Studies on the antibacterial activity of dodecylglycerol. Its limited metabolism and inhibition of glycerolipid and lipoteichoic acid biosynthesis in Streptococcus mutans BHT.

Brissette, Janice L.; Cabacungan, E; Pieringer, Ronald A.

doi:10.1016/s0021-9258(19)84568-4

Cited by 34 publications

(4 citation statements)

References 37 publications

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“…Interestingly, DDG was found to inhibit bacterial growth by activating bacterial enzymes that break down the cell wall . Later studies showed that DDG also inhibited metabolic processes associated with peptidoglycan synthesis , as well as lipid and lipoteichoic acid synthesis . The wide range of metabolic activities affected by DDG treatment suggests that DDG disturbs bacterial cell membranes through a nonspecific mechanism, in turn, affecting the function of numerous, membrane-associated bacterial enzymes .…”

Section: Introductionmentioning

confidence: 99%

“…15 Later studies showed that DDG also inhibited metabolic processes associated with peptidoglycan synthesis 15,16 as well as lipid and lipoteichoic acid synthesis. 17 The wide range of metabolic activities affected by DDG treatment suggests that DDG disturbs bacterial cell membranes through a nonspecific mechanism, in turn, affecting the function of numerous, membrane-associated bacterial enzymes. 17 Although GML and DDG exhibit overlapping antibacterial activities, the aforementioned studies indicate that there are mechanistic distinctions between the two compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

“…17 The wide range of metabolic activities affected by DDG treatment suggests that DDG disturbs bacterial cell membranes through a nonspecific mechanism, in turn, affecting the function of numerous, membrane-associated bacterial enzymes. 17 Although GML and DDG exhibit overlapping antibacterial activities, the aforementioned studies indicate that there are mechanistic distinctions between the two compounds. Such questions have spurred efforts to better understand the molecular self-assembly of DDG in the context of explaining its biological activity.…”

Section: ■ Introductionmentioning

confidence: 99%

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Characterizing the Membrane-Disruptive Behavior of Dodecylglycerol Using Supported Lipid Bilayers

et al. 2019

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Monoglycerides are esterified adducts of fatty acid and glycerol molecules that disrupt phospholipid membranes, leading to a wide range of biological functions such as antimicrobial activity. Among monoglycerides, glycerol monolaurate (GML) exhibits particularly high antimicrobial activity, although enzymatic hydrolysis of its ester group can diminish potency. Consequently, there have been efforts to identify more chemically stable versions of GML, most notably its alkylglycerol ether equivalent called dodecylglycerol (DDG). However, despite high structural similarity, biological studies indicate that DDG and GML are not functionally equivalent and it has been speculated that the two compounds might have different interaction profiles with phospholipid membranes. To address this outstanding question, herein, we employed supported lipid bilayer (SLB) platforms to experimentally characterize the interactions of DDG with phospholipid membranes. Quartz crystal microbalance-dissipation experiments identified that DDG causes concentration-dependent membrane morphological changes in SLBs and the overall extent of membrane remodeling events was greater than that caused by GML. In addition, time-lapsed fluorescence microscopy imaging experiments revealed that DDG causes extensive membrane tubulation that is distinct from how GML induces membrane budding. We discuss how differences in the head group properties of DDG and GML contribute to distinct membrane interaction profiles, offering insight into how the molecular design of DDG not only improves chemical stability but also enhances membrane-disruptive activity.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Characterizing the Membrane-Disruptive Behavior of Dodecylglycerol Using Supported Lipid Bilayers

et al. 2019

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“…The downregulation of the dlt operon has been shown to lead to increased sensitivity to cationic antimicrobial peptides by increasing the negative charge on the membrane (Maria-Neto et al, 2015). However, this downregulation has also been correlated to increased resistance to membrane damaging agents such as monolaurin and its derivative dodecyl glycerol in E. faecalis AR01/DGVS and Staphylococcus mutans, respectively (Dufour et al, 2007;Brissette et al, 1986). This suggests that there may be a correlation between the dlt mutations and membrane associated damage, which is the reason for the observed changes in these genes.…”

Section: Correlating Gene Expression Level Changes In Efc3c and Efc3py To Adaptation To Coesmentioning

confidence: 99%

The mechanism of resistance to conjugated oligoelectrolytes in enterococcus faecalis

Chilambi¹

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Regulation of neuronal differentiation in neuron‐enriched primary cultures from embryonic rat cerebra by platelet activating factor and the structurally related glycerol ether lipid, dodecylglycerol

Ved

Gustow

Pieringer

1991

J of Neuroscience Research

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Primary cultures enriched in neurons dissociated from embryonic rat cerebra were used to demonstrate that platelet activating factor and the structurally related ether glycerolipid, dodecylglycerol, are readily taken up in small amounts by neurons and that they stimulate the differentiation of neurons. The stimulation of neuronal differentiation was observed as a precocious development of axon-like extensions which correlated with a concentration-dependent increase in neuronal-specific enzyme activities. This stimulation of morphological and neurochemical factors by either platelet activating factor or dodecylglycerol was almost completely abolished by triazolam, a known inhibitor of platelet activating factor function. Neither platelet activating factor nor dodecylglycerol at the concentrations used to achieve stimulation of neuronal differentiation compromised the plasma membrane, as indicated by the lack of leakage of cytoplasmic lactic acid dehydrogenase.

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Studies on the antibacterial activity of dodecylglycerol. Its limited metabolism and inhibition of glycerolipid and lipoteichoic acid biosynthesis in Streptococcus mutans BHT.

Cited by 34 publications

References 37 publications

Characterizing the Membrane-Disruptive Behavior of Dodecylglycerol Using Supported Lipid Bilayers

Characterizing the Membrane-Disruptive Behavior of Dodecylglycerol Using Supported Lipid Bilayers

The mechanism of resistance to conjugated oligoelectrolytes in enterococcus faecalis

Regulation of neuronal differentiation in neuron‐enriched primary cultures from embryonic rat cerebra by platelet activating factor and the structurally related glycerol ether lipid, dodecylglycerol

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