Effect of Xanthone and 1-Hydroxy Xanthone on the Dipole Potential of Lipid Membranes

Cejas, Jimena P.; Rosa, Antonio Sebastián; Pérez, Hugo Alejandro; Alarcón, L. M.; Menéndez, Cintia A.; Appignanesi, Gustavo A.; Disalvo, Anibal; Frías, María A.

doi:10.1016/j.colcom.2018.08.001

Cited by 7 publications

(2 citation statements)

References 44 publications

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“…Xanthone's molecular characteristics make it insoluble in water, as well as having a high solubility to organic solvents. Nonpolluting characters cause most xanthone compounds to have some biological effects that can affect the membrane [ 32 ].…”

Section: Discussionmentioning

confidence: 99%

In Vitro Antiplasmodial, Heme Polymerization, and Cytotoxicity of Hydroxyxanthone Derivatives

Zakiah

Syarif

Mustofa

et al. 2021

Journal of Tropical Medicine

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The previous study showed that xanthone had antiplasmodial activity. Xanthone, with additional hydroxyl groups, was synthesized to increase its antiplasmodial activity. One of the strategies to evaluate a compound that can be developed into an antimalarial drug is by testing its mechanism in inhibiting heme polymerization. In acidic condition, hematin can be polymerized to β-hematin in vitro, which is analog with hemozoin in Plasmodium. This study was conducted to evaluate the antiplasmodial activity of hydroxyxanthone derivative compounds on two strains of Plasmodium falciparum 3D-7 and FCR-3, to assess inhibition of heme polymerization activity and determine the selectivity of hydroxyxanthone derivative compounds. The antiplasmodial activity of each compound was tested on Plasmodium falciparum 3D-7 and FCR-3 with 72 hours incubation period, triplicated in three replications with the microscopic method. The compound that showed the best antiplasmodial activity underwent flow cytometry assay. Heme polymerization inhibition test was performed using the in vitro heme polymerization inhibition activity (HPIA) assay. The antiplasmodial activity and heme polymerization inhibition activity were expressed as the 50% inhibitory concentration (IC50). In vitro cytotoxicity was tested using the MTT assay method on Vero cell lines to determine its selectivity index. The results showed that among 5-hydroxyxanthone derivative compounds, the 1,6,8-trihydroxyxanthone had the best in vitro antiplasmodial activity on both 3D-7 and FCR-3 Plasmodium falciparum strains with IC50 values of 6.10 ± 2.01 and 6.76 ± 2.38 μM, respectively. The 1,6,8-trihydroxyxanthone showed inhibition activity of heme polymerization with IC50 value of 2.854 mM and showed the high selectivity with selectivity index of 502.2–556.54. In conclusion, among 5-hydroxyxanthone derivatives tested, the 1,6,8-trihydroxyxantone showed the best antiplasmodial activity and has heme polymerization inhibition activity and high selectivity.

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Section: Discussionmentioning

confidence: 99%

In Vitro Antiplasmodial, Heme Polymerization, and Cytotoxicity of Hydroxyxanthone Derivatives

Zakiah

Syarif

Mustofa

et al. 2021

Journal of Tropical Medicine

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“…In particular, the carbonyl groups are located in a plane running along the glycerol backbone and, in consequence, they appear to have a special influence on the interfacial properties since their affinity for water can be modified by curvature, phase state, and other topological features. ,, In addition, these groups have been described to participate in the formation of defects upon deformation of the bilayer, giving place to spontaneous or induced curvatures . Fourier transform infrared (FTIR) data report that in each of the sn1 and sn2 chains the carbonyl (CO) groups present hydrated and nonhydrated distributions, as a consequence of fluctuations in CO orientation. , As reported before, its presence may modulate the relative hydration of phosphate and acyl chains .…”

Section: Introductionmentioning

confidence: 99%

Modulation of Interfacial Hydration by Carbonyl Groups in Lipid Membranes

et al. 2020

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The lack of carbonyl groups and the presence of ether bonds give the lipid interphase a different water organization around the phosphate groups that affects the compressibility and electrical properties of lipid membranes. Generalized polarization of 14:0 Diether PC in correlation with FTIR analysis indicates a higher level of polarizability of water molecules in the membrane phase around the phosphate groups both below and above T m . This reorganization of water promotes a different response in compressibility and dipole moment of the interphase which is related to different H-bonding of water molecules with PO and CO groups.

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Dipole moment in medicinal research: green and sustainable approach

Das,

Banik

2024

Green Approaches in Medicinal Chemistry for Sustainable Drug Design

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Effect of Xanthone and 1-Hydroxy Xanthone on the Dipole Potential of Lipid Membranes

Cited by 7 publications

References 44 publications

In Vitro Antiplasmodial, Heme Polymerization, and Cytotoxicity of Hydroxyxanthone Derivatives

In Vitro Antiplasmodial, Heme Polymerization, and Cytotoxicity of Hydroxyxanthone Derivatives

Modulation of Interfacial Hydration by Carbonyl Groups in Lipid Membranes

Dipole moment in medicinal research: green and sustainable approach

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