Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures

İlkay Konçe; Senem Akkoç; Zehra Üstün; Ebru Çubuk Demiralay

Article Details

Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures

Authors:

İlkay Konçe | Senem Akkoç | Zehra Üstün | Ebru Çubuk Demiralay

Publisher:

Marmara University

Main Topics:

Pharmaceutical Sciences | Pharmaceutical Chemistry

Journal:

Journal of Research in Pharmacy Vol.26 Issue 3, pp.655-662

Document Type:

Article

Publication Date:

6/2025

Document Language:

English

Document ID (Org No.):

2001346862

pISSN:

2630-6344

Keywords:

Abstract:

 The ionizationprotonation pKa constant, which is a physicochemical parameter that directly affects the pharmacokinetic properties of a drug such as absorption, distribution, metabolism, and excretion ADME, is currently determined by analytical methods. The effect of pH of the mobile phase on the chromatographic behavior of 1-2- methylbenzonitrile-3-benzylbenzimidazolium bromide 2 which its synthesis, fully characterization, and antiproliferative activity properties were studied previously, and the protonation constant pKa value were determined in this study. The pKa value of compound 2, benzimidazolium salt, was determined by the reverse-phase liquid chromatographic RPLC method at 25 ºC. sspKa values were evaluated using retention time tR in acetonitrile-water binary mixtures with acetonitrile ACN percentages of 40, 45, 50 and 55 vv. The aqueous pKa wwpKa value of the synthesized compound was calculated from the sspKa value using the macroscopic parameters dielectric constant and mole fraction which play an important role in the solvent properties. Obtained wwpKa values were found to be 11.290 and 11.241, respectively. In addition, the degree of ionization of the related compound was calculated using the wwpKa values.

 The ionizationprotonation pKa constant, which is a physicochemical parameter that directly affects the pharmacokinetic properties of a drug such as absorption, distribution, metabolism, and excretion ADME, is currently determined by analytical methods. The effect of pH of the mobile phase on the chromatographic behavior of 1-2- methylbenzonitrile-3-benzylbenzimidazolium bromide 2 which its synthesis, fully characterization, and antiproliferative activity properties were studied previously, and the protonation constant pKa value were determined in this study. The pKa value of compound 2, benzimidazolium salt, was determined by the reverse-phase liquid chromatographic RPLC method at 25 ºC. sspKa values were evaluated using retention time tR in acetonitrile-water binary mixtures with acetonitrile ACN percentages of 40, 45, 50 and 55 vv. The aqueous pKa wwpKa value of the synthesized compound was calculated from the sspKa value using the macroscopic parameters dielectric constant and mole fraction which play an important role in the solvent properties. Obtained wwpKa values were found to be 11.290 and 11.241, respectively. In addition, the degree of ionization of the related compound was calculated using the wwpKa values.

 The ionizationprotonation pKa constant, which is a physicochemical parameter that directly affects the pharmacokinetic properties of a drug such as absorption, distribution, metabolism, and excretion ADME, is currently determined by analytical methods. The effect of pH of the mobile phase on the chromatographic behavior of 1-2- methylbenzonitrile-3-benzylbenzimidazolium bromide 2 which its synthesis, fully characterization, and antiproliferative activity properties were studied previously, and the protonation constant pKa value were determined in this study. The pKa value of compound 2, benzimidazolium salt, was determined by the reverse-phase liquid chromatographic RPLC method at 25 ºC. sspKa values were evaluated using retention time tR in acetonitrile-water binary mixtures with acetonitrile ACN percentages of 40, 45, 50 and 55 vv. The aqueous pKa wwpKa value of the synthesized compound was calculated from the sspKa value using the macroscopic parameters dielectric constant and mole fraction which play an important role in the solvent properties. Obtained wwpKa values were found to be 11.290 and 11.241, respectively. In addition, the degree of ionization of the related compound was calculated using the wwpKa values.

 The ionizationprotonation pKa constant, which is a physicochemical parameter that directly affects the pharmacokinetic properties of a drug such as absorption, distribution, metabolism, and excretion ADME, is currently determined by analytical methods. The effect of pH of the mobile phase on the chromatographic behavior of 1-2- methylbenzonitrile-3-benzylbenzimidazolium bromide 2 which its synthesis, fully characterization, and antiproliferative activity properties were studied previously, and the protonation constant pKa value were determined in this study. The pKa value of compound 2, benzimidazolium salt, was determined by the reverse-phase liquid chromatographic RPLC method at 25 ºC. sspKa values were evaluated using retention time tR in acetonitrile-water binary mixtures with acetonitrile ACN percentages of 40, 45, 50 and 55 vv. The aqueous pKa wwpKa value of the synthesized compound was calculated from the sspKa value using the macroscopic parameters dielectric constant and mole fraction which play an important role in the solvent properties. Obtained wwpKa values were found to be 11.290 and 11.241, respectively. In addition, the degree of ionization of the related compound was calculated using the wwpKa values.

Article Details

Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures

Authors:

İlkay Konçe | Senem Akkoç | Zehra Üstün | Ebru Çubuk Demiralay

Publisher:

Marmara University

Main Topics:

Pharmaceutical Sciences | Pharmaceutical Chemistry

Journal:

Journal of Research in Pharmacy Vol.26 Issue 3, pp.655-662

Document Type:

Article

Publication Date:

6/2025

Document Language:

English

Document ID (Org No.):

2001346862

pISSN:

2630-6344

Benzimidazolium salt

hydro-organic mixture

pKa value

macroscopic parameter

Issues

Article Details

Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures

Authors: İlkay Konçe | Senem Akkoç | Zehra Üstün | Ebru Çubuk Demiralay

Publisher: Marmara University

Main Topics: Pharmaceutical Sciences | Pharmaceutical Chemistry

Journal: Journal of Research in Pharmacy Vol.26 Issue 3, pp.655-662

Document Type: Article

Publication Date: 6/2025

Document Language: English

Document ID (Org No.): 2001346862

pISSN: 2630-6344

Benzimidazolium salt

hydro-organic mixture

pKa value

macroscopic parameter

Issues

Authors:

İlkay Konçe | Senem Akkoç | Zehra Üstün | Ebru Çubuk Demiralay

Publisher:

Marmara University

Main Topics:

Pharmaceutical Sciences | Pharmaceutical Chemistry

Journal:

Journal of Research in Pharmacy Vol.26 Issue 3, pp.655-662

Document Type:

Article

Publication Date:

6/2025

Document Language:

English

Document ID (Org No.):

2001346862

pISSN:

2630-6344