Exploring how structural changes to new Licarin A derivatives effects their bioactive properties against rapid growing mycobacteria and biofilm formation

Alvarenga, Dalila Junqueira; Matias, Laira Maria Faria; Oliveira, Lucas Martins de; Leão, Luiz Paulo Melchior de Oliveira; Hawkes, Jamie Anthony; Raimundo, Breno Vilas Boas; Castro, Lívia de Figueiredo Diniz; Campos, Marli Matiko Anraku de; Siqueira, Fallon dos Santos; Santos, Thiago dos; Carvalho, Diogo Teixeira

doi:10.1016/j.micpath.2020.104203

Cited by 15 publications

(15 citation statements)

References 42 publications

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“…Pharmacological properties of eugenol have been extensively highlighted, especially involving its antibacterial and antifungal properties [17–22] . Our research group has previously demonstrated that synthetic compounds obtained from natural phenylpropanoids, such as eugenol or its analogs (dihydroeugenol and isoeugenol), have important antimicrobial activity and that hybrids obtained from phenylpropanoids and sulfonamide moieties have important antitumor activity [23–30] . Taking advantage of the molecular hybridization strategy (and the well‐established antibacterial potential of eugenol and sulfonamide‐based drugs separately) herein we present for the first time the antibacterial activity of eugenol and dihydroeugenol‐based hybrids bearing the sulfonamide functionality ( Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Azevedo-Barbosa

Vale

Rossi

et al. 2021

Chemistry & Biodiversity

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Using molecular hybridization, specific sulfonamide derivatives of eugenol were synthesized with subtle modifications in the allylic chain of the eugenol subunit (and also in the nature of the substituent group in the sulfonamide aromatic ring) which allowed us to study the influence of structural changes on the antimicrobial potential of the hybrids. Antimicrobial test results showed that most of the synthesized hybrid compounds showed good activity with better results than the parent compounds. Molecular docking studies of the hybrids with the essential bacterial enzyme DHPS showed complexes with low binding energies, suggesting that DHPS could be a possible target for the antibacterial sulfonamide‐eugenol hybrids. Furthermore, most of the final compounds presented similar docking poses to that of the crystallographic ligand sulfamethoxazole. The results obtained allow us to conclude that these are promising compounds for use as new leads in the search for new antibacterial sulfonamides.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Azevedo-Barbosa

Vale

Rossi

et al. 2021

Chemistry & Biodiversity

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“…Licarin A is a neolignan with a dihydrobenzofuran structure that exhibits anti-inflammatory and antibacterial effects [31,32]. The decrease in licarin A content may be due to structural rearrangement and conversion to isoeugenol [33] (Figure 3F).…”

Section: Chemical Transformation Mechanismsmentioning

confidence: 99%

Study on the processing chemistry of Fructus Psoraleae by a combination of untargeted and targeted metabolomics

Dai

Fei

et al. 2022

J of Separation Science

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Fructus Psoralea is widely used to treat osteoporosis and skin inflammatory diseases. Because of the side effects on the liver, renal and cardiovascular systems, it is processed to salt‐processed Fructus Psoraleae to meet the requirements of clinical use. However, the mechanisms involved in the transformation of the chemical components are unclear. In this study, ultra‐high‐performance liquid chromatography quadrupole time‐of‐flight mass spectrometry was used to analyze the chemical profiles of this herbal medicine and the chemical transformation mechanism involved during the salt processing was studied. A total of 83 compounds were identified. Principal component analysis and orthogonal partial least squares discriminate analysis were used to observe the distribution trend of all samples and visualize the difference. Raw and processed Fructus Psoraleae were clearly clustered into two groups. Furthermore, 17 marker compounds were identified as primary contributors to their differences based on t‐test analysis (p < 0.01) and orthogonal partial least squares discriminate analysis (variable importance for the projection > 1). Finally, ultra‐high performance liquid chromatography coupled with triple quadrupole tandem mass spectrometry was used to evaluate the quality of Fructus Psoraleae by simultaneous analysis of 13 components highly related to efficacy. There were variations in the contents of 13 chemicals of Fructus Psoraleae and salt‐processed products. The results of untargeted and targeted metabolomics revealed that salt processing affected the chemical composition of Fructus Psoraleae.

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“…Previous studies have shown that bacteria’s rapid, nonspecific adhesion to the hydrophilic and lipophilic groups on the catheter surface is the initial cause of catheter infection ( Liu et al, 2017 ; Alvarenga et al, 2020 ; Li et al, 2020 ). The effect of bacterial adhesion depends on the microscopic topography and chemical properties of the catheter surface, as well as the characteristics of the bacteria ( Monzillo et al, 2012 ; Liu et al, 2017 ; Yu et al, 2017 ; Faustino et al, 2020 ; Yu et al, 2021 ).…”

Section: Introductionmentioning

confidence: 99%

SiO2 nanosphere coated tough catheter with superhydrophobic surface for improving the antibacteria and hemocompatibility

Zhang

Zhu

et al. 2023

Front. Bioeng. Biotechnol.

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Catheter infection is the most common complication after vascular catheter placement, which seriously threatens the survival of critically ill patients. Although catheters with antibacterial drug coatings have been used, catheter infections have not been effectively resolved. In this research, a SiO2 nanosphere-coated PTFE catheter (PTFE-SiO2) with enhanced antibacterial and excellent mechanical properties was prepared via dopamine as a graft bridge. The microscopic morphology results show that the nanospheres are uniformly dispersed on the surface of the catheter. The physicochemical characterization confirmed that PTFE-SiO2 had reliable bending resistance properties, superhydrophobicity, and cytocompatibility and could inhibit thrombosis. Antibacterial results revealed that PTFE-SiO2 could hinder the reproduction of E. coli and S. aureus. This research demonstrates the hydroxyl-rich materials obtained by hydroboration oxidation have the advantages of better dispersion of functional coatings, indicating their potential for helpful modification of catheters.

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Exploring how structural changes to new Licarin A derivatives effects their bioactive properties against rapid growing mycobacteria and biofilm formation

Cited by 15 publications

References 42 publications

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Study on the processing chemistry of Fructus Psoraleae by a combination of untargeted and targeted metabolomics

SiO2 nanosphere coated tough catheter with superhydrophobic surface for improving the antibacteria and hemocompatibility

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