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Interaction of Phthalates with Lipid Bilayer Membranes

  • Zobia Naz
    Zobia Naz
    Third World Center for Science and Technology, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
    More by Zobia Naz
  • Roshan Shrestha
    Roshan Shrestha
    Molecular Microbiology and Structural Biochemistry (MMSB), UMR 5086 CNRS & University of Lyon, Lyon 69007, France
    More by Roshan Shrestha
  • Syed Tarique Moin
    Syed Tarique Moin
    Third World Center for Science and Technology, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
  • , and 
  • Luca Monticelli*
    Luca Monticelli
    Molecular Microbiology and Structural Biochemistry (MMSB), UMR 5086 CNRS & University of Lyon, Lyon 69007, France
    *Email: [email protected]
    More by Luca Monticelli
Cite this: J. Phys. Chem. B 2022, 126, 25, 4679–4688
Publication Date (Web):June 16, 2022
https://doi.org/10.1021/acs.jpcb.2c02007
Copyright © 2022 American Chemical Society

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    Abstract

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    Phthalates are esters of phthalic acid, widely used as additives in the manufacture of plastics. They are not covalently linked to polymer chains and can easily leach out, disperse in the environment, and get into contact with living organisms. Several short chain phthalates are classified as endocrine disruptors or hormonal active agents, and have also been reported to promote various kinds of cancer. However, the biological effects of longer chain analogues are less well known. Moreover, little is known on the permeation of phthalates and their metabolites through biological membranes and on their effects on the physical properties of membranes. Here we explore the interaction of a group of phthalates and their main metabolites with model biological membranes. We focus on three industrially relevant phthalates, with acyl chains of different sizes, and their monoester metabolites. We use molecular dynamics simulations to predict the distribution in model membranes, as well as permeabilities and effects on the structural, dynamic, and elastic properties of the membranes. We find that alterations of membrane properties are significant and only weakly affected by the size of acyl chains, suggesting that modifications of molecular size may not be sufficient to reduce the impact of this class of molecules on the environment and health.

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    Cited By

    This article is cited by 1 publications.

    1. Yanbo Sun, Jia Li, Yan Du, Hongyu Niu, Chuang Li, Changhai Liang. Ultrauniform Ru Nanoclusters as Efficient Hydrogenation Catalysts for Phthalates. Industrial & Engineering Chemistry Research 2023, 62 (18) , 6897-6907. https://doi.org/10.1021/acs.iecr.3c00130

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