Academic Journal
Novel 1,2,3-Thiadiazole-based Hydrazone and 1,3,4-Oxadiazole hybrids as promising agents against Streptococcus mutans: Synthesis, biological evaluation, and molecular modeling studies.
| Τίτλος: | Novel 1,2,3-Thiadiazole-based Hydrazone and 1,3,4-Oxadiazole hybrids as promising agents against Streptococcus mutans: Synthesis, biological evaluation, and molecular modeling studies. |
|---|---|
| Συγγραφείς: | Kurtuluş İG; Faculty of Engineering, Department of Chemistry, Organic Chemistry Division, Istanbul University-Cerrahpasa, Istanbul 34320, Turkey., Başpınar Küçük H; Faculty of Engineering, Department of Chemistry, Organic Chemistry Division, Istanbul University-Cerrahpasa, Istanbul 34320, Turkey. Electronic address: baspinar@iuc.edu.tr., Kahya SE; School of Pharmacy, Department of Pharmacognosy, Istanbul Medipol University, Istanbul 34810, Türkiye., Karadağ AE; School of Pharmacy, Department of Pharmacognosy, Istanbul Medipol University, Istanbul 34810, Türkiye., Ghazy S; Computational Biology and Molecular Simulations Laboratory, Department of Biophysics, School of Medicine, Bahçesehir University, Istanbul 34353, Türkiye; Lab for Innovative Drugs (Lab4IND), Computational Drug Design Center (HİTMER), Bahçesehir University, İstanbul 34353, Türkiye., Durdağı S; Computational Biology and Molecular Simulations Laboratory, Department of Biophysics, School of Medicine, Bahçesehir University, Istanbul 34353, Türkiye; Lab for Innovative Drugs (Lab4IND), Computational Drug Design Center (HİTMER), Bahçesehir University, İstanbul 34353, Türkiye; Systems Biology Lab, Biruni University Scientific Research Center, Biruni University, İstanbul, Turkiye; Molecular Therapy Lab, Department of Pharmaceutical Chemistry, School of Pharmacy, Bahçesehir University, Istanbul 34353, Türkiye. Electronic address: serdar.durdagi@bau.edu.tr. |
| Πηγή: | Bioorganic chemistry [Bioorg Chem] 2026 Aug 05; Vol. 177, pp. 109935. Date of Electronic Publication: 2026 Apr 30. |
| Τύπος έκδοσης: | Journal Article |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Elsevier Country of Publication: United States NLM ID: 1303703 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1090-2120 (Electronic) Linking ISSN: 00452068 NLM ISO Abbreviation: Bioorg Chem Subsets: MEDLINE |
| Imprint Name(s): | Publication: Amsterdam : Elsevier Original Publication: New York, London, Academic Press. |
| Ιατρικοί όροι (MeSH): | Streptococcus mutans*/drug effects , Streptococcus mutans*/enzymology , Hydrazones*/pharmacology , Hydrazones*/chemistry , Hydrazones*/chemical synthesis , Oxadiazoles*/pharmacology , Oxadiazoles*/chemistry , Oxadiazoles*/chemical synthesis , Thiadiazoles*/chemistry , Thiadiazoles*/pharmacology , Thiadiazoles*/chemical synthesis , Anti-Bacterial Agents*/pharmacology , Anti-Bacterial Agents*/chemical synthesis , Anti-Bacterial Agents*/chemistry, Antioxidants/pharmacology ; Antioxidants/chemical synthesis ; Antioxidants/chemistry ; Biphenyl Compounds/antagonists & inhibitors ; Microbial Sensitivity Tests ; Molecular Docking Simulation ; Molecular Structure ; Quantitative Structure-Activity Relationship ; Models, Molecular ; Dose-Response Relationship, Drug ; Structure-Activity Relationship |
| Περίληψη: | Tooth decay is a widespread chronic condition affecting nearly 50% of the global population, with Streptococcus mutans identified as the primary causative agent. The growing challenge of antimicrobial resistance highlights the need for new antibacterial agents. In this study, a series of novel 1,2,3-thiadiazole-based hydrazone (3a-f) and 1,3,4-oxadiazole (4a-f) hybrid compounds were designed, synthesized, and evaluated for their antimicrobial and antioxidant activities. All compounds were structurally characterized by FT-IR, 1H NMR, 13C NMR, and LC-MS analyses. An integrated in silico workflow combining molecular docking and binary QSAR analysis was applied to key S. mutans virulence-associated enzymes-glucosyltransferase B (GtfB), glucosyltransferase C (GtfC), and sortase A (SrtA)-to provide mechanistic insight into antibacterial activity. Docking studies revealed stable binding of the synthesized compounds within the catalytic domains of these targets, with compounds 3d and 4d showing favorable interaction patterns consistent with their strong in vitro antibacterial activity. Binary QSAR predictions further supported the antibacterial potential of the most active derivatives. Biological screening revealed selective antimicrobial activity against S. mutans, particularly for compounds 3d and 4d. Antioxidant activity assessed by DPPH• and ABTS•+ assays showed that compound 4d exhibited moderate ABTS•+ scavenging activity (IC (Copyright © 2026 Elsevier Inc. All rights reserved.) |
| Competing Interests: | Declaration of competing interest There are no conflicts of interest. |
| Contributed Indexing: | Keywords: 1,2,3-Thiadiazole; 1,3,4-Oxadiazole; Hydrazone; Streptococcus mutans |
| Substance Nomenclature: | 0 (Hydrazones) 0 (Oxadiazoles) 0 (Thiadiazoles) 20O2F20OUR (1,3,4-oxadiazole) 0 (Anti-Bacterial Agents) 0 (Antioxidants) 0 (Biphenyl Compounds) |
| Entry Date(s): | Date Created: 20260503 Date Completed: 20260716 Latest Revision: 20260716 |
| Update Code: | 20260716 |
| DOI: | 10.1016/j.bioorg.2026.109935 |
| PMID: | 42070308 |
| Βάση Δεδομένων: | MEDLINE |
| ISSN: | 1090-2120 |
|---|---|
| DOI: | 10.1016/j.bioorg.2026.109935 |