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Solvent Effects on Protonation Constants of Imatinib in Different Aqueous Solutions of Methanol at T = 298.15 K

  • PHYSICAL CHEMISTRY OF SOLUTIONS
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Abstract

Imatinib (Gleevec) is a drug that is applied to treat cancer. It inhibits the Bcr-Abl tyrosine-kinase and therefore, it can slow growth or result in programmed cell death of certain types of cancer cells. In 2001, the United States approved this drug. The protonation constants of imatinib were determined in mixed solvent of water and methanol containing 40, 50, 60, 70, and 80% (v/v) of methanol, using a combination of spectrophotometric and potentiometric methods at T = 298.15 K and constant ionic strength (0.1 mol dm–3 NaClO4). The obtained protonation constants were analyzed using Kamlet, Abboud, and Taft parameters. In this study, a good linear relationship was obtained between protonation constants (on the logarithmic scale) and dielectric constant (ɛ) of the water-methanol solvent. Dual-parameter correlation of log K versus π* (dipolarity/polarizability) and α (hydrogen-bond donor acidity), as well as versus π* and β (hydrogen-bond acceptor basicity) and multi-parameter π*, α, and β, gave good results for various mole fraction of methanol in methanol-water solvent. Finally, the results are discussed in terms of the solvent effect (increasing of mole fraction of methanol in methanol-water solvent) on the protonation constants.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran

    Tahereh Valizadeh & Farhoush Kiani

  2. Chemistry Department, Shahid Beheshti University, G.C., Evin, Tehran, Iran

    Farrokh Gharib

  3. Department of Physics, Faculty of Science, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran

    Fatemeh Zabihi

  4. Division of Computational Physics, Institute for Computational Science, Ton Duc Thang University, Ho Chi Minh City, Vietnam

    Fardad Koohyar

  5. Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City, Vietnam

    Fardad Koohyar

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  1. Tahereh Valizadeh
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  2. Farhoush Kiani
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  3. Farrokh Gharib
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  4. Fatemeh Zabihi
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  5. Fardad Koohyar
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Correspondence to Fardad Koohyar.

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Tahereh Valizadeh, Kiani, F., Gharib, F. et al. Solvent Effects on Protonation Constants of Imatinib in Different Aqueous Solutions of Methanol at T = 298.15 K. Russ. J. Phys. Chem. 94, 88–94 (2020). https://doi.org/10.1134/S0036024420010331

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  • DOI: https://doi.org/10.1134/S0036024420010331

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