Novel indole derivatives containing a thiosemicarbazide moiety as potential antioxidant agents for fresh beef preservation
- 1Department of Light Industry and Chemical Engineering, Guizhou Light Industry Polytechnic University, Guiyang, China
Abstract
Oxidative stress is implicated in numerous pathological processes. Developing efficient, safe small-molecule antioxidants is of great medicinal interest. In this work, ten new indole derivatives bearing a thiosemicarbazide moiety (4a–4j) were synthesized and fully characterized by 1H NMR, 13C NMR, and HRMS. In vitro antioxidant assays indicated that all target compounds showed obvious free radical scavenging potency. Among them, compound 2-(3-(1H-indol-3-yl)propanoyl)-N-(4-chlorophenyl)hydrazine-1-carbothioamide (4i) displayed the strongest in vitro ABTS radical scavenging activity with an IC50 = 0.96 μg/mL, remarkably lower than that of vitamin C (1.87 μg/mL). Compound 4i also exhibited excellent in vitro DPPH scavenging efficiency (IC50 = 2.95 μg/mL). Molecular docking and 100 ns molecular dynamics simulations predicted that compound 4i stably bound to the catalytic pocket of human peroxiredoxin 5 (PDB ID: 1HD2). Meanwhile, in silico ADMET and drug-likeness predictions suggested favorable physicochemical properties, acceptable safety, and compliance with Lipinski’s rule of five. Furthermore, application in a raw beef patty model revealed that compound 4i effectively retarded myoglobin oxidation, suppressed pH elevation, and preserved red-color stability during refrigerated storage, exhibiting superior color-protection performance. Collectively, these findings highlight compound 4i as a promising dual-purpose candidate, deserving further investigation both as an antioxidant lead for drug discovery and as a potential protective agent for raw meat preservation, with additional enzyme-level and food-safety assessments required.
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BibTeX
@article{wang2026novel,
title = {{Novel indole derivatives containing a thiosemicarbazide moiety as potential antioxidant agents for fresh beef preservation}},
author = {Tao Wang and Lingling Xiao and Yanling Ren and Maozhao Wu and Yongfei Liu and Jian Tang and Shoumei Wan and Jing Peng},
journal = {Frontiers in Chemistry},
year = {2026},
month = oct,
doi = {10.3389/fchem.2026.1994186},
url = {https://doi.org/10.3389/fchem.2026.1994186},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Novel indole derivatives containing a thiosemicarbazide moiety as potential antioxidant agents for fresh beef preservation
AU - Tao Wang
AU - Lingling Xiao
AU - Yanling Ren
AU - Maozhao Wu
AU - Yongfei Liu
AU - Jian Tang
AU - Shoumei Wan
AU - Jing Peng
PY - 2026
DA - 2026/10/12
JO - Frontiers in Chemistry
DO - 10.3389/fchem.2026.1994186
UR - https://doi.org/10.3389/fchem.2026.1994186
AB - Oxidative stress is implicated in numerous pathological processes. Developing efficient, safe small-molecule antioxidants is of great medicinal interest. In this work, ten new indole derivatives bearing a thiosemicarbazide moiety (4a–4j) were synthesized and fully characterized by 1H NMR, 13C NMR, and HRMS. In vitro antioxidant assays indicated that all target compounds showed obvious free radical scavenging potency. Among them, compound 2-(3-(1H-indol-3-yl)propanoyl)-N-(4-chlorophenyl)hydrazine-1-carbothioamide (4i) displayed the strongest in vitro ABTS radical scavenging activity with an IC50 = 0.96 μg/mL, remarkably lower than that of vitamin C (1.87 μg/mL). Compound 4i also exhibited excellent in vitro DPPH scavenging efficiency (IC50 = 2.95 μg/mL). Molecular docking and 100 ns molecular dynamics simulations predicted that compound 4i stably bound to the catalytic pocket of human peroxiredoxin 5 (PDB ID: 1HD2). Meanwhile, in silico ADMET and drug-likeness predictions suggested favorable physicochemical properties, acceptable safety, and compliance with Lipinski’s rule of five. Furthermore, application in a raw beef patty model revealed that compound 4i effectively retarded myoglobin oxidation, suppressed pH elevation, and preserved red-color stability during refrigerated storage, exhibiting superior color-protection performance. Collectively, these findings highlight compound 4i as a promising dual-purpose candidate, deserving further investigation both as an antioxidant lead for drug discovery and as a potential protective agent for raw meat preservation, with additional enzyme-level and food-safety assessments required.
SN - 2296-2646
ER -