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

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).

Chitosan as Valuable Excipient for Oral and Topical Carvedilol Delivery Systems

“…The method is cheap, easy to perform, and there are no severe conditions (temperature, pH, or pressure) that may affect the API. In the literature, kneading is described as one of the key and most frequently used methods of obtaining complexes [ 15 , 31 , 32 ].…”

Synthesis and antihyperlipidaemic activity of a new piperine derivative

“…In particular, N-leucinylpiperamide showed twice-lower cytotoxicity to the cell line than the simvastatin at the 8 µM concentration. Piperine, as an alkaloid with poor solubility, requires modifications for its increased pharmaceutical activities [10,11]. The structure of piperine is suitable for chemical modifications; therefore, it can present an advantage in developing novel derivatives with various therapeutic activities [26].…”

“…Thus, piperine and its derivatives may significantly modulate lipid parameters and lead the compound to develop new potential antihyperlipidemic drug candidates. However, its biological applications are denied due to its low aqueous solubility [6,10], which is a significant barrier to drug development. Therefore, one main concern is the development of the formulations to increase its solubility [11,12].…”

“…Therefore, one main concern is the development of the formulations to increase its solubility [11,12]. Many studies have shown that improving the solubility of piperine affects its bioavailability and increases pharmacological activity [10]. Introduction of amino acids is one way to increase the water solubility of non-soluble compounds.…”

Nano‐Cocrystals of Piperine‐Succinic Acid: Physicochemical Characterization and Dissolution Rate Studies

“…Piperine is practically insoluble in water, resulting in poor bioavailability and the limited use of piperine in pharmaceutical preparations [1,11–13] . Based on the Biopharmaceutical Classification System (BCS), piperine is a class II compound (i. e., low water solubility and high permeability) [14] .…”