Biocompatible Carbon Nanotubes Generated by Functionalization with Glycodendrimers†
Peng Wu
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
These authors contributed equally to the work.
Search for more papers by this authorXing Chen
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
These authors contributed equally to the work.
Search for more papers by this authorNancy Hu
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
Search for more papers by this authorUn Chong Tam
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
Search for more papers by this authorOla Blixt
Carbohydrate Synthesis and Protein Expression Core D, Consortium for Functional Glycomics, The Scripps Research Institute, La Jolla, CA 92037 (USA)
Search for more papers by this authorAlex Zettl Prof.
Department of Physics, University of California
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)
Search for more papers by this authorCarolyn R. Bertozzi Prof.
Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California
The Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA), Fax: (+1) 510-643-2628
Search for more papers by this authorPeng Wu
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
These authors contributed equally to the work.
Search for more papers by this authorXing Chen
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
These authors contributed equally to the work.
Search for more papers by this authorNancy Hu
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
Search for more papers by this authorUn Chong Tam
Department of Chemistry, University of California, Berkeley, CA 94720 (USA)
Search for more papers by this authorOla Blixt
Carbohydrate Synthesis and Protein Expression Core D, Consortium for Functional Glycomics, The Scripps Research Institute, La Jolla, CA 92037 (USA)
Search for more papers by this authorAlex Zettl Prof.
Department of Physics, University of California
Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA)
Search for more papers by this authorCarolyn R. Bertozzi Prof.
Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California
The Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA), Fax: (+1) 510-643-2628
Search for more papers by this authorThis work was supported by the Director, Office of Energy Research, Office of Basic Energy Sciences, Division of Materials Sciences, of the U.S. Department of Energy under Contract No. DE-AC03-76SF00098, within the Interfacing Nanostructures Initiative and NIH (K99M080585-01). Portions of this work were performed at the Molecular Foundry, Lawrence Berkeley National Laboratory, which is supported by the Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231. 9 c was provided by Consortium for functional Glycomics.
Graphical Abstract
Protective coatings: Glycodendrimers can function as homogeneous bioactive coatings that mitigate the cytotoxicity of single-walled carbon nanotubes (SWNTs). The bifunctional glycodendrimers (see picture) have peripheral carbohydrate units and a pyrene tail capable of binding SWNT surfaces through π–π interaction. Cells cultured with glycodendrimer-coated SWNTs proliferate at the same rate as untreated cells.
Supporting Information
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References
- 1Y. Lin, S. Taylor, H. P. Li, K. A. S. Fernando, L. W. Qu, W. Wang, L. R. Gu, B. Zhou, Y. P. Sun, J. Mater. Chem. 2004, 14, 527.
- 2D. Tasis, N. Tagmatarchis, A. Bianco, M. Prato, Chem. Rev. 2006, 106, 1105.
- 3R. S. Kane, A. D. Stroock, Biotechnol. Prog. 2007, 23, 316.
- 4A. Star, E. Tu, J. Niemann, J. C. P. Gabriel, C. S. Joiner, C. Valcke, Proc. Natl. Acad. Sci. USA 2006, 103, 921.
- 5S. S. Wong, E. Joselevich, A. T. Woolley, C. L. Cheung, C. M. Lieber, Nature 1998, 394, 52.
- 6K. Kostarelos, L. Lacerda, G. Pastorin, W. Wu, S. Wieckowski, J. Luangsivilay, S. Godefroy, D. Pantarotto, J. P. Briand, S. Muller, M. Prato, A. Bianco, Nat. Nanotechnol. 2007, 2, 108.
- 7N. W. Shi Kam, M. O'Connell, J. A. Wisdom, H. J. Dai, Proc. Natl. Acad. Sci. USA 2005, 102, 11600.
- 8Z. Liu, W. B. Cai, L. N. He, N. Nakayama, K. Chen, X. M. Sun, X. Y. Chen, H. J. Dai, Nat. Nanotechnol. 2007, 2, 47.
- 9V. L. Colvin, Nat. Biotechnol. 2003, 21, 1166.
- 10D. X. Cui, F. R. Tian, C. S. Ozkan, M. Wang, H. J. Gao, Toxicol. Lett. 2005, 155, 73.
- 11G. Jia, H. F. Wang, L. Yan, X. Wang, R. J. Pei, T. Yan, Y. L. Zhao, X. B. Guo, Environ. Sci. Technol. 2005, 39, 1378.
- 12A. Magrez, S. Kasas, V. Salicio, N. Pasquier, J. W. Seo, M. Celio, S. Catsicas, B. Schwaller, L. Forro, Nano Lett. 2006, 6, 1121.
- 13M. S. Arnold, M. O. Guler, M. C. Hersam, S. I. Stupp, Langmuir 2005, 21, 4705.
- 14C. M. Sayes, F. Liang, J. L. Hudson, J. Mendez, W. H. Guo, J. M. Beach, V. C. Moore, C. D. Doyle, J. L. West, W. E. Billups, K. D. Ausman, V. L. Colvin, Toxicol. Lett. 2006, 161, 135.
- 15H. Dumortier, S. Lacotte, G. Pastorin, R. Marega, W. Wu, D. Bonifazi, J. P. Briand, M. Prato, S. Muller, A. Bianco, Nano Lett. 2006, 6, 1522.
- 16X. Chen, G. S. Lee, A. Zettl, C. R. Bertozzi, Angew. Chem. 2004, 116, 6237; Angew. Chem. Int. Ed. 2004, 43, 6111.
- 17X. Chen, U. C. Tam, J. L. Czlapinski, G. S. Lee, D. Rabuka, A. Zettl, C. R. Bertozzi, J. Am. Chem. Soc. 2006, 128, 6292.
- 18D. Rabuka, R. Parthasarathy, G. S. Lee, X. Chen, J. T. Groves, C. R. Bertozzi, J. Am. Chem. Soc. 2007, 129, 5462.
- 19C. C. Lee, J. A. MacKay, J. M. J. Frechet, F. C. Szoka, Nat. Biotechnol. 2005, 23, 1517.
- 20Y. Kim, S. C. Zimmerman, Curr. Opin. Chem. Biol. 1998, 2, 733.
- 21S. Svenson, D. A. Tomalia, Adv. Drug Delivery Rev. 2005, 57, 2106.
- 22S. Campidelli, C. Sooambar, E. L. Diz, C. Ehli, D. M. Guldi, M. Prato, J. Am. Chem. Soc. 2006, 128, 12544.
- 23Y. P. Sun, W. J. Huang, Y. Lin, K. F. Fu, A. Kitaygorodskiy, L. A. Riddle, Y. J. Yu, D. L. Carroll, Chem. Mater. 2001, 13, 2864.
- 24M. Holzinger, J. Abraha, P. Whelan, R. Graupner, L. Ley, F. Hennrich, M. Kappes, A. Hirsch, J. Am. Chem. Soc. 2003, 125, 8566.
- 25P. Wu, M. Malkoch, J. N. Hunt, R. Vestberg, E. Kaltgrad, M. G. Finn, V. V. Fokin, K. B. Sharpless, C. J. Hawker, Chem. Commun. 2005, 5775.
- 26W. B. Turnbull, J. F. Stoddart, Rev. Mol. Biotechnol. 2002, 90, 231.
- 27M. J. Cloninger, Curr. Opin. Chem. Biol. 2002, 6, 742.
- 28H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056;
Angew. Chem. Int. Ed. 2001, 40, 2004.
10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
- 29J.-F. Lutz, Angew. Chem. 2007, 119, 1036;
10.1002/ange.200604050 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 1018.
- 30P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Frechet, K. B. Sharpless, V. V. Fokin, Angew. Chem. 2004, 116, 4018; Angew. Chem. Int. Ed. 2004, 43, 3928.
- 31C. J. Hawker, K. L. Wooley, Science 2005, 309, 1200.
- 32F. Fazio, M. C. Bryan, O. Blixt, J. C. Paulson, C. H. Wong, J. Am. Chem. Soc. 2002, 124, 14397.
- 33Glycodendrimer nomenclature: Man=α-D-mannopyranoside, Gal=β-D-galactopyranoside, Lac=1,4-(β-D-galactopyranosyl)-β-D-glucopyranoside; [G-2] denotes generation 2 and [G-3] denotes generation 3. [G-2] Man, [G-2] Gal, [G-2] Lac, [G-3] Man, [G-3] Gal, and [G-3] Lac denote the corresponding glycodendrimers.
- 34G. N. Reeke, J. W. Becker, G. M. Edelman, J. Biol. Chem. 1975, 250, 1525.