Structural functions of antimicrobial long-chain alcohols and phenols

Kubo, Isao; Muroi, Hisae; Kubo, Aya

doi:10.1016/0968-0896(95)00081-q

Cited by 159 publications

(134 citation statements)

References 22 publications

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“…The correlation between the IC 50 and logP values of local anesthetics, phenothiazines, and alcohols obeys the Meyer-Overton rule even in yeast (Uesono et al 2011) (Figure 1B). The rule is confirmed in yeast between the growth-inhibitory activities of volatile anesthetics and their lipophilicities (Keil et al 1996), the growth-inhibitory activities of alcohols and their chain lengths (lipophilicity) (Kato and Shibasaki 1980;Kubo et al 1995), and the IC 50 values of QACs and their chain lengths (Uesono et al 2011). These observations indicate that the mechanism that determines the Meyer-Overton rule, the lipid theory, is conserved in yeast.…”

supporting

confidence: 54%

“…To explain the cutoff and the luciferase inhibition by anesthetics, protein theory assumes that the target proteins, such as neurotransmitter receptors and ion channels, might have anesthetic-binding pockets of limited size as their hydrophobic sites that are unable to fit long-chain compounds larger than the cutoff length. However, the cutoff of long-chain alcohols was observed in the growth-inhibitory activity in microorganisms, indicating that the phenomenon is not specific for anesthesia of animals (Kato and Shibasaki 1980;Kubo et al 1995). Pharmacologic analysis of yeast has revealed that cationic TMAs, which have anesthetic activity in animals (Curtis and Scurlock 1981), do not lose their inhibitory activities, i.e., actin polarization and translation initiation, even if they have long alkyl chains (C 6 -C 18 ).…”

Section: Discussionmentioning

confidence: 99%

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Local Anesthetics and Antipsychotic Phenothiazines Interact Nonspecifically with Membranes and Inhibit Hexose Transporters in Yeast

et al. 2016

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Action mechanisms of anesthetics remain unclear because of difficulty in explaining how structurally different anesthetics cause similar effects. In Saccharomyces cerevisiae, local anesthetics and antipsychotic phenothiazines induced responses similar to those caused by glucose starvation, and they eventually inhibited cell growth. These drugs inhibited glucose uptake, but additional glucose conferred resistance to their effects; hence, the primary action of the drugs is to cause glucose starvation. In hxt 0 strains with all hexose transporter (HXT) genes deleted, a strain harboring a single copy of HXT1 (HXT1s) was more sensitive to tetracaine than a strain harboring multiple copies (HXT1m), which indicates that quantitative reduction of HXT1 increases tetracaine sensitivity. However, additional glucose rather than the overexpression of HXT1/2 conferred tetracaine resistance to wild-type yeast; therefore, Hxts that actively transport hexoses apparently confer tetracaine resistance. Additional glucose alleviated sensitivity to local anesthetics and phenothiazines in the HXT1m strain but not the HXT1s strain; thus, the glucose-induced effects required a certain amount of Hxt1. At low concentrations, fluorescent phenothiazines were distributed in various membranes. At higher concentrations, they destroyed the membranes and thereby delocalized Hxt1-GFP from the plasma membrane, similar to local anesthetics. These results suggest that the aforementioned drugs affect various membrane targets via nonspecific interactions with membranes. However, the drugs preferentially inhibit the function of abundant Hxts, resulting in glucose starvation. When Hxts are scarce, this preference is lost, thereby mitigating the alleviation by additional glucose. These results provide a mechanism that explains how different compounds induce similar effects based on lipid theory.

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supporting

confidence: 54%

Section: Discussionmentioning

confidence: 99%

Local Anesthetics and Antipsychotic Phenothiazines Interact Nonspecifically with Membranes and Inhibit Hexose Transporters in Yeast

et al. 2016

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“…Long-chain primary alcohols (alkan-1-ol or CnOH, where n is the number of carbons in aliphatic chain) display several biological activities (Fujita et al, 2008;Kubo et al, 1995;Pringle et al, 1981). The most widely known are their general anaesthetic properties (Pringle et al, 1981), which are believed to result from their interactions with biological membranes.…”

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confidence: 99%

Effect of alkan-1-ols on the structure of dopc model membrane

Kondela

Gallová

Hauß

et al. 2017

European Pharmaceutical Journal

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“…The amphipatic structure allows surfactants to form polymeric micelles, which can incorporate an active ingredient and subsequently act as an efficient drug carrier through the membrane. The antimicrobial activity of the surfactant itself is usually related to the length of the fatty acid chain, a key factor that determines solubility of the molecule (Ingram and Buttke, 1984;Garg and Muller, 1993;Kubo et al, 1995;Lee et al, 1998;Malina and Shai, 2005).…”

Section: Introductionmentioning

confidence: 99%

Efficacy of alcohol alkoxylate surfactants differing in the molecular structure of the hydrophilic portion to control Phytophthora nicotianae in tomato substrate culture

2007

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Phytophthora nicotianae is a common and destructive pathogen of numerous ornamental, agronomic and horticultural crops such as tomato, tobacco and citrus. Three monobranched C 13 alcohol alkoxylate non-ionic surfactants were evaluated for in vitro inhibitory activity against the different asexual structures of P. nicotianae. The same surfactants, labelled MBA1301, MBA1303 and MBA1306, were tested for their in vivo control capacity against P. nicotianae root rot of tomato (Lycopersicon esculentum) under glasshouse conditions. MBA1301, MBA1303 and MBA1306 differ in the molecular structure of the hydrophilic portion. The molecular weight of MBA1301 is comparable to that of MBA1303 and is eight times lower than that of MBA1306. The main in vitro activity for MBA1301 and MBA1303 was a direct lytic effect on the zoospores. Zoospore lysis was already observed in the presence of 1 mg ml À1 of these two surfactants and almost no zoospores survived an addition of 5 mg ml À1 surfactant. In addition, MBA1301 and MBA1303 reduced sporangia formation at a concentration of 5 mg ml À1 . Both surfactants only affect mycelium growth at concentrations as high as 100 mg ml À1 . MBA1306 did not show any effect on sporangia formation, zoospore release and mycelium growth of P. nicotianae at a concentration 10 times that of the other two surfactants. A good in vivo control of P. nicotianae on tomato in substrate culture was obtained for MBA1301 and MBA1303 whereas the control capacity of MBA1306 was significantly lower. The results of this research indicate that non-ionic alcohol alkoxylate surfactants can be used to control tomato root rot caused by P. nicotianae in substrate culture. In addition, the size rather than the arrangement of the polymers in the hydrophilic portion of the surfactant molecule determines the efficacy to control tomato root rot caused by P. nicotianae in substrate culture. r

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Structural functions of antimicrobial long-chain alcohols and phenols

Cited by 159 publications

References 22 publications

Local Anesthetics and Antipsychotic Phenothiazines Interact Nonspecifically with Membranes and Inhibit Hexose Transporters in Yeast

Local Anesthetics and Antipsychotic Phenothiazines Interact Nonspecifically with Membranes and Inhibit Hexose Transporters in Yeast

Effect of alkan-1-ols on the structure of dopc model membrane

Efficacy of alcohol alkoxylate surfactants differing in the molecular structure of the hydrophilic portion to control Phytophthora nicotianae in tomato substrate culture

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