Improved non-covalent biofunctionalization of multi-walled carbon nanotubes using carbohydrate amphiphiles with a butterfly-like polyaromatic tail

Nano Research

Volumn 3, Issue 11, 2010, Pages 764-778

  Assali, Mohyeddin ^a   Leal, Manuel Pernía ^a   Fernández, Inmaculada ^b   Romero Gomez, Pablo ^c   Baati, Rachid ^d   Khiar, Noureddine ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c INSTITUTO DE CIENCIA DE MATERIALES DE SEVILLA   (Spain)

^d UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Biocompatible system; Carbohydrates; Carbon nanotubes; Click chemistry; Non covalent functionalization; Tetrabenzo a,c,g,i fluorene

Indexed keywords

EID: 84904977465     PISSN: 19980124     EISSN: 19980000     Source Type: Journal    
DOI: 10.1007/s12274-010-0044-2     Document Type: Article

References (62)

1. Ijima, S. Helical microtubules of graphitic carbon. Nature 1991, 354, 56-58.
2. Tanaka, K.; Yamabe, T.; Fukui, K. The Science and Technology of Carbon Nanotubes; Elsevier: Oxford U. K., 1999.
3. Dresselhaus, M. S.; Dresselhaus, G.; Avouris, P. Carbon Nanotubes: Synthesis, Structure, Properties and Applications; Springer-Verlag: Berlin, 2000.
4. Lu, F.; Gu, L.; Meziani, M. J.; Wang, X.; Luo, P. G.; Veca, L. M.; Cao, L.; Sun, Y. P. Advances in bioapplications of carbon nanotubes. Adv. Mater. 2009, 21, 139-152.
5. Liu, Z.; Tabakman, S.; Welsher, K.; Dai, H. Carbon nanotubes in biology and medicine: In vitro and in vivodetection, imaging and drug delivery. Nano Res. 2009, 2, 85-120.
6. Byon, H. R.; Choi, H. C. Network single-walled carbon nanotube-field effect transistors (SWNT-FETs) with increased schottky contact area for highly sensitive biosensor applications. J. Am. Chem. Soc. 2006, 128, 2188-2189.
7. Cherukuri, P.; Bachilo, S. M.; Litovsky. S. H.; Weisman, R. B. Near-infrared fluorescence microscopy of single-walled carbon nanotubes in phagocytic cells. J. Am. Chem. Soc. 2004, 126, 15638-15639.
8. Porter, A. E.; Gass, M.; Muller, K.; Skepper, J. N.; Midgley, P. A.; Welland, M. Direct imaging of single-walled carbon nanotubes in cells. Nat. Nanotechnol. 2007, 2, 713-717.
9. Welsher, K.; Liu, Z.; Daranciang, D.; Dai, H. Selective probing and imaging of cells with single walled carbon nanotubes as near-infrared fluorescent molecules. Nano Lett. 2008, 8, 586-590.
10. Bianco, A.; Kostarelos, K.; Prato, M. Applications of carbon nanotubes in drug delivery. Curr. Opin. Chem. Biol. 2005, 9, 674-679.
11. Bhirde, A. A.; Patel, V.; Gavard, J.; Zhang, G.; Sousa, A. A.; Masedunskas, A.; Leapman, R. D.; Weigert, R.; Gutkind, J. S.; Rusling, J. F. Targeted killing of cancer cells in vivo and in vitro with EGF-directed carbon nanotube-based drug delivery. ACS Nano 2009, 3, 307-316.
12. Kam, N. W. S.; Dai, H. Carbon nanotubes as intracellular protein transporters generalityand biological functionality. J. Am. Chem. Soc. 2005, 127, 6021-6026.
13. Pantarotto, D.; Briand, J. P.; Prato, M.; Bianco, A. Translocation of bioactive peptides across cell membranes by carbon nanotubes. Chem. Commun. 2004, 16-17.
14. Liu, Y.; Wu, D. C.; Zhang, W. D.; Jiang, X.; He, C. B.; Chung, T. S.; Goh, S. H.; Leong, K. W. Polyethylenimine-grafted multiwalled carbon nanotubes for secure noncovalent immobilization and efficient delivery of DNA. Angew. Chem. Int. Ed. 2005, 44, 4782-4785.
15. Liu, Z.; Winters, M.; Holodniy, M.; Dai, H. siRNA delivery into human T cells and primary cells with carbon nanotube transporters. Angew. Chem. Int. Ed. 2007, 46, 2023-2027.
16. Yang, R.; Yang, X.; Zhang, Z.; Zhang, Y.; Wang, S.; Cai, Z.; Jia, Y.; Ma, Y.; Zheng, C.; Lu, Y.; Roden, R.; Chen, Y. Single walled carbon nanotubes-mediated in vivo and in vitrodelivery of siRNA into antigen-presenting cells. Gene Ther. 2006, 13, 1714-1723.
17. Kam, N. W. S.; O'Connell, M.; Wisdom, J. A.; Dai, H. Carbon nanotubes as multifunctional biological transporters and near-infrared agents for selective cancer cell destruction. Proc. Natl. Acad. Sc. USA. 2005, 102, 11600-11605.
18. Chakravarty, P.; Marches, R.; Zimmerman, N. S.; Swafford, A. D. E.; Bajaj, P.; Musselman, I. H.; Pantano, P.; Draper, R. K.; Vitetta. E. S. Thermal ablation of tumor cells with antibody-functionalized single-walled carbon nanotubes. Proc. Nat. Acad. Sci. USA 2008, 105, 8697-8702.
19. Gannon, C. J.; Cherukuri, P.; Yakobson, B. I.; Cognet, L.; Kanzius, J. S.; Kittrell, C.; Weisman, R. B.; Pasquali, M.; Schmidt, H. K.; Smalley, R. E.; Curley, S. A. Carbon nanotube-enhanced thermal destruction of cancer cells in a noninvasive radiofrequency field. Cancer 2007, 110, 2654-2665.
20. Singh, R.; Pantarotto, D.; Lacerda, L.; Pastorin, G.; Klumpp, C.; Prato, M.; Bianco, A.; Kostarelos, K. Tissue biodistribution and blood clearance rates of intravenously administered carbon nanotube radiotracers. Proc. Natl. Acad. Sci. USA 2006, 103, 3357-3362.
21. Liu, Z.; Davis, C.; Cai, W.; He, L.; Chen, X.; Dai, H. Circulation and long-term fate offunctionalized, biocompatible single-walled carbon nanotubes in mice probed by Raman spectroscopy. Proc. Natl. Acad. Sci. USA 2008, 105, 1410-1415.
22. Schipper, M. L.; Nakayama-Ratchford, N.; Davis, C. R.; Kam, N. W. S.; Chu, P.; Liu, Z.; Sun, X.; Dai, H.; Gambhir, S. S. A pilot toxicology study of single-walled carbon nanotubes in a small sample of mice. Nature Nanotech. 2008, 3, 216-221.
23. Sudibya, H. G.; Ma, J.; Dong, X.; Ng, S.; Li, L. J.; Liu, X. W.; Chen, P. Interfacing glycosylated carbon-nanotube-network devices with living cells to detect dynamic secretion of biomolecules. Angew. Chem. Int. Ed. 2009, 48, 2723-2726.
24. Tasis, D.; Tagmatarchis, N.; Bianco, A.; Prato, M. Chemistry of carbon nanotubes. Chem. Rev. 2006, 106, 1105-1136.
25. Britz, D. A.; Khlobystov, A. N. Noncovalent interactions of molecules with single walled carbon nanotubes. Chem. Soc. Rev. 2006, 35, 637-659.
26. Hahn, U.; Engmann, S.; Oelsner, C.; Ehli, C.; Guldi, D. M.; Torres, T. Immobilizing water-soluble dendritic electron donors and electron acceptors-phtalocyanines and perylendiimide-onto single Wall carbon nanotubes. J. Am. Chem. Soc. 2010, 132, 6392-6401.
27. Chen, R. J.; Zhang, Y.; Wang, D.; Dai, H. Noncovalent sidwall functionalization of single-walled carbon nanotubes for protein immobilization. J. Am. Chem. Soc. 2001, 123, 3838-3839.
28. Nakashima, N.; Tomonari, Y.; Murakami, H. Water-soluble single-walled carbon nanotubes via non-covalent sidewall-functionalization with a pyrene-carrying ammonium ion. Chem. Lett. 2002, 638-639.
29. Georgakilas, V.; Tzitzios, V.; Gournis, D.; Petridis, D. Attachement of magnetic nanoparticles on carbon nanotubes and their soluble derivatives. Chem Mater. 2005, 17, 1613-1617.
30. Liu, Z.; Sun, X.; Nakayama-Ratchford, N.; Dai, H. Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery. ACS Nano 2007, 1, 50-56.
31. Richard, C.; Balavoine, F.; Schultz, P.; Moreau, N.; Mioskowski, C. Immobilization ofhistidine-tagged proteins on functionalized carbon nanotubes. J. Bionanosci. 2007, 1, 106-113.
32. Ali-Boucetta, H.; Al-Jamal, K. T.; McCarthy, D.; Prato, M.; Bianco, A.; Kostarelos, K. Multiwalled carbon nanotube-doxorubicin supramolecular complexes for cancer therapeutics. Chem Commun. 2008, 459-461.
33. Liu, Z.; Fan, A. C.; Rakhra, K.; Sherlock, S.; Goodwin, A.; Chen, X.; Yang, Q.; Felsher, D. W.; Dai, H. Supramolecular stacking of doxorubicin on carbon nanotubes for in vivo cancer therapy. Angew. Chem. Int. Ed. 2009, 48, 7668-7672.
34. Simmons, T. J.; Bult, J.; Hashim, D. P.; Linhardt, R. J.; Ajayan, P. M. Noncovalent functionalization as an alternative to oxidative acid treatment ofsingle wall carbon nanotubes with applications for polymer composites. ACS Nano 2009, 3, 865-870.
35. Peigney, A.; Laurent, C.; Flahaut, E.; Bacsa, R. R.; Rousset, A. Specific surface area of carbon nanotubes and bundles of carbon nanotubes. Carbon 2001, 39, 507-514.
36. Astronomo, R. A.; Burton, D. R. Carbohydrate vaccines: Developing sweet solutions to sticky situations? Nature Rev. Drug Discover. 2010, 9, 308-324.
37. Dube, D. H.; Bertozzi, C. R; Glycans in cancer and inflammation-potential for therapeutics and diagnostics. Nature Rev. Drug Discover. 2005, 4, 477-488.
38. Seeberger, P. H.; Werz, D. B. Synthesis and medical applications of oligosaccharides. Nautre 2007, 446, 1046-1051.
39. Lundquist, J. J.; Toone, E. J. The cluster glycoside effect. Chem. Rev. 2002, 102, 555-578.
40. Mammen, M.; Choi, S. K.; Whitesides, G. M. Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors Angew. Chem. Int. Ed. 1998, 37, 2754-2794.
41. Chen, X.; Tam, U. C.; Czlapinski, J. L.; Lee, G. S.; Rabuka, D.; Zettl, A.; Bertozzi, C. R. Interfacing carbon nanotubes with living cells. J. Am. Chem. Soc. 2006, 128, 6292-6293.
42. Wang, H.; Gu, L.; Lin, Y.; Lu, F.; Meziani, M. J.; Luo, P. G.; Wang, W.; Cao, L.; Sun, Y. P. Unique aggregation of anthrax (bacillus anthracis) spores by sugar-coated single-walled carbon nanotubes. J. Am. Chem. Soc. 2006, 128, 13364-13365.
43. Khiar, N.; Pernía Leal, M.; Baati, R.; Ruhlmann, C.; Mioskowski, C.; Schultz, P.; Fernández, I. Tailoring carbon nanotube surfaces with glyconanorings: New bionanomaterials with specific lectin affinity. Chem. Commun. 2009, 27, 4121-4123.
44. Assali, M.; Pernía Leal, M.; Fernández, I.; Baati, R.; Mioskowski, C.; Khiar, N. Non-covalent functionalization of carbon nanotubes with glycolipids: Glyconanomaterials with specific lectin-affinity. Soft Matter 2009, 5, 948-950.
45. Andersson, C. H.; Lahmann, M.; Oscarson, S.; Grennberg, H. Reversible non-covalent derivatisation of carbon nanotubes with glycosides. Soft Matter 2009, 5, 2713-2716.
46. Zhang, J.; Lee, J. K.; Wu, Y.; Murray, R. W. Photo-luminescence and electronic interaction of anthracene derivatives adsorbed on sidewalls of single-walled carbon nanotubes. Nano Lett. 2003, 3, 403-407.
47. Paloniemi, H.; Ääritalo, T.; Laiho, T.; Liuke, H.; Kocharova, N.; Haapkka, K.; Terzi, F.; Seeber, R.; Lukkari, J. Water-soluble full-lenght single-wall carbon nanotube polyelectrolytes: Preparation and characterization. J. Phys. Chem. B. 2005, 109, 8634-8642.
48. Kar, T.; Bettinger, H. F.; Scheiner, S.; Roy, A. K. Non-covalent π-π-stacking and CH-π interactions of aromatics on the surface of single-wallcarbon nanotubes: An MP2 study. J. Phys. Chem. C. 2008, 112, 20070-20075.
49. Brown, A. P.; Anson, F. C. Molecular anchors for the attachment of metal complexes to graphite electrode surfaces. J. Electroanal. Chem. 1977, 83, 203-206.
50. Pérez, E. M.; Martín, N. Curves ahead: Molecular receptors for fullerenes based on concave-convex complementarity. Chem. Soc. Rev. 2008, 37, 1512-1519.
51. Brown, A. R.; Irving, S. L.; Ramage, R. Affinity purification of synthetic peptides and proteins on porous graphitised carbon. Tetrahedron Letters. 1993, 34, 7129-7132.
52. Brown, A. R.; Irving, S. L.; Ramage, R.; Raphy, G. (17-Tetrabenzo [a, c, g, i] fluorenyl) methyl chloroformate (TbfmocCl) a reagent for the rapid and efficient purification of synthetic peptides and proteins. Tetrahedron 1995, 51, 11815-11830.
53. Ramage, R.; Wahl, F. O. 4-(17-Tetrabenzo [a, c, g, i] fluorenyl-methyl)-41′, 4″-dimethoxytrityl chloride: A hydrophobic 5′-protecting group for the separation of synthetic oligonucleotides. Tetrahedron Letters 1993, 34, 7133-7136.
54. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
55. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1, 2, 3]-Triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002, 67, 3057-3064.
56. Hay, A. M.; Hobbs-Dewitt, S.; MacDonald, A. A.; Ramage, R. Use of tetrabenzo [a, c, g, i] fluorene as an anchor group for the solid/solution phase synthesis of the quinolone antibacterial, ciprofloxacin. Synthesis 1999, 11, 1979-1985.
57. Yang, Z.; Chen, X.; Chen, C.; Li, W.; Zhang, H.; Xu, L.; Yi, B. Noncovalent-wrapped sidewall functionalization of multiwalled carbon nanotubes with polyimide. Polymer Composites, 2007, 28, 36-41.
58. Brown, S. D. M.; Jorio, A.; Dresselhaus, M. S.; Dresselhaus, G. Observations of the D-band feature in the raman spectra of carbon nanotubes. Phys. Rev. B. 2001, 64, 073403.
59. Yang, Q.; Shuai, Li.; Zhou, J.; Lu, F.; Pan, X. Functionalization of multiwalled carbon nanotubes by pyrene-labeled hydroxypropyl cellulose. J. Phys. Chem. B 2008, 112, 12934-12939.
60. D'Souza, F.; Ito, O. Supramolecular donor-acceptor hybrids of porphyrins/phthalocyanines with fullerenes/carbon nano-tubes: Electron transfer, sensing, switching, and catalytic applications. Chem. Commun. 2009, 4913-4928.
61. Banerjee, R.; Das, K.; Ravishankar, R.; Suguna, K.; Surolia, A.; Vijayan, A. M. Conformation, protein-carbohydrate interactions and a novel subunit association in the refined structure of peanut lectin-lactose complex. J. Mol. Biol. 1996, 259, 281-296.
62. Balavoine, F.; Schultz, P.; Richard, C.; Mallouh, M.; Ebbesen, T. W.; Mioskowski, C. Helical crystallization of proteins on carbon nanotubes: A first step towards the development of new biosensors. Angew. Chem. Int. Ed. 1999, 38, 1912-1915.