Novel phenolic antimicrobials enhanced activity of iminodiacetate prodrugs against biofilm and planktonic bacteria

Walsh, Danica J.; Livinghouse, Tom; Durling, Greg M.; Arnold, Adrienne; Brasier, Whitney; Berry, Luke; Goeres, Darla M.; Stewart, Philip S.

doi:10.1111/cbdd.13768

Cited by 3 publications

(8 citation statements)

References 73 publications

(80 reference statements)

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“…To the original 25 mL round-bottom flask equipped with its magnetic stirring bar was added anhydrous DMF (3.0 mL) under nitrogen. The stirred mixture was cooled to 0 °C in an ice bath, and bromomethyl acetate (243 μL, 2.5 mmol, 2.5 equiv) was added dropwise. The reactant mixture was stirred for 30 min at 0 °C and then for an additional 12 h at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters

Mikesell,

Livinghouse

2023

J. Org. Chem.

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A rapid and highly practical one-flask procedure for the positionally selective preparation of (acyloxy)methyl N-(2hydroxybenzyl)iminodiacetate and related diesters from iminodiacetic acid and phenols is described. The key to this multicomponent phenol-Mannich condensation resides in the use of cesium iminodiacetate as the reaction partner. This protocol has been applied in an unusually direct synthesis of the intracellular fluorescent dye Calcein blue AM, for which scant experimental and spectroscopic data are presently available.

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Section: Methodsmentioning

confidence: 99%

Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters

Mikesell,

Livinghouse

2023

J. Org. Chem.

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“…The Gram-negative bacterium selected for this study, Pseudomonas aeruginosa, is opportunistic, exhibits multi-drug resistance, and has a pronounced propensity to form biofilms. The Gram-positive bacterium selected for this study, Staphylococcus epidermidis, has the ability to form biofilms and has been implicated in chronic urinary tract infections, as well as persistent infections on medical devices [26][27][28]. Staphylococcus epidermidis strain ATCC 35984 was chosen as a representative Grampositive organism with well-documented biofilm-forming ability.…”

Section: Biological Evaluationmentioning

confidence: 99%

“…The minimum inhibitory concentrations (MICs) of all compounds against S. epidermidis and P. aeruginosa were determined using a modified 96-well plate assay previously described by Walsh et. al., [26][27][28]. In short, Costar polystyrene 96-well plates were prepared with 150 µL of TSB and serial dilutions of the compound in dimethyl sulfoxide (DMSO).…”

Section: Microbiologymentioning

confidence: 99%

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Novel Nitro-Heteroaromatic Antimicrobial Agents for the Control and Eradication of Biofilm-Forming Bacteria

et al. 2021

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The synthesis and biological activity of several novel nitrothiazole, nitrobenzothiazole, and nitrofuran containing antimicrobial agents for the eradication of biofilm-forming Gram-negative and Gram-positive pathogens is described. Nitazoxanide (NTZ), nitrofurantoin, and furazolidone are commercial antimicrobials which were used as models to show how structural modification improved activity toward planktonic bacteria via minimum inhibitory concentration (MIC) assays and biofilms via minimum biofilm eradication concentration (MBEC) assays. Structure–activity relationship (SAR) studies illustrate the ways in which improvements have been made to the aforementioned antimicrobial agents. It is of particular interest in this regard that the introduction of a chloro substituent at the 5-position of NTZ (analog 1b) resulted in marked activity enhancement, as did the replacement of the 2-acetoxy substituent in the latter compound with a basic amine group (analog 7b). It is also of importance that analog 4a, which is a simple methacrylamide, displayed noteworthy activity against S. epidermidis biofilms. These lead compounds identified to have high activity towards biofilms provide promise as starting points in future pro-drug studies.

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“…In recent years, natural antimicrobial compounds have seemed to be suitable anti-QS and antibiofilm agents and many experiments determined the antimicrobial potential of many natural compounds against biofilm formation. Phenolic compounds have been shown to be effective in inhibiting the formation of biofilms and cell growth in pathogenic bacteria [ 19 ]. Moreover, these agents have shown modulatory effects on antibiotic resistance in S. aureus and S. epidermidis by inhibiting the function of efflux pumps, which are one of the important factors in biofilm maturation [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Role of RNAIII in Resistance to Antibiotics and Antimicrobial Agents in Staphylococcus epidermidis Biofilms

Minich

Lišková

Kormanová

et al. 2022

IJMS

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Staphylococcus epidermidis is a known opportunistic pathogen and is one of the leading causes of chronic biofilm-associated infections. Biofilm formation is considered as a main strategy to resist antibiotic treatment and help bacteria escape from the human immune system. Understanding the complex mechanisms in biofilm formation can help find new ways to treat resistant strains and lower the prevalence of nosocomial infections. In order to examine the role of RNAIII regulated by the agr quorum sensing system and to what extent it influences biofilm resistance to antimicrobial agents, deletion mutant S. epidermidis RP62a-ΔRNAIII deficient in repressor domains with a re-maining functional hld gene was created. A deletion strain was used to examine the influence of oxacillin in combination with vanillin on biofilm resistance and cell survival was determined. Utilizing real-time qPCR, confocal laser scanning microscopy (CLSM), and crystal violet staining analyses, we found that the RNAIII-independent controlled phenol soluble modulins (PSMs) and RNAIII effector molecule have a significant role in biofilm resistance to antibiotics and phenolic compounds, and it protects the integrity of biofilms. Moreover, a combination of antibiotic and antimicrobial agents can induce methicillin-resistant S. epidermidis biofilm formation and can lead to exceedingly difficult medical treatment.

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Novel phenolic antimicrobials enhanced activity of iminodiacetate prodrugs against biofilm and planktonic bacteria

Abstract: This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.

Cited by 3 publications

References 73 publications

Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters

Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters

Novel Nitro-Heteroaromatic Antimicrobial Agents for the Control and Eradication of Biofilm-Forming Bacteria

Role of RNAIII in Resistance to Antibiotics and Antimicrobial Agents in Staphylococcus epidermidis Biofilms

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