Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action

Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observ...
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Autor*in:	Melina Di Liberto [verfasserIn] María V. Rodriguez [verfasserIn] Luis Espinoza [verfasserIn] Marcela Raimondi [verfasserIn] Susana Zacchino [verfasserIn] Alejandro Madrid [verfasserIn] Laura Svetaz [verfasserIn] Héctor Carrasco [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2012

Schlagwörter:	eugenol derivatives antifungal activity mechanism of antifungal action lipophilicity SAR

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 17(2012), 1, Seite 1002-1024
Übergeordnetes Werk:	volume:17 ; year:2012 ; number:1 ; pages:1002-1024

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules17011002

Katalog-ID:	DOAJ039046672

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520			\|a Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity.
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spelling	10.3390/molecules17011002 doi (DE-627)DOAJ039046672 (DE-599)DOAJe0ba9c86c4404acbb08df3ef781317c5 DE-627 ger DE-627 rakwb eng QD241-441 Melina Di Liberto verfasserin aut Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action 2012 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity. eugenol derivatives antifungal activity mechanism of antifungal action lipophilicity SAR Organic chemistry María V. Rodriguez verfasserin aut Luis Espinoza verfasserin aut Marcela Raimondi verfasserin aut Susana Zacchino verfasserin aut Alejandro Madrid verfasserin aut Laura Svetaz verfasserin aut Héctor Carrasco verfasserin aut In Molecules MDPI AG, 2003 17(2012), 1, Seite 1002-1024 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:17 year:2012 number:1 pages:1002-1024 https://doi.org/10.3390/molecules17011002 kostenfrei https://doaj.org/article/e0ba9c86c4404acbb08df3ef781317c5 kostenfrei http://www.mdpi.com/1420-3049/17/1/1002/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 17 2012 1 1002-1024
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allfieldsSound	10.3390/molecules17011002 doi (DE-627)DOAJ039046672 (DE-599)DOAJe0ba9c86c4404acbb08df3ef781317c5 DE-627 ger DE-627 rakwb eng QD241-441 Melina Di Liberto verfasserin aut Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action 2012 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity. eugenol derivatives antifungal activity mechanism of antifungal action lipophilicity SAR Organic chemistry María V. Rodriguez verfasserin aut Luis Espinoza verfasserin aut Marcela Raimondi verfasserin aut Susana Zacchino verfasserin aut Alejandro Madrid verfasserin aut Laura Svetaz verfasserin aut Héctor Carrasco verfasserin aut In Molecules MDPI AG, 2003 17(2012), 1, Seite 1002-1024 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:17 year:2012 number:1 pages:1002-1024 https://doi.org/10.3390/molecules17011002 kostenfrei https://doaj.org/article/e0ba9c86c4404acbb08df3ef781317c5 kostenfrei http://www.mdpi.com/1420-3049/17/1/1002/ kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 17 2012 1 1002-1024
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callnumber-first	Q - Science
author	Melina Di Liberto
spellingShingle	Melina Di Liberto misc QD241-441 misc eugenol derivatives misc antifungal activity misc mechanism of antifungal action misc lipophilicity misc SAR misc Organic chemistry Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action
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topic_title	QD241-441 Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action eugenol derivatives antifungal activity mechanism of antifungal action lipophilicity SAR
topic	misc QD241-441 misc eugenol derivatives misc antifungal activity misc mechanism of antifungal action misc lipophilicity misc SAR misc Organic chemistry
topic_unstemmed	misc QD241-441 misc eugenol derivatives misc antifungal activity misc mechanism of antifungal action misc lipophilicity misc SAR misc Organic chemistry
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title	Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action
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title_full	Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action
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title_auth	Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action
abstract	Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity.
abstractGer	Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity.
abstract_unstemmed	Twenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity.
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title_short	Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action
url	https://doi.org/10.3390/molecules17011002 https://doaj.org/article/e0ba9c86c4404acbb08df3ef781317c5 http://www.mdpi.com/1420-3049/17/1/1002/ https://doaj.org/toc/1420-3049
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Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy-5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 µg mL−1. 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Antifungal Activity of Eugenol Analogues. Influence of Different Substituents and Studies on Mechanism of Action

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