Synthesis and Antioxidant Characterization of Trolox Conjugates
Ginsberg, Benjamin
Ginsberg, Benjamin
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Abstract
Mitochondria are an essential organelle that generates reactive oxidative species (ROS) as a side product of metabolism, which causes irreversible damage to its components. Ongoing research investigates the use of mitochondria targeting antioxidants to prevent oxidative damage that leads to organelle dysfunction and associated human diseases. This project looks to investigate the synthesis and viability of new peptide-like molecules that can localize to the mitochondria and provide antioxidant function. Trolox a water-soluble analog of vitamin E, is known to be cell-permeable and possess antioxidant function. Utilizing its carboxylic acid residue to form a peptide bond, Trolox was attached to the N-terminal of an amino acid to share these properties. The amino acids used include histidine (His), and 2-thiohistidine (2TH) which is the amino acid analog of ergothioneine a vitamin like compound found in humans that has antioxidant properties. The antioxidant activity of these molecules was quantified utilizing a radical scavenging assay to represent an aqueous environment, while a lipid peroxidation assay was used to represent a lipophilic environment more representative of the mitochondrial membranes. Results from these experiments showed that Trolox-2TH was significantly better for radical scavenging in aqueous conditions. However, both Trolox-2TH & Trolox-His showed significance as lipid peroxidation inhibitors. This suggests that the 2TH offered significant radical scavenging in comparison to the histidine residue, yet the 2TH does not offer a significant difference in preventing lipid peroxidation. This implies that the peptide bond improves the hydrophobicity of the Trolox compound, so that the vitamin E like residue can offer antioxidant properties in the hydrophobic lipid environment. Since the 2TH compound did not offer a significant increase in inhibition, Trolox is likely the main contributor towards this antioxidant property and could be attached to other peptides to improve their antioxidant abilities.
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Date
1/1/2026
Student Status
Junior (Graduating in 2027)
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Poster
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Biochemistry
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College of Arts and Sciences
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Physical Science