Multifunctional dendrimer-modified multiwalled carbon nanotubes: Synthesis, characterization, and in vitro cancer cell targeting and imaging

Biomacromolecules

Volumn 10, Issue 7, 2009, Pages 1744-1750

  Shi, Xiangyang ^a   Su, He Wang ^b   Shen, Mingwu ^a   Antwerp, Mary E ^b   Chen, Xisui ^b   Li, Chang ^b   Petersen, Elijah J ^c   Huang, Qingguo ^d   Weber Jr , Walter J ^c   Baker Jr , James R ^b  

^a DONGHUA UNIVERSITY   (China)

^b UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

^c UNIVERSITY OF MICHIGAN   (United States)

^d UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CANCER CELLS; CANCER-TARGETING; FLUORESCEIN ISOTHIOCYANATE; FOLIC ACIDS; IN-VITRO; NANOMEDICINE; PAMAM DENDRIMER; POLYAMIDOAMINE DENDRIMERS; PRIMARY AMINE GROUPS; WATER DISPERSIBLE;

AMINES; CARBON NANOTUBES; CELL MEMBRANES; CONFOCAL MICROSCOPY; DENDRIMERS; DRUG DELIVERY; FLOW CYTOMETRY; FUNCTIONAL POLYMERS; LIGANDS; MEDICAL IMAGING; MEDICAL NANOTECHNOLOGY; ORGANIC ACIDS;

MULTIWALLED CARBON NANOTUBES (MWCN);

CARBON NANOTUBE; DENDRIMER; FLUORESCEIN ISOTHIOCYANATE; FOLIC ACID; MULTI WALLED NANOTUBE; POLYAMIDOAMINE; WATER;

ACETYLATION; ARTICLE; BIOCOMPATIBILITY; CANCER CELL; CONFOCAL MICROSCOPY; CONTROLLED STUDY; CYTOTOXICITY; DIAGNOSTIC IMAGING; FLOW CYTOMETRY; HUMAN; HUMAN CELL; PRIORITY JOURNAL; SYNTHESIS;

DENDRIMERS; DIAGNOSTIC IMAGING; DRUG DELIVERY SYSTEMS; HUMANS; NANOTUBES, CARBON; NEOPLASMS;

EID: 67650500319     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm9001624     Document Type: Article

References (65)

1. 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. Cellular uptake of functionalized carbon nanotubes is independent of functional group and cell type. Nat. Nanotechnol. 2007, 2, 108-113.
2. Liu, Z.; Cai, W. B.; He, L. N.; Nakayama, N.; Chen, K.; Sun, X. M.; Chen, X. Y.; Dai, H. J. In vivo biodistribution and highly efficient tumour targeting of carbon nanotubes in mice. Nat. Nanotechnol. 2007, 2, 47-52.
3. Yan, X.; He, Q.; Wang, K.; Duan, L.; Cui, Y.; Li, J. Transition of cationic dipeptide nanotubes into vesicles and oligonucleotide delivery. Angew. Chem., Int. Ed. 2007, 46, 2431-2434.
4. Yang, Y.; He, Q.; Duan, L.; Cui, Y.; Li, J. Assembled alginate/chitosan nanotubes for biological application. Biomaterials 2007, 28, 3083-3090.
5. Ajayan, P. M. Nanotubes from carbon. Chem. Rev. 1999, 99, 1787-1800.
6. Hersam, M. C. Progress towards monodisperse single-walled carbon nanotubes. Nat. Nanotechnol. 2008, 3, 387-394.
7. Kam, N. W. S.; Dai, H. J. Carbon nanotubes as intracellular protein transporters: Generality and biological functionality. J. Am. Chem. Soc. 2005, 127, 6021-6026.
8. Kam, N. W. S.; Dai, H. J. Single walled carbon nanotubes for transport and delivery of biological cargos. Phys. Status Solidi B 2006, 243, 3561-3566.
9. Kam, N. W. S.; Liu, Z. A.; Dai, H. J. 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.
10. Pantarotto, D.; Briand, J. P.; Prato, M.; Bianco, A. Translocation of bioactive peptides across cell membranes by carbon nanotubes. Chem. Commun. 2004, 16-17.
11. Liu, Z.; Winters, M.; Holodniy, M.; Dai, H. J. siRNA delivery into human T cells and primary cells with carbon-nanotube transporters. Angew. Chem., Int. Ed. 2007, 46, 2023-2027.
12. Kam, N. W. S.; Liu, Z.; Dai, H. J. 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.
13. Bianco, A.; Prato, M. Can carbon nanotubes be considered useful tools for biological applications. Adv. Mater. 2003, 15, 1765-1768.
14. Pantarotto, D.; Singh, R.; McCarthy, D.; Erhardt, M.; Briand, J. P.; Prato, M.; Kostarelos, K.; Bianco, A. Functionalized carbon nanotubes for plasmid DNA gene delivery. Angew. Chem., Int. Ed. 2004, 43, 5242-5246.
15. 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: Toward the construction of nanotube-based gene delivery vectors. J. Am. Chem. Soc. 2005, 127, 4388-4396.
16. Bianco, A.; Kostarelos, K.; Prato, M. Applications of carbon nanotubes in drug delivery. Curr. Opin. Chem. Biol. 2005, 9, 674-679.
17. Liu, Z.; Davis, C.; Cai, W. B.; He, L.; Chen, X. Y.; Dai, H. J. Circulation and long-term fate of functionalized, biocompatible singlewalled carbon nanotubes in mice probed by Raman spectroscopy. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 1410-1415.
18. 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.
19. Lacerda, L.; Bianco, A.; Prato, M.; Kostarelos, K. Carbon nanotubes as nanomedicines: From toxicology to pharmacology. Adv. Drug Delivery Rev. 2006, 58, 1460-1470.
20. Lacerda, L.; Pastorin, G.; Gathercole, D.; Buddle, J.; Prato, M.; Bianco, A.; Kostarelos, K. Intracellular trafficking of carbon nanotubes by confocal laser scanning microscopy. Adv. Mater. 2007, 19, 1480-1484.
21. McDevitt, M. R.; Chattopadhyay, D.; Kappel, B. J.; Jaggi, J. S.; Schiffman, S. R.; Antczak, C.; Njardarson, J. T.; Brentjens, R.; Scheinberg, D. A. Tumor targeting with antibody-functionalized, radiolabeled carbon nanotubes. J. Nucl. Med. 2007, 48, 1180-1189.
22. Shao, N.; Lu, S.; Wickstrom, E.; Panchapakesan, B. Integrated molecular targeting of IGF1R and HER2 surface receptors and destruction of breast cancer cells using single wall carbon nanotubes. Nanotechnology 2007, 18, 315101/1-315101/9.
23. Kam, N. W. S.; O'Connell, M.; Wisdom, J. A.; Dai, H. J. Carbon nanotubes as multifunctional biological transporters and near-infrared agents for selective cancer cell destruction. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11600-11605.
24. 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.
25. 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.
26. Dhar, S.; Liu, Z.; Thomale, J.; Dai, H.; Lippard, S. J. Targeted singlewall carbon nanotube-mediated Pt(IV) prodrug delivery using folate as a homing device. J. Am. Chem. Soc. 2008, 130, 11467-11476.
27. Shen, M.; Wang, S. H.; Shi, X.; Chen, X.; Huang, Q.; Petersen, E. J.; Pinto, R. A.; Baker, J. R., Jr.; Weber, W. J., Jr. Polyethyleneiminemediated functionalization of multiwalled carbon nanotubes: Synthesis, characterization, and in vitro toxicity assay. J. Phys. Chem. C 2009, 113, 3150-3156.
28. Yang, W. R.; Thordarson, P.; Gooding, J. J.; Ringer, S. P.; Braet, F. Carbon nanotubes for biological and biomedical applications. Nano-technology 2007, 18, 412001/1-412001/12.
29. Newkome, G. R.; Moorefield, C. N.; Vogtle, F. Dendritic Molecules: Concepts, Syntheses, Perspectives; Wiley-VCH: New York, 1997.
30. Tomalia, D. A.; Frechet, J. M. J. Dendrimers and Other Dendritic Polymers; John Wiley & Sons, Ltd.: New York, 2001.
31. Kukowska-Latallo, J. F.; Candido, K. A.; Cao, Z.; Nigavekar, S. S.; Majoros, I. J.; Thomas, T. P.; Balogh, L. P.; Khan, M. K.; Baker, J. R., Jr. Nanoparticle targeting of anticancer drug improves therapeutic response in animal model of human epithelial cancer. Cancer Res. 2005, 65, 5317-5324.
32. Majoros, I. J.; Myc, A.; Thomas, T.; Mehta, C. B.; Baker, J. R. PAMAM dendrimer-based multifunctional conjugate for cancer therapy: Synthesis, characterization, and functionality. Biomacromolecules 2006, 7, 572-579.
33. Majoros, I. J.; Thomas, T. P.; Mehta, C. B.; Baker, J. R., Jr. PAMAM dendrimer-based multifunctional engineered nanodevice for cancer therapy. J. Med. Chem. 2005, 48, 5892-5899.
34. Patri, A. K.; Kukowska-Latallo, J. F.; Baker, J. R., Jr. Targeted drug delivery with dendrimers: comparison of the release kinetics of covalently conjugated drug and non-covalent drug inclusion complex. Adv. Drug Delivery Rev. 2005, 57, 2203-2214.
35. Shukla, R.; Thomas, T. P.; Peters, J. L.; Desai, A. M.; Kukowska-Latallo, J.; Patri, A. K.; Kotlyar, A.; Baker, J. R. HER2 specific tumor targeting with dendrimer conjugated anti-HER2 mAb. Bioconjugate Chem. 2006, 17, 1109-1115.
36. Thomas, T. P.; Majoros, I. J.; Kotlyar, A.; Kukowska-Latallo, J. F.; Bielinska, A.; Myc, A.; Baker, J. R., Jr. Targeting and inhibition of cell growth by an engineered dendritic nanodevice. J. Med. Chem. 2005, 48, 3729-3735.
37. Shi, X.; Lee, I.; Baker, J. R., Jr. Acetylation of dendrimer-entrapped gold and silver nanoparticles. J. Mater. Chem. 2008, 18, 586-593.
38. Shi, X.; Wang, S.; Meshinchi, S.; Van Antwerp, M.; Bi, X.; Lee, I.; Baker, J. R., Jr. Dendrimer-entrapped gold nanoparticles as a platform for cancer-cell targeting and imaging. Small 2007, 3, 1245-1252.
39. Shi, X.; Wang, S.; Sun, H.; Baker, J. R., Jr. Improved biocompatibility of surface functionalized dendrimer-entrapped gold nanoparticles. Soft Matter 2007, 3, 71-74.
40. Lesniak, W.; Bielinska, A. U.; Sun, K.; Janczak, K. W.; Shi, X.; Baker, J. R., Jr.; Balogh, L. P. Silver/dendrimer nanocomposites as biomarkers: Fabrication, characterization, in vitro toxicity, and intracellular detection. Nano Lett. 2005, 5, 2123-2130.
41. Shi, X.; Ganser, T. R.; Sun, K.; Balogh, L. P.; Baker, J. R., Jr. Characterization of crystalline dendrimer-stabilized gold nanoparticles. Nanotechnology 2006, 17, 1072-1078.
42. Shi, X.; Sun, K.; Baker, J. R., Jr. Spontaneous formation of functionalized dendrimer-stabilized gold nanoparticles. J. Phys. Chem. C 2008, 112, 8251-8258.
43. Shi, X.; Thomas, T. P.; Myc, L. A.; Kotlyar, A.; Baker, J. R., Jr. Synthesis, characterization, and intracellular uptake of carboxylterminated poly(amidoamine) dendrimer-stabilized iron oxide nanoparticles. Phys. Chem. Chem. Phys. 2007, 9, 5712-5720.
44. Shi, X.; Wang, S. H.; Swanson, S. D.; Ge, S.; Cao, Z.; Van Antwerp, M. E.; Landmark, K. J.; Baker, J. R., Jr. Dendrimer-functionalized shell-crosslinked iron oxide nanoparticles for in vivo magnetic resonance imaging of tumors. Adv. Mater. 2008, 20, 1671-1678.
45. Wang, S.; Shi, X.; Van Antwerp, M.; Cao, Z.; Swanson, S. D.; Bi, X.; Baker, J. R., Jr. Dendrimer-functionalized iron oxide nanoparticles for specific targeting and imaging of cancer cells. Adv. Funct. Mater. 2007, 17, 3403-3050.
46. Lu, X.; Imae, T. Size-controlled in situ synthesis of metal nanoparticles on dendrimer-modified carbon nanotubes. J. Phys. Chem. C 2007, 111, 2416-2420.
47. Lu, X.; Imae, T. Dendrimer-mediated synthesis of water-dispersible carbon-nanotube-supported oxide nanoparticles. J. Phys. Chem. C 2007, 111, 8459-8462.
48. Vijayaraghavan, G.; Stevenson, K. J. Synergistic assembly of dendrimer-templated platinum catalysts on nitrogen-doped carbon nanotube electrodes for oxygen reduction. Langmuir 2007, 23, 5279-5282.
49. Campidelli, S.; Sooambar, C.; Lozano-Diz, E.; Ehli, C.; Guldi, D. M.; Prato, M. Dendrimer-functionalized single-wall carbon nanotubes: Synthesis, characterization, and photoinduced electron transfer. J. Am. Chem. Soc. 2006, 128, 12544-12552.
50. Davis, J. J.; Coleman, K. S.; Azamian, B. R.; Bagshaw, C. B.; Green, M. L. H. Chemical and biochemical sensing with modified single walled carbon nanotubes. Chem.-Eur. J. 2003, 9, 3732-3739.
51. Pan, B. F.; Cui, D. X.; Gao, F.; He, R. Growth of multi-amine terminated poly(amidoamine) dendrimerson the surface of carbon nanotubes. Nanotechnology 2006, 17, 2483-2489.
52. Wu, P.; Chen, X.; Hu, N.; Tam, U. C.; Blixt, O.; Zettl, A.; Bertozzi, C. R. Biocompatible carbon nanotubes generated by functionalization with glycodendrimers. Angew. Chem., Int. Ed. 2008, 47, 5022-5025.
53. Petersen, E. J.; Huang, Q. G.; Weber, W. J. Ecological uptake and depuration of carbon nanotubes by Lumbriculus variegatus. Environ. Health Perspect. 2008, 116, 496-500.
54. Petersen, E. J.; Huang, Q. G.; Weber, W. J. Bioaccumulation of radiolabeled carbon nanotubes by Eisenia foetida. Environ. Sci. Technol. 2008, 42, 3090-3095.
55. Majoros, I. J.; Keszler, B.; Woehler, S.; Bull, T.; Baker, J. R., Jr. Acetylation of poly(amidoamine) dendrimers. Macromolecules 2003, 36, 5526-5529.
56. Shi, X.; Bányai, I.; Rodriguez, K.; Islam, M. T.; Lesniak, W.; Balogh, P.; Balogh, L.; Baker, J. R., Jr. Electrophoretic mobility and molecular distribution studies of poly(amidoamine) dendrimers of defined charges. Electrophoresis 2006, 27, 1758-1767.
57. Villa, C. H.; McDevitt, M. R.; Escorcia, F. E.; Rey, D. A.; Bergkvist, M.; Batt, C. A.; Scheinberg, D. A. Synthesis and biodistribution of oligonucleotide-functionalized, tumor-targetable carbon nanotubes. Nano Lett. 2008, 8, 4221-4228.
58. Chen, J.; Chen, S.; Zhao, X.; Kuznetsova, L. V.; Wong, S. S.; Ojima, I. Functionalized single-walled carbon nanotubes as rationally designed vehicles for tumor-targeted drug delivery. J. Am. Chem. Soc. 2008, 130, 16778-16785.
59. Hu, X.; Wang, T.; Qu, X.; Dong, S. In situ synthesis and characterization of multiwalled carbon nanotube/Au nanoparticle composite materials. J. Phys. Chem. B 2006, 110, 853-857.
60. Davoren, M.; Herzog, E.; Casey, A.; Cottineau, B.; Chambers, G.; Byrne, H. J.; Lyng, F. M. In vitro toxicity evaluation of single walled carbon nanotubes on human A549 lung cells. Toxicol. in Vitro 2007, 21, 438-448.
61. Keogh, S. M.; Hedderman, T. G.; Gregan, E.; Farrell, G.; Chambers, G.; Byrne, H. J. Spectroscopic analysis of single-walled carbon nanotubes and semiconjugated polymer composites. J. Phys. Chem. B 2004, 108, 6233-6241.
62. Campbell, I. G.; Jones, T. A.; Foulkes, W. D.; Trowsdale, J. Folatebinding protein is a marker for ovarian cancer. Cancer Res. 1991, 51, 5329-5338.
63. Ross, J. F.; Chaudhuri, P. K.; Ratnam, M. Differential regulation of folate receptor isoforms in normal and malignant tissues in vivo and in established cell lines. Physiologic and clinical implications. Cancer 1994, 73, 2432-2443.
64. Weitman, D.; Lark, R. H.; Coney, L. R.; Fort, D. W.; Frasca, V.; Surawski, V. R.; Kamen, B. A. Distribution of the folate receptor GP38 in normal and malignant cell lines and tissues. Cancer Res. 1992, 52, 3396-3401.
65. 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.