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Partition coefficient determination of a series of isoindolines-2-substituted and its correlation with their antiproliferative activity on HeLa cells

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Abstract

In this study, the partition coefficients (Log P) of two series of isoindolines-2-substituted were calculated from the equation obtained for the multilinear correlation between the electronic properties: the highest occupied molecular orbital and the lowest unoccupied molecular orbital energies, and the steric property volume, and the experimental Log P values were determined for some representative isoindolines. Log P values calculated under quantum chemistry were compared with Log P values obtained by the Log P calculation software ALOGPS 2.1 server; the Log P values calculated showed a better correlation with experimental Log P values than those obtained by means of the software. Log P values calculated were also correlated with the antiproliferative activity of some isoindolines-2-substituted determined on HeLa cells, and the correlation obtained shows a quadratic relationship between Log P values calculated and the antiproliferative activity of isoindolines-2-substituted, suggesting a significant effect of Log P values on biological activity of isoindolines.

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Acknowledgments

The authors are grateful to CONACYT for the scholarships—No. 254974 to CRTM, SIP-COFAA/IPN, CONACYT (132353), and ICyTDF (PIRIVE09-9)—for providing thefinancial support, and thank Brenda Trejo for helping in language editing.

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Authors and Affiliations

  1. Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina del Instituto Politécnico Nacional, Plan de San Luis y Díaz Mirón, 11340, México, D.F., México

    Cynthia R. Trejo Muñoz, Elvia Mera Jiménez, José Correa-Basurto & José G. Trujillo Ferrara

  2. Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado, Postal 14-740, 07000, México, D.F., México

    Cynthia R. Trejo Muñoz & Teresa Mancilla Percino

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  1. Cynthia R. Trejo Muñoz
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  2. Teresa Mancilla Percino
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  3. Elvia Mera Jiménez
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  4. José Correa-Basurto
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  5. José G. Trujillo Ferrara
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Correspondence to Teresa Mancilla Percino.

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Trejo Muñoz, C.R., Mancilla Percino, T., Mera Jiménez, E. et al. Partition coefficient determination of a series of isoindolines-2-substituted and its correlation with their antiproliferative activity on HeLa cells. Med Chem Res 22, 4039–4045 (2013). https://doi.org/10.1007/s00044-012-0399-x

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