Preparation and Characterization of Inclusion Complexes of β-Cyclodextrin−BITC and β-Cyclodextrin−PEITC

Abstract

Benzyl isothiocyanate (BITC) and phenylethyl isothiocyanate (PEITC) are two poorly water-soluble plant components that can form inclusion complexes with β-cyclodextrin (β-CD), namely, β-cyclodextrin−BITC and β-cyclodextrin−PEITC, that are two water-soluble complexes. The inclusion complexes were prepared by two independent processes: physical mixing and coprecipitation. The content of guest molecules in the complexes was measured by UV spectrophotometry. Response surface design (RSD) was applied to optimize the preparation conditions of said complexes. The results showed that the embedding ratios for β-CD−BITC and β-CD−PEITC were 94.9% and 94.1%, respectively. Variance analysis revealed that the mass ratio and the inclusion temperature were two important factors in terms of inclusion action. The optimum conditions for the inclusion of β-CD−BITC were a mass ratio of 0.17 and an inclusion temperature of 57.99 °C, and those for β-CD−PEITC were a mass ratio of 0.0057 and an inclusion temperature of 64.87 °C. The inclusion complexes prepared were qualified by thermal methods [thermogravimetry (TG) and differential scanning calorimetry (DSC)], Fourier transform infrared (FTIR) spectroscopy, and X-ray powder diffraction (XRD). The thermal analysis of β-CD and the two complexes indicated that an interaction between the guest and host molecules did occur. BITC and PEITC could be partially embedded in the hydrophobic cavity of β-CD, so the formation of the said complexes was established. The X-ray and FTIR results support this indication of inclusion behavior.

Chemopreventive glucosinolate accumulation in various broccoli and collard tissues: Microfluidic-based targeted transcriptomics for by-product valorization

“…Relatively low QR inducing activity of root samples despite of high glucosinolate and HP concentration could be explained by volatility of HPs in root samples. As mentioned previously, PEITC and erucin have very low water solubility, which has been previously reported [ 19 , 26 ]. Previous studies could not detect PEITC in hydrolyzed watercress extracts due to water solubility [ 31 ].…”

“…For both broccoli and collards, relatively small amounts of PEITC (1.32 and 1.56 μmol/g DW, , respectively) were detected in root tissues compared to its precursor, gluconasturtiin (16.9 and 20.8 μmol/g DW, respectively) in the same tissues. This discrepancy is probably due to its lower solubility in water compared to other compounds, which has been previously reported [ 19 , 26 ]. Although SF has a water solubility of 8.0 mg/mL, PEITC has only 0.051 mg/mL of water solubility [ 27 ].…”

Synthesis, Physiochemical and Biological evaluation of Inclusion Complex of Benzyl Isothiocyanate encapsulated in cyclodextrins for triple negative breast cancer

“…The thermogram of the sonochemically formed complexes showed a peak shift at around 105 °C. The shift of peak to the lower temperature and intensification/deepening of the peak around 220 °C could be attributed to the change in the properties followed by complete complexation thus, confirming the interaction between BITC and CDs (30). The high thermal stability of the complexes was proved by the non-isothermal thermogravimetric analysis conducted in our previous work (29).…”

Insights about stabilization of sulforaphane through microencapsulation

“…The inclusion complex kept antibacterial activity, and then the authors speculate that they also should keep the pharmacological properties. Yuan, Yao, Shen & Mao (2009) optimized the formation of benzyl- and phenyl isothiocyanates inclusion complexes using β-cyclodextrin, through response surface methodology. They concluded that temperature and mass ratio were the most significant factors that affect encapsulation.…”