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Physicochemical and Biochemical Profiling of Diphenyl Diselenide

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Abstract

The objective of the present study was to evaluate the physicochemical and biochemical profiling of diphenyl diselenide (PhSe)2, a selenoorganic compound with biological activity. Experimental protocols were established for chemical stability in isotonic phosphate buffer (PBS) pH 7.4 and in simulated gastric and intestinal fluids, biological stability (bovine serum albumin (BSA) and plasma), solubility in PBS pH 7.4, distribution coefficient (Log D) in octanol/PBS, and determination of free (PhSe)2 concentrations in BSA and plasma by using liquid chromatography with ultraviolet detection and tandem mass spectrometry. (PhSe)2 was found to be chemically stable and not susceptible to degradation in plasma. The aqueous solubility was 0.98 ± 0.072 μM and the Log D in octanol/PBS system was found to be 3.13. The percentage of unbound fractions of (PhSe)2 obtained by equilibrium dialysis from BSA and plasma incubated with 100 μM (PhSe)2 were 0.69 ± 0.12 and 0.44 ± 0.09 %, respectively. The findings indicated that (PhSe)2 presents chemical and biological stability. Though, the compound showed low aqueous solubility, high Log D value and high binding to plasmatic protein. These data contribute to the knowledge of the toxicokinetic properties of (PhSe)2 and further explain its low bioavailability in experimental models.

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Acknowledgments

The financial support by IMED.UL, FAPERGS, CAPES, and CNPq is gratefully acknowledged; and also the Universidade de Lisboa and the Universidade Federal de Santa Maria. FCT Fundação para a Ciência e Tecnologia (REDE/1518/REM/2005) financial support for the LC-MS/MS equipment. Prigol M is recipient of PNPD/CAPES fellowship.

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Authors and Affiliations

  1. Universidade Federal do Pampa (UNIPAMPA), Campus Itaqui, CEP 97.650-000, Itaqui, RS, Brazil

    Marina Prigol

  2. Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, Santa Maria, CEP 97105-900, RS, Brazil

    Marina Prigol, Cristina W. Nogueira & Gilson Zeni

  3. iMed UL Faculdade de Farmácia, Universidade de Lisboa, Av. das Forças Armadas, 1649-003, Lisbon, Portugal

    Maria Rosário Bronze & Luís Constantino

  4. ITQB/IBET, Av. da República-EAN, 2780-157, Oeiras, Portugal

    Maria Rosário Bronze

Authors
  1. Marina Prigol
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  2. Cristina W. Nogueira
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  3. Gilson Zeni
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  4. Maria Rosário Bronze
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  5. Luís Constantino
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Correspondence to Marina Prigol.

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ESM 1

Chromatogram of extracted fragment (m/z 189) obtained in the analysis of a BSA sample (0 and 1 h) and b plasma sample (0 and 1 h) hour using a LC-MS/MS operating in scan mode (GIF 32.9 KB)

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Prigol, M., Nogueira, C.W., Zeni, G. et al. Physicochemical and Biochemical Profiling of Diphenyl Diselenide. Appl Biochem Biotechnol 169, 885–893 (2013). https://doi.org/10.1007/s12010-012-0042-9

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  • DOI: https://doi.org/10.1007/s12010-012-0042-9

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