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Volume 15
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Article

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

by
Lala Stepanyan
1,†,
Tatevik Sargsyan
1,2,†,
Valentina Mittova
3,
Zurab R. Tsetskhladze
3,
Nino Motsonelidze
3,
Ekaterine Gorgoshidze
3,
Niccolò Nova
4,
Monika Israyelyan
1,
Hayarpi Simonyan
2,
Franco Bisceglie
4,
Lusine Sahakyan
1,2,
Karapet Ghazaryan
2 and
Giovanni N. Roviello
5,*
1
Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia
2
Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia
3
Faculty of Medicine, University Geomedi, 4 King Solomon II Str., 0114 Tbilisi, Georgia
4
Department of Chemical Science, Life and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy
5
Institute of Biostructures and Bioimaging (IBB), Italian National Council for Research (CNR), Area di Ricerca Site and Headquarters, Via Pietro Castellino 111, 80131 Naples, Italy
*
Author to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Biomolecules 2025, 15(7), 933; https://doi.org/10.3390/biom15070933
Submission received: 30 April 2025 / Revised: 13 June 2025 / Accepted: 22 June 2025 / Published: 26 June 2025
(This article belongs to the Special Issue State of the Art and Perspectives in Antimicrobial Peptides)
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Abstract

We report on the synthesis and characterization of a novel fluorenyl-methoxycarbonyl (Fmoc)-containing thioxo-triazole-bearing dipeptide 5, 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 Peonia 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.
Keywords: fluorenyl-methoxycarbonyl; fmoc; thioxo-triazole; antioxidant properties; antimicrobial activity; bovine serum albumin; BSA; DNA modulation; bioactive peptides; Caucasus-endemic plants fluorenyl-methoxycarbonyl; fmoc; thioxo-triazole; antioxidant properties; antimicrobial activity; bovine serum albumin; BSA; DNA modulation; bioactive peptides; Caucasus-endemic plants

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MDPI and ACS Style

Stepanyan, L.; Sargsyan, T.; Mittova, V.; Tsetskhladze, Z.R.; Motsonelidze, N.; Gorgoshidze, E.; Nova, N.; Israyelyan, M.; Simonyan, H.; Bisceglie, F.; et al. 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 2025, 15, 933. https://doi.org/10.3390/biom15070933

AMA Style

Stepanyan L, Sargsyan T, Mittova V, Tsetskhladze ZR, Motsonelidze N, Gorgoshidze E, Nova N, Israyelyan M, Simonyan H, Bisceglie F, et al. 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. 2025; 15(7):933. https://doi.org/10.3390/biom15070933

Chicago/Turabian Style

Stepanyan, Lala, Tatevik Sargsyan, Valentina Mittova, Zurab R. Tsetskhladze, Nino Motsonelidze, Ekaterine Gorgoshidze, Niccolò Nova, Monika Israyelyan, Hayarpi Simonyan, Franco Bisceglie, and et al. 2025. "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 15, no. 7: 933. https://doi.org/10.3390/biom15070933

APA Style

Stepanyan, L., Sargsyan, T., Mittova, V., Tsetskhladze, Z. R., Motsonelidze, N., Gorgoshidze, E., Nova, N., Israyelyan, M., Simonyan, H., Bisceglie, F., Sahakyan, L., Ghazaryan, K., & Roviello, G. N. (2025). 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, 15(7), 933. https://doi.org/10.3390/biom15070933

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