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
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(93 views) Stepanyan L, Sargsyan T, Mittova V, Tsetskhladze ZR, Motsonelidze N, Gorgoshidze E, Nova N, Israyelyan M, Simonyan H, Bisceglie F, Sahakyan L, Ghazaryan K, Roviello GN
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;tatev-sargsyan@ysu.am (T.S.); lusine_sahakyan@ysu.am (L.S.)2Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia3 Faculty of Medicine, University Geomedi, 4 King Solomon II Str., 0114 Tbilisi, Georgia;valentina.mittova@geomedi.edu.ge (V.M.); zurab.tsetskhladze@geomedi.edu.ge (Z.R.T.);ekaterine.gorgoshidze@geomedi.edu.ge (E.G.)4 Department of Chemical Science, Life and Environmental Sustainability, University of Parma, Parco Areadelle Scienze 17/A, 43124 Parma, Italy; niccolo.nova@studenti.unipr.it (N.N.)5Institute of Biostructures and Bioimaging (IBB), Italian National Council for Research (CNR), Area di RicercaSite and Headquarters, Via Pietro Castellino 111, 80131 Naples, Italy* Correspondence: giovanni.roviello@cnr.it† These authors contributed equally to this work.
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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 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.
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
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