Determination of ionization constants (PKA) of β-hydroxy-β-arylalkanoic acids using high-pressure liquid chromatography
Abstract
pKa values of five β-hydroxy-β-arylalkanoic acids and ibuprofen were determined using the RP-HPLC method. Stationary phase was octadecyl modified (C-18) silica gel, and mobile phase was a mixture of methanol and one of nine different buffers (60:40, v/v). wspH values were measured after mixing methanol with an appropriate buffer. The mean retention time of each compound was plotted against wspH of each mobile phase. The inflection point of each sigmoidal curve represented wspK a of the compound. Using wspK a in already known equations for the specific methanol/buffer mixture, wwpK a values were calculated. Obtained pKa values for synthesized compounds were in a narrow range from 3.34-3.81 and pKa for ibuprofen was 4.45. Predicted pKa values for these compounds in SPARC software showed good correlation with experimental pKa values (R2=0.8048).
Keywords:
dissociation constant / anti-inflammatory compounds / ibuprofen / liquid chromatographySource:
Kragujevac Journal of Science, 2018, 40, 103-111Publisher:
- Univerzitet u Kragujevcu - Prirodno-matematički fakultet, Kragujevac
Funding / projects:
- Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-MESTD-Basic Research (BR or ON)-172041)
Collections
Institution/Community
PharmacyTY - JOUR AU - Savić, Jelena AU - Marković, Bojan AU - Vitnik, Vesna AU - Dilber, Sanda PY - 2018 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3032 AB - pKa values of five β-hydroxy-β-arylalkanoic acids and ibuprofen were determined using the RP-HPLC method. Stationary phase was octadecyl modified (C-18) silica gel, and mobile phase was a mixture of methanol and one of nine different buffers (60:40, v/v). wspH values were measured after mixing methanol with an appropriate buffer. The mean retention time of each compound was plotted against wspH of each mobile phase. The inflection point of each sigmoidal curve represented wspK a of the compound. Using wspK a in already known equations for the specific methanol/buffer mixture, wwpK a values were calculated. Obtained pKa values for synthesized compounds were in a narrow range from 3.34-3.81 and pKa for ibuprofen was 4.45. Predicted pKa values for these compounds in SPARC software showed good correlation with experimental pKa values (R2=0.8048). PB - Univerzitet u Kragujevcu - Prirodno-matematički fakultet, Kragujevac T2 - Kragujevac Journal of Science T1 - Determination of ionization constants (PKA) of β-hydroxy-β-arylalkanoic acids using high-pressure liquid chromatography IS - 40 SP - 103 EP - 111 DO - 10.5937/KgJSci1840103S ER -
@article{ author = "Savić, Jelena and Marković, Bojan and Vitnik, Vesna and Dilber, Sanda", year = "2018", abstract = "pKa values of five β-hydroxy-β-arylalkanoic acids and ibuprofen were determined using the RP-HPLC method. Stationary phase was octadecyl modified (C-18) silica gel, and mobile phase was a mixture of methanol and one of nine different buffers (60:40, v/v). wspH values were measured after mixing methanol with an appropriate buffer. The mean retention time of each compound was plotted against wspH of each mobile phase. The inflection point of each sigmoidal curve represented wspK a of the compound. Using wspK a in already known equations for the specific methanol/buffer mixture, wwpK a values were calculated. Obtained pKa values for synthesized compounds were in a narrow range from 3.34-3.81 and pKa for ibuprofen was 4.45. Predicted pKa values for these compounds in SPARC software showed good correlation with experimental pKa values (R2=0.8048).", publisher = "Univerzitet u Kragujevcu - Prirodno-matematički fakultet, Kragujevac", journal = "Kragujevac Journal of Science", title = "Determination of ionization constants (PKA) of β-hydroxy-β-arylalkanoic acids using high-pressure liquid chromatography", number = "40", pages = "103-111", doi = "10.5937/KgJSci1840103S" }
Savić, J., Marković, B., Vitnik, V.,& Dilber, S.. (2018). Determination of ionization constants (PKA) of β-hydroxy-β-arylalkanoic acids using high-pressure liquid chromatography. in Kragujevac Journal of Science Univerzitet u Kragujevcu - Prirodno-matematički fakultet, Kragujevac.(40), 103-111. https://doi.org/10.5937/KgJSci1840103S
Savić J, Marković B, Vitnik V, Dilber S. Determination of ionization constants (PKA) of β-hydroxy-β-arylalkanoic acids using high-pressure liquid chromatography. in Kragujevac Journal of Science. 2018;(40):103-111. doi:10.5937/KgJSci1840103S .
Savić, Jelena, Marković, Bojan, Vitnik, Vesna, Dilber, Sanda, "Determination of ionization constants (PKA) of β-hydroxy-β-arylalkanoic acids using high-pressure liquid chromatography" in Kragujevac Journal of Science, no. 40 (2018):103-111, https://doi.org/10.5937/KgJSci1840103S . .