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

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

Abstract

The ionization/protonation (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% (v/v). 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.

Keywords

References

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Details

Primary Language

English

Subjects

Pharmaceutical Sciences, Pharmaceutical Chemistry

Journal Section

Research Article

Authors

İlkay Konçe
0000-0003-3542-7090
Türkiye

Senem Akkoç
0000-0002-1260-9425
Türkiye

Zehra Üstün
0000-0002-7061-6279
Türkiye

Ebru Çubuk Demiralay ^*
0000-0002-6270-7509
Türkiye

Publication Date

June 28, 2025

Submission Date

October 19, 2021

Acceptance Date

February 23, 2022

Published in Issue

Year 2022 Volume: 26 Number: 3

IZ

https://izlik.org/JA95MR77ZW

Cite

RIS / Bibtex

APA

Konçe, İ., Akkoç, S., Üstün, Z., & Çubuk Demiralay, E. (2025). Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures. Journal of Research in Pharmacy, 26(3), 655-662. https://izlik.org/JA95MR77ZW

AMA

1.Konçe İ, Akkoç S, Üstün Z, Çubuk Demiralay E. Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures. J. Res. Pharm. 2025;26(3):655-662. https://izlik.org/JA95MR77ZW

Chicago

Konçe, İlkay, Senem Akkoç, Zehra Üstün, and Ebru Çubuk Demiralay. 2025. “Liquid Chromatographic Determination of PKa Value of 1- (2-Methylbenzonitrile)-3-Benzylbenzimidazolium Bromide As a Drug Candidate in Acetonitrile-Water Binary Mixtures”. Journal of Research in Pharmacy 26 (3): 655-62. https://izlik.org/JA95MR77ZW.

EndNote

Konçe İ, Akkoç S, Üstün Z, Çubuk Demiralay E (June 1, 2025) Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures. Journal of Research in Pharmacy 26 3 655–662.

IEEE

[1]İ. Konçe, S. Akkoç, Z. Üstün, and E. Çubuk Demiralay, “Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures”, J. Res. Pharm., vol. 26, no. 3, pp. 655–662, June 2025, [Online]. Available: https://izlik.org/JA95MR77ZW

ISNAD

Konçe, İlkay - Akkoç, Senem - Üstün, Zehra - Çubuk Demiralay, Ebru. “Liquid Chromatographic Determination of PKa Value of 1- (2-Methylbenzonitrile)-3-Benzylbenzimidazolium Bromide As a Drug Candidate in Acetonitrile-Water Binary Mixtures”. Journal of Research in Pharmacy 26/3 (June 1, 2025): 655-662. https://izlik.org/JA95MR77ZW.

JAMA

1.Konçe İ, Akkoç S, Üstün Z, Çubuk Demiralay E. Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures. J. Res. Pharm. 2025;26:655–662.

MLA

Konçe, İlkay, et al. “Liquid Chromatographic Determination of PKa Value of 1- (2-Methylbenzonitrile)-3-Benzylbenzimidazolium Bromide As a Drug Candidate in Acetonitrile-Water Binary Mixtures”. Journal of Research in Pharmacy, vol. 26, no. 3, June 2025, pp. 655-62, https://izlik.org/JA95MR77ZW.

Vancouver

1.İlkay Konçe, Senem Akkoç, Zehra Üstün, Ebru Çubuk Demiralay. Liquid Chromatographic Determination of pKa Value of 1- (2-methylbenzonitrile)-3-benzylbenzimidazolium bromide as a Drug Candidate in Acetonitrile-Water Binary Mixtures. J. Res. Pharm. [Internet]. 2025 Jun. 1;26(3):655-62. Available from: https://izlik.org/JA95MR77ZW