دورية أكاديمية
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Thiourea derivatives containing 4-arylthiazoles and d-glucose moiety: design, synthesis, antimicrobial activity evaluation, and molecular docking/dynamics simulations.

التفاصيل البيبلوغرافية
العنوان: Thiourea derivatives containing 4-arylthiazoles and d-glucose moiety: design, synthesis, antimicrobial activity evaluation, and molecular docking/dynamics simulations.
المؤلفون: Thanh ND; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn., Lan PH; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Institute of Science and Technology, Ministry of Public Security of Vietnam 47 Pham Van Dong Cau Giay Ha Noi Vietnam., Hai DS; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Institute of Science and Technology, Ministry of Public Security of Vietnam 47 Pham Van Dong Cau Giay Ha Noi Vietnam., Anh HH; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn., Giang NTK; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Institute of Science and Technology, Ministry of Public Security of Vietnam 47 Pham Van Dong Cau Giay Ha Noi Vietnam., Van HTK; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Faculty of Chemical Technology, Viet Tri University of Industry Tien Kien Lam Thao Phu Tho Vietnam., Toan VN; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Institute of New Technology, Military Institute of Science and Technology (Ministry of Military) 17 Hoang Sam Cau Giay Ha Noi Vietnam., Tri NM; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Institute of New Technology, Military Institute of Science and Technology (Ministry of Military) 17 Hoang Sam Cau Giay Ha Noi Vietnam., Toan DN; Faculty of Chemistry, University of Science (Vietnam National University, Hanoi) 19 Le Thanh Tong Ha Noi Vietnam nguyendinhthanh@hus.edu.vn.; Faculty of Chemistry, Thai Nguyen University of Education 20 Luong Ngoc Quyen Thai Nguyen Vietnam.
المصدر: RSC medicinal chemistry [RSC Med Chem] 2023 Apr 19; Vol. 14 (6), pp. 1114-1130. Date of Electronic Publication: 2023 Apr 19 (Print Publication: 2023).
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101759460 Publication Model: eCollection Cited Medium: Internet ISSN: 2632-8682 (Electronic) Linking ISSN: 26328682 NLM ISO Abbreviation: RSC Med Chem Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: Cambridge : Royal Society of Chemistry, [2020]-
مستخلص: Some substituted glucose-conjugated thioureas containing 1,3-thiazole ring, 4a-h, were synthesized by the reaction of the corresponding substituted 2-amino-4-phenyl-1,3-thiazoles 2a-h with 2,3,4,6-tetra- O -acetyl-β-d-glucopyranosyl isocyanate. The antibacterial and antifungal activities of these thiazole-containing thioureas were estimated using a minimum inhibitory concentration protocol. Among these compounds, 4c, 4g, and 4h were better inhibitors with MIC = 0.78-3.125 μg mL -1 . These three compounds were also tested for their ability to inhibit S. aureus enzymes, including DNA gyrase, DNA topoisomerase IV (Topo IV), and dihydrofolate reductase, and compound 4h was found to be a strong inhibitor with IC 50 = 1.25 ± 0.12, 67.28 ± 1.21, and 0.13 ± 0.05 μM, respectively. Induced-fit docking and MM-GBSA calculations were performed to observe the binding efficiencies and steric interactions of these compounds. The obtained results showed that compound 4h is compatible with the active site of S. aureus DNA gyrase 2XCS with four H-bond interactions with residues Ala1118, Met1121, and F:DC11 and also three interactions with F:DG10 (two interactions) and F:DC11 (one interaction). Molecular dynamics simulation in a water solvent system showed that ligand 4h had active interactions with enzyme 2XCS through residues Ala1083, Glu1088, Ala1118, Gly1117, and Met1121.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
References: Arch Pharm (Weinheim). 2022 Jun;355(6):e2100481. (PMID: 35355329)
Eur J Med Chem. 2015 Jun 5;97:911-27. (PMID: 25455640)
Pathog Glob Health. 2020 Dec;114(8):426-450. (PMID: 33115375)
Antibiotics (Basel). 2020 Oct 14;9(10):. (PMID: 33066400)
Chem Pharm Bull (Tokyo). 2015;63(3):225-36. (PMID: 25757494)
Eur J Med Chem. 2020 Feb 15;188:112016. (PMID: 31926469)
Molecules. 2022 Jun 21;27(13):. (PMID: 35807236)
Elife. 2021 Jul 19;10:. (PMID: 34279221)
Nature. 2010 Aug 19;466(7309):935-40. (PMID: 20686482)
Microorganisms. 2020 Feb 20;8(2):. (PMID: 32093370)
Eur J Med Chem. 2015 Jun 5;97:699-718. (PMID: 25934508)
Bioorg Med Chem Lett. 2003 Sep 1;13(17):2929-32. (PMID: 14611860)
Bioorg Med Chem. 2022 Jan 1;53:116506. (PMID: 34890996)
Molecules. 2020 Jun 15;25(12):. (PMID: 32549386)
Chem Biol Drug Des. 2006 Jan;67(1):83-4. (PMID: 16492153)
Med Chem Res. 2018;27(9):2125-2140. (PMID: 30220831)
Nucleic Acids Res. 2006;34(15):e104. (PMID: 16936317)
Pestic Biochem Physiol. 2021 Feb;172:104766. (PMID: 33518053)
Dermatology. 2015;231(4):304-11. (PMID: 26440444)
J Mol Biol. 2019 Mar 29;431(7):1481-1493. (PMID: 30776430)
J Chem Theory Comput. 2021 Jul 13;17(7):4291-4300. (PMID: 34096718)
Biomed Pharmacother. 2018 Jul;103:923-938. (PMID: 29710509)
Curr Drug Discov Technol. 2018;15(3):214-228. (PMID: 28901248)
Chem Cent J. 2017 Apr 7;11(1):32. (PMID: 29086809)
Proteins. 2011 Oct;79(10):2794-812. (PMID: 21905107)
J Agric Food Chem. 2021 Apr 7;69(13):3848-3858. (PMID: 33780242)
Chemotherapy. 2008;54(4):245-59. (PMID: 18587237)
Mol Cell Proteomics. 2013 Jan;12(1):237-44. (PMID: 23028061)
Phys Chem Chem Phys. 2014 Aug 21;16(31):16719-29. (PMID: 24999761)
Pain Pract. 2013 Apr;13(4):316-31. (PMID: 22931375)
Sci Rep. 2015 Jul 27;5:12583. (PMID: 26212886)
Int J Mol Sci. 2023 Jan 13;24(2):. (PMID: 36675148)
J Org Chem. 2000 Mar 10;65(5):1566-8. (PMID: 10814126)
Nat Biotechnol. 2017 Jul 12;35(7):639. (PMID: 28700556)
J Org Chem. 2010 Apr 2;75(7):2327-32. (PMID: 20201494)
J Agric Food Chem. 2017 Feb 1;65(4):745-751. (PMID: 28055187)
Proteins. 2004 May 1;55(2):351-67. (PMID: 15048827)
تواريخ الأحداث: Date Created: 20230626 Latest Revision: 20240420
رمز التحديث: 20240420
مُعرف محوري في PubMed: PMC10285754
DOI: 10.1039/d3md00010a
PMID: 37360390
قاعدة البيانات: MEDLINE
الوصف
تدمد:2632-8682
DOI:10.1039/d3md00010a