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HPLC study of the host–guest complexation between fluorescent glutathione derivatives and β-cyclodextrin

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Abstract

RP-HPLC and the van’t Hoff law were used to study the association in which β-cyclodextrin forms inclusion complexes with aminothiol–phthaldialdehyde derivatives prepared from either glutathione (GSH) or γ-glutamylcysteine (γ-glucys) and either naphthalene-2,3-dicarboxaldehyde (NDA) or o-phthaldialdehyde (OPA). Elution was carried out at pH 8.5, the derivatization pH which gave the highest fluorescence signal during batch experiments. The variation of the retention factor (k) was monitored as a function of column temperature (10–35 °C) and β-cyclodextrin concentration (0–5 mM) in the mobile phase. Apparent binding constants, enthalpy and entropy were calculated from van’t Hoff plots for the complexation reaction. These data lay the groundwork for the improvement of high throughput GSH quantification methods using fluorimetry in biological and vegetal samples.

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Abbreviations

K f :

Apparent association constant

CD:

Cyclodextrin

γ-glucys:

γ-Glutamyl-l-cysteine

GSH:

Glutathione

NDA:

Naphthalene-2,3-dicarboxaldehyde

OPA:

o-Phthaldialdehyde

k :

Retention factor

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Acknowledgements

The authors are grateful to Dr. Christian Ruby and Dr. Khalil Hanna (LCPME, Nancy, France) for helpful discussions during the preparation of this manuscript, and to Pr. John Almy for English language editing.

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  1. Stéphanie Marchand

    Present address: UMR 1219 Œnologie, Université de Bordeaux, INRA, ISVV, 33140, Villenave d’Ornon, France

Authors and Affiliations

  1. Laboratoire de Chimie Physique et Microbiologie pour l’Environnement, UMR 7564 CNRS, Faculty of Pharmacy, Nancy-University, BP 80403, 54001, Nancy Cedex, France

    Stéphanie Marchand, Aldona Guzek & Pierre Leroy

  2. EA 3452 “Cibles thérapeutiques, formulation et expertise préclinique du médicament”, Faculty of Pharmacy, Nancy-University, BP 80403, 54001, Nancy Cedex, France

    Pierre Leroy

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  1. Stéphanie Marchand
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Correspondence to Stéphanie Marchand.

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Marchand, S., Guzek, A. & Leroy, P. HPLC study of the host–guest complexation between fluorescent glutathione derivatives and β-cyclodextrin. J Incl Phenom Macrocycl Chem 66, 409–416 (2010). https://doi.org/10.1007/s10847-009-9619-5

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  • DOI: https://doi.org/10.1007/s10847-009-9619-5

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