Enhancing solubility and stability of piperine using β-cyclodextrin derivatives: computational and experimental investigations

Piperine (PP), a natural alkaloid found in black pepper, possesses significant bioactivities. However, its use in pharmaceutical applications is hindered by low water solubility and susceptibility to UV light degradation. To overcome these challenges, we investigated the potential of β-cyclodextrin (βCD) and its derivatives with dimethyl (DMβCD), hydroxy-propyl (HPβCD) and sulfobutyl-ether (SBEβCD) substitutions to enhance the solubility and stability of PP. This study employed computational and experimental approaches to examine the complexation between PP and βCDs. The results revealed the formation of two types of inclusion complexes: the P-form and M-form involving the insertion of piperidine moiety and the methylene-di-oxy-phenyl moiety, respectively.

These complexes primarily rely on van der Waals interactions. Among the three derivatives, the PP/SBEβCD complex exhibited the highest stability followed by HPβCD, as attributed to maximum atom contacts and minimal solvent accessibility. Solubility studies confirmed the formation of inclusion complexes in a 1:1 ratio. Notably, the stability constant of the inclusion complex was approximately two-fold higher with SBEβCD and HPβCD compared to βCD. The DSC thermograms provided confirmation of the formation of the inclusion complex between the host and guest. These findings highlight the potential of βCD derivatives to effectively encapsulate PP, improving its solubility and presenting new opportunities for its pharmaceutical applications.

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Saba Ali, Phattharapawn Saokaew, Aamir Aman, Duangjai Todsaporn, Kamonpan Sanachai, Kuakarun Krusong, Supot Hannongbua, Peter Wolschann, Panupong Mahalapbutr & Thanyada Rungrotmongkol (2024) Enhancing solubility and stability of piperine using β-cyclodextrin derivatives: computational and experimental investigations, Journal of Biomolecular Structure and Dynamics, DOI: 10.1080/07391102.2024.2305696

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