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PubMed1999

Role of TNF-alpha in the induction of fungicidal activity of mouse peritoneal exudate cells against Cryptococcus neoformans by IL-12 and IL-18.

We have recently demonstrated that two IFN-gamma-inducing cytokines, interleukin (IL)-12 and IL-18, synergistically induced the fungicidal activity of mouse peritoneal exudate cells (PEC) against Cryptococcus neoformans through NK cell production of interferon (IFN)-gamma and nitric oxide (NO) synthesis. In the present study, we further dissected these effects by examining the involvement of tumor necrosis factor (TNF)-alpha in the induction of IL-12/IL-18-stimulated PEC fungicidal activity. The addition of neutralizing anti-TNF-alpha mAb significantly suppressed IL-12/IL-18-stimulated PEC anticryptococcal activity. This effect was ascribed to the inhibition of macrophage NO synthesis, but not of IFN-gamma production by NK cells, because the same treatment inhibited the former response, but not the latter one. On the other hand, combined treatment with IL-12 and IL-18 synergistically induced the production of TNF-alpha by PEC and this effect was almost completely abrogated by neutralizing anti-IFN-gamma mAb. The cell type producing TNF-alpha among PEC was mostly macrophage. TNF-alpha significantly promoted macrophage NO production and anticryptococcal activity induced by IFN-gamma, and furthermore anti-TNF-alpha mAb partially inhibited these responses. Considered together, our results indicated that TNF-alpha contributed to the potentiation of IL-12/IL-18-induced PEC fungicidal activity against C. neoformans through enhancement of IFN-gamma-induced production of NO by macrophages, but not through increased production of IFN-gamma by NK cells.

Animals↗
PubMed1989

Fungicidal activity of cilofungin (LY121019) alone and in combination with anticapsin or other antifungal agents.

Cilofungin (LY121019) was shown to have potent fungicidal activity against clinical isolates of Candida albicans and Candida tropicalis but not Candida parapsilosis. Fungicidal activity was evident against both replicating and non-replicating Candida albicans and was progressive over the first 12 h of incubation. The combination of cilofungin (LY121019) with anticapsin but not with amphotericin B, ketoconazole or 5-fluorocytosine resulted in synergistic fungicidal activity. This compound warrants further investigation of its safety and efficacy in the treatment of Candida infections.

Alanine↗
PubMed2003

Evidence for chromosomal determination of fungicidal activity in strains of Lactobacillus brevis and Lactobacillus fermentum isolated from fermented foods.

The genetic basis of the fungicidal activity of strains of Lactobacillus brevis and L. fermentum isolated from indigenous fermented foods was determined. A 5.5-kb plasmid was isolated from L. brevis while L. Fermentum was found to harbor no plasmid. Plasmid curing indicated no correlation between the plasmid and the fungicidal activity of the Lactobacillus species. The fungicidal activity of the isolated organisms can be supposed to be mediated by the chromosome. No antibiotic resistance genetic markers were detected on the plasmid and hence it was classified as cryptic.

Anti-Bacterial Agents↗
PubMed1987

Detection of point-mutation mutagens in Aspergillus nidulans: comparison of methionine suppressors and arginine resistance induction by fungicides.

In the present study we describe the effect of 4 fungicides on the induction of point mutations in strains biA1 methG1 (induction of methionine suppressors) and 118 (induction of arginine resistance) of Aspergillus nidulans. Captan, which was used as a known mutagen, Daconil 2787 and Dithane M-45 were effective in inducing these mutations, whereas the fungicide Cercobin caused no significant increase in the induction frequency of the point mutations selected. Actually, a decrease in the frequency of methionine suppressors was observed in relation to those occurring spontaneously. However, this effect could not be considered antimutagenic because the revertants were more sensitive to the fungicide than the biA1 methG1 strain. Although the induction of methionine suppressors was more convenient because it permits the visualization of several morphological types, the 118 strain system also proved to be effective in detecting point-mutation induction.

Antifungal Agents↗
PubMed1985

Synthesis and spectroscopic and fungicidal characterization of hydroxamic acids and their metal chelates.

Hydroxamic acid chelates of the type ML2, ML2', and ML2" where M = Cu(II), Ni(II) or Co(II) and L = N,2'-diphenylacetohydroxamic acid (N,2'-DPAHA), L' = 2,2'-diphenylacetohydroxamic acid (2,2'-DPAHA), and L" = 2-phenylacetohydroxamic acid (2-PAHA) have been isolated and characterized on the basis of elemental analysis and infrared and magnetic data. These metal chelates were screened for their fungicidal activity. The testing against fungi has been carried out by slide germination technique against Alternaria alternata and by inhibition zone technique against Fusarium oxysporum and Aspergillus flavus. The fungicidal activity of chelates and their parent ligand has been compared with the commercial fungicide, Dithane M-45, screened under similar conditions.

Antifungal Agents↗
PubMed1995

Estimating the risks and benefits of pesticides: considering the agroecosystem and integrated pest management in the use of EBDC fungicides on apples.

Calculating the risks and benefits of agricultural pesticides determines whether a pesticide will be registered for use on commodities. Historically, the US Environmental Protection Agency (EPA) has used very conservative estimates of health risks, particularly in the absence of data regarding actual use patterns of the pesticide and actual pesticide residue at the point of food purchase. However, when grower groups and manufacturers were faced with the problem of losing the ethylene bisdithiocarbamate (EBDC) fungicides, they approached EPA offering to provide hard data in place of estimates. Plant pathologists familiar with apple agroecosystems pointed out that different fungicides have highly specific uses in integrated pest management (IPM) programs, and that banning EBDC use on apples would probably raise total pesticide use in apples by compromising the pesticide reductions obtained under existing IPM programs. In addition, an early study showed that use-patterns could significantly reduce the amount of EBDC residue on apples. This approach led to a more realistic appraisal of both risks and benefits of the fungicides, lowering risks and raising benefits. The process ended with a registration prescribing use-patterns which result in minimal residue at harvest, thus providing valuable tools for use in IPM programs.

Journal Article↗
PubMed2006

Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles.

Polyfluorinated 2-benzylthiobenzothiazoles 3a-l are prepared via a microwave-assisted, one-pot procedure. The advantages, such as good to excellent yields, shorter reaction time (14-21min), readily available starting material, and simple purification procedure, distinguish the present protocol from other existing methods used for the synthesis of 2-benzylthiobenzothiazoles. Bioassay indicated that most of the compounds showed significant fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, and Dothiorella gregaria at a dosage of 50microg/mL. Interestingly, compared to the control of commercial fungicide, triadimefon, compound 3c exhibited much higher activities against R. solani, B. cinereapers, and D. gregaria, which showed that the polyfluorinated 2-benzylthiobenzothiazoles can be used as lead compound for developing novel fungicides.

Antifungal Agents↗
PubMed2005

Synergistic fungicidal activity of Cu(2+) and allicin, an allyl sulfur compound from garlic, and its relation to the role of alkyl hydroperoxide reductase 1 as a cell surface defense in Saccharomyces cerevisiae.

Cu(2+) showed a dose-dependent fungicidal activity against Saccharomyces cerevisiae cells, and its lethal effect was extremely enhanced in the presence of allicin, an allyl sulfur compound from garlic. The fungicidal activity of Cu(2+) was unaffected or rather attenuated by other sulfur-containing compounds such as N-acetyl-cysteine, l-cysteine or dithiothreitol. Ca(2+) could absolutely protect against the lethal effect of Cu(2+) itself, but showed no protection against the fungicidal activity of Cu(2+) newly generated in combination with allicin. Cu(2+) accelerated an endogenous generation of reactive oxygen species (ROS) in S. cerevisiae cells at a lethal concentration, but such intracellular oxidative stress induction was not observed during cell death progression upon treatment with Cu(2+) and allicin. A surfactant, sodium N-lauroyl sarcosinate (SLS), enhanced the solubilization of a few proteins including alkyl hydroperoxide reductase 1 (AHP1) in intact cells, accounting for the absence of this protein in the extract from allicin-treated cells. Allicin-treated cells were rendered extremely sensitive to the subsequent Cu(2+) treatment as in the case of SLS-treated cells. Allicin-treated cells and SLS-treated cells similarly showed an increased sensitivity to exogenously added tert-butyl hydroperoxide (t-BOOH), an organic peroxide that is detoxified by the action of AHP1. Our study suggests that allicin influences the mode of cell surface localization or the related function of AHP1 as a defense against phospholipid peroxidation by the external action of Cu(2+).

Anti-Infective Agents↗
PubMed2001

Structures of trihydroxynaphthalene reductase-fungicide complexes: implications for structure-based design and catalysis.

BACKGROUND: Trihydroxynaphthalene reductase catalyzes two intermediate steps in the fungal melanin biosynthetic pathway. The enzyme, a typical short-chain dehydrogenase, is the biochemical target of three commercial fungicides. The fungicides bind preferentially to the NADPH form of the enzyme. RESULTS: Three X-ray structures of the Magnaporthe grisea enzyme complexed with NADPH and two commercial and one experimental fungicide were determined at 1.7 A (pyroquilon), 2.0 A (2,3-dihydro-4-nitro-1H-inden-1-one, 1), and 2.1 A (phthalide) resolutions. The chemically distinct inhibitors occupy similar space within the enzyme's active site. The three inhibitors share hydrogen bonds with the side chain hydroxyls of Ser-164 and Tyr-178 via a carbonyl oxygen (pyroquilon and 1) or via a carbonyl oxygen and a ring oxygen (phthalide). Active site residues occupy similar positions among the three structures. A buried water molecule that is hydrogen bonded to the NZ nitrogen of Lys-182 in each of the three structures likely serves to stabilize the cationic form of the residue for participation in catalysis. CONCLUSIONS: The pro S hydrogen of NADPH (which is transferred as a hydride to the enzyme's naphthol substrates) is directed toward the carbonyl carbon of the inhibitors that mimic an intermediate along the reaction coordinate. Modeling tetrahydroxynaphthalene and trihydroxynaphthalene in the active site shows steric and electrostatic repulsion between the extra hydroxyl oxygen of the former substrate and the sulfur atom of Met-283 (the C-terminal residue), which accounts, in part, for the 4-fold greater substrate specificity for trihydroxynaphthalene over tetrahydroxynaphthalene.

Antifungal Agents↗
PubMed2002

The fungicidal activity of novel nanoemulsion (X8W60PC) against clinically important yeast and filamentous fungi.

Surfactant nanoemulsions are water in oil preparations that proved to have a broad spectrum biocidal activity against a variety of microorganisms including Gram-positive and Gram-negative bacteria, spores and enveloped viruses. These preparations are non-toxic to the skin, mucous membrane and gastrointestinal tissues at biocidal concentrations. In this study, 0.1% of the nanoemulsion designated X8W60PC has shown fungicidal activity against yeast including Candida albicans and C. tropicalis in 15 minutes. C. tropicalis was more sensitive than C. albicans, which required a longer time or a higher concentration of the nanoemulsion to achieve killing. Neutral to slightly alkaline pH was more effective in killing the yeast cells than acidic pH. Using the minimum inhibitory concentration assay, 0.08% of the nanoemulsion was inhibitory to C. albicans, and parapsilosis and filamentous fungi including Microsporum gypseum, Trichophyton mentagrophytes, Trichophyton rubrum, Aspergillus fumigatus and Fusarium oxysporum. None of the individual ingredients was as effective a fungicidal as the nanoemulsion at equivalent concentration. This shows that the nanoemulsion structure is an important factor in the anti-fungal activity. The X8W60PC has great potential as a topical anti-fungal agent and further investigation into the mechanism of fungicidal action is warranted.

Antifungal Agents↗
PubMed2004

Structure and fungicidal activity of a synthetic antimicrobial peptide, P18, and its truncated peptides.

P18 (KWKLFKKIPKFLHLAKKF-NH2) is an antimicrobial peptide designed from a cecropin A-magainin 2 hybrid that has potent antibacterial activity without hemolytic activity against human erythrocytes. In this study, P18 displayed potent fungicidal activity (MIC: 12.5 approximately 25 microM) against pathogenic fungi, Candida albicans, Trichosporon beigelii, Aspergillus flavus and Fusarium oxyspovrum. The central Pro9 residue and the entire sequence of P18 are essential for its full fungicidal activity. Circular dichroism analysis suggested that the higher alpha-helical content of the peptides did not correlate with the stronger fungicidal activity.

Animals↗
PubMed1998

Different susceptibilities of yeasts and conidia of Penicillium marneffei to nitric oxide (NO)-mediated fungicidal activity of murine macrophages.

Penicillium marneffei is an important opportunistic fungal pathogen. Host defence mechanisms against P. marneffei are not fully understood. We investigated the fungicidal activity of murine peritoneal macrophages against two forms of P. marneffei, conidia and yeast cells, and the involvement of the NO-mediated killing system. Peritoneal macrophages suppressed the intracellular growth of P. marneffei yeast cells and conidia. The number of live yeast cells within macrophages was significantly reduced by activation of macrophages by interferon-gamma (IFN-gamma), while a similar response was not observed with conidia. IFN-gamma-induced macrophage fungicidal activity against yeast cells was mediated by NO and was almost completely inhibited by N(G)-monomethyl-L-arginine (L-NMMA), a competitive inhibitor of NO synthesis, while N(G)-monomethyl-D-arginine (D-NMMA), an optical isomer of L-NMMA, did not show any influence. NO production by macrophages stimulated with IFN-gamma was significantly enhanced when these macrophages were cultured with P. marneffei yeast cells, while conidia did not enhance macrophage NO production. Furthermore, yeast cells were more susceptible to the killing effect of chemically generated NO than conidia. Our results indicate that the yeast form of P. marneffei is more sensitive to the fungicidal activity of IFN-gamma-stimulated macrophages than conidia, and suggest that the different effects of two forms of P. marneffei on macrophage NO production and their different susceptibilities to NO may be reasons for the present findings.

Animals↗
PubMed1998

Genetic and biochemical studies establish that the fungicidal effect of a fully depeptidized inhibitor of Cryptococcus neoformans myristoyl-CoA:protein N-myristoyltransferase (Nmt) is Nmt-dependent.

Cryptococcus neoformans is a fungal pathogen that causes chronic meningitis in 10% of patients with AIDS. Genetic and biochemical studies were conducted to determine whether myristoyl-CoA:protein N-myristoyltransferase (Nmt) is a target for development of a new class of fungicidal drugs. A single copy of a conditional lethal C. neoformans NMT allele was introduced into the fungal genome by homologous recombination. The allele (nmt487D) produces temperature-sensitive myristic acid auxotrophy. This phenotype is due, in part, to under-myristoylation of a cellular ADP ribosylation factor (Arf) and can be rescued by forced expression of human Nmt. Two isogenic strains with identical growth kinetics at 35 degreesC were used to test the biological effects of an Nmt inhibitor. CPA8 contained a single copy of wild type C. neoformans NMT. HMC1 contained nmt487D plus 10 copies of human NMT. Since a single copy of nmt487D will not support growth at 35 degreesC, survival of HMC1 depends upon its human Nmt. ALYASKLS-NH2, an inhibitor derived from an Arf, was fully depeptidized: p-[(2-methyl-1-imidazol-1-yl)butyl]phenyl-acetyl was used to represent the GLYA tetrapeptide, whereas SKLS was replaced with a chiral tyrosinol scaffold. Kinetic studies revealed Ki (app) values of 1.8 +/- 1 and 9 +/- 2.4 microM for purified fungal and human Nmts, respectively. The minimal inhibitory concentration of the compound was 2-fold lower for CPA8 compared with HMC1. A single dose of 100 microM produced a 5-fold greater inhibition of protein synthesis in CPA8 versus HMC1. The strain specificity of these responses indicates that the fungicidal effect was Nmt-dependent. These two strains may be useful for screening chemical libraries for Nmt-based fungicidal compounds with relatively little activity against the human enzyme.

Acyltransferases↗
PubMedDate not supplied

Neutral red assay in minimum fungicidal concentrations of antifungal agents.

We assayed the fungicidal effects of antifungal agents using neutral red staining. Fungal elements of Trichophyton mentagrophytes and T. rubrum were treated with various concentrations of antifungal agents in 96-well filtration plates and then stained with neutral red. The amount of neutral red incorporated by the surviving viable cells was determined from the automated spectrophotometric readings at 550 nm. The minimum fungicidal concentrations (MFCs) of antifungal agents determined by this assay correlated well with those determined by conventional assay. This newly developed procedure should provide a rapid, reproducible, quantitative, qualitative and semi-automated susceptibility test for determination of the MFCs of the fungicidal agents.

Antifungal Agents↗
PubMed2000

Experimental paracoccidioidomycosis of the Syrian hamster: fungicidal activity and production of inflammatory cytokines by macrophages.

Phagocytic cells play an important role in nonspecific resistance to fungal infection by mediating an inflammatory response and by a direct fungicidal action. In this study, the functional activity of peritoneal macrophages obtained from hamsters experimentally infected with strain Pb18 of Paracoccidioides brasiliensis was evaluated during 16 weeks of infection. The results showed that macrophages had a higher spreading ability associated with increased production of tumor necrosis factor alpha (TNF-alpha) and enhanced fungicidal activity during the early periods of infection. TNF-alpha levels remained elevated during all periods studied, while low levels of interleukin-1 beta (IL-1 beta) were produced during the infection. A necrotic area with dead fungi was observed at the inoculation site and the infection disseminated only to liver and lymph nodes in a few animals. These results suggest that during the early stages of infection with P. brasiliensis, macrophage activation by the high levels of TNF-alpha limited fungal dissemination. In contrast, in the later stages of infection, high levels of TNF-alpha were observed while the fungicidal activity of macrophages was lower and the animals presented loss of vitality resulting in their death. These observations suggest a complex role of TNF-alpha in experimental paracoccidioidomycosis of Syrian hamsters, involving not only resistance but also pathogenesis.

Animals↗
PubMed2002

CAY-I, a fungicidal saponin from Capsicum sp. fruit.

Saponins are steroidal or terpenoid-based glycosides with surface active properties. A steroidal saponin, CAY-1, with a molecular weight of 1243.35 Da, was isolated and purified to homogeneity from commercially available dry, ground fruit of Capsicum frutescens. CAY-1 was shown to be a potent fungicide for the germinating conidia of Aspergillus flavus, A. fumigatus, A. parasiticus and A. niger with species-dependent LD90 values between 3 and 20 microM. Activity against some Aspergillus species was affected by the test medium used. In vitro assays, CAY-1 was effective against Pneumocystis carinii (IC50): 9.5 microM) and Candida albicans (IC90: 6.2 microM). CAY-1 had no effect on the viability of the nongerminating conidia of the two filamentous fungi, P. carinii and C. albicans, nor on the conidial type of Fusarium oxysporum. It was ineffective against the bacteria Enterobacter agglomerans, Bacillus subtilis, Escherichia coli and Staphylococcus aureus. CAY-1 was not cytotoxic to A 549 lung carcinoma cells or HeLa cells at effective fungicidal concentrations. The results indicate that CAY-1 is an effective fungicide for Aspergillus species, C. albicans and P. carinii at concentrations below the threshold for mammalian cell toxicity.

Antifungal Agents↗
PubMed2002

Fungicidal activities of commonly used disinfectants and antifungal pharmaceutical spray preparations against clinical strains of Aspergillus and Candida species.

The antifungal efficacy of commercial chemical disinfectants and pharmaceutical antifungal agents against medically important moulds and yeast species was investigated. Chlorine, phenol, sodium dodecyl sulfate and quaternary ammonium salts were the chemical disinfectants, and bifonazole and terbinafine were the antifungal pharmaceutical products tested against clinical isolates of Aspergillus and Candida species. Fungal inocula were obtained from conidial preparations of two A. ochraceus strains and yeast cells of C. albicans, C. krusei and C. parapsilosis. The antifungal activities were evaluated either by determining the kill rate in a cell suspension media at different contact periods, or by examining the viability and growth on plates sprayed with the active ingredient. Chlorine (1%) was the only disinfectant with the ability to cause a rapid inactivation of all five strains. Phenol (5%) was equally effective against Candida species; however, a number of A. ochraceus conidia were able to survive this treatment for up to 1 h. Benzalkonium chloride (0.5%) and cetrimide (0.5%) were also able to disinfect the three Candida species rapidly; however, these two quaternary ammonium compounds were relatively ineffective against A. ochraceus. In spray experiments, quaternary ammonium compounds had a fungicidal activity against Candida species and were fungistatic against A. ochraceus conidia. All five fungal strains were able to resist 0.5% sodium dodecyl sulfate, present either in the suspension solution or on the sprayed plate. Of the two pharmaceutical antifungal products tested, bifonazole (1%) were essentially ineffective against all five strains. Terbinafine (1%) had a fungicidal activity against A. ochraceus and C. parapsilosis. In suspension experiments, an exposure to 0.01% terbinafine required a contact period of 1 h for a complete inactivation of A. ochraceus conidia and an onset of fungicidal effect on C. parapsilosis yeast cells. Terbinafine was only moderately effective against C. albicans and was completely ineffective against C. krusei.

Antifungal Agents↗
PubMed2006

Biocide uptake in contact lenses and loss of fungicidal activity during storage of contact lenses.

PURPOSE: With recent outbreaks of Fusarium keratitis related to contact lens wear, studies were conducted to determine the biocide uptake during lens storage, and the resulting effect on antifungal activity of related products. METHODS: ACUVUE 2 (etafilcon A) soft, hydrophilic contact lenses (group IV) were soaked from 1 hour to 7 days in OPTI-FREE Express and OPTI-FREE RepleniSH multipurpose disinfecting solutions with POLYQUAD (polyquaternium-1) and ALDOX (myristamidopropyl dimethylamine) biocides and multipurpose solutions, Bausch & Lomb ReNu with MoistureLoc (Alexidine), ReNu MultiPlus (polyhexamethylene biguanide [PHMB]), and AMO Complete MoisturePLUS (PHMB). Storage solutions were tested to evaluate the effect of preservative uptake on the residual biocide activity against Fusarium solani. RESULTS: Approximately 30% to 60% of the PHMB and Alexidine were depleted by 6 hours, with comparable loss of antimicrobial activity. Decreasing activity was noted with corresponding decreases in active concentration throughout the course of the evaluation. The POLYQUAD systems retained nearly 100% of the biocide and fungicidal activity and maintained their concentration in the solution. CONCLUSIONS: OPTI-FREE Express and OPTI-FREE RepleniSH multipurpose disinfecting solutions maintained fungicidal efficacy after storage of lenses. The Alexidine- and PHMB-based multipurpose solutions tested showed significant uptake of preservative into group IV lenses, resulting in a decrease in the residual activity of the storage solution. The POLYQUAD systems showed a low uptake of biocide and maintained fungicidal efficacy against F. solani.

Antifungal Agents↗