The Effect of Ion Pairing Reagents in the Retention Profile of Zwitterionic Cephalosporins
The retention of three zwitterionic cephalosporins, Cefepime, Cefpirome, and Ceftazidime, in a broad pH range was studied by means of reversed phase high performance liquid chromatography (RP-HPLC) and reversed phase ion-pair liquid chromatography (RP-IPC), using an octadecylsilane stationary phase...
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Published in | Journal of liquid chromatography & related technologies Vol. 26; no. 6; pp. 937 - 952 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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Colchester
Taylor & Francis Group
01.04.2003
Taylor & Francis |
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Abstract | The retention of three zwitterionic cephalosporins, Cefepime, Cefpirome, and Ceftazidime, in a broad pH range was studied by means of reversed phase high performance liquid chromatography (RP-HPLC) and reversed phase ion-pair liquid chromatography (RP-IPC), using an octadecylsilane stationary phase and acetonitrile as organic modifier. Sodium hexane-, heptane-, and octane-sulphonate and tetrabutylammonium hydroxide were used as sources of counter ions in ion pair chromatography. The presence of the permanently charged quaternary nitrogen in the cephalosporin molecules leads to zwitterionic species over a broad pH range, masking the carboxylic acid function and stabilizing the retention. The effect of the counter ion depends on the ionization state of the compounds. Formation of ion pairs with the opposite charged center of the molecules led to significant increase in retention. At pH values favoring the zwitterionic species a decrease in retention was observed as a result of the disruption of the intramolecular interactions and the deliberation of the free charge. The extent of ion pair formation and the competition with the zwitterionic species, depended on the counter ion concentration in the mobile phase and was reflected in retention. The effect of the size of the counter anion alkyl chain on retention was investigated at different pH as well. |
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AbstractList | The retention of three zwitterionic cephalosporins, Cefepime, Cefpirome, and Ceftazidime, in a broad pH range was studied by means of reversed phase high performance liquid chromatography (RP-HPLC) and reversed phase ion-pair liquid chromatography (RP-IPC), using an octadecylsilane stationary phase and acetonitrile as organic modifier. Sodium hexane-, heptane-, and octane-sulphonate and tetrabutylammonium hydroxide were used as sources of counter ions in ion pair chromatography. The presence of the permanently charged quaternary nitrogen in the cephalosporin molecules leads to zwitterionic species over a broad pH range, masking the carboxylic acid function and stabilizing the retention. The effect of the counter ion depends on the ionization state of the compounds. Formation of ion pairs with the opposite charged center of the molecules led to significant increase in retention. At pH values favoring the zwitterionic species a decrease in retention was observed as a result of the disruption of the intramolecular interactions and the deliberation of the free charge. The extent of ion pair formation and the competition with the zwitterionic species, depended on the counter ion concentration in the mobile phase and was reflected in retention. The effect of the size of the counter anion alkyl chain on retention was investigated at different pH as well. |
Author | Pistos, C. M. Tsantili-Kakoulidou, A. Koupparis, M. |
Author_xml | – sequence: 1 givenname: C. M. surname: Pistos fullname: Pistos, C. M. organization: Division of Pharmaceutical Chemistry, Department of Pharmacy , University of Athens – sequence: 2 givenname: A. surname: Tsantili-Kakoulidou fullname: Tsantili-Kakoulidou, A. email: tsantili@pharm.uoa.gr organization: Division of Pharmaceutical Chemistry, Department of Pharmacy , University of Athens – sequence: 3 givenname: M. surname: Koupparis fullname: Koupparis, M. organization: Laboratory of Analytical Chemistry, Department of Chemistry , University of Athens |
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Cites_doi | 10.1002/qsar.19970160407 10.1002/qsar.19900090202 10.1016/S0378-5173(99)00150-7 10.1016/S0021-9673(00)91700-X 10.1016/S0378-5173(97)00137-3 10.1002/hlca.19950780304 10.1002/qsar.19890080302 10.1023/A:1011001914685 10.1016/S0378-4347(98)00256-4 10.1023/A:1018977225919 10.1023/A:1012076022420 10.1016/0021-9673(92)85199-4 10.1021/js980170y 10.1021/cr9601019 10.1023/A:1015963128124 10.1016/S0021-9673(01)95994-1 10.1016/0378-5173(81)90018-1 10.1016/S0021-9673(97)01213-2 |
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Keywords | Chemical analysis Phase composition Cefepime Cefpirome Chromatographic retention Lactam Ion pair HPLC chromatography Zwitterion Mobile phase Antibiotic Reversed phase chromatography Cephalosporin derivatives pH Qualitative analysis Antibacterial agent Ceftazidime |
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SubjectTerms | Analysis Biological and medical sciences Cefepime Cefpirome Ceftazidime General pharmacology High performance liquid chromatography Ion-pair liquid chromatography Medical sciences Pharmacology. Drug treatments Zwitterions |
Title | The Effect of Ion Pairing Reagents in the Retention Profile of Zwitterionic Cephalosporins |
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