Synthesis of Gold Glyconanoparticles: Possible Probes for the Exploration of Carbohydrate‐Mediated Self‐Recognition of Marine Sponge Cells.

Souza, Adriana Carvalho de; Halkes, Koen M.; Meeldijk, Johannes D.; Verkleij, Arie J.; Vliegenthart, Johannes F.G.; Kamerling, Johannis P.

doi:10.1002/chin.200501177

Cited by 4 publications

(6 citation statements)

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“…The generation of the 1-SH-and 2-SH-decorated gold nanoparticles β-D-GlcpNAc3S-(1→3)-α-L-Fucp-(1→O) (CH 2 ) 3 S(CH 2 ) 6 S-@-Au (Au-1) and β-D-Galp4,6(R)Pyr-(1→4)-β-D-GlcpNAc-(1→3)-α-L-Fucp-(1→O)(CH 2 ) 3 S (CH 2 ) 6 S-@-Au (Au-2) have been reported earlier [11,24]. The mean diameter and the carbohydrate-weight percentage of the particles are 1.82±0.8 nm (36%) for Au-1, and 1.59± 0.5 nm (53%) for Au-2.…”

Section: Transmission Electron Microscopysupporting

confidence: 55%

“…Ultraviolet (UV) and surface plasmon resonance (SPR) spectroscopy of a synthetic β-D-GlcpNAc3S-(1→3)-α-LFucp-(1→O) fragment multivalently presented on bovine serum albumin (BSA) strongly supported the existence of true Ca 2+ -induced carbohydrate-carbohydrate interactions as a major force in the MAF aggregation phenomenon [9,10]. Moreover, transmission electron microscopy (TEM) imaging of gold glyconanoparticles coated with β-D-GlcpNAc3S-(1→3)-α-L-Fucp-(1→O)(CH 2 ) 3 S(CH 2 ) 6 SH (1-SH) (Scheme 1) and related structures, in the presence or absence of Ca 2+ -ions, has given valuable information on the mechanism of this disaccharide self-recognition [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Adhesion forces in the self-recognition of oligosaccharide epitopes of the proteoglycan aggregation factor of the marine sponge Microciona prolifera

et al. 2008

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Cell aggregation in the marine sponge Microciona prolifera is mediated by a multimillion molecular-mass aggregation factor, termed MAF. Earlier investigations revealed that the cell aggregation activity of MAF depends on two functional domains: (i) a Ca 2+ -independent cellbinding domain and (ii) a Ca 2+ -dependent proteoglycan self-interaction domain. Structural analysis of involved carbohydrate fragments of the proteoglycan in the selfassociation established a sulfated disaccharideRecent UV, SPR, and TEM studies, using BSA conjugates and gold nanoparticles of the synthetic sulfated disaccharide, clearly demonstrated self-recognition on the disaccharide level in the presence of Ca 2+ -ions. To determine binding forces of the carbohydrate-carbohydrate interactions for both synthetic MAF oligosaccharides, atomic force microscopy (AFM) studies were carried out. It turned out that, in the presence of Ca 2+ -ions, the force required to separate the tip and sample coated with a self-assembling monolayer of thiol-spacer-containing β-D-GlcpNAc-(1→3)-α-L-Fucp-(1→O)(CH 2 ) 3 S(CH 2 ) 6 S-was found to be quantized in integer multiples of 30±6 pN. No binding was observed between the two monolayers in the absence of Ca 2+ -ions. Cd 2+ -ions could partially induce the selfinteraction. In contrast, similar AFM experiments with thiol-spacer-containing β-D-Galp4,6(R)Pyr-(1→4)-β-DGlcpNAc-(1→3)-α-L-Fucp-(1→O)(CH 2 ) 3 S(CH 2 ) 6 S-did not show a binding in the presence of Ca 2+ -ions. Also TEM experiments of gold nanoparticles coated with the pyruvated trisaccharide could not make visible aggregation in the presence of Ca 2+ -ions. It is suggested that the selfinteraction between the sulfated disaccharide fragments is stronger than that between the pyruvated trisaccharide.

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Section: Transmission Electron Microscopysupporting

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Adhesion forces in the self-recognition of oligosaccharide epitopes of the proteoglycan aggregation factor of the marine sponge Microciona prolifera

et al. 2008

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“…This approach therefore necessitated precise, chemically-synthesized carbohydrate ligands to mediate CD62 binding and detection. Nano-sized particles (16)(17)(18)(19)(20) have been functionalized with carbohydrates for the elegant in vitro study of carbohydrate-mediated interactions, such as those mediating marine sponge interactions (17). The platforms for these particles have focused on nanosized gold (17)(18)(19) and cadmium sulfide (CdS) (19)(20)(21).…”

mentioning

confidence: 99%

“…Nano-sized particles (16)(17)(18)(19)(20) have been functionalized with carbohydrates for the elegant in vitro study of carbohydrate-mediated interactions, such as those mediating marine sponge interactions (17). The platforms for these particles have focused on nanosized gold (17)(18)(19) and cadmium sulfide (CdS) (19)(20)(21). Although these are often highly convenient and flexible, they also have disadvantages, such as the toxicity (22) of CdS-based fluorescent quantum dots and the ligand-lability of gold clusters (23,24), which is exacerbated in biological media (25).…”

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confidence: 99%

Glyconanoparticles allow pre-symptomatic in vivo imaging of brain disease

Kasteren

Campbell

Serres

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

255

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Initial recruitment of leukocytes in inflammation associated with diseases such as multiple sclerosis (MS), ischemic stroke, and HIV-related dementia, takes place across intact, but activated brain endothelium. It is therefore undetectable to symptom-based diagnoses and cannot be observed by conventional imaging techniques, which rely on increased permeability of the blood–brain barrier (BBB) in later stages of disease. Specific visualization of the early-activated cerebral endothelium would provide a powerful tool for the presymptomatic diagnosis of brain disease and evaluation of new therapies. Here, we present the design, construction and in vivo application of carbohydrate-functionalized nanoparticles that allow direct detection of endothelial markers E-/P-selectin (CD62E/CD62P) in acute inflammation. These first examples of MRI-visible glyconanoparticles display multiple copies of the natural complex glycan ligand of selectins. Their resulting sensitivity and binding selectivity has allowed acute detection of disease in mammals with beneficial implications for treatment of an expanding patient population suffering from neurological disease.

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“…The other SH group can then be linked to gold nanoparticles to form water-soluble gold glyconanoparticles, which are important model systems for interaction studies [65]. A thiomethylation reaction can take place in the solid state, as was demonstrated in the photoreaction of a toluene dispersion of crystals of a tetraphenylaminotriazine derivative having eight pendant N-allyl chains in the presence of CH 3 SH [66].…”

Section: Hào Additionmentioning

confidence: 99%