Papulacandins - The relationship between chemical structure and effect on glucan synthesis in yeast.

Römmele, Günter; Traxler, Peter; Wehrli, W.

doi:10.7164/antibiotics.36.1539

Cited by 42 publications

(16 citation statements)

References 4 publications

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“…Hydrogenation of the two fatty acids, or even removal of the shorter fatty acids in the galactose unit have only small effects on the inhibition of glucan biosynthesis, although it completely abolishes growth inhibition. The presence of the long fatty acid is essential for activity [106]. It seems that the configuration of the fatty acid is important for penetration into the cells, thus reaching the target site to block 1,3-glucan synthase.…”

Section: From Papulacandins and Echinocandins To Drugs Against Fungalmentioning

confidence: 99%

Fungal Metabolites for the Control of Biofilm Infections

Estrela

Abraham

2016

Agriculture

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Many microbes attach to surfaces and produce a complex matrix of polymers surrounding their cells, forming a biofilm. In biofilms, microbes are much better protected against hostile environments, impairing the action of most antibiotics. A pressing demand exists for novel therapeutic strategies against biofilm infections, which are a grave health wise on mucosal surfaces and medical devices. From fungi, a large number of secondary metabolites with antimicrobial activity have been characterized. This review discusses natural compounds from fungi which are effective against fungal and bacterial biofilms. Some molecules are able to block the cell communication process essential for biofilm formation (known as quorum sensing), others can penetrate and kill cells within the structure. Several targets have been identified, ranging from the inhibition of quorum sensing receptors and virulence factors, to cell wall synthesizing enzymes. Only one group of these fungal metabolites has been optimized and made it to the market, but more preclinical studies are ongoing to expand the biofilm-fighting arsenal. The broad diversity of bioactive compounds from fungi, their activities against various pathogens, and the multi-target trait of some molecules are promising aspects of fungal secondary metabolites. Future screenings for biofilm-controlling compounds will contribute to several novel clinical applications.

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Section: From Papulacandins and Echinocandins To Drugs Against Fungalmentioning

confidence: 99%

Fungal Metabolites for the Control of Biofilm Infections

Estrela

Abraham

2016

Agriculture

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“…The papulacandins A–E were isolated from the fermentation broths of Papularia sphaerosperma [3]. They block the synthesis of β-(1,3)-D-glucan by inhibition of β-(1,3)-D-glucan synthase [9–12]. The β-(1,3)-D-glucan is an integral and essential component of the fungal cell wall [13] and the dominant glucan in the cell wall of most medically important fungi, and therefore it is a target that is being actively pursued [14].…”

Section: Introductionmentioning

confidence: 99%

“…Apparently, the situation is different for the related disaccharide saricandan carrying different acyl chains, for which the monosaccharide analogue was not active [29]. Removing the galactose acyl chain from papulacandin B results in material that can still inhibit the target (in a spheroplasts glucan synthesis assay) but cannot reach the target site of C. albicans [12]. The same is true for the hydrogenated form of papulacandin D [12].…”

Section: Introductionmentioning

confidence: 99%

“…Removing the galactose acyl chain from papulacandin B results in material that can still inhibit the target (in a spheroplasts glucan synthesis assay) but cannot reach the target site of C. albicans [12]. The same is true for the hydrogenated form of papulacandin D [12]. Clearly some form of unsaturation is needed to maintain biological activity, but it is not known to what extent unsaturation (and alkylation and/or hydroxylation) needs to be present for the compound to reach the target site.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and antifungal properties of papulacandin derivatives

Kaaden

Breukink²,

Pieters

2012

Beilstein J. Org. Chem.

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SummaryDerivatives of an antifungal agent that targets the β-(1,3)-D-glucan synthase, papulacandin D, were synthesized and tested for activity. The papulacandin D structure contains a challenging benzannulated spiroketal unit, which is introduced in a palladium-catalyzed cross-coupling reaction of a glycal silanolate and an aryl iodide followed by an oxidative spiroketalization. Four different variants were made, differing in the nature of the acyl side chain with respect to the length, and in the number and stereochemistry of the double bonds. Moderate biological activity was observed for the derivatives with a side chain based on palmitic acid and linoleic acid.

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“…Papulacandins A, B, and C contain a spirocyclic diglycoside and two unsaturated FA, linked as esters to two hydroxyl groups of the diglycosides. Papulacandin D, a monosaccharide relative, is the simplest member of the family (44,45,48). The common opportunistic infection in AIDS patients, Pneumocystis carinii pneumonia, has been effectively overcome by newer members of the papulacandin family, Mer-WF3010 4 and L-687-781 5 (49-51).…”

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confidence: 99%

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

Dembitsky

2005

Lipids

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Polyether glycosidic ionophores and macrocyclic glycosides are of great interest, especially for the medicinal and pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antibiotics, anticancer agents, or in industry. More than 300 interesting and unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

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Papulacandins - The relationship between chemical structure and effect on glucan synthesis in yeast.

Cited by 42 publications

References 4 publications

Fungal Metabolites for the Control of Biofilm Infections

Fungal Metabolites for the Control of Biofilm Infections

Synthesis and antifungal properties of papulacandin derivatives

Astonishing diversity of natural surfactants: 2. Polyether glycosidic ionophores and macrocyclic glycosides

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