Experimental and Theoretical Study of Emodin Interaction with Phospholipid Bilayer and Linoleic Acid
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Applied Magnetic Resonance
ORIGINAL PAPER
Experimental and Theoretical Study of Emodin Interaction with Phospholipid Bilayer and Linoleic Acid O. Yu. Selyutina1,2 · P. A. Kononova1 · N. E. Polyakov1,2 Received: 30 June 2020 / Revised: 23 July 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract 1 H NMR technique, optical spectrophotometry and molecular dynamics simulations have been applied to study the effect of the lipid composition on emodin interaction with the lipid bilayer. The special attention was paid on the presence of the unsaturated fatty acid linoleic acid in the lipid bilayer. Emodin (1,3,8‐trihydroxy‐6‐ methylanthraquinone) is a natural anthraquinone which shows a wide spectrum of biological activity including anticancer, anti-inflammatory, antiviral, antibacterial, neuroprotective and others. It is assumed that the location of emodin in the lipid membrane is important for its biological activity. It was demonstrated that in the presence of linoleic acid, the pKa value of the emodin significantly increases. Molecular dynamics simulations show that these changes can be associated with the interaction of emodin and linoleic acid inside the bilayer. Also, it was shown that the order of deprotonation positions in the POPC bilayer differs from the deprotonation order in aqueous solution.
1 Introduction Drug–membrane interactions are widely studied nowadays for several reasons. Firstly, a lot of drugs has intracellular targets and they must overcome a membrane barrier to reach this target. On the other hand, lipids participate in the interaction of proteins with the cell barrier and also regulate the distribution and localization of peripheral proteins to membrane domains. Also, changes in the lipid structure are often related to the development of numerous diseases [1]. Emodin (1,3,8‐trihydroxy‐6‐methylanthraquinone, Fig. 1) is a natural anthraquinone contained in some plants including Rheum palmatum, Polygonum cuspidatum or Aloe vera. These herbs are widely used in traditional medicine in different countries [2]. Emodin has * O. Yu. Selyutina [email protected] 1
Institute of Chemical Kinetics and Combustion, Institutskaya St., 3, 630090 Novosibirsk, Russia
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Institute of Solid State Chemistry and Mechanochemistry, Kutateladze St., 18, 630128 Novosibirsk, Russia
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Fig. 1 The chemical structure of emodin
a wide spectrum of biological activities. A number of researches are focused on its anti-inflammatory, anticancer, antiviral, antibacterial, anti‐allergic, anti‐osteoporotic, anti‐diabetic, immunosuppressive, neuroprotective and hepatoprotective activities [2, 3]. The anticancer activity of anthraquinones, including emodin, is related to its association with DNA duplex or with generation of reactive oxygen species, which could damage cell membranes [4]. Membrane-related effects of emodin is the subject of several papers [5, 6]. Because of the its hydrophobicity, emodin interaction with cell membranes may play an im
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