Hemisyntheses and In-silico Study of New Analogues of Carlina Oxide from Carthamus Caeruleus Roots
| Autor: | Joëlle Pérard, Mohammed El Amine Dib, Zoheir Arrar, Imane Rihab Mami, Tabet Zatla Amina |
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| Přispěvatelé: | Université de Tlemcen, Cibles Thérapeutiques et conception de médicaments (CiTCoM - UMR 8038), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP) |
| Rok vydání: | 2021 |
| Předmět: |
In silico
Carthamus [CHIM.THER]Chemical Sciences/Medicinal Chemistry Plant Roots reductive amination Molecular Docking Simulation Enterococcus faecalis law.invention Steam distillation 03 medical and health sciences 0302 clinical medicine Column chromatography law Carlina oxide Drug Discovery Furans Vilsmeier-Haack reaction Essential oil 030304 developmental biology chemistry.chemical_classification 0303 health sciences Molecular Structure biology [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry General Medicine DNA gyrase inhibitors biology.organism_classification Combinatorial chemistry Computer Science Applications Enzyme chemistry 13. Climate action Docking (molecular) Alkynes 030220 oncology & carcinogenesis Molecular docking Software |
| Zdroj: | Combinatorial Chemistry and High Throughput Screening Combinatorial Chemistry and High Throughput Screening, Bentham Science Publishers, 2021, 24, pp.1503-1513. ⟨10.2174/1386207323999201103214141⟩ |
| ISSN: | 1386-2073 |
| DOI: | 10.2174/1386207323999201103214141 |
| Popis: | Aim and Objective: Nowadays, developing effective antibiotics for bacteria control has become difficult due to increased resistance to the available medicines in the market. Essential oils have very interesting biological properties; some of their components have very powerful antiviral and antibacterial properties. Carthamus caeruleus is a plant that has antibacterial and antioxidant activity due to the presence of an acetylenic compound, Carlina oxide. The aim of this work was to provide for the first time the chemical modifications to the structure of Carlina oxide and the in-silico study of these analogues. Materials and Methods: The essential oil of Carthamus caeruleus was extracted by steam distillation in a Clevenger-type apparatus. Carlina oxide component was separated by column chromatography. Five new analogues were synthetized and identified by spectroscopic analyses (RMN, IR and SM). Molecular docking simulation study was performed using Molecular Operating Environment software (MOE) on three enzymes of bacterial origin (Streptococcus pyogenesis and Enterococcus faecalis). Results: Five new compounds derived from Carlina oxide were synthesized (IM8-IM12), and their structures were characterized by infrared (IR), 1H and 13C nuclear magnetic resonance (NMR). The new synthesized compounds were evaluated as mSpeB, DHFR from Enterococcus faecalis and DNA gyrase inhibitors by a docking analysis using MOE. These results show interesting ligand interactions with the three enzymes, and the best result was attributed to the complexes formed with IM9, which had the lowest score. Conclusion: In fact, these new compounds could lead to powerful approaches for the research and development of new antibiotics. |
| Databáze: | OpenAIRE |
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