Investigation of Antimicrobial and Anti-Inflammatory Efficacy of Newly Synthesized Pyrogallol-Coumarin Hybrids: <i>In Vitro</i> and <i>In Silico</i> Studies

Investigation of Antimicrobial and Anti-Inflammatory Efficacy of Newly Synthesized Pyrogallol-Coumarin Hybrids: <i>In Vitro</i> and <i>In Silico</i> Studies

<b>Background:</b> The aim of this study is to present the synthesis of two new compounds with promising antimicrobial and anti-inflammatory properties using precursors that contain pyrogallol and coumarin units. <b>Methods:</b> The characterization of the obtained compounds...

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Main Authors: Dušica Simijonović, Edina Avdović, Sandra Jovičić Milić, Marko Antonijević, Dejan Milenković, Katarina Marković, Mirjana Grujović, Danijela Lj. Stojković, Milan Dekić, Zoran Marković
Format: Article
Language:English
Published: MDPI AG 2024-11-01
Series:Pharmaceutics
Subjects:
pyrogallol-coumarin hybrids
anti-inflammatory effect
antimicrobial activity
molecular docking
molecular dynamics simulations
Online Access:https://www.mdpi.com/1999-4923/16/11/1472
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Summary:<b>Background:</b> The aim of this study is to present the synthesis of two new compounds with promising antimicrobial and anti-inflammatory properties using precursors that contain pyrogallol and coumarin units. <b>Methods:</b> The characterization of the obtained compounds (<b>PCHs</b>) (<i>E</i>)-<i>N</i>′-(1-(2,4-dioxochroman-3-ylidene)ethyl)-2,3,4-trihydroxybenzohydrazide (<b>PCH-1</b>) and (<i>E</i>)-<i>N</i>′-(1-(2,4-dioxochroman-3-ylidene)ethyl)-3,4,5-trihydroxybenzohydrazide (<b>PCH-2</b>) was performed using various spectroscopic methods in combination with the DFT methods. To evaluate antimicrobial and anti-inflammatory activities, <b>PCHs</b> were tested against 13 different types of microorganisms and soybean lipoxygenase. To determine the specific mechanisms of anti-LOX activity, molecular docking and molecular dynamics studies were performed. <b>Results:</b> These compounds had the most potent antibacterial activity against the bacterium <i>Proteus mirabilis</i> ATCC 12453, with a MIC value of 31.125 µg/mL. In addition, three standard bacterial species were chosen to evaluate the antibiofilm activity of tested substances. The results showed that the strongest effect of <b>PCH-2</b> was noticed on the biofilm formation of <i>Staphylococcus aureus</i> ATCC 25923 (BIC<sub>50</sub> at 378 µg/mL). The anti-LOX results indicate that <b>PCHs</b> have excellent activity with the IC<sub>50</sub> value for <b>PCH-1</b> = 38.12 μM and <b>PCH-2</b> = 34.12 μM. <b>Conclusions:</b> The obtained in vitro and in silico results confirm the strong inhibitory potential of the investigated compounds.
ISSN:1999-4923

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