Experimental and Theoretical Study of Emodin Interaction with Phospholipid Bilayer and Linoleic Acid

Selyutina, Olga Yu.; Kononova, Polina A.; Polyakov, Nikolay E.

doi:10.1007/s00723-020-01233-x

Cited by 7 publications

(5 citation statements)

References 27 publications

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“…Therefore, for another chelator, thiosemicarbazone Dp44mT which is even more lipophilic than anthraquinones (log P = 2.19 [ 49 , 50 ]), it was shown that it cannot penetrate deeply into the lipid bilayer, remaining bound to the surface and staying outside the bilayer for a significant part of the time [ 47 ]. For anthraquinone emodin, it was shown that it is bonded to the surface of the lipid bilayer and oriented parallel to it [ 47 , 51 ].…”

Section: Resultsmentioning

confidence: 99%

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The Interaction of Anthracycline Based Quinone-Chelators with Model Lipid Membranes: 1H NMR and MD Study

2023

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Anthracycline antibiotics, e.g., doxorubicin, daunomycin, and other anthraquinones, are an important family of antitumor agents widely used in chemotherapy, which is currently the principal method for treating many malignancies. Thus, development of improved antitumor drugs with enhanced efficacy remains a high priority. Interaction of anthraquinone-based anticancer drugs with cell membranes attracts significant attention due to its importance in the eventual overcoming of multidrug resistance (MDR). The use of drugs able to accumulate in the cell membrane is one of the possible ways of overcoming MDR. In the present work, the aspects of interaction of anthraquinone 2-phenyl-4-(butylamino)naphtho[2,3-h]quinoline-7,12-dione) (Q1) with a model membrane were studied by means of NMR and molecular dynamics simulations. A fundamental shortcoming of anthracycline antibiotics is their high cardiotoxicity caused by reactive oxygen species (ROS). The important feature of Q1 is its ability to chelate transition metal ions responsible for ROS generation in vivo. In the present study, we have shown that Q1 and its chelating complexes penetrated into the lipid membrane and were located in the hydrophobic part of the bilayer near the bilayer surface. The chelate complex formation of Q1 with metal ions increased its penetration ability. In addition, it was found that the interaction of Q1 with lipid molecules could influence lipid mobility in the bilayer. The obtained results have an impact on the understanding of molecular mechanisms of Q1 biological activity.

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Section: Resultsmentioning

confidence: 99%

“…These results differed from the data obtained earlier for another anthraquinone, emodin. Emodin could form hydrogen bonds with lipid bilayer surface groups and is located predominantly on the membrane surface [ 51 ].…”

Section: Resultsmentioning

confidence: 99%

The Interaction of Anthracycline Based Quinone-Chelators with Model Lipid Membranes: 1H NMR and MD Study

2023

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“…It is known that pKa values of drugs and proteins can be significantly changed in a lipid environment [ 46 , 47 ]. pKa values can also be affected by hydrogen bonding [ 48 ].…”

Section: Discussionmentioning

confidence: 99%

“…A schematic representation of the proposed mechanism of GA interaction with ETM in bilayer is summarized in Figure 10. It is known that pKa values of drugs and proteins can be significantly changed in a lipid environment [46,47]. pKa values can also be affected by hydrogen bonding [48].…”

Section: Discussionmentioning

confidence: 99%

The Interaction of the Transmembrane Domain of SARS-CoV-2 E-Protein with Glycyrrhizic Acid in Lipid Bilayer

2023

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The interaction of the transmembrane domain of SARS-CoV-2 E-protein with glycyrrhizic acid in a model lipid bilayer (small isotropic bicelles) is demonstrated using various NMR techniques. Glycyrrhizic acid (GA) is the main active component of licorice root, and it shows antiviral activity against various enveloped viruses, including coronavirus. It is suggested that GA can influence the stage of fusion between the viral particle and the host cell by incorporating into the membrane. Using NMR spectroscopy, it was shown that the GA molecule penetrates into the lipid bilayer in a protonated state, but localizes on the bilayer surface in a deprotonated state. The transmembrane domain of SARS-CoV-2 E-protein facilitates deeper GA penetration into the hydrophobic region of bicelles at both acidic and neutral pH and promotes the self-association of GA at neutral pH. Phenylalanine residues of the E-protein interact with GA molecules inside the lipid bilayer at neutral pH. Furthermore, GA influences the mobility of the transmembrane domain of SARS-CoV-2 E-protein in the bilayer. These data provide deeper insight into the molecular mechanism of antiviral activity of glycyrrhizic acid.

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“…According to current research, the biological activity of emodin, including its antimicrobial properties, depends on its interactions with components of biological membranes [101,102].…”

Section: Antimicrobial Activitymentioning

confidence: 99%

The Health Benefits of Emodin, a Natural Anthraquinone Derived from Rhubarb—A Summary Update

Stompor-Gorący

2021

IJMS

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Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a naturally occurring anthraquinone derivative found in roots and leaves of various plants, fungi and lichens. For a long time it has been used in traditional Chinese medicine as an active ingredient in herbs. Among other sources, it is isolated from the rhubarb Rheum palmatum or tuber fleece-flower Polygonam multiflorum. Emodin has a wide range of biological activities, including diuretic, antibacterial, antiulcer, anti-inflammatory, anticancer and antinociceptive. According to the most recent studies, emodin acts as an antimalarial and antiallergic agent, and can also reverse resistance to chemotherapy. In the present work the potential therapeutic role of emodin in treatment of inflammatory diseases, cancers and microbial infections is analysed.

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Experimental and Theoretical Study of Emodin Interaction with Phospholipid Bilayer and Linoleic Acid

Cited by 7 publications

References 27 publications

The Interaction of Anthracycline Based Quinone-Chelators with Model Lipid Membranes: 1H NMR and MD Study

The Interaction of Anthracycline Based Quinone-Chelators with Model Lipid Membranes: 1H NMR and MD Study

The Interaction of the Transmembrane Domain of SARS-CoV-2 E-Protein with Glycyrrhizic Acid in Lipid Bilayer

The Health Benefits of Emodin, a Natural Anthraquinone Derived from Rhubarb—A Summary Update

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