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Charge-Transfer Reaction of Chloranilic Acid with Crizotinib: Spectrophotometric Study, Computational Modeling and Use in Development of Microwell Assay for Crizotinib

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Abstract

The reaction of chloranilic acid (CA) with crizotinib (CZT); a novel drug used for treatment of non-small cell lung cancer) was investigated in different solvents of varying dielectric constants and polarity indices. The reaction resulted in the formation of a violet-colored product. Spectrophotometric investigations confirmed that the reaction proceeded through CT complex formation. The molar absorptivity of the CT complex produced was found to be linearly correlated with the dielectric constant and polarity index of the solvent. The association constant of the CA–CZT CT complex and the stoichiometric ratio of CA:CZT were determined. Computational molecular modeling for the CT complex between CA and CZT was conducted, the sites of interaction on CZT molecule were determined, and the mechanism of the reaction was postulated. The reaction was employed as a basis for the development of a novel 96-microwell assay for CZT. In this assay, the absorbances of the CA–CZT CT complex solutions were measured by a microwell-plate absorbance reader. The CZT limits of detection and quantitation are 8.8 and 26.4 μg·mL−1, respectively. The assay was successfully applied to the analysis of CZT in its bulk form and capsules with good accuracy and precision. The assay described herein has great practical value as it has high throughput and consumes minimum volume of organic solvent, thus it reduces the exposures of the analysts to the toxic effects of organic solvents, and significantly reduces the analysis cost.

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Acknowledgments

The authors would like to extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the research group Project No. RGP-VPP-225.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia

    Ibrahim A. Darwish & Nasr Y. Khalil

  2. Department of Pharmaceutical Chemistry, College of Pharmacy, Women Student-Medical Studies & Sciences Sections, King Saud University, P.O. Box 11495, Riyadh, 22452, Saudi Arabia

    Jamilah M. Alshehri & Nourah Z. Alzoman

  3. Department of Medicinal Chemistry, Faculty of Pharmacy, Assiut University, Assiut, 71526, Egypt

    Hamdy M. Abdel-Rahman

Authors
  1. Ibrahim A. Darwish
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  2. Jamilah M. Alshehri
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  3. Nourah Z. Alzoman
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  4. Nasr Y. Khalil
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  5. Hamdy M. Abdel-Rahman
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Correspondence to Ibrahim A. Darwish.

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Darwish, I.A., Alshehri, J.M., Alzoman, N.Z. et al. Charge-Transfer Reaction of Chloranilic Acid with Crizotinib: Spectrophotometric Study, Computational Modeling and Use in Development of Microwell Assay for Crizotinib. J Solution Chem 43, 1282–1295 (2014). https://doi.org/10.1007/s10953-014-0203-2

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