Accumulation of <i>O</i>‐GlcNAc‐Displaying CdTe Quantum Dots in Cells in the Presence of ATP

Niikura, Kenichi; Nishio, Takashi; Akita, Hidetaka; Matsuo, Yasutaka; Kamitani, Ryosuke; Kogure, Kentaro; Harashima, Hideyoshi; Ijiro, Kuniharu

doi:10.1002/cbic.200600496

Cited by 30 publications

(20 citation statements)

References 35 publications

(39 reference statements)

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“…In our previous study, we have shown that classical NLS-coated QDs are transported into the nucleus only in the presence of additional cytosolic factors. [11] In contrast, the nuclear import of sugar-displaying QDs did not require additional cytosolic factors. This corresponds closely to the results of a previous report on the nuclear import of glycosylated BSA.…”

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confidence: 92%

“…[11] Ligand exchange occurring on the surface of the QDs was confirmed by MALDI-ToF mass spectrometry. Ligands immobilized on inorganic nanoparticles, such as QDs, were detached from the surface during the laser deposition process, and the mass corresponding to the molecular weight of neoglycolipids was clearly detected (Figure 1 B).…”

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confidence: 99%

“…The cellotriose(Glcb1-4Glcb1-4Glc)-lipid 7 is a trisaccharide that is composed of only a b-linked glucose, thus lipid 7 was used as a control to a-linked glucose. Neoglycolipids were synthesized based on a previously described method [10,11] by starting from fully acetylated carbohydrates, hexa(ethyleneglycol) and 11-bromoundecene.CdTe nanocrystals that had been stabilized with mercaptopropionic acid (MPA) were prepared in water as described by Yang et al[12] Sugar-displaying CdTe QDs were synthesized by surface exchange from MPA to the neoglycolipid in water (Figure 1 A), and then purified by using spin filtration.[11] Ligand exchange occurring on the surface of the QDs was confirmed by MALDI-ToF mass spectrometry. Ligands immobilized on inorganic nanoparticles, such as QDs, were detached from the surface during the laser deposition process, and the mass corresponding to the molecular weight of neoglycolipids was clearly detected (Figure 1 B).…”

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Oligosaccharide‐Mediated Nuclear Transport of Nanoparticles

et al. 2008

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The transport of nanoparticles into the cellular nucleus is a potentially important technique because it can open the way to a wide range of applications, including the sequence-specific detection of genomic DNA, efficient DNA transfection, and the specific entry of drugs into the nucleus.[1] It has been reported that the nuclear import of proteins larger than 40 kD does not occur by passive diffusion.[2] Similarly, the nuclear import of macromolecules or particles is strictly regulated. Therefore, the nuclear import of nanoparticles that contain gold nanoparticles and quantum dots has been achieved by coating the surface with classical nuclear localization signals (NLS), that is, short, highly positively charged peptides.[3] However, the problem remains that positively charged particles can interact with serum protein, resulting in rapid clearance from the plasma compartment.[4] Because the cationic NLS interacts with negatively charged DNA, NLS peptides do not work as efficient signals for transport of DNA into the nucleus; [5] this implies that the use of peptide-based cationic NLS might be limited when using DNA-displaying nanoparticles.Monsigny et al. have shown that sugars can also work as nuclear localization signals. [6][7][8][9] The neoglycoproteins, BSA (bovine serum albumin)-glucose, BSA-mannose and BSA-fucose are rapidly transported into the nucleus of HeLa cells, whereas BSA without chemical modifications is not. Because carbohydrates normally show high biocompatibility and water solubility, they are suitable for use in the modification of synthetic carriers and nanoparticles. Previously, however, only the application of these carbohydrate signals to the nuclear import of proteins was examined, and there are no reports on the effectiveness of carbohydrate signals for the nuclear import of artificial materials, such as nanoparticles and polymers. Previous reports that used BSA have focused only on monosaccharides as a signal. In this paper, we expand the varieties of carbohydrates tested from monosaccharides to oligosaccharides in the search for an efficient signal that is applicable to the nuclear import of nanoparticles. Herein, we present our unique finding that nanoparticles (quantum dots) that display oligo a-glucopyranoside on their surface are readily transported into the nucleus of digitonin-permeabilized HeLa cells. Semiconductor QDs have a diameter of several nanometers and their specific transport inside the cell can be readily achieved through the display of multiple ligands on their surface. As far as we know, this is the first report to describe the import of nanoparticles into the nucleus without the use of cationic NLS.Because BSA that has been substituted with a-glucopyranoside has been reported to be efficiently transported into the cell nucleus, [6] we synthesized neoglycolipids that contain various carbohydrates comprised of different numbers of glucose units (Scheme 1). In addition to a-monoglucopyranoside-lipid 3, we synthesized maltose(Glca1-4Glc)-lipid 4, maltotriose(Glca1-4Glc...

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Oligosaccharide‐Mediated Nuclear Transport of Nanoparticles

et al. 2008

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“…It was observed than GlcNAc-QDs accumulate in the endoplasmic reticulum in the presence of ATP. 160 When oligosaccharides 161 were attached to the QDs, the fluorescence intensity measured in the nucleus showed different degree of accumulation depending on the sugar covering QDs.…”

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confidence: 99%

Multivalent glycoconjugates in medicinal chemistry

Fernández-Bolaños¹,

Maya²,

Oliete³

2012

Carbohydrate Chemistry

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“…Covalent approaches include in situ protocols, for example, based on the addition of thiol-functionalized neoglycoconjugates to QD precursor solutions (De la Fuente and Penadés, 2005; Mukhopadhyay et al, 2009). The ligand exchange protocol is similar to the synthesis of gold glyconanomaterials, where the original capping agents can be replaced by thiol-derivatized glycoconjugates (Babu et al, 2007; Chen et al, 2008; Niikura et al, 2007, 2008; Robinson et al., 2005). QD glyconanomaterials have also been prepared by post-modification protocols similar to gold nanoparticles (Higuchi et al, 2008; Kikkeri et al, 2009b; Sandros et al, 2007).…”

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confidence: 99%

Glyconanomaterials for biosensing applications

Hao

Neranon

Ramström

et al. 2016

Biosensors and Bioelectronics

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Nanomaterials constitute a class of structures that have unique physiochemical properties and are excellent scaffolds for presenting carbohydrates, important biomolecules that mediate a wide variety of important biological events. The fabrication of carbohydrate-presenting nanomaterials, glyconanomaterials, is of high interest and utility, combining the features of nanoscale objects with biomolecular recognition. The structures can also produce strong multivalent effects, where the nanomaterial scaffold greatly enhances the relatively weak affinities of single carbohydrate ligands to the corresponding receptors, and effectively amplifies the carbohydrate-mediated interactions. Glyconanomaterials are thus an appealing platform for biosensing applications. In this review, we discuss the chemistry for conjugation of carbohydrates to nanomaterials, summarize strategies, and tabulate examples of applying glyconanomaterials in in vitro and in vivo sensing applications of proteins, microbes, and cells. The limitations and future perspectives of these emerging glyconanomaterials sensing systems are furthermore discussed.

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Accumulation of O‐GlcNAc‐Displaying CdTe Quantum Dots in Cells in the Presence of ATP

Cited by 30 publications

References 35 publications

Oligosaccharide‐Mediated Nuclear Transport of Nanoparticles

Oligosaccharide‐Mediated Nuclear Transport of Nanoparticles

Multivalent glycoconjugates in medicinal chemistry

Glyconanomaterials for biosensing applications

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