Umbelliferone esters with antibacterial activity produced by lipase-mediated biocatalytic pathway

Soares, Vitor; Marini, Maíra Barcellos; Paula, L. A. de; Gabry, Patrick Soares; Amaral, Ana Cláudia F.; Malafaia, Camila Adão; Leal, Ivana Corrêa Ramos

doi:10.1007/s10529-020-03014-9

Cited by 16 publications

(9 citation statements)

References 13 publications

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“…With regard to antibacterial compounds, the imines and their analogues are reported to exhibit inhibition activity against Gram-positive and Gram-negative bacteria [ 13 ]. Ester compounds exhibit antimicrobial and antifungal inhibition activities against some Gram-positive and Gram-negative bacteria, having antifungal and antioxidant activity [ 14 , 15 , 16 , 17 ]. Evidence suggests hydrazide to have noteworthy antibacterial potential [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Evaluation of Novel Benzamidine Derivatives: Newer Antibiotics for Periodontitis Treatment

et al. 2022

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Periodontal disease (PD) is complex polymicrobial disease which destroys tooth-supporting tissue. Although various synthetic inhibitors of periodontitis-triggering pathogens have been recognized, their undesirable side effects limit their application. Hence, the present study intended to perform the synthesis, characterization, antimicrobial evaluation, and cytotoxicity analysis of novel benzamidine analogues (NBA). This study involved the synthesis of novel imino bases of benzamidine (4a–c), by reacting different aromatic aldehydes with 2-(4-carbamimidoylphenoxy) acetohydrazide (3), which was synthesized by the hydrazination of ethyl 2-(4-carbamimidoylphenoxy) acetate (2), the derivative of 4-hydroxybenzene carboximidamide (1). This was followed by characterization using FTIR, 1H, 13C NMR and mass spectrometry. All synthesized compounds were further tested for antimicrobial potential against PD-triggering pathogens by the micro broth dilution method. The cytotoxicity analysis of the NBA against HEK 293 cells was conducted using an MTT assay. The present study resulted in a successful synthesis of NBA and elucidated their structures. The synthesized NBA exhibited significant antimicrobial activity values between 31.25 and 125 µg/mL against tested pathogens. All NBA exhibited weak cytotoxicity against HEK 293 cells at 7.81 µg, equally to chlorhexidine at 0.2%. The significant antimicrobial activity of NBA against PD-triggering pathogens supports their potential application in periodontitis treatment.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Evaluation of Novel Benzamidine Derivatives: Newer Antibiotics for Periodontitis Treatment

et al. 2022

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“…Immune cells destroy bacteria by migrating cells to the inflammation site and are responsible for phagocytosis [ 36 ], resulting in bacterial death. When an infection arises, the pathogen-associated molecular patterns of pathogens are recognized by pattern recognition receptors, which then activate non-specific immune cells [ 37 ]. Neutrophil cells act as the first line of defense against pathogens during infection by performing the initial phagocytosis of cell debris and dead immune cells.…”

Section: Discussionmentioning

confidence: 99%

“…Blood glucose and cortisol levels are common stress indicators [ 29 ]. Increased blood glucose is usually caused by stress or infection [ 37 ]. Induction of Salmonella lipopolysaccharide decreases glucagon-like peptide 1 production and increases Homeostatic Model Assessment for Insulin Resistance, leading to glucose regulation [ 38 ].…”

Section: Discussionmentioning

confidence: 99%

Aeromonas hydrophila induction method in adult zebrafish (Danio rerio) as animal infection models

et al. 2023

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Background and Aim: Zebrafish are frequently used as model organisms in scientific research as their genes mirror those of humans. Aeromonas hydrophila bacteria can infect humans and animals, mainly fish. This study aimed to identify the concentration and route of A. hydrophila infection in adult zebrafish. Zebrafish had been used as a challenge test by analyzing their hematological profiles, blood glucose levels, and survival rates. Materials and Methods: Induction of cell supernatant free (CSF) from A. hydrophila bacteria in adult zebrafish was carried out via bath immersion (BI), intraperitoneal injection (IPI), intramuscular injection (IMI), and healthy zebrafish as a control (C). The bacterial concentrations were 107, 109, and 1011 colony-forming units (CFU)/mL. At 24 h post-infection, the outcomes of infection were evaluated based on survival rates, hematological profiles, and blood glucose levels. A one-way analysis of variance with a confidence level of 95% was employed to examine the data. Results: In the BI, IPI, and IMI treatment groups, the survival rate of the fish reached a peak of 100%, 22%–100%, and 16%–63%, respectively, compared with the injection technique. In the IMI2 group, a 109 CFU/mL bacterial concentration was determined to correspond to the lethal dosage 50. All infection groups had lower erythrocyte and hemoglobin counts but higher leukocyte counts than the control group. The blood sugar levels of the healthy and infected groups were not significantly different. Conclusion: The route of A. hydrophila infection through Intramuscular injection with a concentration of 109 CFU/mL indicated a high performance compared to other techniques. This method could be developed as a reproducible challenge test.

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“…Enol esters, such as vinyl derivatives, are by far the most used acyl donors. [9] After acyl transfer, the leaving enol tautomerizes to its keto form thus making the reaction irreversible. [10] Vinyl esters are often liquid at reaction temperatures and used on large scale and even under solvent-free conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Other activated acyl donors that can be accepted by acyltransferases have been described in the literature. Enol esters, such as vinyl derivatives, are by far the most used acyl donors [9] . After acyl transfer, the leaving enol tautomerizes to its keto form thus making the reaction irreversible [10] .…”

Section: Introductionmentioning

confidence: 99%

Expanding the Substrate Scope of Acyltransferase LovD9 for the Biosynthesis of Statin Analogues

García‐Marquina

Núñez‐Franco

Grajales‐Hernández

et al. 2023

Chemistry A European J

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This study identifies new acyl donors for manufacturing statin analogues through the acylation of monacolin J acid by the laboratory evolved acyltransferase LovD9. Vinyl and p-nitrophenyl esters have emerged as alternate substrates for LovD9-catalyzed acylation. While vinyl esters can reach product yields as high as the ones obtained by α-dimethyl butyryl-S-methyl-3-mercaptopropionate (DMB-SMMP), the thioester for which LovD9 was evolved, p-nitrophenyl esters display a reactivity even higher than DMB-SMMP for the first acylation step yet the acylation product yield is lower. The reaction mechanisms were elucidated through quantum mechanics (QM) calculations.

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Umbelliferone esters with antibacterial activity produced by lipase-mediated biocatalytic pathway

Cited by 16 publications

References 13 publications

Synthesis, Characterization and Biological Evaluation of Novel Benzamidine Derivatives: Newer Antibiotics for Periodontitis Treatment

Synthesis, Characterization and Biological Evaluation of Novel Benzamidine Derivatives: Newer Antibiotics for Periodontitis Treatment

Aeromonas hydrophila induction method in adult zebrafish (Danio rerio) as animal infection models

Expanding the Substrate Scope of Acyltransferase LovD9 for the Biosynthesis of Statin Analogues

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