Functionalized Fullerenes in Water. The First 10 Years of Their Chemistry, Biology, and Nanoscience

Accounts of Chemical Research

Volumn 36, Issue 11, 2003, Pages 807-815

  Nakamura, Eiichi ^a   Isobe, Hiroyuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; FULLERENE DERIVATIVE; METAL COMPLEX; PLASMID DNA; PROTEIN; PROTEINASE INHIBITOR; SCAVENGER; WATER;

ACUTE TOXICITY; ARTICLE; BILAYER MEMBRANE; BIOLOGY; CELL; DEGENERATIVE DISEASE; DNA VECTOR; DRUG ACCUMULATION; DRUG DNA BINDING; DRUG EXCRETION; DRUG PROTEIN BINDING; DRUG SOLUBILITY; DRUG SYNTHESIS; GENE DELIVERY SYSTEM; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; NANOPARTICLE; NEUROPROTECTION; NONHUMAN; ORGANIC CHEMISTRY; PHOTOCHEMICAL QUENCHING; PHOTOCHEMISTRY; PHOTOTOXICITY; SUPRAMOLECULAR CHEMISTRY;

ANIMALS; FULLERENES; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; NANOTECHNOLOGY; PHOTOCHEMISTRY; WATER;

EID: 0344393787     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar030027y     Document Type: Article

References (81)

1. Tokuyama H.; Yamago, S.; Nakamura, E.; Shiraki, T.; Sugiura, Y. Photo-induced biochemical activity of fullerene carboxylic acid. J. Am. Chem. Soc. 1993, 115, 7918-7919.
2. Friedman, S. H.; DeCamp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification. J. Am. Chem. Soc. 1993, 115, 6506-6509. Sijbesma, R.; Srdanov, G.; Wudl, F.; Castoro, J. A.; Wilkins, C.; Friedman, S. H.; DeCamp, D. L.; Kenyon, G. L. Synthesis of a fullerene derivative for the inhibition of HIV enzymes. J. Am. Chem. Soc. 1993, 115, 6510-6512.
3. Friedman, S. H.; DeCamp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification. J. Am. Chem. Soc. 1993, 115, 6506-6509. Sijbesma, R.; Srdanov, G.; Wudl, F.; Castoro, J. A.; Wilkins, C.; Friedman, S. H.; DeCamp, D. L.; Kenyon, G. L. Synthesis of a fullerene derivative for the inhibition of HIV enzymes. J. Am. Chem. Soc. 1993, 115, 6510-6512.
4. 60 fullerene. Antimicrob. Agents Chemother. 1993, 37, 1707-1710.
5. Da Ros, T.; Prato, M. Medicinal chemistry with fullerenes and fullerene derivatives. Chem. Commun. 1999, 663-669. Wilson, S. R. Nanomedicine: fullerene and carbon nanotube biology. In Perspectives of Fullerene Nanotechnology; Osawa E., Eds.; Kluwer Academic: Dordrecht, 2002; pp 155-163.
6. Da Ros, T.; Prato, M. Medicinal chemistry with fullerenes and fullerene derivatives. Chem. Commun. 1999, 663-669. Wilson, S. R. Nanomedicine: fullerene and carbon nanotube biology. In Perspectives of Fullerene Nanotechnology; Osawa E., Eds.; Kluwer Academic: Dordrecht, 2002; pp 155-163.
7. 70, in water. Preparation and characterization. Langmuir 2001, 17, 6013-6017.
8. 70, in water. Preparation and characterization. Langmuir 2001, 17, 6013-6017.
9. 60 fullerene derivatives. Acc. Chem. Res. 2000, 33, 695-703.
10. 60-based electroactive organofullerenes. Chem. Rev. 1998, 98, 2527-2547.
11. Hirsch, A. Chemistry of the fullerenes; Thieme: Stuttgart, 1994. Diederich, F.; Kessinger, R. Regio- and stereoselective multiple functionalization of fullerenes. In Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 2000; pp 189-218.
12. Hirsch, A. Chemistry of the fullerenes; Thieme: Stuttgart, 1994. Diederich, F.; Kessinger, R. Regio- and stereoselective multiple functionalization of fullerenes. In Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 2000; pp 189-218.
13. Osawa, E. Superaromaticity. Kagaku 1970, 25, 854-863; Chem. Abst. 1971, 74 (15), 75698v.
14. Osawa, E. Superaromaticity. Kagaku 1970, 25, 854-863; Chem. Abst. 1971, 74 (15), 75698v.
15. 60-Buckminsterfullerene. Nature 1985, 318, 162-163.
16. 60-A new form of carbon. Nature 1990, 347, 354-358.
17. Korobov, M. V.; Smith, A. L. Solubility of the fullerenes. In Fullerenes: Chemistry, physics, and technology; Kadish, K. M., Ruoff, R. S., Eds.; Wiley: New York, 2000; pp 53-89.
18. Yamakoshi, Y. N.; Yagami, T.; Fukuhara, K.; Sueyoshi, S.; Miyata, N. Solubilization of fullerenes into water with poly(vinylpyrrolidone) applicable to biological tests. J. Chem. Soc., Chem. Commun. 1994, 517-518.
19. Diederich, F.; Gómez-López, M. Supramolecular fullerene chemistry. Chem. Soc. Rev. 1999, 28, 263-277.
20. 60 fullerene functionalization. J. Am. Chem. Soc. 1992, 114, 10154-10157.
21. 60. J. Am. Chem. Soc. 1993, 115, 1594-1595.
22. Ando, R.; Morinaka, Y.; Tokuyama, H.; Isaka M.; Nakamura, E. A new class of proteinase inhibitor. Cyclopropenone-containing inhibitor of papain. J. Am. Chem. Soc. 1993, 115, 1174-1175.
23. Irie, K.; Nakamura, Y.; Ohigashi, H.; Tokuyama, H.; Yamago, S.; Nakamura, E. Photocytotoxicity of water-soluble fullerene derivatives. Biosci., Biotechnol. Biochem. 1996, 60, 1359-1361.
24. Nakamura, E.; Tokuyama, H.; Yamago, S.; Shiraki, T.; Sugiura, Y. Biological activity of water-soluble fullerenes. Structural dependence of DNA cleavage, cytotoxicity and enzyme inhibitory activities. Bull. Soc. Chem. Jpn. 1996, 69, 2143-2151.
25. 60 solutions by Photoirradiation: An EPR Study. J. Am. Chem. Soc. 1998, 120, 12363-12364.
26. 60. J. Am. Chem. Soc. 1999, 121, 464-465.
27. Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Functionalized fullerene as a new artificial vector for transfection. Angew. Chem., Int. Ed. 2000, 39, 4254-4257.
28. Brettreich, M.; Hirsch, A. A highly water-soluble dendro[60]-fullerene. Tetrahedron Lett. 1998, 39, 2731-2734. Schuster, D. I.; Wilson, S. R.; Kirschner, A. N.; Schinazi, R. F.; Schlueter-Wirtz, S.; Tharnish, P.; Barnett, T.; Ermolieff, J.; Tang, J.; Brettreich, M.; Hirsch, A. Evaluation of the anti-HIV potency of a water-soluble dendrimeric fullerene. Proc. Electrochem. Soc. 2000, 11, 267-270.
29. Brettreich, M.; Hirsch, A. A highly water-soluble dendro[60]-fullerene. Tetrahedron Lett. 1998, 39, 2731-2734. Schuster, D. I.; Wilson, S. R.; Kirschner, A. N.; Schinazi, R. F.; Schlueter-Wirtz, S.; Tharnish, P.; Barnett, T.; Ermolieff, J.; Tang, J.; Brettreich, M.; Hirsch, A. Evaluation of the anti-HIV potency of a water-soluble dendrimeric fullerene. Proc. Electrochem. Soc. 2000, 11, 267-270.
30. 60, its suspension in water, and its uptake by human keratinocytes. J. Am. Chem. Soc. 1994, 116, 4517-4518.
31. 60, its suspension in water, and its uptake by human keratinocytes. J. Am. Chem. Soc. 1994, 116, 4517-4518.
32. 14C labeling, absorption, distribution, excretion and acute toxicity. Chem. Biol. 1995, 2, 385-389.
33. Nakamura E.; Yamago, S. Thermal reactions of dipolar trimethylenemethane species. Acc. Chem. Res. 2002, 35, 867-877. Yamago S.; Nakamura, E. [3 + 2] Cycloaddition of trimethylenemethane and its synthetic equivalents. Org. React. 2002, 61, 1-215.
34. Nakamura E.; Yamago, S. Thermal reactions of dipolar trimethylenemethane species. Acc. Chem. Res. 2002, 35, 867-877. Yamago S.; Nakamura, E. [3 + 2] Cycloaddition of trimethylenemethane and its synthetic equivalents. Org. React. 2002, 61, 1-215.
35. Dugan, L. L.; Turetsky, D. M.; Du, C.; Lobner, D.; Wheeler, M.; Almli, C. R.; Shen, C. K.-F.; Luh, T.-Y.; Choi, D. W.; Lin, T.-S. Carboxyfullerenes as neuroprotective agents. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 9434-9439.
36. Cagle, D. W.; Kennel, S. J.; Mirzadeh, S.; Alford, J. M.; Wilson, L. J. In vivo studies of fullerene-based materials using endohedral metallofullerene radiotracers. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 5182-5187.
37. Rajagopalan, P.; Wudl, F.; Schinazi, R. F.; Boudinot, F. D. Pharmacokinetics of a water-soluble fullerene in rats. Antimicrob. Agents Chemother. 1996, 40, 2262-2265.
38. Tabata, Y.; Murakami, Y.; Ikada, Y. Photodynamic effect of polyethylene glycol-modified fullerene on tumor. Jpn. J. Cancer Res. 1997, 88, 11108-1116.
39. 60 tris-adduct on Jurkat cells. J. Photochem. Photobiol., B: Biol. 2002, 67, 157-162.
40. 60 in ambient air and the role of ozone. Geochim. Cosmochim. Acta 1993, 57, 1879-1881.
41. 60 in ambient air and the role of ozone. Geochim. Cosmochim. Acta 1993, 57, 1879-1881.
42. Boutorine, A. S.; Tokuyama, H.; Takasugi, M.; Isobe, H.; Nakamura, E.; Hélène, C. Fullerene-oligonucleotide conjugates: Photoinduced sequence-specific DNA cleavage. Angew. Chem., Int. Ed. Engl. 1994, 33, 2462-2465.
43. 60-linked deoxyoligonucleotide: Evidence for a non-singlet oxygen mechanism. Tetrahedron 1996, 52, 5179-5189.
44. Da Ros T.; Bergamin M.; Vazquez E.; Spalluto G.; Baiti B.; Moro S.; Boutorine A.; Prato M. Synthesis and molecular modeling studies of fullerene-5,6,7-trimethoxyindole-oligonucleotide conjugates as possible probes for study of photochemical reactions in DNA triple helices. Eur. J. Org. Chem. 2002, 405-413.
45. Yamakoshi Y. N.; Yagami T.; Sueyoshi S.; Miyata N. Acridine adduct of [60]fullerene with enhanced DNA-cleaving activity. J. Org. Chem. 1996, 61, 7236-7237.
46. Chi, Y.; Canteenwala, T.; Chen, H. H. C.; Jeng, U.-S.; Lin, T.-L.; Chiang, L. Y. Free radical scavenging and photodynamic functions of micelle-like hydrophilic hexa(sulfobutyl)fullerene (FC4S). In Perspectives of Fullerene Nanotechnology; Osawa E., Eds.; Kluwer Academic: Dordrecht, 2002; pp 165-183.
47. 60 with the poly(N-vinylpyrrolidone) complex. Mol. Cryst. Liq. Cryst. Sci. Technol., C: Mol. Mater. 1998, 11, 121-124.
48. Wolff, J. A. Gene Therapeutics: Methods and applications of direct gene transfer, Birkhäuser: Boston, 1993.
49. Isobe, H.; Tomita, N.; Jinno, S.; Okayama, H.; Nakamura, E. Synthesis and transfection capability of multi-functionalized fullerene polyamine. Chem. Lett. 2001, 1214-1215.
50. 60 derivative: Nanorods and vesicles. Angew. Chem., Int. Ed. 1999, 38, 2403-2405.
51. 60 derivative: Nanorods and vesicles. Angew. Chem., Int. Ed. 1999, 38, 2403-2405.
52. Isobe, H.; Tomita, N.; Nakamura, E. One-step multiple-addition of amine to [60]fullerene. Synthesis of tetra(amino)fullerene epoxide under photochemical aerobic conditions. Org. Lett. 2002, 3663-3666.
53. Kato, H.; Kanazawa, Y.; Okumura, M.; Taninaka, A.; Yokawa, T.; Shinohara, H. Lanthanoid endohedral metallofullerenols for MRI contrast agents. J. Am. Chem. Soc. 2003, 125, 4391-4397.
54. 10 as a MRI contrast agent. J. Am. Chem. Soc. 2003, 125, 5471-5478.
55. Mirkin, C. A.; Caldwell, W. B. Thin film, fullerene-based materials. Tetrahedron 1996, 52, 5113-5130.
56. 60 carboxylic acid. Langmuir 1995, 11, 660-665.
57. Sano, M.; Oishi, K. Ishi-i, T.; Shinkai, S. Vesicle formation and its fractal distribution by bola-amphiphilic [60]fullerene. Langmuir 2000, 16, 3773-3776.
58. Georgakilas, V.; Pellarini, F.; Prato, M.; Guldi, D. M.; Mlle-Franco, M. ; Zerbetto, F. Supramolecular self-assembled fullerene nanostructures. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5075-5080.
59. -. A water soluble hydrocarbon anion. Chem. Lett. 2000, 1098-1099.
60. Zhou, S.; Burger, C.; Chu, B.; Sawamura, M.; Nagahama, N.; Toganoh, M.; Hackler, U. E.; Isobe, H.; Nakamura, E. Spherical bilayer vesicles of fullerene based surfactants in water: A laser light scattering study. Science 2001, 291, 1944-1947.
61. Sawamura, M.; Kawai, K.; Matsuo, Y.; Kanie, K.; Kato T.; Nakamura, E. Stacking of conical mesogens with a fullerene apex into polar columns in crystals and liquid crystals. Nature 2002, 419, 702-705.
62. Isobe, H.; Sugiyama, S.; Fukui, K.-i.; Iwasawa, Y.; Nakamura, E. Atomic force microscope studies on condensation of plasmid DNA with functionalized fullerene. Angew. Chem., Int. Ed. 2001, 40, 3364-3367.
63. Kawaura, C.; Noguchi, A.; Furuno, T.; Nakanishi, M. Atomic force microscopy for studying gene transfection mediated by cationic liposomes with a cationic cholesterol derivative. FEBS Lett. 1998, 421, 69-72.
64. Chen, B.-X.; Wilson, S. R.; Das, N.; Coughlin, D. J. Erlanger, B. F. Antigenicity of fullerenes: Antibodies specific for fullerenes and their characteristics. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 10809-10813.
65. 60. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 12193-12197.
66. Erlanger, B. F.; Chen, B.-X.; Zhu, M.; Brus, L. Binding of an antifullerene IgG monoclonal antibody to single wall carbon nanotubes. Nano Lett. 2001, 1, 465-467.
67. Stork G.; Nakamura, E. A simplified total synthesis of cytochalasins via macrocyclic Diels-Alder reaction. J. Am. Chem. Soc. 1983, 105, 5510-5511. Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Total Synthesis of (±)-cortisone. Double hydroxylation reaction for corticoid synthesis. J. Am. Chem. Soc. 1989, 111, 6257-6265.
68. Stork G.; Nakamura, E. A simplified total synthesis of cytochalasins via macrocyclic Diels-Alder reaction. J. Am. Chem. Soc. 1983, 105, 5510-5511. Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Total Synthesis of (±)-cortisone. Double hydroxylation reaction for corticoid synthesis. J. Am. Chem. Soc. 1989, 111, 6257-6265.
69. 60. J. Org. Chem. 1997, 62, 5034-5041.
70. Nakamura, M.; Isobe, H.; Nakamura, E. Cyclopropenone acetal-Synthesis and reactions. Chem. Rev. 2003, 203, 1295-1326.
71. Sawamura, M.; likura, H.; Nakamura, E. The first pentahapto fullerene metal complexes. J. Am. Chem. Soc. 1996, 118, 12850-12851.
72. 5-fullerene metal complexes. Pure Appl. Chem. 2001, 73, 355-359.
73. 70. J. Am. Chem. Soc. 1998, 120, 8285-8286.
74. Isobe, H.; Ohbayashi, A.; Sawamura, M.; Nakamura, E. A cage with fullerene end caps. J. Am. Chem. Soc. 2000, 122, 2669-2670.
75. Isobe, H.; Mashima, H.; Yorimitsu, H.; Nakamura, E. Org. Lett. 2003, 5, 4461-4464.
76. Sawamura, M.; Kuninobu, Y.; Toganoh, M.; Matsuo, Y.; Yamanaka, M.; Nakamura, E. Hybrid of ferrocene and fullerene. J. Am. Chem. Soc. 2002, 124, 9354-9355.
77. Nakamura, E.; Tahara, K.; Matsuo, Y.; Sawamura, M.; Synthesis, structure and aromaticity of a hoop-shaped cyclic benzenoid [10]-cyclophenacene. J. Am. Chem. Soc. 2003, 125, 2834-2835. Hoffmann, R. Thoughts on aesthetics and visualization in chemistry. HILI 2003, 9, 7-11.
78. Nakamura, E.; Tahara, K.; Matsuo, Y.; Sawamura, M.; Synthesis, structure and aromaticity of a hoop-shaped cyclic benzenoid [10]-cyclophenacene. J. Am. Chem. Soc. 2003, 125, 2834-2835. Hoffmann, R. Thoughts on aesthetics and visualization in chemistry. HILI 2003, 9, 7-11.
79. 70 in flames. Nature 1991, 352, 139-141.
80. URL of Frontier Carbon: http://www.f-carbon.com/
81. http://www.absbowling.co.jp/