The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport
We report on the synthesis and characterization of a novel fluorenyl-methoxycarbonyl (Fmoc)-containing thioxo-triazole-bearing dipeptide <b>5</b>, evaluated for potential therapeutic applications. The compound was tested for its antioxidant and antimicrobial properties, demonstrating sig...
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2025-06-01
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| author | Lala Stepanyan Tatevik Sargsyan Valentina Mittova Zurab R. Tsetskhladze Nino Motsonelidze Ekaterine Gorgoshidze Niccolò Nova Monika Israyelyan Hayarpi Simonyan Franco Bisceglie Lusine Sahakyan Karapet Ghazaryan Giovanni N. Roviello |
| author_facet | Lala Stepanyan Tatevik Sargsyan Valentina Mittova Zurab R. Tsetskhladze Nino Motsonelidze Ekaterine Gorgoshidze Niccolò Nova Monika Israyelyan Hayarpi Simonyan Franco Bisceglie Lusine Sahakyan Karapet Ghazaryan Giovanni N. Roviello |
| author_sort | Lala Stepanyan |
| collection | DOAJ |
| description | We report on the synthesis and characterization of a novel fluorenyl-methoxycarbonyl (Fmoc)-containing thioxo-triazole-bearing dipeptide <b>5</b>, evaluated for potential therapeutic applications. The compound was tested for its antioxidant and antimicrobial properties, demonstrating significant effects in scavenging reactive oxygen species (ROS) and inhibiting microbial growth, particularly when combined with plant extracts from an endemic <i>Peonia</i> species from the Caucasus. Circular dichroism (CD) binding studies with bovine serum albumin (BSA) and calf thymus DNA revealed important interactions, suggesting the dipeptide’s potential in biomedically relevant conditions that involve DNA modulation. Molecular docking and CD spectra deconvolution provided additional insights into the binding mechanisms and structural characteristics of the formed complexes with the biomolecular targets. The Fmoc group enhances the dipeptide’s lipophilicity, which may facilitate its interaction with cellular membranes, supporting efficient drug delivery. A computational evaluation at the ωB97XD/aug-cc-pVDZ level of theory was carried out, confirming the experimental results and revealing a powerful potential of the peptide as an antioxidant, through FMOs, MEP analysis, and antioxidant mechanism assessments. Together, these findings suggest that this dipeptide could be valuable as an antimicrobial and antioxidant agent, with potential applications in pathologies involving oxidative stress, DNA modulation, and microbial infections. |
| format | Article |
| id | doaj-art-363b8ab7828d4fc19ca3cf1f9ebc21da |
| institution | DOAJ |
| issn | 2218-273X |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj-art-363b8ab7828d4fc19ca3cf1f9ebc21da2025-08-20T02:45:45ZengMDPI AGBiomolecules2218-273X2025-06-0115793310.3390/biom15070933The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug TransportLala Stepanyan0Tatevik Sargsyan1Valentina Mittova2Zurab R. Tsetskhladze3Nino Motsonelidze4Ekaterine Gorgoshidze5Niccolò Nova6Monika Israyelyan7Hayarpi Simonyan8Franco Bisceglie9Lusine Sahakyan10Karapet Ghazaryan11Giovanni N. Roviello12Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan Str., Yerevan 0056, ArmeniaScientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan Str., Yerevan 0056, ArmeniaFaculty of Medicine, University Geomedi, 4 King Solomon II Str., 0114 Tbilisi, GeorgiaFaculty of Medicine, University Geomedi, 4 King Solomon II Str., 0114 Tbilisi, GeorgiaFaculty of Medicine, University Geomedi, 4 King Solomon II Str., 0114 Tbilisi, GeorgiaFaculty of Medicine, University Geomedi, 4 King Solomon II Str., 0114 Tbilisi, GeorgiaDepartment of Chemical Science, Life and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyScientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan Str., Yerevan 0056, ArmeniaInstitute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, ArmeniaDepartment of Chemical Science, Life and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyScientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan Str., Yerevan 0056, ArmeniaInstitute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, ArmeniaInstitute of Biostructures and Bioimaging (IBB), Italian National Council for Research (CNR), Area di Ricerca Site and Headquarters, Via Pietro Castellino 111, 80131 Naples, ItalyWe report on the synthesis and characterization of a novel fluorenyl-methoxycarbonyl (Fmoc)-containing thioxo-triazole-bearing dipeptide <b>5</b>, evaluated for potential therapeutic applications. The compound was tested for its antioxidant and antimicrobial properties, demonstrating significant effects in scavenging reactive oxygen species (ROS) and inhibiting microbial growth, particularly when combined with plant extracts from an endemic <i>Peonia</i> species from the Caucasus. Circular dichroism (CD) binding studies with bovine serum albumin (BSA) and calf thymus DNA revealed important interactions, suggesting the dipeptide’s potential in biomedically relevant conditions that involve DNA modulation. Molecular docking and CD spectra deconvolution provided additional insights into the binding mechanisms and structural characteristics of the formed complexes with the biomolecular targets. The Fmoc group enhances the dipeptide’s lipophilicity, which may facilitate its interaction with cellular membranes, supporting efficient drug delivery. A computational evaluation at the ωB97XD/aug-cc-pVDZ level of theory was carried out, confirming the experimental results and revealing a powerful potential of the peptide as an antioxidant, through FMOs, MEP analysis, and antioxidant mechanism assessments. Together, these findings suggest that this dipeptide could be valuable as an antimicrobial and antioxidant agent, with potential applications in pathologies involving oxidative stress, DNA modulation, and microbial infections.https://www.mdpi.com/2218-273X/15/7/933fluorenyl-methoxycarbonylfmocthioxo-triazoleantioxidant propertiesantimicrobial activitybovine serum albumin |
| spellingShingle | Lala Stepanyan Tatevik Sargsyan Valentina Mittova Zurab R. Tsetskhladze Nino Motsonelidze Ekaterine Gorgoshidze Niccolò Nova Monika Israyelyan Hayarpi Simonyan Franco Bisceglie Lusine Sahakyan Karapet Ghazaryan Giovanni N. Roviello The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport Biomolecules fluorenyl-methoxycarbonyl fmoc thioxo-triazole antioxidant properties antimicrobial activity bovine serum albumin |
| title | The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport |
| title_full | The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport |
| title_fullStr | The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport |
| title_full_unstemmed | The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport |
| title_short | The Synthesis, Characterization, and Biological Evaluation of a Fluorenyl-Methoxycarbonyl-Containing Thioxo-Triazole-Bearing Dipeptide: Antioxidant, Antimicrobial, and BSA/DNA Binding Studies for Potential Therapeutic Applications in ROS Scavenging and Drug Transport |
| title_sort | synthesis characterization and biological evaluation of a fluorenyl methoxycarbonyl containing thioxo triazole bearing dipeptide antioxidant antimicrobial and bsa dna binding studies for potential therapeutic applications in ros scavenging and drug transport |
| topic | fluorenyl-methoxycarbonyl fmoc thioxo-triazole antioxidant properties antimicrobial activity bovine serum albumin |
| url | https://www.mdpi.com/2218-273X/15/7/933 |
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