Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-l-arabino-hexopyranosides

Rauter, Amélia P.; Lucas, Susana D.; Almeida, Tânia Santos de; Sacoto, Diana; Ribeiro, Verónica; Justino, Jorge; Neves, Ana; Silva, Filipa; Oliveira, M. Conceição; Ferreira, Maria João; Santos, M. Soledade C.S.; Barbosa, Ester F.G.

doi:10.1016/j.carres.2004.11.020

Cited by 31 publications

(12 citation statements)

References 29 publications

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“…With increasing dose levels of the tested complexes, antifungal activity for the most part was enhanced. In a few circumstances, inconsistent data on %MIZ was observed in this study either with increasing application dosage or over time as seen in some studies [14][15][16]30]; these data could not be explained with high degree of certainty but may be related to either the hydrophilic nature of some micro-organisms during growth or due to the higher permeation potential of the diluted compound into the fungal cell wall. L 1 is most potent, exhibiting high potential fungistatic activity with significantly (p < 0.001) much higher MIZ above 13% on average, particularly in cultures of A. niger and A. fumigatus, when compared with other complexes.…”

Section: In Vitro Antifungal Activitycontrasting

confidence: 68%

“…Disc diffusion assay. A disc application technique of Rauter and co-workers [16] was employed in vitro to evaluate the antifungal activities. Mature conidia of fungal isolates were harvested from PDA plates and suspended in Ringer's solution; spore suspensions were standardized with a haemocytometer (1 Â 10 4 conidia mL À1 ).…”

Section: In Vitro Antifungal Activitymentioning

confidence: 99%

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Synthesis, characterization, and in vitro antibacterial and antifungal studies of tin(IV) thiohydrazide complexes

Mishra

Tiwari

et al. 2011

Journal of Coordination Chemistry

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Reaction of tin dichloride and tin tetrachloride with cyclohexylamine-N-thiohydrazide (ChaThz) [L 1 ] and 1,3-propanediamine-N-thiohydrazide (PdaThz) [L 2 ] results in [Sn(ChaThz) 2 ] (1), Sn(ChaThz) 2 Cl 2 ] (2), [Sn(PdaThz) 2 ] (3), and [Sn(PdaThz) 2 Cl 2 ] (4), in which the thiohydrazide coordinates to tin through imine nitrogen and thioamide sulfur. The ratio metal : ligand was 1 : 2 for all complexes. The tin(IV) thiohydrazide complexes were characterized by elemental analysis, IR, UV-Vis, 1 H-NMR, 119 Sn NMR, and mass spectral studies. Using the disc diffusion method, the ligands and metal complexes were screened for in vitro antibacterial activities against four pathogenic bacteria, Escherichia coli, Staphylococcus aureus, P. aeruginosa, and Bacillus cereus and for antifungal activities against Aspergillus flavus, A. carbonarius, A. niger, and A. fumigatus. While the tin(IV) complexes exhibited moderate antifungal activities, their parent ligands showed much higher and long-lasting broad spectrum of bioactivity against fungal growth. This was particularly the case for L 1 whose fungal inhibitory activity by the end of the experimental period was comparable and, for the most part, more pronounced than that of AmB. This higher activity of L 1 was maintained specifically against S. Aureus but in general, bacteria were more susceptible to complexes than ligands.

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Section: In Vitro Antifungal Activitycontrasting

confidence: 68%

Section: In Vitro Antifungal Activitymentioning

confidence: 99%

Synthesis, characterization, and in vitro antibacterial and antifungal studies of tin(IV) thiohydrazide complexes

Mishra

Tiwari

et al. 2011

Journal of Coordination Chemistry

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“…The O-nucleophiles were chosen in order to obtain potentially bioactive glycosides such as octyl glycosides, which have been reported to present surface active and antimicrobial properties [46] and flavonoid glycosides, known to possess a diversity of bioactivities and to display a remarkable array of biochemical and pharmacological actions, with repercussion on inflammation, heart diseases and cancer. Thus, the condensation of flavonoids with sugars leading to new derivatives for structure/bioactivity relationship studies is a matter of relevance for this type of research.…”

Section: Reaction Of 346-tri-o-benzyl-d-glucal With Nucleophiles Camentioning

confidence: 99%

Acid zeolites as efficient catalysts for O- and S-glycosylation

Rauter

Almeida

Xavier

et al. 2007

Journal of Molecular Catalysis A: Chemical

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“…All lipids were obtained from Avanti Polar Lipids (Alabaster, AL), except LPS (Escherichia coli O55:B5) that was purchased from Fluka (Buchs, Switzerland). Dodecyl 2,6-dideoxy-b-L-arabino-hexopyranoside (DAHP) was a kind gift from Prof. Pilar Rauter (University of Lisbon, Portugal) and synthesized as described elsewhere (25). Acetate buffer (5 mM sodium acetate, 150 mM NaCl) was used in all the fluorescence studies.…”

Section: Methodsmentioning

confidence: 99%

Fold-Unfold Transitions in the Selectivity and Mechanism of Action of the N-Terminal Fragment of the Bactericidal/Permeability-Increasing Protein (rBPI21)

Domingues

Lopes²,

Santos

et al. 2009

Biophysical Journal

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Septic or endotoxic shock is a common cause of death in hospital intensive care units. In the last decade numerous antimicrobial peptides and proteins have been tested in the search for an efficient drug to treat this lethal disease. Now in phase III clinical trials, rBPI(21), a recombinant N-terminal fragment of the bactericidal/permeability-increasing protein (BPI), is a promising drug to reduce lesions caused by meningococcal sepsis. We correlated structural and stability data with functional information of rBPI(21) bound to both model systems of eukaryotic and bacterial membranes. On interaction with membranes, rBPI(21) loses its conformational stability, as studied by circular dichroism. This interaction of rBPI(21) at membrane level was higher in the presence of negatively charged phospholipid relatively to neutral ones, with higher partition coefficients (K(p)), suggesting a preference for bacterial membranes over mammalian membranes. rBPI(21) binding to membranes is reinforced when its disulfide bond is broken due to conformational changes of the protein. This interaction is followed by liposome aggregation due to unfolding, which ensures protein aggregation, and interfacial localization of rBPI(21) in membranes, as studied by extensive quenching by acrylamide and 5-deoxylstearic acid and not by 16-deoxylstearic acid. An uncommon model of the selectivity and mechanism of action is proposed, where membrane induces unfolding of the antimicrobial protein, rBPI(21). The unfolding ensures protein aggregation, established by protein-protein interaction at membrane surface or between adjacent membranes covered by the unfolded protein. This protein aggregation step may lead to membrane perturbation.

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Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-l-arabino-hexopyranosides

Cited by 31 publications

References 29 publications

Synthesis, characterization, and in vitro antibacterial and antifungal studies of tin(IV) thiohydrazide complexes

Synthesis, characterization, and in vitro antibacterial and antifungal studies of tin(IV) thiohydrazide complexes

Acid zeolites as efficient catalysts for O- and S-glycosylation

Fold-Unfold Transitions in the Selectivity and Mechanism of Action of the N-Terminal Fragment of the Bactericidal/Permeability-Increasing Protein (rBPI21)

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