Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots
Glycans are expected to be one of the potential signal molecules for controlling drug targeting/delivery or long-term circulation of biopharmaceuticals. However, the effect of the carbohydrates of artificially glycosylated derivatives on in vivo dynamic distribution profiles after intravenous inject...
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| Veröffentlicht in: | Journal of the American Chemical Society 2011-08, Vol.133 (32), p.12507-12517 |
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| creator | Ohyanagi, Tatsuya Nagahori, Noriko Shimawaki, Ken Hinou, Hiroshi Yamashita, Tadashi Sasaki, Akira Jin, Takashi Iwanaga, Toshihiko Kinjo, Masataka Nishimura, Shin-Ichiro |
| description | Glycans are expected to be one of the potential signal molecules for controlling drug targeting/delivery or long-term circulation of biopharmaceuticals. However, the effect of the carbohydrates of artificially glycosylated derivatives on in vivo dynamic distribution profiles after intravenous injection of model animals remains unclear due to the lack of standardized methodology and a suitable platform. We report herein an efficient and versatile method for the preparation of multifunctional quantum dots (QDs) displaying common synthetic glycosides with excellent solubility and long-term stability in aqueous solution without loss of quantum yields. Combined use of an aminooxy-terminated thiol derivative, 11,11′-dithio bis[undec-11-yl 12-(aminooxyacetyl)amino hexa(ethyleneglycol)], and a phosphorylcholine derivative, 11-mercaptoundecylphosphorylcholine, provided QDs with novel functions for the chemical ligation of ketone-functionalized compounds and the prevention of nonspecific protein adsorption concurrently. In vivo near-infrared (NIR) fluorescence imaging of phosphorylcholine self-assembled monolayer (SAM)-coated QDs displaying various simple sugars (glyco-PC-QDs) after administration into the tail vein of the mouse revealed that distinct long-term delocalization over 2 h can be achieved in cases of QDs modified with α-sialic acid residue (Neu5Ac-PC-QDs) and control PC-QDs, while QDs bearing other common sugars, such as α-glucose (Glc-PC-QDs), α-mannose (Man-PC-QDs), α-fucose (Fuc-PC-QDs), lactose (Lac-PC-QDs), β-glucuronic acid (GlcA-PC-QDs), N-acetyl-β-d-glucosamine (GlcNAc-PC-QDs), and N-acetyl-β-d-galactosamine (GalNAc-PC-QDs) residues, accumulated rapidly (5–10 min) in the liver. Sequential enzymatic modifications of GlcNAc-PC-QDs gave Galβ1,4GlcNAc-PC-QDs (LacNAc-PC-QDs), Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (Le x -PC-QDs), Neu5Acα2,3Galβ1,4GlcNAc-PC-QDs (sialyl LacNAc-PC-QDs), and Neu5Acα2,3Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (sialyl Le x -PC-QDs) in quantitative yield as monitored by direct matrix-assisted laser desorption ionization time-of-flight mass spectrometry analyses. Live animal imaging uncovered for the first time that Le x -PC-QDs also distributed rapidly in the liver after intravenous injection and almost quenched over 1 h in similar profiles to those of LacNAc-PC-QDs and Lac-PC-QDs. On the other hand, sialyl LacNAc-PC-QDs and sialyl Le x -PC-QDs were still retained stably in the whole body after 2 h, while they showed significantly different in |
| doi_str_mv | 10.1021/ja111201c |
| format | Article |
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However, the effect of the carbohydrates of artificially glycosylated derivatives on in vivo dynamic distribution profiles after intravenous injection of model animals remains unclear due to the lack of standardized methodology and a suitable platform. We report herein an efficient and versatile method for the preparation of multifunctional quantum dots (QDs) displaying common synthetic glycosides with excellent solubility and long-term stability in aqueous solution without loss of quantum yields. Combined use of an aminooxy-terminated thiol derivative, 11,11′-dithio bis[undec-11-yl 12-(aminooxyacetyl)amino hexa(ethyleneglycol)], and a phosphorylcholine derivative, 11-mercaptoundecylphosphorylcholine, provided QDs with novel functions for the chemical ligation of ketone-functionalized compounds and the prevention of nonspecific protein adsorption concurrently. In vivo near-infrared (NIR) fluorescence imaging of phosphorylcholine self-assembled monolayer (SAM)-coated QDs displaying various simple sugars (glyco-PC-QDs) after administration into the tail vein of the mouse revealed that distinct long-term delocalization over 2 h can be achieved in cases of QDs modified with α-sialic acid residue (Neu5Ac-PC-QDs) and control PC-QDs, while QDs bearing other common sugars, such as α-glucose (Glc-PC-QDs), α-mannose (Man-PC-QDs), α-fucose (Fuc-PC-QDs), lactose (Lac-PC-QDs), β-glucuronic acid (GlcA-PC-QDs), N-acetyl-β-d-glucosamine (GlcNAc-PC-QDs), and N-acetyl-β-d-galactosamine (GalNAc-PC-QDs) residues, accumulated rapidly (5–10 min) in the liver. Sequential enzymatic modifications of GlcNAc-PC-QDs gave Galβ1,4GlcNAc-PC-QDs (LacNAc-PC-QDs), Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (Le x -PC-QDs), Neu5Acα2,3Galβ1,4GlcNAc-PC-QDs (sialyl LacNAc-PC-QDs), and Neu5Acα2,3Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (sialyl Le x -PC-QDs) in quantitative yield as monitored by direct matrix-assisted laser desorption ionization time-of-flight mass spectrometry analyses. Live animal imaging uncovered for the first time that Le x -PC-QDs also distributed rapidly in the liver after intravenous injection and almost quenched over 1 h in similar profiles to those of LacNAc-PC-QDs and Lac-PC-QDs. On the other hand, sialyl LacNAc-PC-QDs and sialyl Le x -PC-QDs were still retained stably in the whole body after 2 h, while they showed significantly different in vivo dynamics in the tissue distribution, suggesting that structure/sequence of the neighboring sugar residues in the individual sialyl oligosaccharides might influence the final organ-specific distribution. The present results clearly visualize the evidence of an essential role of the terminal sialic acid residue(s) for achieving prolonged in vivo lifetime and biodistribution of various glyco-PC-QDs as a novel class of functional platforms for nanomaterial-based drug targeting/delivery. A standardized protocol using multifunctional PC-QDs should facilitate live animal imaging of ligand-displayed QDs using versatile NIR fluorescence photometry without influence of size-dependent accumulation/excretion pathway for nanoparticles (e.g., viruses) >10 nm in hydrodynamic diameter by the liver.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja111201c</identifier><identifier>PMID: 21740000</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Carbohydrate Sequence ; Glycoconjugates - analysis ; Glycoconjugates - chemistry ; Mice ; Molecular Sequence Data ; N-Acetylneuraminic Acid - chemistry ; Phosphorylcholine - chemistry ; Quantum Dots ; Spectroscopy, Near-Infrared - methods</subject><ispartof>Journal of the American Chemical Society, 2011-08, Vol.133 (32), p.12507-12517</ispartof><rights>Copyright © 2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-5df284314e2446f26e7c752ed5e73fec19a8f797faa4782a839e21e8498264c53</citedby><cites>FETCH-LOGICAL-a380t-5df284314e2446f26e7c752ed5e73fec19a8f797faa4782a839e21e8498264c53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja111201c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja111201c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27078,27926,27927,56740,56790</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21740000$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ohyanagi, Tatsuya</creatorcontrib><creatorcontrib>Nagahori, Noriko</creatorcontrib><creatorcontrib>Shimawaki, Ken</creatorcontrib><creatorcontrib>Hinou, Hiroshi</creatorcontrib><creatorcontrib>Yamashita, Tadashi</creatorcontrib><creatorcontrib>Sasaki, Akira</creatorcontrib><creatorcontrib>Jin, Takashi</creatorcontrib><creatorcontrib>Iwanaga, Toshihiko</creatorcontrib><creatorcontrib>Kinjo, Masataka</creatorcontrib><creatorcontrib>Nishimura, Shin-Ichiro</creatorcontrib><title>Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Glycans are expected to be one of the potential signal molecules for controlling drug targeting/delivery or long-term circulation of biopharmaceuticals. However, the effect of the carbohydrates of artificially glycosylated derivatives on in vivo dynamic distribution profiles after intravenous injection of model animals remains unclear due to the lack of standardized methodology and a suitable platform. We report herein an efficient and versatile method for the preparation of multifunctional quantum dots (QDs) displaying common synthetic glycosides with excellent solubility and long-term stability in aqueous solution without loss of quantum yields. Combined use of an aminooxy-terminated thiol derivative, 11,11′-dithio bis[undec-11-yl 12-(aminooxyacetyl)amino hexa(ethyleneglycol)], and a phosphorylcholine derivative, 11-mercaptoundecylphosphorylcholine, provided QDs with novel functions for the chemical ligation of ketone-functionalized compounds and the prevention of nonspecific protein adsorption concurrently. In vivo near-infrared (NIR) fluorescence imaging of phosphorylcholine self-assembled monolayer (SAM)-coated QDs displaying various simple sugars (glyco-PC-QDs) after administration into the tail vein of the mouse revealed that distinct long-term delocalization over 2 h can be achieved in cases of QDs modified with α-sialic acid residue (Neu5Ac-PC-QDs) and control PC-QDs, while QDs bearing other common sugars, such as α-glucose (Glc-PC-QDs), α-mannose (Man-PC-QDs), α-fucose (Fuc-PC-QDs), lactose (Lac-PC-QDs), β-glucuronic acid (GlcA-PC-QDs), N-acetyl-β-d-glucosamine (GlcNAc-PC-QDs), and N-acetyl-β-d-galactosamine (GalNAc-PC-QDs) residues, accumulated rapidly (5–10 min) in the liver. Sequential enzymatic modifications of GlcNAc-PC-QDs gave Galβ1,4GlcNAc-PC-QDs (LacNAc-PC-QDs), Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (Le x -PC-QDs), Neu5Acα2,3Galβ1,4GlcNAc-PC-QDs (sialyl LacNAc-PC-QDs), and Neu5Acα2,3Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (sialyl Le x -PC-QDs) in quantitative yield as monitored by direct matrix-assisted laser desorption ionization time-of-flight mass spectrometry analyses. Live animal imaging uncovered for the first time that Le x -PC-QDs also distributed rapidly in the liver after intravenous injection and almost quenched over 1 h in similar profiles to those of LacNAc-PC-QDs and Lac-PC-QDs. On the other hand, sialyl LacNAc-PC-QDs and sialyl Le x -PC-QDs were still retained stably in the whole body after 2 h, while they showed significantly different in vivo dynamics in the tissue distribution, suggesting that structure/sequence of the neighboring sugar residues in the individual sialyl oligosaccharides might influence the final organ-specific distribution. The present results clearly visualize the evidence of an essential role of the terminal sialic acid residue(s) for achieving prolonged in vivo lifetime and biodistribution of various glyco-PC-QDs as a novel class of functional platforms for nanomaterial-based drug targeting/delivery. A standardized protocol using multifunctional PC-QDs should facilitate live animal imaging of ligand-displayed QDs using versatile NIR fluorescence photometry without influence of size-dependent accumulation/excretion pathway for nanoparticles (e.g., viruses) >10 nm in hydrodynamic diameter by the liver.</description><subject>Animals</subject><subject>Carbohydrate Sequence</subject><subject>Glycoconjugates - analysis</subject><subject>Glycoconjugates - chemistry</subject><subject>Mice</subject><subject>Molecular Sequence Data</subject><subject>N-Acetylneuraminic Acid - chemistry</subject><subject>Phosphorylcholine - chemistry</subject><subject>Quantum Dots</subject><subject>Spectroscopy, Near-Infrared - methods</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1qGzEURkVpaJy0i75A0aaELCaVNJqRZmnc_Bgc0tbNepA1V7GMRnKlmYBfIU8dOU6y6uZeLpx74PsQ-krJBSWM_tgoSikjVH9AE1oxUlSU1R_RhBDCCiHr8hidpLTJJ2eSfkLHjAqeLzJBT_N-G-KgvAYcDF5a5azGU207_AeS7UZIeO7c2FuvBujwaocX9hHw1NteOTzv1YP1D_g-7eevdUjbdYg7p9fBWQ94Cc4U05SgX7n8fRt8cGoHsZiFF93vUflh7PHPMKTP6Mgol-DL6z5F91eXf2c3xeLuej6bLgpVSjIUVWeY5CXlwDivDatBaFEx6CoQpQFNGyWNaIRRigvJlCwbYBQkbySrua7KU3R28G5j-JfzDW1vkwbnlIcwplbKsiSiaUQmzw-kjiGlCKbdxhw77lpK2n3z7Xvzmf32ah1XPXTv5FvVGfh-AJRO7SaM0eeQ_xE9AzYxiu0</recordid><startdate>20110817</startdate><enddate>20110817</enddate><creator>Ohyanagi, Tatsuya</creator><creator>Nagahori, Noriko</creator><creator>Shimawaki, Ken</creator><creator>Hinou, Hiroshi</creator><creator>Yamashita, Tadashi</creator><creator>Sasaki, Akira</creator><creator>Jin, Takashi</creator><creator>Iwanaga, Toshihiko</creator><creator>Kinjo, Masataka</creator><creator>Nishimura, Shin-Ichiro</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20110817</creationdate><title>Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots</title><author>Ohyanagi, Tatsuya ; Nagahori, Noriko ; Shimawaki, Ken ; Hinou, Hiroshi ; Yamashita, Tadashi ; Sasaki, Akira ; Jin, Takashi ; Iwanaga, Toshihiko ; Kinjo, Masataka ; Nishimura, Shin-Ichiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-5df284314e2446f26e7c752ed5e73fec19a8f797faa4782a839e21e8498264c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Animals</topic><topic>Carbohydrate Sequence</topic><topic>Glycoconjugates - analysis</topic><topic>Glycoconjugates - chemistry</topic><topic>Mice</topic><topic>Molecular Sequence Data</topic><topic>N-Acetylneuraminic Acid - chemistry</topic><topic>Phosphorylcholine - chemistry</topic><topic>Quantum Dots</topic><topic>Spectroscopy, Near-Infrared - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ohyanagi, Tatsuya</creatorcontrib><creatorcontrib>Nagahori, Noriko</creatorcontrib><creatorcontrib>Shimawaki, Ken</creatorcontrib><creatorcontrib>Hinou, Hiroshi</creatorcontrib><creatorcontrib>Yamashita, Tadashi</creatorcontrib><creatorcontrib>Sasaki, Akira</creatorcontrib><creatorcontrib>Jin, Takashi</creatorcontrib><creatorcontrib>Iwanaga, Toshihiko</creatorcontrib><creatorcontrib>Kinjo, Masataka</creatorcontrib><creatorcontrib>Nishimura, Shin-Ichiro</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ohyanagi, Tatsuya</au><au>Nagahori, Noriko</au><au>Shimawaki, Ken</au><au>Hinou, Hiroshi</au><au>Yamashita, Tadashi</au><au>Sasaki, Akira</au><au>Jin, Takashi</au><au>Iwanaga, Toshihiko</au><au>Kinjo, Masataka</au><au>Nishimura, Shin-Ichiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2011-08-17</date><risdate>2011</risdate><volume>133</volume><issue>32</issue><spage>12507</spage><epage>12517</epage><pages>12507-12517</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Glycans are expected to be one of the potential signal molecules for controlling drug targeting/delivery or long-term circulation of biopharmaceuticals. However, the effect of the carbohydrates of artificially glycosylated derivatives on in vivo dynamic distribution profiles after intravenous injection of model animals remains unclear due to the lack of standardized methodology and a suitable platform. We report herein an efficient and versatile method for the preparation of multifunctional quantum dots (QDs) displaying common synthetic glycosides with excellent solubility and long-term stability in aqueous solution without loss of quantum yields. Combined use of an aminooxy-terminated thiol derivative, 11,11′-dithio bis[undec-11-yl 12-(aminooxyacetyl)amino hexa(ethyleneglycol)], and a phosphorylcholine derivative, 11-mercaptoundecylphosphorylcholine, provided QDs with novel functions for the chemical ligation of ketone-functionalized compounds and the prevention of nonspecific protein adsorption concurrently. In vivo near-infrared (NIR) fluorescence imaging of phosphorylcholine self-assembled monolayer (SAM)-coated QDs displaying various simple sugars (glyco-PC-QDs) after administration into the tail vein of the mouse revealed that distinct long-term delocalization over 2 h can be achieved in cases of QDs modified with α-sialic acid residue (Neu5Ac-PC-QDs) and control PC-QDs, while QDs bearing other common sugars, such as α-glucose (Glc-PC-QDs), α-mannose (Man-PC-QDs), α-fucose (Fuc-PC-QDs), lactose (Lac-PC-QDs), β-glucuronic acid (GlcA-PC-QDs), N-acetyl-β-d-glucosamine (GlcNAc-PC-QDs), and N-acetyl-β-d-galactosamine (GalNAc-PC-QDs) residues, accumulated rapidly (5–10 min) in the liver. Sequential enzymatic modifications of GlcNAc-PC-QDs gave Galβ1,4GlcNAc-PC-QDs (LacNAc-PC-QDs), Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (Le x -PC-QDs), Neu5Acα2,3Galβ1,4GlcNAc-PC-QDs (sialyl LacNAc-PC-QDs), and Neu5Acα2,3Galβ1,4(Fucα1,3)GlcNAc-PC-QDs (sialyl Le x -PC-QDs) in quantitative yield as monitored by direct matrix-assisted laser desorption ionization time-of-flight mass spectrometry analyses. Live animal imaging uncovered for the first time that Le x -PC-QDs also distributed rapidly in the liver after intravenous injection and almost quenched over 1 h in similar profiles to those of LacNAc-PC-QDs and Lac-PC-QDs. On the other hand, sialyl LacNAc-PC-QDs and sialyl Le x -PC-QDs were still retained stably in the whole body after 2 h, while they showed significantly different in vivo dynamics in the tissue distribution, suggesting that structure/sequence of the neighboring sugar residues in the individual sialyl oligosaccharides might influence the final organ-specific distribution. The present results clearly visualize the evidence of an essential role of the terminal sialic acid residue(s) for achieving prolonged in vivo lifetime and biodistribution of various glyco-PC-QDs as a novel class of functional platforms for nanomaterial-based drug targeting/delivery. A standardized protocol using multifunctional PC-QDs should facilitate live animal imaging of ligand-displayed QDs using versatile NIR fluorescence photometry without influence of size-dependent accumulation/excretion pathway for nanoparticles (e.g., viruses) >10 nm in hydrodynamic diameter by the liver.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21740000</pmid><doi>10.1021/ja111201c</doi><tpages>11</tpages></addata></record> |
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| subjects | Animals Carbohydrate Sequence Glycoconjugates - analysis Glycoconjugates - chemistry Mice Molecular Sequence Data N-Acetylneuraminic Acid - chemistry Phosphorylcholine - chemistry Quantum Dots Spectroscopy, Near-Infrared - methods |
| title | Importance of Sialic Acid Residues Illuminated by Live Animal Imaging Using Phosphorylcholine Self-Assembled Monolayer-Coated Quantum Dots |
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