Synthesis of glycosylated porphyrins as neutral ionophores for a berberine-sensitive electrode.
For preparing a berberine-sensitive electrode, 5,10,15,20-tetrakis[2-(2,3,4,6-tetraacetyl-beta-D-glucopyranosyl)-1-O- phenyl]porphyrin (T(o-glu)PPH2) was synthesized from the reaction of pyrrole with ortho-acetylglycosylated benzaldehyde by Lindsay's method. The electrode based on T(o-glu)PPH2 with an optimized membrane composition exhibits Nernstian response to berberine in the concentration range 2.4 x 10(-7)-5.0 x 10(-3) mol L-1, with a pH range from 3.9 to 10.2, and a fast response time of 30 s. The electrode shows fair selectivity towards berberine with respect to common co-existing species. T(o-glu)PPH2 shows better potentiometric response characteristics comparing to chloro[5,10,15,20-tetrakis[2-(2,3,4,6-tetraacetyl-beta-D- glucopyranosyl)-1-O-phenyl]-porphinato]-manganese (MnT(o-glu)PPCl) and better selectivity towards berberine than tetraphenylporphyrin (TPPH2). The effect of the composition of the electrode membrane has been studied and the experimental conditions optimized. The contents of berberine in pharmaceutical tablets were determined by direct potentiometry and the results agreed with values obtained by the pharmacopoeia method.
Institute for Chemometrics and Chemical Sensing Technology, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P.R. China.
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D001599:Berberine / Q000032:analysis*; D004563:Electrochemistry; D004586:Electrophoresis / Q000379:methods*; D006031:Glycosylation; D006863:Hydrogen-Ion Concentration; D017736:Ion-Selective Electrodes; D008566:Membranes / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis*; D013607:Tablets / Q000737:chemistry
C423404:5,10,15,20-tetrakis(2-(2,3,4,6-tetraacetylglucopyranosyl)-1-O-phenyl)porphyrin; D004364:Pharmaceutical Preparations; D011166:Porphyrins; D013607:Tablets; D001599:Berberine