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Antioxidant properties of diorganoyl diselenides and ditellurides: modulation by organic aryl or naphthyl moiety

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Abstract

Diorganoyl dichalcogenide compouds can have antioxidant activity in different in vitro and in vivo models. Here, we have compared the potential antioxidant activity of 1-dinaphthyl diselenide (1-NapSe)2, 2-dinaphthyl diselenide (2-NapSe)2, 1-dinaphthyl distelluride (1-NapTe)2, 2-dinaphthyl ditelluride (2-NapTe)2 with their well-studied analogs diphenyl diselenide ((PhSe)2) and diphenyl telluride ((PhTe)2). (PhSe)2, (PhTe)2, and naphthalene analogs-inhibited Fe(II)-induced lipid peroxidation, catalytically decomposed hydrogen peroxide and oxidized thiols, such as dithiothreitol (DTT), Cysteine (CYS), dimercaptopropionic acid (DMPS), and thiophenol (PhSH). (PhSe)2 was the less potent of the tested compounds against Fe(II)-induced lipid peroxidation in brain homogenates and the change in the organic moiety from an aryl to naphthyl group increased considerably the antioxidant potency of diselenide compounds. However, the change from aryl to naphthyl had little effect on the thio-peroxidase-like activity of diorganoyl dichalcogenides. These results suggest that minor changes in the organic moiety of aromatic diselenide compounds can modify profoundly their capacity to inhibit iron-induced lipid peroxidation. The pharmacological properties of organochalcogens are thought to be linked to their capacity of modulating oxidative stress. Consequently, it becomes important to explore the toxicological properties of dinaphthyl diselenides and ditellurides.

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Acknowledgments

Mohammad Ibrahim is specifically grateful for the financial support of TWAS and CNPq. M. Ibrahim is a beneficiary of the TWAS-CNPq postgraduate (doctoral) and Matheus Santos (PRAE-UFSM) fellowship program. João B.T. da Rocha gratefully acknowledges the financial support of CNPq, INCT for Excitoxicity and Neuroprotection, IBNet-FINEP, FAPERGS, CAPES, CAPES/SAUX, FAPERS-PRONEX-CNPQ, and VITAE.

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Authors and Affiliations

  1. Programa de Pós-Graduação em Ciências Biológicas-Bioquímica Toxicológica, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria, RS, CEP 97105-900, Brazil

    Mohammad Ibrahim, Waseem Hassan, Daiane Francine Meinerz, Matheus dos Santos, Claudia V. Klimaczewski, Anna M. Deobald, Cristina W. Nogueira, Nilda B. V. Barbosa & Joao B. T. Rocha

  2. Institute of Chemical Sciences, University of Peshawar, Peshawar, 25120, Khyber Pakhtunkhwa, Pakistan

    Waseem Hassan

  3. Universidade do Vale Paraiba (UNIVAP), Instituto de Pesquisa e Desenvolvimento (P&D), Sao Jose Dos Campos, SP, CEP 12244000, Brazil

    Maricilia S. Costa

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  1. Mohammad Ibrahim
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  2. Waseem Hassan
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  9. Nilda B. V. Barbosa
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  10. Joao B. T. Rocha
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Correspondence to Joao B. T. Rocha.

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Ibrahim, M., Hassan, W., Meinerz, D.F. et al. Antioxidant properties of diorganoyl diselenides and ditellurides: modulation by organic aryl or naphthyl moiety. Mol Cell Biochem 371, 97–104 (2012). https://doi.org/10.1007/s11010-012-1426-4

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