Salt effects on mixed composition membranes containing an antioxidant lipophilic edaravone derivative: a computational-experimental study.

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  • Additional Information
    • Source:
      Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Electronic Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: MEDLINE
    • Publication Information:
      Original Publication: Cambridge, UK : Royal Society of Chemistry, c2003-
    • Subject Terms:
      Antioxidants*/pharmacology ; Phosphatidylcholines*/chemistry; Calcium Chloride ; Edaravone ; Lipid Bilayers/chemistry ; Molecular Dynamics Simulation ; Salts ; Sodium Chloride ; Water/chemistry
    • Abstract:
      The protection of lipid membranes against oxidation avoids diseases associated with oxidative stress. As a strategy to contrast it, functionalized lipids with antioxidant activity are used to become part of membranes thus protecting them. For this purpose, a lipophilic edaravone derivative has been synthesized, adding a C18 saturated chain to the original structure. The antioxidant activity of C18-Edv has been demonstrated in our previous work. In this study, molecular dynamics simulations have been performed to define the effects of NaCl, MgCl 2 , KCl, and CaCl 2 salts on a palmitoyl-oleoyl- sn -glycero-phosphocholine (POPC) lipid bilayer encapsulating C18-Edv. The results showed how different salts influence POPC lateral diffusion, and the movements of C18-Edv heads, which are antioxidant moieties, were correlated to the ability of C18-Edv molecules to protect membranes. MgCl 2 showed a negative impact leading to C18-Edv clusterization and membrane stretching, while KCl and NaCl showed a moderate influence on the mixed lipid membrane structure. CaCl 2 increased the exposure of the C18-Edv heads to the lipid-water interface, resulting in the salt with a higher propensity to guarantee protection against radicals in the aqueous phase. Finally, C18-Edv-POPC liposomes have been prepared following the simulation conditions, and then an experimental Oxygen Radical Absorbance Capacity (ORAC) assay has been performed to confirm the in silico predicted results.
    • Accession Number:
      0 (Antioxidants)
      0 (Lipid Bilayers)
      0 (Phosphatidylcholines)
      0 (Salts)
      059QF0KO0R (Water)
      451W47IQ8X (Sodium Chloride)
      M4I0D6VV5M (Calcium Chloride)
      S798V6YJRP (Edaravone)
    • Publication Date:
      Date Created: 20220713 Date Completed: 20220729 Latest Revision: 20220804
    • Publication Date:
      20240829
    • Accession Number:
      10.1039/d2ob01143c
    • Accession Number:
      35822625