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Solubility of Thiophene-, Furan- and Pyrrole-2-Carboxaldehyde Phenylhydrazone Derivatives in 2.82 mol⋅L−1 Aqueous DMSO at 298.15 K, Inhibition of Lymphoproliferation and Tubulin Polymerization: A Study Based on the Scaled Particle Theory

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Abstract

In this work, the solubilities of nine phenylhydrazone derivatives in water and in 2.82 mol⋅L−1 aqueous DMSO at 298.15 K, expressed on the molar fraction scale, are reported. The estimated value of the standard Gibbs energy for transferring the solute from water to 2.82 mol⋅L−1 DMSO, \(\Delta G^{0}_{\mathrm{W}\rightarrow \mathrm{mix}}\), for each system, indicates that it is a spontaneous process. Some of the phenylhydrazone derivatives inhibited the induction of T lymphocyte proliferation by phytohaemagglutinin (PHA) but only DPCT and NPCF efficiently inhibited Guinea pig brain tubulin polymerization. Scaled Particle Theory (SPT) was used to interpretate solubility and biological activity results. Based on the results we suggested that the difference in the work of cavity creation ΔΔG c, associated with the transfer of the phenylhydrazone derivatives from water to 2.82 mol⋅L−1 aqueous DMSO, is the dominant factor in the magnitude of \(\Delta G^{0}_{\mathrm{W}\rightarrow \mathrm{mix}}\). The later quantity was considered to be an indirect measurement of the hydrophobic character of these derivatives, and it can be used to interpret the biological results.

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Authors and Affiliations

  1. Departamento de Investigación en Tecnología de los Materiales y el Ambiente (DITeMA), Instituto Venezolano de Investigaciones Científicas (IVIC), Avenida 74 con calle 14A, Maracaibo, República Bolivariana de Venezuela

    Ysaías J. Alvarado & Gladys Ferrer-Amado

  2. Laboratorio de Inmunología y Oncología, Departamento de Medicina, Facultad de Medicina, Universidad de Alcalá, Alcalá de Henares, Madrid, España

    Melchor Álvarez-Mon & María Esther San Antonio-Sánchez

  3. Laboratorio de Fisiología Molecular, Centro de Biofísica y Bioquímica, Instituto Venezolano de Investigaciones Científicas (IVIC), Carretera Panamericana Km 11, Apartado 21827, Caracas, 1020-A, República Bolivariana de Venezuela

    Joanna Baricelli, Miguel A. Rocafull & Luz E. Thomas

  4. Laboratorio de Electrónica Molecular(LEM), Departamento de Química, Facultad Experimental de Ciencias, La Universidad del Zulia, Ap. 526, Grano de Oro, Módulo No. 2, Maracaibo, Estado Zulia, República Bolivariana de Venezuela

    Ysaías J. Alvarado, José Caldera-Luzardo, Néstor Cubillán, Victoria Mancilla & José Ojeda-Andara

  5. Laboratorio de Farmacología, Facultad de Medicina, La Universidad del Zulia, Maracaibo, Estado Zulia, República Bolivariana de Venezuela

    Manzur Hassanhi

  6. Laboratorio de Diseño de Fármacos, Departamento de Farmacia, Centro de Química Bio-activa, Universidad Central de las Villas, Santa Clara, Cuba

    Yovani Marrero-Ponce

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  1. Ysaías J. Alvarado
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  2. Melchor Álvarez-Mon
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Alvarado, Y.J., Álvarez-Mon, M., Baricelli, J. et al. Solubility of Thiophene-, Furan- and Pyrrole-2-Carboxaldehyde Phenylhydrazone Derivatives in 2.82 mol⋅L−1 Aqueous DMSO at 298.15 K, Inhibition of Lymphoproliferation and Tubulin Polymerization: A Study Based on the Scaled Particle Theory. J Solution Chem 39, 1099–1112 (2010). https://doi.org/10.1007/s10953-010-9568-z

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