Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study
With the increasing global burden of diabetes mellitus type 2, the search for the new drugs, with better pharmacological profile is continued. As a part of this surge, the synthesis, pharmacological in vitro and computational evaluation of five, simple carbamate derivatives, against carbohydrate dig...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2023-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300058S.pdf |
| _version_ | 1797393670019743744 |
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| author | Suručić Relja V. Jevtić Ivana I. Stanojković Tatjana P. Popović-Đorđević Jelena B. |
| author_facet | Suručić Relja V. Jevtić Ivana I. Stanojković Tatjana P. Popović-Đorđević Jelena B. |
| author_sort | Suručić Relja V. |
| collection | DOAJ |
| description | With the increasing global burden of diabetes mellitus type 2, the search for the new drugs, with better pharmacological profile is continued. As a part of this surge, the synthesis, pharmacological in vitro and computational evaluation of five, simple carbamate derivatives, against carbohydrate digestive enzyme α-glucosidase, is disclosed herein. Results of the experimental and computational assessment indicated that examined carbamates deterred the activity of α-glucosidase with acceptable IC50 values ranging from 65.34 to 79.89 μM compared to a standard drug acarbose (109.71 μM). Similarly, the studied compounds displayed in silico binding affinity for α-glucosidase enzyme with significant binding energies. Preliminary toxicity profiles of studied carbamates against three cancerous cell lines indicated their poor activity, suggesting that significant structural modifications have to be made to improve their anticancer efficiency. Results of the present study indicate that the examined carbamates were able to virtually or experimentally interact with an important target of diabetes mellitus type 2. Additionally, a new pharmacophore model is proposed featuring hydrogen bond donating carbamate –NH group, hydrogen bond accepting carbamate –OCH3 group and hydrophobic stabilization of aromatic moieties. |
| first_indexed | 2024-03-09T00:07:08Z |
| format | Article |
| id | doaj.art-5d75f104217845ffb0e1b41784c2aef9 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-03-09T00:07:08Z |
| publishDate | 2023-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-5d75f104217845ffb0e1b41784c2aef92023-12-12T13:08:19ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212023-01-0188111089110210.2298/JSC220923058S0352-51392300058SAntidiabetic potential of simple carbamate derivatives: Comparative experimental and computational studySuručić Relja V.0https://orcid.org/0000-0003-1599-6210Jevtić Ivana I.1https://orcid.org/0000-0002-7653-2420Stanojković Tatjana P.2https://orcid.org/0000-0001-9178-9200Popović-Đorđević Jelena B.3https://orcid.org/0000-0003-4057-3826University of Banja Luka, Faculty of Medicine, Banja Luka, Bosnia and HerzegovinaUniversity of Belgrade, Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Belgrade, Republic of SerbiaUniversity of Belgrade, Institute for Oncology and Radiology of Serbia, Belgrade, SerbiaUniversity of Belgrade, Faculty of Agriculture, Department of Chemistry and Biochemistry, Belgrade, SerbiaWith the increasing global burden of diabetes mellitus type 2, the search for the new drugs, with better pharmacological profile is continued. As a part of this surge, the synthesis, pharmacological in vitro and computational evaluation of five, simple carbamate derivatives, against carbohydrate digestive enzyme α-glucosidase, is disclosed herein. Results of the experimental and computational assessment indicated that examined carbamates deterred the activity of α-glucosidase with acceptable IC50 values ranging from 65.34 to 79.89 μM compared to a standard drug acarbose (109.71 μM). Similarly, the studied compounds displayed in silico binding affinity for α-glucosidase enzyme with significant binding energies. Preliminary toxicity profiles of studied carbamates against three cancerous cell lines indicated their poor activity, suggesting that significant structural modifications have to be made to improve their anticancer efficiency. Results of the present study indicate that the examined carbamates were able to virtually or experimentally interact with an important target of diabetes mellitus type 2. Additionally, a new pharmacophore model is proposed featuring hydrogen bond donating carbamate –NH group, hydrogen bond accepting carbamate –OCH3 group and hydrophobic stabilization of aromatic moieties.https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300058S.pdfdiabetes mellitushofmann rearrangementmolecular dockingα-glucosidasemolecular dynamics simulation |
| spellingShingle | Suručić Relja V. Jevtić Ivana I. Stanojković Tatjana P. Popović-Đorđević Jelena B. Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study Journal of the Serbian Chemical Society diabetes mellitus hofmann rearrangement molecular docking α-glucosidase molecular dynamics simulation |
| title | Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study |
| title_full | Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study |
| title_fullStr | Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study |
| title_full_unstemmed | Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study |
| title_short | Antidiabetic potential of simple carbamate derivatives: Comparative experimental and computational study |
| title_sort | antidiabetic potential of simple carbamate derivatives comparative experimental and computational study |
| topic | diabetes mellitus hofmann rearrangement molecular docking α-glucosidase molecular dynamics simulation |
| url | https://doiserbia.nb.rs/img/doi/0352-5139/2023/0352-51392300058S.pdf |
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