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Reaction of 5-Aminosalicylic Acid with Peroxyl Radicals: Protection and Recovery by Ascorbic Acid and Amino Acids

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Purpose

The aims of the study are to analyze the interaction between 5-aminosalicylic acid (5-ASA) and peroxyl radicals and to evaluate the effect of some endogenous compounds such as ascorbic acid and amino acids on the oxidation of 5-ASA induced by 2,2′-azo-bis(2-amidinopropane) dihydrochloride.

Methods

The consumption and/or the recovery of 5-ASA (7.6 μM) exposed to a peroxyl radical source [2,2′-azo-bis(2-amidinopropane)] was followed by techniques such as spectrofluorescence, high-performance liquid chromatography, and differential pulse voltammetry.

Results

5-Aminosalicylic acid was found to readily react with peroxyl radicals at micromolar concentrations and to protect c-Phycocyanin in a very similar fashion to that shown by Trolox. Exposure of 5-ASA to peroxyl radicals led to its oxidation into the corresponding quinone-imine. Disappearance of 5-ASA was prevented by tryptophan, cysteine, glutathione, and ascorbic acid. Furthermore, some of these compounds induced the partial (cysteine and glutathione) or total (ascorbic acid) recovery of 5-ASA when added after its almost total consumption.

Conclusions

5-Aminosalicylic acid is a very efficient peroxyl radical scavenger. The 5-ASA oxidation by peroxyl radicals was prevented by ascorbic acid, cysteine, and glutathione. In addition, 5-ASA can be regenerated by these endogenous compounds, which would be a valuable mechanism to preserve 5-ASA in tissues undergoing oxidative stress conditions.

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Acknowledgment

This work was partially supported by grants FONDECYT (3040002 and 1040736).

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Authors and Affiliations

  1. Instituto de Nutricíon y Tecnología de los Alimentos (INTA), Universidad de Chile, El Líbano 5524, Macul, Santiago, Chile

    Camilo López-Alarcón, Claudia Rocco, Eduardo Lissi, Catalina Carrasco, J. Arturo Squella, Luis Nuñez-Vergara & Hernan Speisky

Authors
  1. Camilo López-Alarcón
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  2. Claudia Rocco
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  3. Eduardo Lissi
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  4. Catalina Carrasco
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  5. J. Arturo Squella
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  6. Luis Nuñez-Vergara
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  7. Hernan Speisky
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Correspondence to Hernan Speisky.

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López-Alarcón, C., Rocco, C., Lissi, E. et al. Reaction of 5-Aminosalicylic Acid with Peroxyl Radicals: Protection and Recovery by Ascorbic Acid and Amino Acids. Pharm Res 22, 1642–1648 (2005). https://doi.org/10.1007/s11095-005-6948-y

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  • DOI: https://doi.org/10.1007/s11095-005-6948-y

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