Browsing by Subject "Catechin"

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    3,4,5-Trimethoxybenzoate of Catechin, an Anticarcinogenic Semisynthetic Catechin, Modulates the Physical Properties of Anionic Phospholipid Membranes
    (MDPI, 2022-05-03) Aranda, Elisa; Teruel, José A.; Antonio Ortiz, Antonio; Pérez-Cárceles, María Dolores; Rodríguez-López, José N.; Aranda, Francisco J.; Bioquímica y Biología Molecular A
    3,4,5-Trimethoxybenzoate of catechin (TMBC) is a semisynthetic catechin which shows strong antiproliferative activity against malignant melanoma cells. The amphiphilic nature of the molecule suggests that the membrane could be a potential site of action, hence the study of its inter action with lipid bilayers is mandatory in order to gain information on the effect of the catechin on the membrane properties and dynamics. Anionic phospholipids, though being minor components of the membrane, possess singular physical and biochemical properties that make them physiologically essential. Utilizing phosphatidylserine biomimetic membranes, we study the interaction between the catechin and anionic bilayers, bringing together a variety of experimental techniques and molecular dynamics simulation. The experimental data suggest that the molecule is embedded into the phos phatidylserine bilayers, where it perturbs the thermotropic gel to liquid crystalline phase transition. In the gel phase, the catechin promotes the formation of interdigitation, and in the liquid crystalline phase, it decreases the bilayer thickness and increases the hydrogen bonding pattern of the interfacial region of the bilayer. The simulation data agree with the experimental ones and indicate that the molecule is located in the interior of the anionic bilayer as monomer and small clusters reaching the carbonyl region of the phospholipid, where it also disturbs the intermolecular hydrogen bonding between neighboring lipids. Our observations suggest that the catechin incorporates well into phos phatidylserine bilayers, where it produces structural changes that could affect the functioning of the membrane
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    Anticarcinogenic trimethoxybenzoate of catechin stabilizes the liquid crystalline bilayer phase in phosphatidylethanolamine membranes
    (Elsevier, 2022-11-11) Aranda, Elisa; Teruel, José A.; Ortiz, Antonio; Pérez-Cárceles, María Dolores; Rodríguez-López, José N.; Aranda, Francisco J.; Bioquímica y Biología Molecular A
    The anticarcinogenic properties of catechins stand out among the great variety of biological actions attributed to these compounds. The capacity of catechins to interact with lipids and their participation in membrane related processes points out to the membrane as their potential site of action. Phosphatidylethanolamine is an abundant phospholipid in mammalian membranes that has tendency to form non lamellar phases, it is associated with important cellular processes, and it has been related to cancer. In order to shed light into the molecular effect of the anticarcinogenic 3,4,5- trimethoxybenzoate of catechin (TMBC) on lipid polymorphism and membrane structure and dynamics, we present a combined experimental and computational study of the interaction between this semisyn thetic catechin and biomimetic membranes composed of unsaturated phosphatidylethanolamine. Our experimental evidence reveals that TMBC is readily incorporated into unsaturated phos phatidylethanolamine system where it is able to shift the gel to liquid crystalline phase transition tem perature to lower values, decreasing the cooperativity and the enthalpy change of the transition. The presence of TMBC is able to promote the formation of gel phase immiscibility and to block the formation of the inverted hexagonal phase. In the bilayer liquid crystalline phase, the catechin decreases the inter lamellar repeat distance, it increases the fluidity of the membrane, and it alters the hydrogen bond pat tern of the interfacial region of the bilayer. Our molecular dynamics results concur with the experimental data and locate TMBC forming different domains near the interfacial region of the bilayer where it mod ifies the lateral pressure profile of the membrane leading to a stabilization of the bilayer in the liquid crystalline phase and to a potential alteration of the function of the membrane
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    Effects of a Semisynthetic Catechin on Phosphatidylglycerol Membranes: A Mixed Experimental and Simulation Study
    (MDPI, 2023-01-03) Aranda, Elisa; Teruel, José A.; Ortiz, Antonio; Pérez-Cárceles, María Dolores; Rodríguez-López, José N.; Aranda, Francisco J.; Bioquímica y Biología Molecular A
    Catechins have been shown to display a great variety of biological activities, prominent among them are their chemo preventive and chemotherapeutic properties against several types of cancer. The amphiphilic nature of catechins points to the membrane as a potential target for their actions. 3,4,5-Trimethoxybenzoate of catechin (TMBC) is a modified structural analog of catechin that shows significant antiproliferative activity against melanoma and breast cancer cells. Phosphatidylglycerol is an anionic membrane phospholipid with important physical and biochemical characteristics that make it biologically relevant. In addition, phosphatidylglycerol is a preeminent component of bacterial membranes. Using biomimetic membranes, we examined the effects of TMBC on the structural and dynamic properties of phosphatidylglycerol bilayers by means of biophysical techniques such as differential scanning calorimetry, X-ray diffraction and infrared spectroscopy, together with an analysis through molecular dynamics simulation. We found that TMBC perturbs the thermotropic gel to liquid-crystalline phase transition and promotes immiscibility in both phospholipid phases. The modified catechin decreases the thickness of the bilayer and is able to form hydrogen bonds with the carbonyl groups of the phospholipid. Experimental data support the simulated data that locate TMBC as mostly forming clusters in the middle region of each monolayer approaching the carbonyl moiety of the phospholipid. The presence of TMBC modifies the structural and dynamic properties of the phosphatidylglycerol bilayer. The decrease in membrane thickness and the change of the hydrogen bonding pattern in the interfacial region of the bilayer elicited by the catechin might contribute to the alteration of the events taking place in the membrane and might help to understand the mechanism of action of the diverse effects displayed by catechins.