactive sites are obtained by Molecular Electrostatic Potential. Using DFT theory NLO studies carried out. The topological studies like ELF and LOL carried on the compound to know the electron density and binding nature around an atom. The weak interactions are identified by non-covalent interactions (NCI) and RDG. Furthermore, in-silico molecular docking and dynamics simulations were carried out, complemented by ADMET predictions to assess interactions between this derivative and the active sites of ESR1 (Estrogen Receptor Alpha) after a pharmacological network study. The findings demonstrated strong binding affinity of the synthesized 1,2,3-triazole-thiosemicarbazone hybrid with ESR1, displaying a binding energy score of -6.48 Kcal mol <sup>-1</sup> , and also confirmed the notable stability of the complex through molecular dynamics studies.<br /> (Copyright © 2025 Elsevier Ltd. All rights reserved.) |
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| ISSN: | 1476-928X |
| DOI: | 10.1016/j.compbiolchem.2025.108580 |