In Vitro Evaluation of Antibacterial and Antifungal Properties of Some New 1, 3, 4-Oxadiazole Derivatives Containing Phenyl Group

Zarrabi, Nakisa; Souldozi, Ali; SarveAhrabi, Yasin

doi:10.29252/iem.6.3.177

Cited by 4 publications

(4 citation statements)

References 26 publications

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“…Finally, the plates were closed and they were incubated for 24 hours at 37°C for bacterial samples and 48 hours at 35°C for fungal samples. After the time mentioned, the plates were examined for the presence of growth inhibition zone (15).…”

Section: Inhibition Zonementioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

SarveAhrabi

Ahrabi

Souldozi

2021

Avicenna J Clin Microbiol Infect

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Background: New drugs must be designed and synthesized for combating resistant pathogens. In this study, antibacterial and antifungal activities of 4 new derivatives of 1,3,4-oxadiazole were assessed against 8 bacterial and 2 fungal pathogens. Methods: To this end, the cinnamic acid derivatives were dissolved in acetonitrile solvent and N-iso-ciano-imino-triphenyl-phosphorane was added to the above-mentioned solution, followed by applying Petroleum ether and Ethyl acetate as solvent and base. Then, antimicrobial susceptibility tests were used to determine inhibition zone diameter, minimum inhibitory concentration, the minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC) values. Results: The chemical structure of all compounds was characterized with infrared spectra, 1H-NMR, and 13C-NMR. A variety of inhibitory effects were observed by the synthesized compounds. Methoxyphenyl derivative (3c) affected bacterial strains, especially Streptococcus mutans. Other compounds also had antibacterial properties. Additionally, compound 3c showed the greatest effect on fungal samples, especially Aspergillus flavus. Conclusions: In general, our new derivatives of 1,3,4-oxadiazole are able to destroy Gram-positive bacteria. In addition, developing new derivatives of 1,3,4-oxadiazole in future research can improve therapeutic properties. It seems that with the addition of other functional groups and increasing the destructive power of compounds, inhibitory effects on fungal samples can also be observed.

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Section: Inhibition Zonementioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

SarveAhrabi

Ahrabi

Souldozi

2021

Avicenna J Clin Microbiol Infect

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“…Therefore, exploring new antibacterial agents and modern methods to defeat microbial resistance is essential and is considered as a priority in medical studies (9). Research has shown that various synthesized products containing the central ring of 1, 3, 4-oxadiazole can inhibit the growth of gram-negative bacteria in certain concentrations (10). Many studies have investigated the antibacterial properties of different 1, 3, 4-oxadiazole derivatives on E. faecalis strains in order to provide pharmaceutical structures against this bacterium (11)(12)(13)(14).…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Evaluation of Biological Activity of a New Series of Oxadiazole Compounds Against Esp Gene Expression in Enterococcus faecalis Biofilm

2021

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Background: The enterococcal surface protein (Esp) is a high-molecular-weight surface protein of biofilm creating agent in Enterococcus faecalis. Oxadiazoles have a wide range of biological activities. Objective: This research aimed to examine the impact of new oxadiazole derivatives on the expression of Esp, playing an important role in promoting the biofilm formation ability of drug-resistant E. faecalis strains. Method: 1, 3, 4-oxadiazole derivatives were synthesized through a one-step synthesis. E. faecalis strains were collected and isolated from hospitals in Tehran. The antimicrobial properties of the synthesized materials against the isolated strains were investigated. RNA, DNA, and cDNA were extracted, and the relative expression of Esp in E. faecalis isolates was evaluated by real-time PCR. Docking study was performed by AutoDock vina software, and the resulting docking poses were analyzed using Discovery Studio 4.5 Client software. Results: The use of synthesized derivatives changed the Esp expression level in different isolates compared to the control sample. The two compounds containing naphthalene (4f) and methoxyphenyl (4g) caused respectively a 2-fold and a 3-fold decrease in Esp expression compared to the control sample. The compound 4f with the best binding energy among the compounds (-9.2) had the most hydrogen and hydrophobic bonds with the receptor-binding site. Conclusions: 1, 3, 4-oxadiazole derivatives, especially naphthalene and methoxyphenyl, act as inhibitors of bacterial biofilm formation and can be used in the pharmaceutical and biological industries.

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“…isomers of this 5-membered heterocycle, including 1, 2, 4-oxadiazole 1, 2, 3-oxadiazole 1, 2, 5-oxadiazole, and 1, 3, 4-oxadiazole (8). 1, 3, 4-oxadiazoles are of special importance due to their prominent biological properties such as antibacterial (7), antifungal (9), anti-tuberculosis (10) and anti-cancer (11) properties. The introduction of 1, 3, 4-oxadiazole ring to the inhibitors can change their polarity and flexibility, as well as their metabolic stability (12).…”

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confidence: 99%

Evaluation of the Antibacterial and Investigation of the Molecular Docking of New Derivatives of 1, 3, 4-Oxadiazole as Inhibitors of Quorum Sensing System in the Human PathogenPseudomonas Aeruginosa

Ghameshlouei

Ahrabi

Souldozi

et al. 2021

Avicenna J Clin Microbiol Infect

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Background: Oxadiazoles are a group of anti-inflammatory compounds that have a wide range of activity due to their higher efficacy. Pseudomonas aeruginosa is an opportunistic pathogen and a major pathogen of nosocomial infections. This study aimed to evaluate the antibacterial and investigation of the molecular docking of new derivatives of 1, 3, 4-oxadiazole against P. aeruginosa, in vitro & in silico. Materials and Methods: Four new derivatives were synthesized and added to our previous synthetic derivatives of 1, 3, 4-oxadiazole. The antibacterial activity of all derivatives was measured based on three standard species of P. aeruginosa using inhibition zone (IZ) and minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. Then, employing the computational design of the drug by the molecular docking method, the inhibitory effect of synthetic compounds on the LasR regulatory protein of P. aeruginosa quorum sensing system was investigated, which plays an important role in regulating the expression of pathogenic genes in bacteria. Results: The chemical structures of new compounds were characterized by IR spectra and 1H-NMR. A variety of inhibitory effects were observed by the synthesized compounds – compound 4d and 4g, in particular. Also, the inhibitory effect of these two compounds on the LasR regulatory protein under the control of the quorum sensing system in P. aeruginosa was demonstrated by molecular docking. Conclusions: The results of this study showed that the two compounds containing the functional group of naphthalene and fluorophenyl have a significant effect on the inhibition of P. aeruginosa, as well as on the LasR protein of this bacterium.

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In Vitro Evaluation of Antibacterial and Antifungal Properties of Some New 1, 3, 4-Oxadiazole Derivatives Containing Phenyl Group

Cited by 4 publications

References 26 publications

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

Synthesis and Antimicrobial Evaluation of New Series of 1,3,4-Oxadiazole Containing Cinnamic Acid Derivatives

In Vitro and In Silico Evaluation of Biological Activity of a New Series of Oxadiazole Compounds Against Esp Gene Expression in Enterococcus faecalis Biofilm

Evaluation of the Antibacterial and Investigation of the Molecular Docking of New Derivatives of 1, 3, 4-Oxadiazole as Inhibitors of Quorum Sensing System in the Human PathogenPseudomonas Aeruginosa

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