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Monatshefte für Chemie - Chemical Monthly

, Volume 146, Issue 1, pp 99–109 | Cite as

Cocrystals of quercetin: synthesis, characterization, and screening of biological activity

  • Miroslav Veverka
  • Tibor Dubaj
  • Ján Gallovič
  • Vladimír Jorík
  • Eva Veverková
  • Martina Danihelová
  • Peter Šimon
Original Paper

Abstract

Cocrystallization of quercetin with 22 cocrystal formers, i.e. phenolic acids, proline, urea, N-acetylcytosine, carnitine, dacarbazine, diflunisal, kojic acid, lactamide, baclofen, pyrazole, edaravone, salicylamide, O-acetylsalicylamide, 2-imidazolidinone, allopurinol, dipyridamole, 5-sulfosalicylic acid, and 4-sulfobenzoic acid resulted in cocrystals with various stoichiometric ratios. The cocrystals were characterized by FT-IR, DSC, and XRPD. Some of them were non-hygroscopic and stable to thermal stress. The cocrystals quercetin:pyrazole (1:1), quercetin:imidazolidinone (1:1), and quercetin:baclofen (1:2) were found to be stable at various relative humidity conditions at 20–40 °C for up to 3 months. The in vitro antioxidant activity, cytotoxicity, and serine protease inhibitory activity were tested. The best inhibitory activity to pathophysiological proteases was observed for cocrystals with N-acetylcytosine, carnitine, and kojic acid; these cocrystals were the most potent inhibitors of thrombin. About two times better cytotoxic activity to human cervical cancer cells (HeLa) and human colon cancer cells (Caco-2) in comparison with quercetin itself was observed for quercetin:kojic acid (2:1).

Graphical abstract

Keywords

Solid phase synthesis Drug research Nutraceutical Cytotoxicity Serine protease inhibitory activity Antioxidant activity 

Notes

Acknowledgments

This investigation was supported by the Slovak Research and Development Agency, Grant No. APVV-121-2009 and The Agency of the Ministry of Education, Science, Research and Sport of the Slovak Republic for the Structural Funds of EU ITMS 26240220040 (M. Veverka, J. Gallovič, E. Švajdlenka).

Supplementary material

706_2014_1314_MOESM1_ESM.doc (1.4 mb)
Supplementary material 1 (DOC 1412 kb)

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Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  • Miroslav Veverka
    • 1
  • Tibor Dubaj
    • 2
  • Ján Gallovič
    • 1
  • Vladimír Jorík
    • 2
  • Eva Veverková
    • 3
  • Martina Danihelová
    • 2
  • Peter Šimon
    • 2
  1. 1.EUROFINS BEL/NOVAMANN Ltd.Nové ZámkySlovakia
  2. 2.Faculty of Chemical and Food TechnologySlovak University of TechnologyBratislavaSlovakia
  3. 3.Faculty of Natural SciencesComenius UniversityBratislavaSlovakia

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