Synthesis and comparative lectin-binding affinity of mannosyl-coated β-cyclodextrin-dendrimer constructs

Baussanne, Isabelle; Benito, Juan M.; Mellet, Carmen Ortiz; Fernández, José Manuel Garcı́a; Law, Ho; Defaye, J.

doi:10.1039/b003765f

Cited by 87 publications

(60 citation statements)

References 6 publications

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“…The mono-6-ethylenediamino-6-deoxy-b-cyclodextrin was obtained by treating the corresponding mono-6-O-tosyl derivative [27] with freshly distilled ethylenediamine as previously described [28]. The product was purified by ion exchange chromatography on CM-Sephadex C-25 (NH 4 + form) and the purity and identity of this derivative was checked by TLC, 1 H-and positive-ion FAB-MS.…”

Section: Synthesis Of Monomentioning

confidence: 99%

Immobilization of Xanthine Oxidase on Carbon Nanotubes Through Double Supramolecular Junctions for Biosensor Construction

et al. 2011

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A novel approach for the noncovalent functionalization of single-walled carbon nanotubes with enzymes, using a bcyclodextrin-modified pyrene derivative, mono-6-ethylenediamino-(2-pyrene carboxamido)-6-deoxy-b-cyclodextrin (Pyr-bCD), as a molecular bridge for the construction of a supramolecular assembly between the nanotube surface and an adamantane-modified enzyme, is reported. The Pyr-bCD derivative was synthesized and its stacking to SWNT through p-p interactions accomplished. The functionalized nanotubes showed low capacity for the nonspecific adsorption of proteins, but were able to immobilize adamantane-modified xanthine oxidase via host-guest associations. This double supramolecular junctions-based approach was employed to modify a glassy carbon electrode with the enzyme/nanotubes complex for designing a biosensor device toward xanthine. The biosensor showed fast electroanalytical response (10 s), high sensitivity (5.9 mA/M cm 2 ) low detection limit (2 mM) and high stability.

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Section: Synthesis Of Monomentioning

confidence: 99%

Immobilization of Xanthine Oxidase on Carbon Nanotubes Through Double Supramolecular Junctions for Biosensor Construction

et al. 2011

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“…[25] A retrosynthetic analysis shows that neoglycolipid type I can be obtained in a straightforward manner from the per-O-acetylated mannose-or thiomannose-tethered azide derivative II with a variable spacer and N-(2-propynyl)pentacosa-10,12-diynamide (NPPCDAM, 4; Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Azide–Alkyne Cycloaddition in the Synthesis of Polydiacetylene: “Click Glycoliposome” as Biosensors for the Specific Detection of Lectins

Leal

Assali

Fernández

et al. 2011

Chemistry A European J

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Supramolecular self‐assembly of conjugated diacetylenic amphiphile‐tethered ligands photopolymerize to afford polydiacetylene (PDA) functional liposomes. Upon specific interaction with a variety of biological analytes in aqueous solution, PDA exhibits rapid colorimetric transitions. The PDA nanoassemblies, which are excellent membrane mimics, include an ene–yne polymeric reporter responsible for the chromatic transitions and the molecular recognition elements that are responsible for selective and specific binding to the biological target. A bottleneck in the fabrication of these colorimetric biosensors is the preparation of the diacetylenic monomer embedded with the recognition element of choice. In the present work, we make use of copper‐catalyzed azide–alkyne cycloaddition (CuAAC) as key step in the preparation of sugar‐coated liposome biosensors. The regioselective click ligation of the triacetylenic N‐(2‐propynyl)pentacosa‐10,12‐diynamide (NPPCDAM) with a variety of mannose‐ and lactose‐tethered azides afforded chemo‐ and regioselectively the corresponding 1,2,3‐triazole. The obtained diacetylenic monomers were incorporated efficiently into vesicles to afford functional mannose‐ and lactose‐coated glycoliposomes. The obtained PDA‐based click glycoliposomes have been characterized by using transmission electronic microscopy (TEM), dynamic light scattering (DLS), and UV/Vis spectroscopy. The efficiency of the reported approach was demonstrated by the rapid optimization of the hydrophilic spacer between the lipidic matrix and the mannose head group for the colorimetric detection of Concavalin A.

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“…Mono-6-formyl-CD was prepared by the oxidation in DMSO of the corresponding mono-6-O-tosyl-CD derivative [16] in the presence of 2,4,6-trimethylpyridine at 130°C under N 2 , followed by precipitation and exhaustive washing with ethanol [17]. The monoaldehyde derivative of CD was characterized by conventional NMR technique.…”

Section: Synthesis Of Fe 3 O 4 @Aptes-cd Nanoparticlesmentioning

confidence: 99%

Supramolecular immobilization of redox enzymes on cyclodextrin-coated magnetic nanoparticles for biosensing applications

Díez

Villalonga

et al. 2012

Journal of Colloid and Interface Science

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Synthesis and comparative lectin-binding affinity of mannosyl-coated β-cyclodextrin-dendrimer constructs

Cited by 87 publications

References 6 publications

Immobilization of Xanthine Oxidase on Carbon Nanotubes Through Double Supramolecular Junctions for Biosensor Construction

Immobilization of Xanthine Oxidase on Carbon Nanotubes Through Double Supramolecular Junctions for Biosensor Construction

Copper‐Catalyzed Azide–Alkyne Cycloaddition in the Synthesis of Polydiacetylene: “Click Glycoliposome” as Biosensors for the Specific Detection of Lectins

Supramolecular immobilization of redox enzymes on cyclodextrin-coated magnetic nanoparticles for biosensing applications

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