Functionalized carbon nanotubes in drug design and discovery

Accounts of Chemical Research

Volumn 41, Issue 1, 2008, Pages 60-68

  Prato, Maurizio ^a   Kostarelos, Kostas ^b   Bianco, Alberto ^c  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF LONDON   (United Kingdom)

^c INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON NANOTUBE; DIAGNOSTIC AGENT; DRUG CARRIER;

ANIMAL; ARTICLE; CHEMISTRY; COMMUNICABLE DISEASE; DRUG DESIGN; GENE THERAPY; HUMAN; IMMUNIZATION; METHODOLOGY; NEOPLASM;

ANIMALS; COMMUNICABLE DISEASES; DRUG CARRIERS; DRUG DESIGN; GENE THERAPY; HUMANS; IMMUNIZATION; NANOTUBES, CARBON; NEOPLASMS;

EID: 38949105860     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar700089b     Document Type: Article

References (45)

1. Duncan, R. Polymer conjugates as anticancer nanomedicines. Nat. Rev. Cancer 2006, 6, 688-701.
2. Torchilin, V. P. Recent advances with liposomes as pharmaceutical carriers. Nat. Rev. Drug Discovery 2005, 4, 145-160.
3. Couvreur, P.; Vauthier, C. Nanotechnology: intelligent design to treat complex disease. Pharm. Res. 2006, 23, 1417-1450.
4. Tasis, D.; Tagmatarchis, N.; Bianco, A.; Prato, M. Chemistry of carbon nanotubes. Chem. Rev. 2006, 106, 1105-1136.
5. Bianco, A.; Kostarelos, K.; Partidos, C. D.; Prato, M. Biomedical applications of functionalised carbon nanotubes. Chem. Commun. 2005, 571-577.
6. Bianco, A.; Kostarelos, K.; Prato, M. Applications of carbon nanotubes in drug delivery. Curr. Opin. Chem. Biol. 2005, 9, 674-679.
7. 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.
8. Haddon, R. C. Carbon nanotubes. Acc. Chem. Res. 2002, 35, 997-1113.
9. (a) Sumio Iijima, S.; Ichihashi, T. Single-shell carbon nanotubes of 1-nm diameter. Nature (London) 1993, 363, 603-605.
10. (b) Bethune, D. S.; Klang, C. H.; de Vries, M. S.; Gorman, G.; Savoy, R.; Vazquez, J.; BeyersR. Cobalt-catalysed growth of carbon nanotubes with single-atomic-layer walls. Nature (London) 1993, 363, 605-607.
11. Iijima, S. Helical microtubules of graphitic carbon. Nature (London) 1991, 354, 56-58.
12. Niyogi, S.; Hamon, M. A.; Hu, H.; Zhao, B.; Bhowmik, P.; Sen, R.; Itkis, M. E.; Haddon, R. C. Chemistry of single-walled carbon nanotubes. Acc. Chem. Res. 2002, 35, 1105-1113.
13. Liu, J.; Rinzler, A. G.; Dai, H.; Hafner, J. H.; Bradley, R. K.; Boul, P. J.; Lu, A.; Iverson, T.; Shelimov, K.; Huffman, C. B.; Rodriguez-Macias, F.; Shon, Y. S.; Lee, T. R.; Colbert, D. T.; Smalley, R. E. Fullerene pipes. Science 1998, 280, 1253-1256.
14. Bonifazi, D.; Nacci, C.; Marega, R.; Campidelli, S.; Ceballos, G.; Modesti, S.; Meneghetti, M.; Prato, M. Microscopic and spectroscopic characterization of paintbrush-like single-walled carbon nanotubes. Nano Lett. 2006, 6, 1408-1414.
15. Chen, J.; Hamon, M. A.; Hu, H.; Chen, Y.; Rao, A. M.; Eklund, P. C.; Haddon, R. C. Solution properties of single-walled carbon nanotubes. Science 1998, 282, 95-98.
16. Koshino, M.; Tanaka, T.; Solin, N.; Suenaga, K.; Isobe, H.; Nakamura, E. Imaging of Single Organic Molecules in Motion. Science 2007, 316, 853.
17. Khlobystov, A. N.; Britz, D. A.; Briggs, G. A. D. Molecules in carbon nanotubes. Acc. Chem. Res. 2005, 38, 901-909.
18. Colvin, V. L. The potential environmental impact of engineered nanomaterials. Nat. Biotechnol. 2003, 21, 1166-1170.
19. Sayes, C. M.; Liang, F.; Hudson, J. L.; Mendez, J.; Guo, W.; Beach, J. M.; Moore, V. C.; Doyle, C. D.; West, J. L.; Billups, W. E.; Ausman, K. D.; Colvin, V. L. Functionalization density dependence of single-walled carbon nanotubes cytotoxicity in vitro. Toxicol. Lett. 2006, 16, 135-142.
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. U.S.A. 2006, 103, 3357-3362.
21. Georgakilas, V.; Kordatos, K.; Prato, M.; Guldi, D. M.; Holzinger, M.; Hirsch, A. Organic functionalization of carbon nanotubes. J. Am. Chem. Soc. 2002, 124, 760-761.
22. Georgakilas, V.; Tagmatarchis, N.; Pantarotto, D.; Bianco, A.; Briand, J.-P.; Prato, M. Amino acid functionalisation of water soluble carbon nanotubes. Chem. Commun. 2002, 3050-3051.
23. Wu, W.; Wieckowski, S.; Pastorin, G.; Benincasa, M.; Klumpp, C.; Briand, J.; Gennaro, R.; Prato, M.; Bianco, A. Targeted delivery of Amphotericin B to cells using functionalized carbon nanotubes. Angew. Chem., Int. Ed. 2005, 44, 6358-6362.
24. Pantarotto, D.; Briand, J.-P.; Prato, M.; Bianco, A. Translocation of bioactive peptides across cell membranes by carbon nanotubes. Chem. Commun. 2004, 16-17.
25. Kostarelos, K.; Lacerda, L.; Pastorin, G.; Wu, W.; Wieckowski, S.; Luangsivilay, J.; Godefroy, S.; Pantarotto, D.; Briand, J.-P.; Muller, S.; Prato, M.; Bianco, A. Functionalised carbon nanotube cellular uptake and internalisation mechanism is independent of functional group and cell type. Nat. Nanotechnol. 2007, 2, 108-113.
26. Dumortier, H.; Lacotte, S.; Pastorin, G.; Marega, R.; Wu, W.; Bonifazi, D.; Briand, J.-P.; Prato, M.; Muller, S.; Bianco, A. Functionalized carbon nanotubes are non-cytotoxic and preserve the functionality of primary immune cells. Nano Lett. 2006, 6, 1522-1528.
27. Pantarotto, D.; Singh, R.; McCarthy, D.; Erhardt, M.; Briand, J.-P.; Prato, M.; Kostarelos, K.; Bianco, A. Functionalised carbon nanotubes for plasmid DNA gene delivery. Angew. Chem., Int. Ed. 2004, 43, 5242-5246.
28. Lacerda, L.; Pastorin, G.; Gathercole, D.; Prato, M.; Bianco, A.; Kostarelos, K. Intracellular trafficking of carbon nanotubes by confocal laser scanning microscopy. Adv. Mater. 2007, 19, 1480-1484.
29. Kam, N. W. S.; Dai, H. Carbon nanotubes as intracellular protein transporters: generality and biological functionality. J. Am. Chem. Soc. 2005, 127, 6021-6026.
30. Kam, N. W. S.; Liu, Z.; Dai, H. Carbon nanotubes as intracellular transporters for proteins and DNA: an investigation of the uptake mechanism and pathway. Angew. Chem., Int. Ed. 2006, 45, 577-581.
31. Kateb, B.; Van Handel, M.; Zhang, L.; Bronikowski, M. J.; Manohara, H.; Badiea, B. Internalization of MWCNTs by microglia: Possible application in immunotherapy of brain tumors. NeuroImage 2007, 37, S9-S17.
32. Lacerda, L.; Pastorin, G.; Wu, W.; Prato, M.; Bianco, A.; Kostarelos, K. Functionalised carbon nanotube autofluorescence as a tool to monitor bundle formation and dissociation in aqueous phases by fluorescence spectrophotometry: the effect of plasmid DNA complexation. Adv. Funct. Mater. 2006, 16, 1839-1846.
33. Singh, R.; Pantarotto, D.; McCarthy, D.; Chaloin, O.; Hoebeke, J.; Partidos, C. D.; Briand, J.-P.; Prato, M.; Bianco, A.; Kostarelos, K. Binding and condensation of Plasmid DNA onto functionalized carbon nanotubes: towards the construction of nanotube-based gene delivery vectors. J. Am. Chem. Soc. 2005, 127, 4388-4396.
34. Kam, N. W. S.; Liu, Z.; Dai, H. Functionalization of carbon nanotubes via cleavable disulfide bonds for efficient intracellular delivery of siRNA and potent gene silencing. J. Am. Chem. Soc. 2005, 127, 12492-12493.
35. Zhang, Z.; Yang, X.; Zhang, Y.; Zeng, B.; Wang, S.; Zhu, T.; Roden, R. B.; Chen, Y.; Yang, R. Delivery of telomerase reverse transcriptase small interfering RNA in complex with positively charged single-walled carbon nanotubes suppresses tumor growth. Clin. Cancer Res. 2006, 12, 4933-4939.
36. Zotchev, S. B. Polyene macrolide antibiotics and their applications in human therapy. Curr. Med. Chem. 2003, 10, 211-223.
37. Pastorin, G.; Wu, W.; Wieckowski, S.; Briand, J.-P.; Kostarelos, K.; Prato, M.; Bianco, A. Double functionalisation of carbon nanotubes for multimodal drug delivery. Chem. Commun. 2006, 1182-1184.
38. Wong, J. M.; Esdaile, J. M. Methotrexate in systemic lupus erythematosus. Lupus 2005, 14, 101-105.
39. Pignatello, R.; Guccione, S.; Forte, S.; Di Giacomo, C.; Sorrenti, V.; Vicari, L.; Uccello Barretta, G.; Balzano, F.; Puglisi, G. Lipophilic conjugates of methotrexate with short-chain alkylamino acids as DHFR inhibitors. Synthesis, biological evaluation, and molecular modeling. Bioorg. Med. Chem. 2004, 12, 2951-2964.
40. Quintana, A.; Raczka, E.; Piehler, L.; Lee, I.; Myc, A.; Majoras, I.; Patri, A. K.; Thomas, T.; Mule, J.; Baker, J. R., Jr. Design and function of a dendrimer-based therapeutic nanodevice targeted to tumor cells through the folate receptor. Pharm. Res. 2002, 19, 1310-1316.
41. Yinghuai, Z.; Peng, A. T.; Carpenter, K.; Maguire, J. A.; Hosmane, N. S.; Takagaki, M. Substituted carborane-appended water-soluble single-wall carbon nanotubes: new approach to boron neutron capture therapy drug delivery. J. Am. Chem. Soc. 2005, 127, 9875-9880.
42. Pantarotto, D.; Hoebeke, J.; Graff, R.; Partidos, C. D.; Briand, J.-P.; Prato, M.; Bianco, A. Synthesis, Structural Characterization and Immunological Properties of Carbon Nanotubes Functionalized with Peptides. J. Am. Chem. Soc. 2003, 125, 6160-6164.
43. Pantarotto, D.; Partidos, C. D.; Hoebeke, J.; Brown, F.; Kramer, E.; Briand, J.-P.; Muller, S.; Prato, M.; Bianco, A. Immunization with peptide-functionalized carbon nanotubes enhances virus-specific neutralizing antibody responses. Chem. Biol. 2003, 10, 961-966.
44. (a) Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C. Methods of Organic Chemistry, Houben-Weyl: Thieme, Stuttgart, 2002; Vol. E22b.
45. (b) Müller, S. Laboratory Techniques in Biochemistry and Molecular Biology, Pillai, S., van der Vliet, P. C., Eds.; Elsevier: Amsterdam, 1999; Vol. 28, pp 79-131.