Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives

Rezende, Celso O.; Oliveira, Larissa Albuquerque; Oliveira, Bruno Assis de; Almeida, Camila G. de; Ferreira, Bianca Silva; Hyaric, Mireille Le; Carvalho, Guilherme S. L.; Lourenço, Maria Cristina S.; Batista, Michel; Marchini, Fabrício Klerynton; Silva, Vânia L.; Diniz, Cláudio Galuppo; Almeida, Mauro Vieira de

doi:10.1111/cbdd.12498

Cited by 14 publications

(7 citation statements)

References 31 publications

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“…GC-MS analysis of active leads disclosed the presence of quinic acid as one of its major compounds. Whereas, amides of QA have been reported for their antimicrobial activity against both Gram-positive and Gram-negative bacterial pathogens ( Rezende et al, 2015 ). Additionally, QA with other phenolic acids have shown significant antiviral, antibacterial, antifungal activity and the non-toxic nature of QA was confirmed by Madin-Darby bovine kidney and Vero cell lines ( Özçelik et al, 2011 ).…”

Section: Discussionmentioning

confidence: 99%

“…Quinic acid is a cyclic polyol, commonly extracted from different medicinal plants including Eucalyptus globules, Hymenocrater calycinus, Tara spinosa, Ageratina adenophora, Urtica dioica , coffee beans and barks of Cinchona genus ( Gohari et al, 2010 ; Zhang et al, 2013 ). The compound has many advantages such as solubility in water, stability at room temperature, less cytotoxicity and also non-degradable nature in gut enzymes produced by bacteria ( Rezende et al, 2015 ). Similarly, undecenoic acid, also known as undecylenic acid naturally occurs in human body (sweat), synthetically derived from castor oil.…”

Section: Introductionmentioning

confidence: 99%

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Synergistic Effect of Quinic Acid Derived From Syzygium cumini and Undecanoic Acid Against Candida spp. Biofilm and Virulence

et al. 2018

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In recent decades, fungal infections have incredibly increased with Candida genus as the major cause of morbidity and mortality in hospitalized and immunocompromised patients. Most of the Candida species are proficient in biofilm formation on implanted medical devices as well as human tissues. Biofilm related Candida infections are very difficult to treat using common antifungal agents owing to their increased drug resistance. To address these issues, the present study investigated the antibiofilm and antivirulent properties of Syzygium cumini derived quinic acid in combination with known antifungal compound undecanoic acid. Initially, antibiofilm potential of S. cumini leaf extract was assessed and the active principles were identified through gas chromatography and mass spectrometry analysis. Among the compounds identified, quinic acid was one of the major compounds. The interaction between quinic acid and undecanoic acid was found to be synergistic in the Fractional inhibitory concentration index (≤0.5). Results of in vitro assays and gene expression analysis suggested that the synergistic combinations of quinic acid and undecanoic acid significantly inhibited virulence traits of Candida spp. such as the biofilm formation, yeast-to-hyphal transition, extracellular polymeric substances production, filamentation, secreted hydrolases production and ergosterol biosynthesis. In addition, result of in vivo studies using Caenorhabditis elegans demonstrated the non-toxic nature of QA-UDA combination and antivirulence effect against Candida spp. For the first time, synergistic antivirulence ability of quinic acid and undecanoic acid was explored against Candida spp. Thus, results obtained from the present study suggest that combination of phytochemicals might be used an alternate therapeutic strategy for the prevention and treatment of biofilm associated Candida infection.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synergistic Effect of Quinic Acid Derived From Syzygium cumini and Undecanoic Acid Against Candida spp. Biofilm and Virulence

et al. 2018

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“…Ten ( 1 – 10 ) amides of quinic acid derivatives were synthesized as previously described [ 43 ]. Compounds were prepared both with and without lipophilic chains to investigate the influence of lipophilicity on antiviral activity (Table 1 ).…”

Section: Methodsmentioning

confidence: 99%

Quinic acid derivatives inhibit dengue virus replication in vitro

Zanello

Koishi

Júnior

et al. 2015

Virol J

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BackgroundDengue is the most prevalent arboviral disease in tropical and sub-tropical areas of the world. The incidence of infection is estimated to be 390 million cases and 25,000 deaths per year. Despite these numbers, neither a specific treatment nor a preventive vaccine is available to protect people living in areas of high risk.ResultsWith the aim of seeking a treatment that can mitigate dengue infection, we demonstrated that the quinic acid derivatives known as compound 2 and compound 10 were effective against all four dengue virus serotypes and safe for use in a human hepatoma cell line (Huh7.5). Both compounds were non-virucidal to dengue virus particles and did not interfere with early steps of the dengue virus life cycle, including binding and internalization. Experiments using a replicon system demonstrated that compounds 2 and 10 impaired dengue virus replication in Huh7.5 cells. Additionally, the anti-dengue virus effects of the quinic acid derivatives were preserved in human peripheral blood mononuclear cells.ConclusionsTaken together, these data suggest that quinic acid derivatives represent a novel chemical class of active compounds that could be used to combat dengue virus infection.Electronic supplementary materialThe online version of this article (doi:10.1186/s12985-015-0443-9) contains supplementary material, which is available to authorized users.

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“…Some natural products, such as macrolides and peptides, break the filter thresholds used in Lipinski's rule [95] . Therefore, attempts have been made to improve the performance of antibiotics by tuning their molecular charge, [96] lipophilicity, [97] and configurations [98] …”

Section: Comparisons Between Antibiotics and Antimicrobial Nanomaterialsmentioning

confidence: 99%

Antibacterial Nanomaterials: Mechanisms, Impacts on Antimicrobial Resistance and Design Principles

et al. 2023

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Antimicrobial resistance (AMR) is one of the biggest threats to the environment and health. AMR rapidly invalidates conventional antibiotics, and antimicrobial nanomaterials have been increasingly explored as alternatives. Interestingly, several antimicrobial nanomaterials show AMR‐independent antimicrobial effects without detectable new resistance and have therefore been suggested to prevent AMR evolution. In contrast, some are found to trigger the evolution of AMR. Given these seemingly conflicting findings, a timely discussion of the two faces of antimicrobial nanomaterials is urgently needed. This review systematically compares the killing mechanisms and structure‐activity relationships of antibiotics and antimicrobial nanomaterials. We then focus on nano‐microbe interactions to elucidate the impacts of molecular initiating events on AMR evolution. Finally, we provide an outlook on future antimicrobial nanomaterials and propose design principles for the prevention of AMR evolution.

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Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives

Cited by 14 publications

References 31 publications

Synergistic Effect of Quinic Acid Derived From Syzygium cumini and Undecanoic Acid Against Candida spp. Biofilm and Virulence

Synergistic Effect of Quinic Acid Derived From Syzygium cumini and Undecanoic Acid Against Candida spp. Biofilm and Virulence

Quinic acid derivatives inhibit dengue virus replication in vitro

Antibacterial Nanomaterials: Mechanisms, Impacts on Antimicrobial Resistance and Design Principles

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