Characterization of an Aryl Piperazine/2-Hydroxypropyl-β-Cyclodextrin Association, a Complex with Antidiabetic Potential

Authors

R. Devine, Maynooth University, Maynooth, Co. Kildare, Ireland
D.S.D. Martin, Maynooth University, Maynooth, Co. Kildare, Ireland
Gemma Kinsella, Technological University DublinFollow
J.B.C. Findlay, Maynooth University, Maynooth, Co. Kildare, Ireland
J.C. Stephens, Maynooth University, Maynooth, Co. Kildare, Ireland

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

3.4 HEALTH BIOTECHNOLOGY, Health-related biotechnology

Publication Details

Results in Chemistry

Abstract

This study explores the molecular association between 4-(thiophen-2-yl)-1-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)butan-1-one (RTC1), an antidiabetic compound recently reported by our research group with challenging aqueous solubility, and 2-hydroxypropyl-β-cyclodextrin (HPBCD). The formation of a RTC1/HPBCD complex resulted in improved solubility. A phase-solubility diagram was used to determine the complex stability constant and stoichiometric ratio. 2D ¹H NMR spectroscopy was utilized to study the molecular interaction between RTC1 and HPBCD in the complex. Differential scanning calorimetry and scanning electron microscopy was also employed to confirm complex formation. In vitro biological evaluation, using a glucose uptake assay, showed that the homogeneous RTC1/HPBCD complex solution showed the same activity to that of RTC1 alone, with no reduction in activity due to the presence of HPBCD.

DOI

https://doi.org/10.1016/j.rechem.2020.100026

Recommended Citation

J.C. Stephens et al. (2020) Characterization of an Aryl Piperazine/2-Hydroxypropyl-β-Cyclodextrin Association, a Complex with Antidiabetic Potential,Results in Chemistry, Vol. 2, January 2020, 100026 DOI:10.1016/j.rechem.2020.100026