TY - JOUR
T1 - Solubility of thiophene-, furan- and pyrrole-2-carboxaldehyde phenylhydrazone derivatives in 2.82 mol̇L -1 aqueous DMSO at 298.15 K, inhibition of lymphoproliferation and tubulin polymerization
T2 - A study based on the scaled particle theory
AU - Alvarado, Ysaías J.
AU - Álvarez-Mon, Melchor
AU - Baricelli, Joanna
AU - Caldera-Luzardo, José
AU - Cubillán, Néstor
AU - Ferrer-Amado, Gladys
AU - Hassanhi, Manzur
AU - Marrero-Ponce, Yovani
AU - Mancilla, Victoria
AU - Rocafull, Miguel A.
AU - San Antonio-Sánchez, María Esther
AU - Ojeda-Andara, José
AU - Thomas, Luz E.
N1 - Funding Information:
Acknowledgements The authors thank to the Fondo Nacional de Ciencia, Tecnología e Innovación (FONACIT, Proyecto de apoyo a Grupos No. G-2005000403), Instituto Zuliano de Investigaciones Tecnológ-icas (INZIT), CONDES-LUZ, Avícola La Rosita S. A. and Petroregional del Lago S. A. (PERLA) for partial financial support of this work. The authors thank Dr. Juan Chirinos Colina for his help in the discussion of this manuscript, and the referees for important observations and very helpful comments on the present work.
PY - 2010/10
Y1 - 2010/10
N2 - 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 mol̇L -1 DMSO, Δ G 0 W → 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 mol̇L -1 aqueous DMSO, is the dominant factor in the magnitude of Δ G 0 W → 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.
AB - 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 mol̇L -1 DMSO, Δ G 0 W → 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 mol̇L -1 aqueous DMSO, is the dominant factor in the magnitude of Δ G 0 W → 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.
KW - Lymphoproliferation
KW - Phenylhydrazone derivatives
KW - SPT
KW - Solubility
KW - Tubulin polimerization
UR - https://www.scopus.com/pages/publications/78049295920
U2 - 10.1007/s10953-010-9568-z
DO - 10.1007/s10953-010-9568-z
M3 - Artículo
AN - SCOPUS:78049295920
SN - 0095-9782
VL - 39
SP - 1099
EP - 1112
JO - Journal of Solution Chemistry
JF - Journal of Solution Chemistry
IS - 8
ER -