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3D-QSAR modeling of maximum steady-state fluxes of some substituted benzenes and quinolone derivatives through polydimethylsiloxane membrane

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Abstract

The maximum steady-state flux of 79 compounds (substituted benzenes, and quinolones and their derivatives) with a wide range of polarity through a PDMS membrane was predicted using a comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) methods. Moreover, the contribution of partial atomic charge to mass transport phenomena was further verified by the correlation of atomic charge to apparent permeability through polydimethylsiloxane (PDMS) membranes. The obtained results indicated superiority of CoMSIA model over CoMFA model. The best CoMSIA model is developed based on the combination of electrostatic and hydrophobic and H-bond acceptor fields (CoMSIA-EHA). The contour maps of electrostatic and hydrophobic and H-bond acceptor fields of CoMSIA model provide an interpretable and logical relationship between chemicals structure and their fluxes, which give useful insights for designing new compounds with higher penetration through the membranes.

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Authors and Affiliations

  1. Chemometics Laboratory, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran

    Seyedeh Mozhgan Behgozin & Mohammad Hossein Fatemi

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  1. Seyedeh Mozhgan Behgozin
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  2. Mohammad Hossein Fatemi
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Correspondence to Mohammad Hossein Fatemi.

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Behgozin, S.M., Fatemi, M.H. 3D-QSAR modeling of maximum steady-state fluxes of some substituted benzenes and quinolone derivatives through polydimethylsiloxane membrane. J IRAN CHEM SOC 15, 1293–1300 (2018). https://doi.org/10.1007/s13738-018-1328-9

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