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Bioactive microparticles (10): thermal and oxidative stability of nicotine and its complex with β-cyclodextrin

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Abstract

The paper presents a comparative thermal and oxidative stability study between nicotine/β-cyclodextrin microparticles and commercial nicotine. It is well known that the nicotine is the bioactive compound in formulations used for smoking cessation and no studies among the stability of nicotine in cyclodextrin-containing formulations were reported. The non-enzymatic and enzymatic oxidation of nicotine can lead to cotinine (an alkaloid/metabolite with a lower toxicity), but another way is the obtaining of the cancerigene N-nitroso-nicotine derivatives by nornicotine derivative intermediates (like nornicotine and myosmine). The present study demonstrates the protecting capacity of β-cyclodextrin for commercial nicotine against thermal and oxidative factors: for the non-complexed nicotine the thermal and oxidative degradation led to a decrease of the relative concentration of nicotine from 96 to 92% for an increasing temperature from 30 to 90 °C (in the presence of air at normal pressure), with an increase of the relative concentration of the corresponding oxidized compounds (like cotinine and furthermore myosmine up to 0.7%, and up to 4.7%, respectively). For the nicotine/β-cyclodextrin complex the interaction selectivity was higher for nicotine and the stability of this bioactive compound against oxidation was also higher in comparison with the non-complexed nicotine (around 98% in all cases).

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Abbreviations

bCD:

β-cyclodextrin

KI:

Kovats Index

TG:

Thermogravimetry

GC-MS:

Gas chromatography-mass spectrometry

SEM:

Scanning electron microscopy

KFT:

Karl Fischer titration

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Acknowledgments

This work was supported by Ministry of Education and Research of Romania [Grant CEEX P-CD 18/2005 and Grant PN2 62072/2008 for KFT]. All authors were members of the research teams in the above mentioned grants. Authors are grateful to Professor Heinz-Dieter Isengard (Hohenheim University, Germany) for the help in Karl Fischer water titration, to Professor Geza Bandur (“Politehnica” University of Timişoara, Romania) for the help in TG analysis, and to Professor Mircea Mracec (“Coriolan Drăgulescu” Institute of Chemistry, Timişoara, Romania) for permission to use the HyperChem molecular modeling package.

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Authors and Affiliations

  1. Faculty of Industrial Chemistry and Environmental Engineering, Organic Chemistry and Technology Department, Politehnica University of Timişoara, P-ţa Victoriei 2, Timişoara, 300006, Romania

    Daniel Ioan Hădărugă

  2. Faculty of Food Processing Technology, Food Quality Department, Banat’s University of Agricultural Sciences and Veterinary Medicine, C. Aradului 119, Timişoara, 300645, Romania

    Nicoleta Gabriela Hădărugă

  3. Faculty of Horticulture and Forestry, Genetic Engineering in Agriculture Department, Banat’s University of Agricultural Sciences and Veterinary Medicine, C. Aradului 119, Timişoara, 300645, Romania

    Gallia Butnaru

  4. Regional Centre of Immunology and Transplant, County Hospital Timişoara, Bv. Iosif Bulbuca 10, Timişoara, 300736, Romania

    Călin Tatu & Alexandra Gruia

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  1. Daniel Ioan Hădărugă
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  2. Nicoleta Gabriela Hădărugă
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Correspondence to Daniel Ioan Hădărugă.

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Hădărugă, D.I., Hădărugă, N.G., Butnaru, G. et al. Bioactive microparticles (10): thermal and oxidative stability of nicotine and its complex with β-cyclodextrin. J Incl Phenom Macrocycl Chem 68, 155–164 (2010). https://doi.org/10.1007/s10847-010-9761-0

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