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Article

Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System

by
Anna Stasiłowicz
1,
Natalia Rosiak
1,
Ewa Tykarska
2,
Maciej Kozak
3,
Jacek Jenczyk
4,
Piotr Szulc
5,
Joanna Kobus-Cisowska
6,
Kornelia Lewandowska
7,
Anita Płazińska
8,
Wojciech Płaziński
9 and
Judyta Cielecka-Piontek
1,*
1
Department of Pharmacognosy, Faculty of Pharmacy, Poznan University of Medical Sciences, Swiecickiego 4, 60-781 Poznań, Poland
2
Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland
3
Department of Macromolecular Physics, Faculty of Physics, Adam Mickiewicz University, Uniwersytetu Poznańskiego 2, 61-614 Poznań, Poland
4
NanoBioMedical Centre, Adam Mickiewicz University, Wszechnicy Piastowskiej 3, 61-614 Poznań, Poland
5
Department of Agronomy, Poznań University of Life Sciences, Dojazd 11, 60-632 Poznań, Poland
6
Department of Gastronomy Sciences and Functional Foods, Faculty of Food Science and Nutrition, Poznań University of Life Sciences, Wojska Polskiego 31, 60-624 Poznań, Poland
7
Institute of Molecular Physics, Polish Academy of Sciences, Smoluchowskiego 17, 60-179 Poznan, Poland
8
Department of Biopharmacy, Faculty of Pharmacy, Medical University of Lublin, Chodzki 4a, 20-093 Lublin, Poland
9
Jerzy Haber Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, Niezapominajek 8, 30-239 Krakow, Poland
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2021, 22(8), 4195; https://doi.org/10.3390/ijms22084195
Submission received: 5 March 2021 / Revised: 9 April 2021 / Accepted: 16 April 2021 / Published: 18 April 2021
(This article belongs to the Collection Bioactive Natural Compounds for Therapeutics and Nutraceutical Applications)
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Abstract

Piperine is an alkaloid that has extensive pharmacological activity and impacts other active substances bioavailability due to inhibition of CYP450 enzymes, stimulation of amino acid transporters and P-glycoprotein inhibition. Low solubility and the associated low bioavailability of piperine limit its potential. The combination of piperine with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) causes a significant increase in its solubility and, consequently, an increase in permeability through gastrointestinal tract membranes and the blood–brain barrier. X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) were used to characterize interactions between piperine and HP-β-CD. The observed physicochemical changes should be combined with the process of piperine and CD system formation. Importantly, with an increase in solubility and permeability of piperine as a result of interaction with CD, it was proven to maintain its biological activity concerning the antioxidant potential (2,2-diphenyl-1-picryl-hydrazyl-hydrate assay), inhibition of enzymes essential for the inflammatory process and for neurodegenerative changes (hyaluronidase, acetylcholinesterase, butyrylcholinesterase).
Keywords: piperine; hydroxypropyl-β-cyclodextrin; solubility; permeability; anti-inflammatory and neuroprotective activity piperine; hydroxypropyl-β-cyclodextrin; solubility; permeability; anti-inflammatory and neuroprotective activity
Graphical Abstract

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MDPI and ACS Style

Stasiłowicz, A.; Rosiak, N.; Tykarska, E.; Kozak, M.; Jenczyk, J.; Szulc, P.; Kobus-Cisowska, J.; Lewandowska, K.; Płazińska, A.; Płaziński, W.; et al. Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System. Int. J. Mol. Sci. 2021, 22, 4195. https://doi.org/10.3390/ijms22084195

AMA Style

Stasiłowicz A, Rosiak N, Tykarska E, Kozak M, Jenczyk J, Szulc P, Kobus-Cisowska J, Lewandowska K, Płazińska A, Płaziński W, et al. Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System. International Journal of Molecular Sciences. 2021; 22(8):4195. https://doi.org/10.3390/ijms22084195

Chicago/Turabian Style

Stasiłowicz, Anna, Natalia Rosiak, Ewa Tykarska, Maciej Kozak, Jacek Jenczyk, Piotr Szulc, Joanna Kobus-Cisowska, Kornelia Lewandowska, Anita Płazińska, Wojciech Płaziński, and et al. 2021. "Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System" International Journal of Molecular Sciences 22, no. 8: 4195. https://doi.org/10.3390/ijms22084195

APA Style

Stasiłowicz, A., Rosiak, N., Tykarska, E., Kozak, M., Jenczyk, J., Szulc, P., Kobus-Cisowska, J., Lewandowska, K., Płazińska, A., Płaziński, W., & Cielecka-Piontek, J. (2021). Combinations of Piperine with Hydroxypropyl-β-Cyclodextrin as a Multifunctional System. International Journal of Molecular Sciences, 22(8), 4195. https://doi.org/10.3390/ijms22084195

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