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Inclusion complex of Tramadol in β-cyclodextrin enhances fluorescence by preventing self-quenching

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Abstract

Fluorescence self-quenching occurs at high concentration. Inhibition of self-quenching by inclusion of fluorescence emitters inside the hydrophobic cavity of β-cyclodextrin (β-CD) has been addressed taking the example of the fluorescence behavior of Tramadol hydrochloride. Indeed complexation by β-CD enhanced fluorescence emission of Tramadol under conditions where self-quenching was operative. A quantitative account of self-quenching and its inhibition by β-CD was done through determination of complexation equilibrium by 1H NMR experiments and a detailed study of absorption and fluorescence properties. Tramadol and β-CD associate as a complex of 1:1 stoichiometry with a formation constant K11 = 260. Complexation of Tramadol by β-CD does not cause modification of its absorbance and fluorescence spectra. Fluorescence self-quenching of Tramadol above ∼ 1 mmol·L−1 was characterized by a Stern–Volmer constant K = 810 L·mol−1. Inhibition of self-quenching by formation of an inclusion complex was manifested by lower Stern–Volmer constants in the presence of β-CD. Such study required a correct account of Inner Filter Effects on fluorescence, which is mandatory in all physicochemical studies using fluorescence where concentrations are rather high.

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Authors and Affiliations

  1. Laboratoire d’Électrochimie, Ingénierie Moléculaire et Catalyse Redox (LEIMCR), University Farhat Abbas, 19000, Sétif, Algeria

    Salima Zidane & Amor Maiza

  2. University of Lyon, Laboratoire d’Automatique et de Génie des Procédés (LAGEP), UMR 5007 CNRS - University Claude Bernard Lyon 1, 69622, Villeurbanne, France

    Salima Zidane & Yves Chevalier

  3. Laboratoire de Chimie Organique Appliquée (LCOA), Groupe de Chimie Bioorganique, Faculty of Sciences, Department of Chemistry, University Badji-Mokhtar, 23000, Annaba, Algeria

    Hocine Bouleghlem

  4. University of Lyon, Centre Commun de RMN, University Claude Bernard Lyon 1, 69616, Villeurbanne, France

    Bernard Fenet

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  1. Salima Zidane
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  2. Amor Maiza
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Correspondence to Yves Chevalier.

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Zidane, S., Maiza, A., Bouleghlem, H. et al. Inclusion complex of Tramadol in β-cyclodextrin enhances fluorescence by preventing self-quenching. J Incl Phenom Macrocycl Chem 93, 253–264 (2019). https://doi.org/10.1007/s10847-018-0874-1

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  • DOI: https://doi.org/10.1007/s10847-018-0874-1

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