Solvent effects on pKa values of some anticancer agents in acetonitrile - Water binary mixtures


ŞANLI S., ALTUN Y., Guven G.

Journal of Chemical and Engineering Data, vol.59, no.12, pp.4015-4020, 2014 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 12
  • Publication Date: 2014
  • Doi Number: 10.1021/je500595w
  • Journal Name: Journal of Chemical and Engineering Data
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4015-4020
  • Uşak University Affiliated: Yes

Abstract

The solute-solvent interactions of four anticancer drugs, daunorubicin, doxorubicin, vincristine sulfate, and 6-thioguanine, have been studied in acetonitrile-water mixtures up to 50 % acetonitrile by volume fraction using a UV/pH titration method. The acidity constants have been calculated with the STAR (stability constants by absorbance readings) program. The interactions between the four anticancer drugs and the solvent studied, acetonitrile-water mixtures, was identified using the microscopic parameters (Kamlet and Taft's solvatochromic parameters: α, β, and π∗). The Kamlet and Taft general equation for pKa1 and pKa2 values of 6-thioguanine, doxorubicin, daunorubicin, and vincristine sulfate was reduced to two terms (the independent term and the hydrogen-bond-donating ability, α) or three terms (the independent term, polarity/polarizability, π∗, and the hydrogen-bond-donating ability, α) using linear regression analysis in acetonitrile-water mixtures. The Kamlet and Taft equations can be used to predict the acidity constants of daunorubicin, doxorubicin, vincristine sulfate, and 6-thioguanine at any acetonitrile composition, which would be helpful in practical work during chromatographic method development. (Chemical Equation Presented).