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Published on: June 10, 2022
Exploring the Mechanism of β-Cyclodextrin-Encased Phenolic Acids Functionalized with TPP for Antioxidant Activity and
Christopher Sbarbaro1, Valeria Márquez-Miranda1, Matías Leal2
1Center for Bioinformatics and Integrative Biology, Facultad de Ciencias de la Vida, Universidad Andrés Bello, Santiago 8370035, Chile.
Abstract:
Oxidative stress on the mitochondria in a human cell is attributed to several life-risking conditions, and as such, the importance of molecular structures packed with antioxidant properties and structural characteristics to enter the cell to help prevent such stress has been substantially relevant in recent years. In this study, we investigated the antioxidant properties of triphenylphosphonium (TPP)-conjugated phenolic acids encapsulated in β-cyclodextrin (β-CD). We synthesized TPP conjugates of caffeic, coumaric, and cinnamic acids and formed inclusion complexes with β-CD. Our results showed successful encapsulation of TPP conjugates in β-CD with high efficiency. The TPP conjugates maintained antioxidant activity, with slight reductions observed in β-CD complexes. Furthermore, cell viability studies showed low cytotoxicity of the dds. Computational analyses revealed that TPP conjugation preserved the chemical reactivity of the phenolic acids. Molecular dynamics simulations demonstrated stable inclusion complexes with β-CD and the free energy calculations indicated that TPP conjugation significantly enhanced the ability of caffeic acid to translocate across mitochondrial membranes. These results highlight the potential of TPP-conjugated phenolic acids encapsulated in β-CD as effective antioxidants with improved mitochondrial targeting capabilities.
Insights
Triphenylphosphonium (TPP)-conjugated phenolic acids encapsulated in beta-cyclodextrin (β-CD) show potent antioxidant activity. These compounds effectively target mitochondria, offering a promising strategy against oxidative stress.
Area of Science:
- Biochemistry and Molecular Biology
- Cell Biology
- Materials Science
Background:
- Mitochondrial oxidative stress is linked to severe health conditions.
- Developing cell-penetrant antioxidants with mitochondrial targeting is crucial.
Purpose of the Study:
- To investigate the antioxidant properties of triphenylphosphonium (TPP)-conjugated phenolic acids.
- To evaluate their encapsulation within beta-cyclodextrin (β-CD) and mitochondrial targeting potential.
Main Methods:
- Synthesis of TPP conjugates of caffeic, coumaric, and cinnamic acids.
- Formation of inclusion complexes with β-CD.
- Assessment of antioxidant activity, cytotoxicity, and computational analysis (molecular dynamics, free energy calculations).
Main Results:
- High-efficiency encapsulation of TPP conjugates in β-CD was achieved.
- TPP conjugates retained significant antioxidant activity; β-CD complexes showed slight reductions.
- Low cytotoxicity was observed. TPP conjugation enhanced mitochondrial translocation of caffeic acid.
Conclusions:
- TPP-conjugated phenolic acids are effective antioxidants.
- Encapsulation in β-CD maintains their activity while improving mitochondrial targeting.
- These compounds show promise for combating mitochondrial oxidative stress.
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