Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots

Ohyanagi, Tatsuya; Nagahori, Noriko; Shimawaki, Ken; Hinou, Hiroshi; Yamashita, Tadashi; Sasaki, Akira; Jin, Takashi; Iwanaga, Toshihiko; Kinjo, Masataka; Nishimura, Shin‐Ichiro

doi:10.1021/ja111201c

Cited by 82 publications

(89 citation statements)

References 90 publications

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“…To amplify the low affinity between simple oligosaccharides and HA, glycan-modified high performance quantum dots (Glyco-PC-QDs) (Ohyanagi et al, 2011) that can be used for live animal imaging by near-infrared fluorescence photometry due to the non-fouling nature of QDs coated by phosphorylcholine self-assembled monolayers were employed. Although colorful Glyco-PC-QDs have proved to become highly sensitive fluorescent probes for direct imaging of living cells and animals by employing common fluorescence microscopic devices (Ohyanagi et al, 2011), no examples have indicated the feasibility of these ligand-conjugated QDs in quantitative analysis aiming for high-throughput screening toward drug discovery research.…”

Section: Discussionmentioning

confidence: 99%

“…Egg yolk sialylated glycopeptide (A2 glycopeptide) was purchased from TCI (Tokyo, Japan). 11-Mercaptoundecylphosphorylcholine (PC-SH) and 11,11'-dithio bis [undec-11-yl 12-(aminooxyacetyl) amino hexa (ethyleneglycol) ] (ao-SH) were synthesized by the procedures reported previously (Holmlin RE et al, 2001;Nagahori et al, 2009;Ohyanagi et al, 2011). The ao-PC-QDs were prepared from the above Qdot 545 ITK, trioctylphosphine oxide (TOPO)-coated QDs (100 L of 1 M solution, 5.8 nm, CdSe/ZnS, λ em = 545 nm), by a general protocol for coating with ao-SH (50%) and PC-SH (50%).…”

Section: Reagents and The Preparation Of A2-pc-qdsmentioning

confidence: 99%

“…The ao-PC-QDs were prepared from the above Qdot 545 ITK, trioctylphosphine oxide (TOPO)-coated QDs (100 L of 1 M solution, 5.8 nm, CdSe/ZnS, λ em = 545 nm), by a general protocol for coating with ao-SH (50%) and PC-SH (50%). Sialylated biantennary N-glycan (A2) prepared by treating A2 glycopeptide with PNGase F (Roche Diagnostics Japan, Tokyo, Japan) was subjected to coupling with ao-PC-QDs by the "glycoblotting" (Nishimura et al, 2005;Ohyanagi et al, 2011) reaction and gave PC-QDs displaying A2 glycans (A2-PC-QDs, Figure 1). Characterization of A2-PC-QDs was performed by 5 direct MALDI-TOFMS (Nagahori et al, 2009;Ohyanagi et al, 2011) and the results showed the advent of an expected molecular ion signal at m/z 3155.7 corresponding to the heterodisulfide A2-S-S-PC instead of disappearance of the signal at m/z 908.7 due to ao-S-S-PC corresponding to free aminooxy-functional groups.…”

Section: Reagents and The Preparation Of A2-pc-qdsmentioning

confidence: 99%

“…Sialylated biantennary N-glycan (A2) prepared by treating A2 glycopeptide with PNGase F (Roche Diagnostics Japan, Tokyo, Japan) was subjected to coupling with ao-PC-QDs by the "glycoblotting" (Nishimura et al, 2005;Ohyanagi et al, 2011) reaction and gave PC-QDs displaying A2 glycans (A2-PC-QDs, Figure 1). Characterization of A2-PC-QDs was performed by 5 direct MALDI-TOFMS (Nagahori et al, 2009;Ohyanagi et al, 2011) and the results showed the advent of an expected molecular ion signal at m/z 3155.7 corresponding to the heterodisulfide A2-S-S-PC instead of disappearance of the signal at m/z 908.7 due to ao-S-S-PC corresponding to free aminooxy-functional groups. As standards or simple model compounds in the competitive binding assay, 2-aminobenzamide (2AB) labeled A2 (2AB-A2, 1) (Dell et al, 2008), and two known sialosides, methyl 5-acetamido-3,5-dideoxy-D-glycero--D-galacto-2-nonulopyranosonic acid (2) (Sauter et al, 1992) and octyl 5-acetamido-3,5-dideoxy-D-glycero--D-galacto-2-nonulopyranosonic acid (3) (Crich and Li, 2007), were also used.…”

Section: Reagents and The Preparation Of A2-pc-qdsmentioning

confidence: 99%

“…According to the versatile synthetic method (Ohyanagi et al, 2011) by combined use of an aminooxy-terminated thiol derivative (ao-SH) and a PC derivative (PC-SH), a novel Glyco-PC-QDs having biantennary N-glycan chains (A2-PC-QDs) was prepared (Figure 1). Concentration of A2-PCQDs dissolved in the stock solution derived from the starting TOPO-coated QDs was determined, at which the fluorescent signal was sufficiently higher than the background of the buffer solution.…”

Section: Preparation Of a New Fluorescent Probe For Fp-based Ha Assaymentioning

confidence: 99%

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Over the past few decades, nanoengineered particles have gained increasing interest for applications in the biomedical realm, including diagnosis, imaging, and therapy. When functionalized with targeting ligands, these particles have the potential to interact with specific cells and tissues, and accumulate at desired target sites, reducing side effects and improve overall efficacy in applications such as vaccination and drug delivery. However, when targeted particles enter a complex biological environment, the adsorption of biomolecules and the formation of a surface coating (e.g., a protein corona) changes the properties of the carriers and can render their behavior unpredictable. For this reason, it is of importance to consider the potential challenges imposed by the biological environment at the early stages of particle design. This review describes parameters that affect the targeting ability of particulate drug carriers, with an emphasis on the effect of the protein corona. We highlight strategies for exploiting the protein corona to improve the targeting ability of particles. Finally, we provide suggestions for complementing current in vitro assays used for the evaluation of targeting and carrier efficacy with new and emerging techniques (e.g., 3D models and flow‐based technologies) to advance fundamental understanding in bio‐nano science and to accelerate the development of targeted particles for biomedical applications.

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Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots

Cited by 82 publications

References 90 publications

Fluorescence polarization-based assay using N-glycan-conjugated quantum dots for screening in hemagglutinin blockers for influenza A viruses

Fluorescence polarization-based assay using N-glycan-conjugated quantum dots for screening in hemagglutinin blockers for influenza A viruses

Multifunctional Glyco‐Nanofibers: siRNA Induced Supermolecular Assembly for Codelivery In Vivo

Particle Targeting in Complex Biological Media

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