Modelling, synthesis and biological evaluation of novel glucuronide-based probes of Vibrio cholerae sialidase

Mann, Maretta; Thomson, Robin Joy; Dyason, Jeffrey Clifford; McAtamney, Sarah; Itzstein, Mark von

doi:10.1016/j.bmc.2005.10.004

Cited by 24 publications

(23 citation statements)

References 38 publications

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“…Established functional assays to assess NA inhibitory activities are based on either fluorescence or chemiluminescence and are reported to be compared to culture-based assays, more predictive in terms of their in vivo susceptibility [ 3 ]. The in vitro NA inhibition assays work with both viral and bacterial NAs, because the enzymes recognize the applied substrates independent of their biological origin [ 16 ]. The use of commercially available bacterial or viral NA-based test systems may be beneficial for a given pathogenic condition.…”

Section: Introductionmentioning

confidence: 99%

Different Inhibitory Potencies of Oseltamivir Carboxylate, Zanamivir, and Several Tannins on Bacterial and Viral Neuraminidases as Assessed in a Cell-Free Fluorescence-Based Enzyme Inhibition Assay

2017

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Neuraminidase is a key enzyme in the life cycle of influenza viruses and is present in some bacterial pathogens. We here assess the inhibitory potency of plant tannins versus clinically used inhibitors on both a viral and a bacterial model neuraminidase by applying the 2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid (MUNANA)-based activity assay. A range of flavan-3-ols, ellagitannins and chemically defined proanthocyanidin fractions was evaluated in comparison to oseltamivir carboxylate and zanamivir for their inhibitory activities against viral influenza A (H1N1) and bacterial Vibrio cholerae neuraminidase (VCNA). Compared to the positive controls, all tested polyphenols displayed a weak inhibition of the viral enzyme but similar or even higher potency on the bacterial neuraminidase. Structure–activity relationship analyses revealed the presence of galloyl groups and the hydroxylation pattern of the flavan skeleton to be crucial for inhibitory activity. The combination of zanamivir and EPs® 7630 (root extract of Pelargonium sidoides) showed synergistic inhibitory effects on the bacterial neuraminidase. Co-crystal structures of VCNA with oseltamivir carboxylate and zanamivir provided insight into bacterial versus viral enzyme-inhibitor interactions. The current data clearly indicate that inhibitor potency strongly depends on the biological origin of the enzyme and that results are not readily transferable. The therapeutic relevance of our findings is briefly discussed.

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Section: Introductionmentioning

confidence: 99%

Different Inhibitory Potencies of Oseltamivir Carboxylate, Zanamivir, and Several Tannins on Bacterial and Viral Neuraminidases as Assessed in a Cell-Free Fluorescence-Based Enzyme Inhibition Assay

2017

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“…Thus, known 2-acetamido-2-deoxy-6-O-trityl D-glucopyranose (14) [22,23] was per-benzoylated with benzoyl chloride in pyridine and subsequently the trityl group was removed using 90% TFA in CH 2 Cl 2 to afford the acceptor 15 in 78% yield. Chloroacetylation of known p-tolyl 3,4-O-isopropylidene-1-thio-β-D-fucopyranose (16) [24,25] with chloroacetic anhydride in pyridine provided the donor 17 in 89% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin

Roy

Mukhopadhyay

2007

Glycoconj J

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Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J(28), isolated from Albizia julibrissin, that showed significant in vitro antitumor activity against HeLa, Bel-7402 and PC-3M-1E8 cancer cell lines is reported. The tetrasaccharide has been synthesized as its p-methoxyphenyl glycoside starting from commercially available D-glucose, L-rhamnose and L-arabinose. The trisaccharide part has been synthesized from commercially available N-acetyl D-glucosamine, D-fucose and D-xylose using simple protecting group manipulations. Sulfuric acid immobilized on silica has been used successfully as a Brönsted acid catalyst for the crucial glycosylation steps.

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“…1 Sialidases or neuraminidases (EC 3.2.1.18) are exoglycosidases that catalyze the cleavage of terminal sialic acids from oligosaccharides and glycoconjugates. They have been found in many organisms including bacteria, viruses, fungi, and mammals.…”

Section: Introductionmentioning

confidence: 99%

“…Sialic acids are negatively charged monosaccharides with a nine-carbon backbone and are often found as the terminal residues of cell-surface glycoconjugates involved in many important cellular events. 1 Sialidases or neuraminidases (EC 3.2.1.18) are exoglycosidases that catalyze the cleavage of terminal sialic acids from oligosaccharides and glycoconjugates. They have been found in many organisms including bacteria, viruses, fungi, and mammals.…”

Section: Introductionmentioning

confidence: 99%

Triazole-linked transition state analogs as selective inhibitors against V. cholerae sialidase

Slack

Shi

et al. 2018

Bioorganic & Medicinal Chemistry

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Sialidases or neuraminidases are enzymes that catalyze the cleavage of terminal sialic acids from oligosaccharides and glycoconjugates. They play important roles in bacterial and viral infection and have been attractive targets for drug development. Structure-based drug design has led to potent inhibitors against neuraminidases of influenza A viruses that have been used successfully as approved therapeutics. However, selective and effective inhibitors against bacterial and human sialidases are still being actively pursued. Guided by crystal structural analysis, several derivatives of 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (Neu5Ac2en or DANA) were designed and synthesized as triazole-linked transition state analogs. Inhibition studies revealed that glycopeptide analog E-(TriazoleNeu5Ac2en)-AKE and compound (TriazoleNeu5Ac2en)-A were selective inhibitors against Vibrio cholerae sialidase, while glycopeptide analog (TriazoleNeu5Ac2en)-AdE selectively inhibited Vibrio cholerae and A. ureafaciens sialidases.

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Modelling, synthesis and biological evaluation of novel glucuronide-based probes of Vibrio cholerae sialidase

Cited by 24 publications

References 38 publications

Different Inhibitory Potencies of Oseltamivir Carboxylate, Zanamivir, and Several Tannins on Bacterial and Viral Neuraminidases as Assessed in a Cell-Free Fluorescence-Based Enzyme Inhibition Assay

Different Inhibitory Potencies of Oseltamivir Carboxylate, Zanamivir, and Several Tannins on Bacterial and Viral Neuraminidases as Assessed in a Cell-Free Fluorescence-Based Enzyme Inhibition Assay

Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin

Triazole-linked transition state analogs as selective inhibitors against V. cholerae sialidase

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