Synthesis and antimicrobial activities of N-substituted imides

Zentz, Frédéric; Valla, Alain; Guillou, Régis Le; Labia, Roger; Mathot, Anne-Gabrielle; Sirot, D.

doi:10.1016/s0014-827x(02)01217-x

Cited by 78 publications

(37 citation statements)

References 25 publications

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“…GlmU inhibitors belong to a maleimide class of compounds that are quite reactive against sulfhydryl-containing enzymes (23) and have poor specificity, making them broad-spectrum antimicrobial compounds (11,31). Although NPM, an analog of NEM, showed antibiofilm activity against all the uropathogens tested ( Fig.…”

Section: Discussionmentioning

confidence: 99%

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Antibiofilm Activity of GlmU Enzyme Inhibitors against Catheter-Associated Uropathogens

Burton

Gawande

Yakandawala

et al. 2006

Antimicrob Agents Chemother

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The colonization of uropathogenic bacteria on urinary catheters resulting in biofilm formation frequently leads to the infection of surrounding tissue and often requires removal of the catheter. Infections associated with biofilms are difficult to treat since they may be more than 1,000 times more resistant to antibiotics than their planktonic counterparts. We have developed an antibiofilm composition comprising an N-acetyl-Dglucosamine-1-phosphate acetyltransferase (GlmU) inhibitor and protamine sulfate, a cationic polypeptide. The antibiofilm activity of GlmU inhibitors, such as iodoacetamide (IDA), N-ethyl maleimide (NEM), and NEM analogs, including N-phenyl maleimide, N,N-(1,2-phenylene)dimaleimide (oPDM), and N-(1-pyrenyl)maleimide (PyrM), was tested against that of catheter-associated uropathogens. Both IDA and NEM inhibited biofilm formation in Escherichia coli. All NEM analogs showed antibiofilm activity against clinical isolates of E. coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Staphylococcus epidermidis, and Enterococcus faecalis. The combination of oPDM with protamine sulfate (PS) enhanced its antibiofilm activity and reduced its effective concentration to as low as 12.5 M. In addition, we found that the in vitro inhibitory activity of oPDM-plus-PS-coated silicone catheters against P. aeruginosa and S. epidermidis colonization was superior to that of catheters coated with silver hydrogel. Confocal scanning laser microscopy further confirmed that the oPDMplus-PS-coated silicone catheters were almost free from bacterial colonization. Thus, a broad-spectrum antibiofilm composition comprising a GlmU inhibitor and protamine sulfate shows promise for use in antiinfective coatings for medical devices, including urinary catheters.Microorganisms can attach to and colonize any biomaterial surface, putting patients at risk for local and systemic infections. More than 900,000 episodes of catheter-associated urinary tract infections occur annually in acute-care hospitals in the United States, accounting for 40% of all nosocomial infections and involving between 10 and 30% of patients with indwelling urinary catheters (30). Catheter-associated urinary tract infection prolongs the hospital stay between an estimated 2.4 and 4.5 days, with resultant increased healthcare costs (15,16). Recent studies have shown that a wide range of persistent catheter-related infections may be related to the ability of bacteria to form biofilms (6, 28). Treatment of device-related infections with conventional antimicrobial agents frequently fails because microorganisms growing in biofilms are more tolerant or phenotypically resistant to antimicrobial agents than planktonic cells (24). The insensitivity of biofilm bacteria to antibiotics is a function of cell wall composition, surface structure, and phenotypic variation in enzymatic activity (8,14). It has also been suggested that the negatively charged exopolysaccharide is very effective in protecting bacterial cells from cationic antibiotics by restricting their permeation (2...

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Section: Discussionmentioning

confidence: 99%

“…Its acetyltransferase activity is inactivated in the presence of thiol-specific reagents, such as iodoacetamide and N-substituted maleimides (21,23). In the recent past, GlmU enzyme inhibitors, which belong to a thiol-specific reagent group, were reported to inactivate bacterial pathogens (11,31).…”

mentioning

confidence: 99%

Antibiofilm Activity of GlmU Enzyme Inhibitors against Catheter-Associated Uropathogens

Burton

Gawande

Yakandawala

et al. 2006

Antimicrob Agents Chemother

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“…Because many of these enzymes are important for growth and survival of micro-organisms, antimicrobial activity of NEM is not surprising. Antimicrobial properties of NEM and other N-substituted maleimides have been already reported [5][6][7][8][9] ; however, none of those studies related antimicrobial activity of substituted maleimides to their physicochemical properties, including chemical reactivity and lipophilicity. In the present work, such correlation has been attempted for 12 various N-substituted maleimides.…”

Section: Introductionmentioning

confidence: 99%

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Salewska

Boros-Majewska

Łącka

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Sodium cyanoborohydride (NaCNBH 3 , 97%) was purchased from Alfa Aesar, TianJin, China. Nhydroxyethyl maleimide (HEMI) was synthesized according to the literature procedures [39,40]. The toluene and dimethyl sulfoxide (DMSO) (analytical grade, provided by Sinopharm Chemical Reagent Co., Shanghai, China) were first dried over CaCl 2 and CaH 2 , respectively, and then distilled prior to use.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and self-assembly behavior of amphiphilic diblock copolymer dextran-block-poly(ε-caprolactone) (DEX-b-PCL) in aqueous media

Zhang¹,

Dou²,

Jin³

2010

Express Polym. Lett.

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Abstract. An amphiphilic diblock copolymer, dextran-block-poly(ε-caprolactone) (DEX-b-PCL), with a series of welldefined chain lengths of each block was prepared by conjugating a dextran chain with a PCL block via aza-Michael addition reaction under mild conditions. For the dextran block, samples with relatively uniform molecular weight, 3.5 and 6.0 kDa, were used, and the PCL blocks were prepared via ring-opening polymerization at defined ratios of ε-caprolactone to initiator in order to give copolymers with mass fraction of dextran (fDEX) ranging from 0.16 to 0.45. When these copolymers were allowed to self-assemble in aqueous solution, the morphology of assembled aggregates varied as a function of fDEX when characterized by transmission electron microscope (TEM), fluorescence microscope (FM) and dynamic laser scattering (DLS). As fDEX decreases gradually from 0.45 to 0.16, the morphology of the copolymer assembly changes from spherical micelles to worm-like micelles and eventually to polymersomes, together with an increase in particle sizes.

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Synthesis and antimicrobial activities of N-substituted imides

Cited by 78 publications

References 25 publications

Antibiofilm Activity of GlmU Enzyme Inhibitors against Catheter-Associated Uropathogens

Antibiofilm Activity of GlmU Enzyme Inhibitors against Catheter-Associated Uropathogens

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Synthesis and self-assembly behavior of amphiphilic diblock copolymer dextran-block-poly(ε-caprolactone) (DEX-b-PCL) in aqueous media

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