Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation
This study introduces a series of novel Alkyl thio-1,2,4-triazole (4a-p) and mercapto-1,2,4-triazole (3a-d) compounds derived from nalidixic acid. The synthesis was streamlined, involving interactions between nalidixic acid hydrazide and various isothiocyanates to yield cyclic and alkyl(aryl) sulfid...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-04-01
|
| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S240584402404235X |
| _version_ | 1827307925013528576 |
|---|---|
| author | Ibrahim Mhaidat Sojoud Banidomi Fadel Wedian Rahaf Badarneh Hasan Tashtoush Waleed Almomani Ghassab M. Al-Mazaideh Naiyf S. Alharbi Muthu Thiruvengadam |
| author_facet | Ibrahim Mhaidat Sojoud Banidomi Fadel Wedian Rahaf Badarneh Hasan Tashtoush Waleed Almomani Ghassab M. Al-Mazaideh Naiyf S. Alharbi Muthu Thiruvengadam |
| author_sort | Ibrahim Mhaidat |
| collection | DOAJ |
| description | This study introduces a series of novel Alkyl thio-1,2,4-triazole (4a-p) and mercapto-1,2,4-triazole (3a-d) compounds derived from nalidixic acid. The synthesis was streamlined, involving interactions between nalidixic acid hydrazide and various isothiocyanates to yield cyclic and alkyl(aryl) sulfide compounds, characterized using 1H NMR, 13C NMR, IR, and elemental analysis. Antioxidant capabilities were quantified through DPPH and ABTS assays, highlighting significant potential, especially for compound 3d, which demonstrated an ABTS IC50 value of 0.397 μM, on par with ascorbic acid (IC50 = 0.87 μM). Antibacterial efficacy was established through MIC assessments against a broad spectrum of Gram-positive and Gram-negative bacteria, including Candida albicans. Compounds 3b, 4e, 4h, 4j, 4i, 4m, and 4o showed broad-spectrum activity, with 4k and 4m exhibiting pronounced potency against E. coli. Molecular docking studies validated the antibacterial potential, with compounds 4f and 4h showing high binding affinities (docking scores of −9.8 and −9.6 kcal/mol, respectively), indicating robust interactions with the bacterial enzyme targets. These scores underscore the compounds' mechanistic basis for their antibacterial action and support their therapeutic promise. Furthermore, compounds 3b, 4i, and 4m, identified through drug-likeness and toxicity predictions, were highlighted for their favorable profiles, suggesting their suitability for oral antibiotic therapies. This comprehensive study, blending synthetic, in vitro, and in silico approaches, emphasizes the triazole derivatives' potential as future candidates for antibiotic and antioxidant applications, particularly spotlighting compounds 3b, 4i, and 4m due to their promising efficacy and safety profiles. |
| first_indexed | 2024-04-24T18:47:29Z |
| format | Article |
| id | doaj.art-7ffb4f7cbff446cb8b031693e31296ac |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-24T18:47:29Z |
| publishDate | 2024-04-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-7ffb4f7cbff446cb8b031693e31296ac2024-03-27T04:52:30ZengElsevierHeliyon2405-84402024-04-01107e28204Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluationIbrahim Mhaidat0Sojoud Banidomi1Fadel Wedian2Rahaf Badarneh3Hasan Tashtoush4Waleed Almomani5Ghassab M. Al-Mazaideh6Naiyf S. Alharbi7Muthu Thiruvengadam8Department of Chemistry, Faculty of Sciences, Yarmouk University, Irbid, 21163, JordanDepartment of Chemistry, Faculty of Sciences, Yarmouk University, Irbid, 21163, JordanDepartment of Chemistry, Faculty of Sciences, Yarmouk University, Irbid, 21163, JordanDepartment of Chemistry, Faculty of Sciences, Yarmouk University, Irbid, 21163, JordanDepartment of Chemistry, Faculty of Sciences, Yarmouk University, Irbid, 21163, JordanDepartment of Basic Medical Sciences, Faculty of Medicine, Yarmouk University, Irbid, 21163, JordanDepartment of Chemistry and Chemical Technology, Tafila Technical University, Tafila, Jordan; Corresponding author.Department of Botany and Microbiology, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi ArabiaDepartment of Crop Science, College of Sanghuh Life Sciences, Konkuk University, Seoul, 05029, South KoreaThis study introduces a series of novel Alkyl thio-1,2,4-triazole (4a-p) and mercapto-1,2,4-triazole (3a-d) compounds derived from nalidixic acid. The synthesis was streamlined, involving interactions between nalidixic acid hydrazide and various isothiocyanates to yield cyclic and alkyl(aryl) sulfide compounds, characterized using 1H NMR, 13C NMR, IR, and elemental analysis. Antioxidant capabilities were quantified through DPPH and ABTS assays, highlighting significant potential, especially for compound 3d, which demonstrated an ABTS IC50 value of 0.397 μM, on par with ascorbic acid (IC50 = 0.87 μM). Antibacterial efficacy was established through MIC assessments against a broad spectrum of Gram-positive and Gram-negative bacteria, including Candida albicans. Compounds 3b, 4e, 4h, 4j, 4i, 4m, and 4o showed broad-spectrum activity, with 4k and 4m exhibiting pronounced potency against E. coli. Molecular docking studies validated the antibacterial potential, with compounds 4f and 4h showing high binding affinities (docking scores of −9.8 and −9.6 kcal/mol, respectively), indicating robust interactions with the bacterial enzyme targets. These scores underscore the compounds' mechanistic basis for their antibacterial action and support their therapeutic promise. Furthermore, compounds 3b, 4i, and 4m, identified through drug-likeness and toxicity predictions, were highlighted for their favorable profiles, suggesting their suitability for oral antibiotic therapies. This comprehensive study, blending synthetic, in vitro, and in silico approaches, emphasizes the triazole derivatives' potential as future candidates for antibiotic and antioxidant applications, particularly spotlighting compounds 3b, 4i, and 4m due to their promising efficacy and safety profiles.http://www.sciencedirect.com/science/article/pii/S240584402404235XAntioxidantAntimicrobialIsothiocyanateAlkyl halideNalidixic acidIn silico |
| spellingShingle | Ibrahim Mhaidat Sojoud Banidomi Fadel Wedian Rahaf Badarneh Hasan Tashtoush Waleed Almomani Ghassab M. Al-Mazaideh Naiyf S. Alharbi Muthu Thiruvengadam Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation Heliyon Antioxidant Antimicrobial Isothiocyanate Alkyl halide Nalidixic acid In silico |
| title | Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation |
| title_full | Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation |
| title_fullStr | Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation |
| title_full_unstemmed | Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation |
| title_short | Antioxidant and antibacterial activities of 5-mercapto(substitutedthio)-4-substituted-1,2,4-triazol based on nalidixic acid: A comprehensive study on its synthesis, characterization, and In silico evaluation |
| title_sort | antioxidant and antibacterial activities of 5 mercapto substitutedthio 4 substituted 1 2 4 triazol based on nalidixic acid a comprehensive study on its synthesis characterization and in silico evaluation |
| topic | Antioxidant Antimicrobial Isothiocyanate Alkyl halide Nalidixic acid In silico |
| url | http://www.sciencedirect.com/science/article/pii/S240584402404235X |
| work_keys_str_mv | AT ibrahimmhaidat antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT sojoudbanidomi antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT fadelwedian antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT rahafbadarneh antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT hasantashtoush antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT waleedalmomani antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT ghassabmalmazaideh antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT naiyfsalharbi antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation AT muthuthiruvengadam antioxidantandantibacterialactivitiesof5mercaptosubstitutedthio4substituted124triazolbasedonnalidixicacidacomprehensivestudyonitssynthesischaracterizationandinsilicoevaluation |