The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

Araújo, Hallysson Douglas Andrade de; Silva, Hianna Arely Milca Fagundes; Júnior, José Guedes da Silva; Albuquerque, Mônica Camelo Pessôa de Azevedo; Coelho, Luana Cassandra Breitenbach Barroso; Aires, André de Lima

doi:10.3390/molecules26195995

Cited by 13 publications

(4 citation statements)

References 61 publications

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“…Furthermore, increasing the UA concentration leads to lower zeta potential values ( Figure 5 a) measured in PBS, which is in accordance with previously published literature [ 23 ] and could be justified by the hydrophobicity of UA [ 24 ]. However, the MNP@5UA_CP sample shows a similar zeta potential value as the pristine sample, which is explained by the significantly reduced loading, i.e., 0.58%.…”

Section: Resultssupporting

confidence: 91%

Usnic Acid-Loaded Magnetite Nanoparticles—A Comparative Study between Synthesis Methods

Chircov,

Bîrcă,

Dănciulescu

et al. 2023

Molecules

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Since cancer is a continuously increasing concern for the general population, more efficient treatment alternatives ought to be developed. In this regard, a promising direction is represented by the use of magnetite nanoparticles (MNPs) to act both as a nanocarrier for the targeted release of antitumoral drugs and as hyperthermia agents. Thus, the present study focused on improving the control upon the outcome properties of MNPs by using two synthesis methods, namely the co-precipitation and microwave-assisted hydrothermal method, for the incorporation of usnic acid (UA), a natural lichen-derived metabolite with proven anticancer activity. The obtained UA-loaded MNPs were thoroughly characterized regarding their morpho-structural and physicochemical properties through X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FT-IR), dynamic light scattering (DLS) and zeta potential, scanning electron microscopy (SEM), and vibrating sample magnetometry (VSM). Results demonstrated the formation of magnetite as the unique mineralogical phase through both types of synthesis, with increased uniformity regarding the drug loading efficiency, size, stability, and magnetic properties obtained through the microwave-assisted hydrothermal method. Furthermore, the cytotoxicity of the nanostructures against the HEK 293T cell line was investigated through the XTT assay, which further proved their potential for anticancer treatment applications.

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Section: Resultssupporting

confidence: 91%

Usnic Acid-Loaded Magnetite Nanoparticles—A Comparative Study between Synthesis Methods

Chircov,

Bîrcă,

Dănciulescu

et al. 2023

Molecules

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“…In an attempt to study the possible mechanism of antiviral action, which was revealed for a number of compounds in experiments on live virus, we performed molecular modeling of the interaction of compounds with the active site of the main protease of SARS-CoV-2. Given the known reactivity of usnic acid [ 54 , 55 ], it was assumed that covalent binding of the SH-group of the catalytic amino acid residue Cys145 is unlikely. Therefore, non-covalent docking to the active site of the main protease was performed.…”

Section: Resultsmentioning

confidence: 99%

(+)-Usnic Acid and Its Derivatives as Inhibitors of a Wide Spectrum of SARS-CoV-2 Viruses

Filimonov

Yarovaya

Zaykovskaya

et al. 2022

Viruses

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In order to test the antiviral activity, a series of usnic acid derivatives were synthesized, including new, previously undescribed compounds. The activity of the derivatives against three strains of SARS-CoV-2 virus was studied. To understand the mechanism of antiviral action, the inhibitory activity of the main protease of SARS-CoV-2 virus was studied using the developed model as well as the antiviral activity against the pseudoviral system with glycoprotein S of SARS-CoV-2 virus on its surface. It was shown that usnic acid exhibits activity against three strains of SARS-CoV-2 virus: Wuhan, Delta, and Omicron. Compounds 10 and 13 also showed high activity against the three strains. The performed biological studies and molecular modeling allowed us to assume that the derivatives of usnic acid bind in the N-terminal domain of the surface glycoprotein S at the binding site of the hemoglobin decay metabolite.

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“…Because of the lack of available GA amount, we were not able to find lethal and semi-lethal concentrations of this compound, which seems to be a limitation of our study. Due to the absence of prior in vivo studies involving GA, we opted to utilize a similar dosage that has been employed for other secondary metabolites, such as atranorin [ 38 , 39 ], or usnic acid [ 40 ]. Accordingly, GA was administered orally at a concentration of 10 mg/kg body weight on a daily basis for a duration of one month, as outlined in the Materials and Methods section.…”

Section: Discussionmentioning

confidence: 99%

The First In Vivo Study Shows That Gyrophoric Acid Changes Behavior of Healthy Laboratory Rats

Simko,

Leskanicova,

Suvakova-Nunhart

et al. 2024

IJMS

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Gyrophoric acid (GA), a lichen secondary metabolite, has attracted more attention during the last years because of its potential biological effects. Until now, its effect in vivo has not yet been demonstrated. The aim of our study was to evaluate the basic physicochemical and pharmacokinetic properties of GA, which are directly associated with its biological activities. The stability of the GA in various pH was assessed by conducting repeated UV-VIS spectral measurements. Microsomal stability in rat liver microsomes was performed using Ultra-Performance LC/MS. Binding to human serum albumin (HSA) was assessed using synchronous fluorescence spectra, and molecular docking analysis was used to reveal the binding site of GA to HSA. In the in vivo experiment, 24 Sprague-Dawley rats (Velaz, Únetice, Czech Republic) were used. The animals were divided as follows. The first group (n = 6) included healthy males as control intact rats (♂INT), and the second group (n = 6) included healthy females as controls (♀INT). Groups three and four (♂GA/n = 6 and ♀GA/n = 6) consisted of animals with daily administered GA (10 mg/kg body weight) in an ethanol-water solution per os for a one-month period. We found that GA remained stable under various pH and temperature conditions. It bonded to human serum albumin with the binding constant 1.788 × 106 dm3mol−1 to reach the target tissue via this mechanism. In vivo, GA did not influence body mass gain, food, or fluid intake during the experiment. No liver toxicity was observed. However, GA increased the rearing frequency in behavioral tests (p < 0.01) and center crossings in the elevated plus-maze (p < 0.01 and p < 0.001, respectively). In addition, the time spent in the open arm was prolonged (p < 0.01 and p < 0.001, respectively). Notably, GA was able to pass through the blood–brain barrier, indicating its ability to permeate into the brain and to stimulate neurogenesis in the hilus and subgranular zone of the hippocampus. These observations highlight the potential role of GA in influencing brain function and neurogenesis.

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The Natural Compound Hydrophobic Usnic Acid and Hydrophilic Potassium Usnate Derivative: Applications and Comparisons

Cited by 13 publications

References 61 publications

Usnic Acid-Loaded Magnetite Nanoparticles—A Comparative Study between Synthesis Methods

Usnic Acid-Loaded Magnetite Nanoparticles—A Comparative Study between Synthesis Methods

(+)-Usnic Acid and Its Derivatives as Inhibitors of a Wide Spectrum of SARS-CoV-2 Viruses

The First In Vivo Study Shows That Gyrophoric Acid Changes Behavior of Healthy Laboratory Rats

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