Academic Journal
Προβολή σε EDS

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.

Λεπτομέρειες βιβλιογραφικής εγγραφής
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 (IC50 = 24.21 ± 0.11 μg/mL). Overall, these findings indicate that thiadiazole-based hydrazone and 1,3,4-oxadiazole frameworks represent promising scaffolds for the development of multifunctional antibiofilm agents targeting oral pathogens.
(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
FullText Text:
  Availability: 0
CustomLinks:
  – Url: https://www.doi.org/10.1016/j.bioorg.2026.109935?
    Name: ScienceDirect (all content) (s7799221)
    Category: fullText
    Text: View record from ScienceDirect
    MouseOverText: View record from ScienceDirect
  – Url: https://resolver.ebsco.com/c/fiv2js/result?sid=EBSCO:cmedm&genre=article&issn=10902120&ISBN=&volume=177&issue=&date=20260805&spage=109935&pages=109935&title=Bioorganic chemistry&atitle=Novel%201%2C2%2C3-Thiadiazole-based%20Hydrazone%20and%201%2C3%2C4-Oxadiazole%20hybrids%20as%20promising%20agents%20against%20Streptococcus%20mutans%3A%20Synthesis%2C%20biological%20evaluation%2C%20and%20molecular%20modeling%20studies.&aulast=Kurtulu%C5%9F%20%C4%B0G&id=DOI:10.1016/j.bioorg.2026.109935
    Name: Full Text Finder (for New FTF UI) (ns324271)
    Category: fullText
    Text: Full Text Finder
    MouseOverText: Full Text Finder
Header DbId: cmedm
DbLabel: MEDLINE
An: 42070308
AccessLevel: 3
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: 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.
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AU" term="%22Kurtuluş+İG%22">Kurtuluş İG</searchLink>; Faculty of Engineering, Department of Chemistry, Organic Chemistry Division, Istanbul University-Cerrahpasa, Istanbul 34320, Turkey.<br /><searchLink fieldCode="AU" term="%22Başpınar+Küçük+H%22">Başpınar Küçük H</searchLink>; Faculty of Engineering, Department of Chemistry, Organic Chemistry Division, Istanbul University-Cerrahpasa, Istanbul 34320, Turkey. Electronic address: baspinar@iuc.edu.tr.<br /><searchLink fieldCode="AU" term="%22Kahya+SE%22">Kahya SE</searchLink>; School of Pharmacy, Department of Pharmacognosy, Istanbul Medipol University, Istanbul 34810, Türkiye.<br /><searchLink fieldCode="AU" term="%22Karadağ+AE%22">Karadağ AE</searchLink>; School of Pharmacy, Department of Pharmacognosy, Istanbul Medipol University, Istanbul 34810, Türkiye.<br /><searchLink fieldCode="AU" term="%22Ghazy+S%22">Ghazy S</searchLink>; 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.<br /><searchLink fieldCode="AU" term="%22Durdağı+S%22">Durdağı S</searchLink>; 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.
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="JN" term="%221303703%22">Bioorganic chemistry</searchLink> [Bioorg Chem] 2026 Aug 05; Vol. 177, pp. 109935. <i>Date of Electronic Publication: </i>2026 Apr 30.
– Name: TypePub
  Label: Publication Type
  Group: TypPub
  Data: Journal Article
– Name: Language
  Label: Language
  Group: Lang
  Data: English
– Name: TitleSource
  Label: Journal Info
  Group: Src
  Data: <i>Publisher: </i><searchLink fieldCode="PB" term="%22Elsevier%22">Elsevier </searchLink><i>Country of Publication: </i>United States <i>NLM ID: </i>1303703 <i>Publication Model: </i>Print-Electronic <i>Cited Medium: </i>Internet <i>ISSN: </i>1090-2120 (Electronic) <i>Linking ISSN: </i><searchLink fieldCode="IS" term="%2200452068%22">00452068 </searchLink><i>NLM ISO Abbreviation: </i>Bioorg Chem <i>Subsets: </i>MEDLINE
– Name: PublisherInfo
  Label: Imprint Name(s)
  Group: PubInfo
  Data: <i>Publication</i>: Amsterdam : Elsevier<br /><i>Original Publication</i>: New York, London, Academic Press.
– Name: SubjectMESH
  Label: MeSH Terms
  Group: Su
  Data: <searchLink fieldCode="MM" term="%22Streptococcus+mutans%22">Streptococcus mutans*</searchLink>/<searchLink fieldCode="MM" term="%22Streptococcus+mutans+drug+effects%22">drug effects</searchLink> <br /><searchLink fieldCode="MM" term="%22Streptococcus+mutans%22">Streptococcus mutans*</searchLink>/<searchLink fieldCode="MM" term="%22Streptococcus+mutans+enzymology%22">enzymology</searchLink> <br /><searchLink fieldCode="MM" term="%22Hydrazones%22">Hydrazones*</searchLink>/<searchLink fieldCode="MM" term="%22Hydrazones+pharmacology%22">pharmacology</searchLink> <br /><searchLink fieldCode="MM" term="%22Hydrazones%22">Hydrazones*</searchLink>/<searchLink fieldCode="MM" term="%22Hydrazones+chemistry%22">chemistry</searchLink> <br /><searchLink fieldCode="MM" term="%22Hydrazones%22">Hydrazones*</searchLink>/<searchLink fieldCode="MM" term="%22Hydrazones+chemical+synthesis%22">chemical synthesis</searchLink> <br /><searchLink fieldCode="MM" term="%22Oxadiazoles%22">Oxadiazoles*</searchLink>/<searchLink fieldCode="MM" term="%22Oxadiazoles+pharmacology%22">pharmacology</searchLink> <br /><searchLink fieldCode="MM" term="%22Oxadiazoles%22">Oxadiazoles*</searchLink>/<searchLink fieldCode="MM" term="%22Oxadiazoles+chemistry%22">chemistry</searchLink> <br /><searchLink fieldCode="MM" term="%22Oxadiazoles%22">Oxadiazoles*</searchLink>/<searchLink fieldCode="MM" term="%22Oxadiazoles+chemical+synthesis%22">chemical synthesis</searchLink> <br /><searchLink fieldCode="MM" term="%22Thiadiazoles%22">Thiadiazoles*</searchLink>/<searchLink fieldCode="MM" term="%22Thiadiazoles+chemistry%22">chemistry</searchLink> <br /><searchLink fieldCode="MM" term="%22Thiadiazoles%22">Thiadiazoles*</searchLink>/<searchLink fieldCode="MM" term="%22Thiadiazoles+pharmacology%22">pharmacology</searchLink> <br /><searchLink fieldCode="MM" term="%22Thiadiazoles%22">Thiadiazoles*</searchLink>/<searchLink fieldCode="MM" term="%22Thiadiazoles+chemical+synthesis%22">chemical synthesis</searchLink> <br /><searchLink fieldCode="MM" term="%22Anti-Bacterial+Agents%22">Anti-Bacterial Agents*</searchLink>/<searchLink fieldCode="MM" term="%22Anti-Bacterial+Agents+pharmacology%22">pharmacology</searchLink> <br /><searchLink fieldCode="MM" term="%22Anti-Bacterial+Agents%22">Anti-Bacterial Agents*</searchLink>/<searchLink fieldCode="MM" term="%22Anti-Bacterial+Agents+chemical+synthesis%22">chemical synthesis</searchLink> <br /><searchLink fieldCode="MM" term="%22Anti-Bacterial+Agents%22">Anti-Bacterial Agents*</searchLink>/<searchLink fieldCode="MM" term="%22Anti-Bacterial+Agents+chemistry%22">chemistry</searchLink><br /><searchLink fieldCode="MH" term="%22Antioxidants%22">Antioxidants</searchLink>/<searchLink fieldCode="MH" term="%22Antioxidants+pharmacology%22">pharmacology</searchLink> ; <searchLink fieldCode="MH" term="%22Antioxidants%22">Antioxidants</searchLink>/<searchLink fieldCode="MH" term="%22Antioxidants+chemical+synthesis%22">chemical synthesis</searchLink> ; <searchLink fieldCode="MH" term="%22Antioxidants%22">Antioxidants</searchLink>/<searchLink fieldCode="MH" term="%22Antioxidants+chemistry%22">chemistry</searchLink> ; <searchLink fieldCode="MH" term="%22Biphenyl+Compounds%22">Biphenyl Compounds</searchLink>/<searchLink fieldCode="MH" term="%22Biphenyl+Compounds+antagonists+%26+inhibitors%22">antagonists & inhibitors</searchLink> ; <searchLink fieldCode="MH" term="%22Microbial+Sensitivity+Tests%22">Microbial Sensitivity Tests</searchLink> ; <searchLink fieldCode="MH" term="%22Molecular+Docking+Simulation%22">Molecular Docking Simulation</searchLink> ; <searchLink fieldCode="MH" term="%22Molecular+Structure%22">Molecular Structure</searchLink> ; <searchLink fieldCode="MH" term="%22Quantitative+Structure-Activity+Relationship%22">Quantitative Structure-Activity Relationship</searchLink> ; <searchLink fieldCode="MH" term="%22Models%2C+Molecular%22">Models, Molecular</searchLink> ; <searchLink fieldCode="MH" term="%22Dose-Response+Relationship%2C+Drug%22">Dose-Response Relationship, Drug</searchLink> ; <searchLink fieldCode="MH" term="%22Structure-Activity+Relationship%22">Structure-Activity Relationship</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: 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, <superscript>1</superscript>H NMR, <superscript>13</superscript>C 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•<superscript>+</superscript> assays showed that compound 4d exhibited moderate ABTS•<superscript>+</superscript> scavenging activity (IC<subscript>50</subscript> = 24.21 ± 0.11 μg/mL). Overall, these findings indicate that thiadiazole-based hydrazone and 1,3,4-oxadiazole frameworks represent promising scaffolds for the development of multifunctional antibiofilm agents targeting oral pathogens.<br /> (Copyright © 2026 Elsevier Inc. All rights reserved.)
– Name: Abstract
  Label: Competing Interests
  Group: Ab
  Data: Declaration of competing interest There are no conflicts of interest.
– Name: SubjectMinor
  Label: Contributed Indexing
  Group:
  Data: <i>Keywords: </i>1,2,3-Thiadiazole; 1,3,4-Oxadiazole; Hydrazone; Streptococcus mutans
– Name: NumberCAS
  Label: Substance Nomenclature
  Group: ID
  Data: 0 (Hydrazones)<br />0 (Oxadiazoles)<br />0 (Thiadiazoles)<br />20O2F20OUR (1,3,4-oxadiazole)<br />0 (Anti-Bacterial Agents)<br />0 (Antioxidants)<br />0 (Biphenyl Compounds)
– Name: DateEntry
  Label: Entry Date(s)
  Group: Date
  Data: <i>Date Created: </i>20260503 <i>Date Completed: </i>20260716 <i>Latest Revision: </i>20260716
– Name: DateUpdate
  Label: Update Code
  Group: Date
  Data: 20260716
– Name: DOI
  Label: DOI
  Group: ID
  Data: 10.1016/j.bioorg.2026.109935
– Name: AN
  Label: PMID
  Group: ID
  Data: 42070308
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=cmedm&AN=42070308
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1016/j.bioorg.2026.109935
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        StartPage: 109935
    Subjects:
      – SubjectFull: Antioxidants pharmacology
        Type: general
      – SubjectFull: Antioxidants chemical synthesis
        Type: general
      – SubjectFull: Antioxidants chemistry
        Type: general
      – SubjectFull: Biphenyl Compounds antagonists & inhibitors
        Type: general
      – SubjectFull: Microbial Sensitivity Tests
        Type: general
      – SubjectFull: Molecular Docking Simulation
        Type: general
      – SubjectFull: Molecular Structure
        Type: general
      – SubjectFull: Quantitative Structure-Activity Relationship
        Type: general
      – SubjectFull: Models, Molecular
        Type: general
      – SubjectFull: Dose-Response Relationship, Drug
        Type: general
      – SubjectFull: Structure-Activity Relationship
        Type: general
      – SubjectFull: Streptococcus mutans drug effects
        Type: general
      – SubjectFull: Streptococcus mutans enzymology
        Type: general
      – SubjectFull: Hydrazones pharmacology
        Type: general
      – SubjectFull: Hydrazones chemistry
        Type: general
      – SubjectFull: Hydrazones chemical synthesis
        Type: general
      – SubjectFull: Oxadiazoles pharmacology
        Type: general
      – SubjectFull: Oxadiazoles chemistry
        Type: general
      – SubjectFull: Oxadiazoles chemical synthesis
        Type: general
      – SubjectFull: Thiadiazoles chemistry
        Type: general
      – SubjectFull: Thiadiazoles pharmacology
        Type: general
      – SubjectFull: Thiadiazoles chemical synthesis
        Type: general
      – SubjectFull: Anti-Bacterial Agents pharmacology
        Type: general
      – SubjectFull: Anti-Bacterial Agents chemical synthesis
        Type: general
      – SubjectFull: Anti-Bacterial Agents chemistry
        Type: general
    Titles:
      – TitleFull: 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.
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Kurtuluş İG
      – PersonEntity:
          Name:
            NameFull: Başpınar Küçük H
      – PersonEntity:
          Name:
            NameFull: Kahya SE
      – PersonEntity:
          Name:
            NameFull: Karadağ AE
      – PersonEntity:
          Name:
            NameFull: Ghazy S
      – PersonEntity:
          Name:
            NameFull: Durdağı S
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 05
              M: 08
              Text: 2026 Aug 05
              Type: published
              Y: 2026
          Identifiers:
            – Type: issn-electronic
              Value: 1090-2120
          Numbering:
            – Type: volume
              Value: 177
          Titles:
            – TitleFull: Bioorganic chemistry
              Type: main
ResultId 1