Antifungal activity of crown ethers

Yagi, Koji; García, Vanessa; Rivas, Ma E.; Salas, Javier; Camargo, Andres; Tabata, Takeo

doi:10.1007/bf00663254

Cited by 13 publications

(8 citation statements)

References 8 publications

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“…for the treatment of dermatomycosis. [17] Leevy et al investigated the antimicrobial activity of several alkyl-substituted lariat ethers on E. coli, B. subtilis, and yeast. [18] Yildiz and co-workers synthesized five new crown ether ligands of the Schiff base type which have activity on various microorganisms.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Dithiacrown Ethers and Evaluation of Their Cytotoxic Activity

et al. 2021

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New derivatives of thiacrown ethers were synthesized based on the domino reaction of 1,5‐bis(2‐formylphenthio)‐3‐oxapentane with ketones containing active methylene group and ammonium acetate. After 24 hours at moderate temperature, the reaction afforded new substances containing both polyether chain S(CH2)2−O−(CH2)2−S and heterocyclic piperidone. Particularly when benzyl acetoacetate was used, the three ‐ component reaction provided a final tetrahydropyridine derivative product containing enamine fragment instead of piperidone as expected. Physico‐chemical methods of analyses including IR, 1H &13C‐NMR and HRMS were used to clarify these structures. Subsequently, the cytotoxicity of five novel derivatives were evaluated on four cancer cells including HeLa (HeLa cervical cancer), Hep‐G2 (human hepatocellular carcinoma), MCF7 (human breast adenocarcinoma), Lu‐1 (human lung adenocarcinoma) and Vero cell. The result showed the potential application of these compounds in terms of biological activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Dithiacrown Ethers and Evaluation of Their Cytotoxic Activity

et al. 2021

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“…15 More extensive studies showed that the simple crowns 12-crown-4, 15-crown-5, and 18-crown-6 had LD 50 values (male white rats) of 3200, 1000, and 700 mg/kg, respectively. 16 Antibacterial 17 and antifungal 18 activities of widely varied crown structures were reported in the early 1980s. Additional antimicrobial activity of various crown ether derivatives has been reported up to the present day.…”

Section: Resultsmentioning

confidence: 99%

“…1, 2, and 3 all mediate potency enhancements when coadministered with erythromycin, kanamycin, rifampicin, or tetracycline against DH5α and K-12 E. coli. Based on the somewhat diverse literature on crown toxicity to bacteria, [13][14][15][16][17][18][19] we anticipated that Gram positive B. subtilis would be the most susceptible organism to hydraphiles and the most likely to show potency enhancements when exposed to low hydraphile doses and antibiotics. In fact, the potency of either erythromycin or tetracycline against B. subtilis (see Table 2) was enhanced only marginally by 2 (administered at ¼ MIC).…”

Section: Comparison Of C 8 Benzyl Hydraphile (1) To C 14 Benzyl Hydramentioning

confidence: 99%

Hydraphiles enhance antimicrobial potency against Escherichia coli, Pseudomonas aeruginosa, and Bacillus subtilis

Patel

Garrad

Stavri

et al. 2016

Bioorganic & Medicinal Chemistry

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Hydraphiles are synthetic amphiphiles that form ion-conducting pores in liposomal membranes. These pores exhibit open-close behavior when studied by planar bilayer conductance techniques. In previous work, we showed that when co-administered with various antibiotics to the DH5α strain of Escherichia coli, they enhanced the drug's potency. We report here potency enhancements at low concentrations of hydraphiles for the structurally and mechanistically unrelated antibiotics erythromycin, kanamycin, rifampicin, and tetracycline against Gram negative E. coli (DH5α and K-12) and Pseudomonas aeruginosa, as well as Gram positive Bacillus subtilis. Earlier work suggested that potency increases correlated to ion transport function. The data presented here comport with the function of hydraphiles to enhance membrane permeability in addition to, or instead of, their known function as ion conductors.

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“…Sadly,t his situation has largely reversed as bacteria have developed resistance to essentially all antibiotics and even to those considered to be medicamentso fl ast resort.I nt he United States alone, hospital-acquired bacterial infections affect approximately two million peoplea nnually and prove fatal to more than 20 000 of those patients. [5] This might have been expected, [6] as numerous reports have appeared that describe the toxic or other biological effects of crown ethers on bacteria, [7] fungi, [8] various tissues, [9] plants, [10] and mammals. This concern has very recently been addressedb yaW hite House initiative.…”

Section: Introductionmentioning

confidence: 97%

“…[3] In previousw ork, we showedt hat hydraphile [4] synthetic cation channel-formers are toxic to Escherichia coli bacteria. [5] This might have been expected, [6] as numerous reports have appeared that describe the toxic or other biological effects of crown ethers on bacteria, [7] fungi, [8] various tissues, [9] plants, [10] and mammals. [11] To our knowledge,h owever, there are only two reports of co-administration of crown-ether-basedc om-poundsa nd antibiotics in addition to our own work.…”

Section: Introductionmentioning

confidence: 99%

Antibiotic Potency against E. coli Is Enhanced by Channel‐Forming Alkyl Lariat Ethers

et al. 2016

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Several N,N'-bis(n-alkyl-4,13-diaza[18]crown-6) lariat ethers were found to significantly enhance the potency of rifampicin and tetracycline, but not erythromycin and kanamycin, against the non-pathogenic DH5α and K-12 strains of Escherichia coli when administered at levels below their minimum inhibitory concentrations (MICs). The enhancements in antibiotic potency observed for the lariat ethers ranged from three- to 20-fold, depending on the strain of E. coli, the antibiotic, and the lengths of the alkyl chains attached at the macroring nitrogen atoms. The dialkyl lariat ethers, previously thought to only be cation carriers, formed well-behaved, ion-conducting pores in soybean asolectin membranes, as judged by planar bilayer conductance measurements. The ability of lariat ethers to form stable pores, which appeared to be aggregated, depended in part on alkyl chain length and in part on the composition of the bilayer membrane in which they were studied.

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Antifungal activity of crown ethers

Cited by 13 publications

References 8 publications

Synthesis of Dithiacrown Ethers and Evaluation of Their Cytotoxic Activity

Synthesis of Dithiacrown Ethers and Evaluation of Their Cytotoxic Activity

Hydraphiles enhance antimicrobial potency against Escherichia coli, Pseudomonas aeruginosa, and Bacillus subtilis

Antibiotic Potency against E. coli Is Enhanced by Channel‐Forming Alkyl Lariat Ethers

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