Analyses of polycyclic aromatic hydrocarbon (PAH) and chiral-PAH analogues-methyl-β-cyclodextrin guest-host inclusion complexes by fluorescence spectrophotometry and multivariate regression analysis
Abstract The negative health impact of polycyclic aromatic hydrocarbons (PAHs) and differences in pharmacological activity of enantiomers of chiral molecules in humans highlights the need for analysis of PAHs and their chiral analogue molecules in humans. Herein, the first use of cyclodextrin guest-host inclusion complexation, fluorescence spectrophotometry, and chemometric approach to PAH (anthracene) and chiral-PAH analogue derivatives (1-(9-anthryl)-2,2,2-triflouroethanol (TFE)) analyses are reported. The binding constants ( K b ), stoichiometry ( n ), and thermodynamic properties (Gibbs free energy (Δ G ), enthalpy (Δ H ), and entropy (Δ S )) of anthracene and enantiomers of TFE-methyl-β-cyclodextrin (Me-β-CD) guest-host complexes were also determined. Chemometric partial-least-square (PLS) regression analysis of emission spectra data of Me-β-CD-guest-host inclusion complexes was used for the determination of anthracene and TFE enantiomer concentrations in Me-β-CD-guest-host inclusion complex samples. The values of calculated K b and negative Δ G suggest the thermodynamic favorability of anthracene-Me-β-CD and enantiomeric of TFE-Me-β-CD inclusion complexation reactions. However, anthracene-Me-β-CD and enantiomer TFE-Me-β-CD inclusion complexations showed notable differences in the binding affinity behaviors and thermodynamic properties. The PLS regression analysis resulted in square-correlation-coefficients of 0.997530 or better and a low LOD of 3.81×10 −7 M for anthracene and 3.48×10 −8 M for TFE enantiomers at physiological conditions. Most importantly, PLS regression accurately determined the anthracene and TFE enantiomer concentrations with an average low error of 2.31% for anthracene, 4.44% for R- TFE and 3.60% for S- TFE. The results of the study are highly significant because of its high sensitivity and accuracy for analysis of PAH and chiral PAH analogue derivatives without the need of an expensive chiral column, enantiomeric resolution, or use of a polarized light. Highlights Guest-host inclusion complexation formation between polycyclic aromatic hydrocarbons anthracene and anthracene chiral derivatives (1-(9-anthryl)-2,2,2-triflouroethanol (TFE)) and methyl-β-cyclodextrin (Me-β-CD) was examined using fluorescence spectroscopy Me-β-CD shows enantiomeric and chiral discrimination of TFE enantiomers. Emission spectra data of anthracene-Me-β-CD and enantiomers of TFE-Me-β-CD-guest-host inclusion complexes was used subjected to chemometric partial-least-square (PLS) regression analysis The values of calculated binding constants and negative Δ G suggest the thermodynamic favorability of anthracene-Me-β-CD and enantiomeric of TFE-Me-β-CD inclusion complexation reactions. The PLS regression analysis resulted in square-correlation-coefficients of ≥0.997530 and a low LOD of 3.48×10 −8 M and accurately determined the anthracene and TFE enantiomer concentrations with low error of ≤4.5%. Graphical abstract [DISPLAY OMISSION]
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