Effect ofp-Substitution of Aryl α-D-Mannosides on Inhibiting Mannose-Sensitive Adhesion ofEscherichia coli – Syntheses and Testing

Kötter, Sven; Kubisch, Jiří; Krallmann-Wenzel, Ulrike; Ehlers, Stefan; Křen, Vladimı́r

doi:10.1002/(sici)1099-0690(199808)1998:8<1669::aid-ejoc1669>3.0.co;2-q

Cited by 32 publications

(21 citation statements)

References 12 publications

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“…A plot of the percentage inhibition against the concentration of inhibitor enabled the extrapolation of the half‐maximal inhibitory concentration (IC 50 , Figures 4, a and S4). The IC 50 of 1950 μ M for α‐ D ‐methyl mannose is in agreement with the literature IC 50 values of 1300–3900 μ M 41,42. Concentrations of discotic molecules higher than 500 μ M could not be achieved because of solubility limits.…”

Section: Resultssupporting

confidence: 90%

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Petkau-Milroy

Brunsveld

2013

Eur J Org Chem

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Supramolecular synthesis, the “bottom‐up” construction of higher‐order structures from monomeric building blocks, represents a flexible approach for the generation of multivalent materials. Here, monovalent building blocks decorated with a single bioactive ligand were synthesized. In water, these supramolecular elements self‐assemble into columnar polymers that display multiple ligands. The supramolecular effect on the binding affinity was evaluated by using an enzyme‐linked lectin assay, and the self‐assembled architecture exhibited a stronger inhibitory power than that of the monovalent bioactive ligand. This so‐called self‐assembling multivalency enables the rapid and flexible generation of multivalent polymers from monovalent building blocks.

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Section: Resultssupporting

confidence: 90%

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Petkau-Milroy

Brunsveld

2013

Eur J Org Chem

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“…In vitro assays, usually used for QSAR studies, include three major components: the biological receptor or target, the native ligand and the test compound. In hemmaglutination inhibition assay, widely applied to test antagonist of FimH‐mediated bacterial adhesion, the bacterial lectin FimH is the receptor, the native ligand is glycosylated cell surface and the test compound is structurally modified α‐ d ‐mannoside. Here, we tested the potency of the ester type of ferrocene–mannose conjugate ( 10 , 12 and 14 ) to efficiently inhibit type 1 fimbriated E. coli HB101 (pPKl4) from agglutinating guinea‐pig erythrocytes.…”

Section: Resultsmentioning

confidence: 99%

Ferrocene conjugates with mannose: synthesis and influence of ferrocene aglycon on mannose‐mediated adhesion of Escherichia coli

Kovačević

Barišić

Ribić

et al. 2012

Applied Organom Chemis

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a Bacterial adhesion, mediated through interaction of bacterial lectins with carbohydrate structures presented on the surface of the host cells, is a prerequisite for infection. Anti-adhesion therapy, based on the inhibition of lectins by suitable carbohydrates, has been considered as a weapon for the combat of microbial diseases. Structural alteration of aglycon portions of mannose derivatives strongly influences their inhibitory potency toward type 1 fimbriated Escherichia coli. Thus several conjugates of mannosecontaining ferrocene aglycon moieties were synthesized and tested. The novel ferrocene conjugates 10, 12 and 14 were obtained by esterification of O-mannosylated propionic acid 1 with ferrocene alcohols R-Fn-(CH 2 ) n -OH (Fn = 1,1'-ferrocenylene; 2, n = 1, R = COOMe; 7, n = 1, R = NHBoc; 8, n = 2, R = H) in the presence of Boc 2 O/DMAP with subsequent debenzylation of the intermediate O-protected esters. Performed hemagglutination inhibitory tests showed that the examined bioorganometallics exhibit better inhibitory activity than known inhibitor methyl a-D-mannoside. Thus ferrocene-mannose conjugate 14 with the dimethylene spacer between ferrocene core and chiral linker displayed the best inhibitory efficiency.

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“…Variation of the p ‐substituent of phenyl mannosides had no big effect. It was shown that neither the reduction of the nitro group in p NPMan (leading to p APMan), nor its deletion (PMan) changed the compound's inhibitory potency to a great extent 67,68. While Sharon and co‐workers had reported a difference between PMan [RIP(PMan) MeMan = 40] and p NPMan [RIP( p NPMan) MeMan = 70], somewhat later this difference could not be confirmed (cf.…”

Section: Rational Design Of Carbohydrate Ligands For the Type 1 Fimentioning

confidence: 99%

Tuning the Redox Potentials of Dinuclear Tungsten Oxo Complexes [(Cp*W(4,4′‐R,R‐2,2′‐bpy)(μ‐O))₂][PF₆]₂ Toward Photochemical Water Splitting

Cremer

Burger

2003

Chemistry A European J

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A series of novel dinuclear tungsten(IV) oxo complexes with disubstituted 4,4'-R,R-2,2'-bipyridyl (R(2)bpy) ligands of the type [(Cp*W(R(2)bpy)(mu-O))(2)][PF(6)](2) (R=NMe(2), tBu, Me, H, Cl) was prepared by hydrolysis of the tungsten(IV) trichloro complexes [Cp*W(R(2)bpy)Cl(3)]. Cyclic voltammetry measurements for the tungsten(IV) oxo compounds provided evidence for one reversible oxidation and two reversible reductions leading to the oxidation states W(V)W(IV), W(IV)W(III) and W(III)W(III). The corresponding complexes [(Cp*W(R(2)bpy)(mu-O))(2)](n+) [PF(6)](n) (n=0 for R=Me, tBu, and 1, 3 for both R=Me) could be isolated after chemical oxidation/reduction of the tungsten(IV) oxo complexes. The crystal structures of the complexes [(Cp*W(R(2)bpy)(mu-O))(2)][BPh(4)](2) (R=NMe(2), tBu) and [(Cp*W(Me(2)bpy)(mu-O))(2)](n+)[PF(6)](n) (n=0, 1, 2, 3) show a cis geometry with a puckered W(2)O(2) four-membered ring for all compounds except [(Cp*W(Me(2)bpy)(mu-O))(2)] which displays a trans geometry with a planar W(2)O(2) ring. Examining the interaction of these novel tungsten oxo complexes with protons, we were able to show that the W(IV)W(IV) complexes [(Cp*W(R(2)bpy)(mu-O))(2)][PF(6) (-)](2) (R=NMe(2), tBu) undergo reversible protonation, while the W(III)W(III) complexes [(Cp*W(R(2)bpy)(mu-O))(2)] transfer two electrons forming the W(IV)W(IV) complex and molecular hydrogen.

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Effect ofp-Substitution of Aryl α-D-Mannosides on Inhibiting Mannose-Sensitive Adhesion ofEscherichia coli – Syntheses and Testing

Cited by 32 publications

References 12 publications

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Ferrocene conjugates with mannose: synthesis and influence of ferrocene aglycon on mannose‐mediated adhesion of Escherichia coli

Tuning the Redox Potentials of Dinuclear Tungsten Oxo Complexes [(Cp*W(4,4′‐R,R‐2,2′‐bpy)(μ‐O))₂][PF₆]₂ Toward Photochemical Water Splitting

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Effect ofp-Substitution of Aryl α-D-Mannosides on Inhibiting Mannose-Sensitive Adhesion ofEscherichia coli – Syntheses and Testing

Cited by 32 publications

References 12 publications

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Self‐Assembling Multivalency – Supramolecular Polymers Assembled from Monovalent Mannose‐Labelled Discotic Molecules

Ferrocene conjugates with mannose: synthesis and influence of ferrocene aglycon on mannose‐mediated adhesion of Escherichia coli

Tuning the Redox Potentials of Dinuclear Tungsten Oxo Complexes [(Cp*W(4,4′‐R,R‐2,2′‐bpy)(μ‐O))2][PF6]2 Toward Photochemical Water Splitting

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Tuning the Redox Potentials of Dinuclear Tungsten Oxo Complexes [(Cp*W(4,4′‐R,R‐2,2′‐bpy)(μ‐O))₂][PF₆]₂ Toward Photochemical Water Splitting