Ion Transfer Behavior of Protonated Phenazopyridine at the Liquid/Liquid Interface Modified by Functionalized Hybrid Mesoporous Silica Membrane†

doi:10.7503/cjcu20180811

Abstract

Abstract:

The transfer behavior of a clinical drug, phenazopyridine hydrochloride, at the water/1,6-dichlorhexane(W/DCH) interface modified by functionalized mesoporous silica membrane was studied by cyclic voltammetry and differential pulse voltammetry. It was found that the phenazopyridine(PAP) can be protonated to form phenazopyridine cation(HPAP⁺) under acidic condition, which can transfer at such a membrane-modified W/DCH interface. According to the relationship between the transfer peak current and the scan rate, as well as the equation of Randles-Sev$\check{c}$ik, the diffusion coefficient of HPAP⁺ in the functionalized hybrid mesoporous silica membrane was calculated to be 5.14×10^-8 cm²/s. In addition, the electrochemical response of ion-transfer of HPAP⁺ at the W/DCH interface modified by functionalized hybrid mesoporous silica membrane is much higher than bare PET membrane, which can improve the electrochemical detection performance of phenazopyridine cation. Moreover, the ionic partition diagram of HPAP⁺ at the W/DCH interface modified by functionalized hybrid mesoporous silica membrane was obtained by differential pulse voltammetry, which can not only understand the distribution of HPAP⁺ under different conditions(pH value and interfacial potential), but also obtain the distribution coefficient and ion-transfer Gibbs free energy of HPAP⁺, which helps to understand the transmembrane process of HPAP⁺ across biological membrane and provide a new electrochemical method to detect phenazopyridine hydrochloride.

Key words: Phenazopyridine, Liquid/liquid interface, Electrochemistry, Ion transfer

CLC Number:

O647

TrendMD:

LIU Shufeng,QIU Haiyan,JIANG Tao,ZHANG Yehua,ZHAO Yun,CHENG Hanwen,CHEN Yong. Ion Transfer Behavior of Protonated Phenazopyridine at the Liquid/Liquid Interface Modified by Functionalized Hybrid Mesoporous Silica Membrane^†[J]. Chem. J. Chinese Universities, 2019, 40(5): 973.

Figures/Tables 9

Scheme 1 Chemical structure of phenazopyridine hydrochloride

Scheme 2 Schematic representation of the electrochemical cell

Fig.1 SEM images of the surface of bare PET membrane(A) and hybrid mesoporous membrane(B)

Scheme 3 Schematic diagram of the electrochemical cell

Fig.2 CVs obtained at the W/DCH interface modified by hybrid mesoporous membrane in the absence(a) and presence(b) of 0.3 mmol/L phenazopyridine hydrochloride at a scan rate of 20 mV/spH=4.0.

Fig.3 CVs obtained at the W/DCH interface modified by hybrid mesoporous membrane in the presence of 0.18 mmol/L phenazopyridine hydrochloride at different scan ratesFrom inner CVs to outer CVs, the scan rates are 5, 15, 20, 25 and 30 mV/s. Inset: the corresponding plot of peak current vs. the square root of scan rate.

Fig.4 CVs of the W/DCH interface modified by hybrid mesoporous membrane(A) and bare PET membrane(B) at increasing concentrations of phenazopyridine hydrochlorideFrom inner CVs to outer CVs, the concentrations of phenazopyridine hydrochloride are 0, 0.18, 0.3, 0.36, 0.42 and 0.54 mmol/L. Inset: the corresponding plots of peak current vs. the concentration of phenazopyridine hydrochloride in aqueous solution.

Fig.5 DPVs of the W/DCH interface modified by hybrid mesoporous membrane(A) and bare PET membrane(B) at increasing concentrations of phenazopyridine hydrochlorideFrom bottom to top, the concentrations of phenazopyridine hydrochloride are 0, 0.18, 0.3, 0.36, 0.42 and 0.54 mmol/L. Inset: the corresponding plots of peak current vs. the concentration of phenazopyridine hydrochloride in aqueous solution.

Fig.6 DPVs of the W/DCH interface modified by hybrid mesoporous membrane in presence of phenazopyridine hydrochloride and TBA+ at different pH values(A) and the corresponding plots of ionic partition diagram of PAP at W/DCH interface(B)The concentrations of phenazopyridine hydrochloride and TBA+ are 0.3 mmol/L, respectively. (B) The dotted line represents the pKa of PAP. Lines 1, 2, and 3 correspond to eqs.(3), (4) and (5), respectively.

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