Fullerenes toxicity and electronic properties

Environmental Chemistry Letters

Volumn 11, Issue 2, 2013, Pages 105-118

  Sergio, Manzetti ^a   Behzadi, Hadi ^b   Otto, Andersen ^c   van der Spoel, David ^d  

^a FJORDFORSK   (Norway)

^b KHARAZMI UNIVERSITY   (Iran)

^c WESTERN NORWAY RESEARCH INSTITUTE   (Norway)

^d UPPSALA UNIVERSITY   (Sweden)

Author keywords

Chemical modifications; Electronic properties; Fullerenes; Mutagenicity; Quantum chemistry; Toxicity prediction

Indexed keywords

BLENDING; ELECTRONIC PROPERTIES; FULLERENES; METABOLITES; MOLECULES; QUANTUM CHEMISTRY; TOXICITY;

C 60; EXOTIC MATERIALS; EXOTIC PRODUCTS; IN-VITRO; INDUSTRIAL CHEMISTRY; MATERIALS AND PRODUCTS; MUTAGENICITY; SCIENTIFIC DEVELOPMENT; TOXICITY PREDICTIONS; TOXICOLOGICAL PROPERTIES;

CHEMICAL MODIFICATION;

EID: 84878203989     PISSN: 16103653     EISSN: 16103661     Source Type: Journal    
DOI: 10.1007/s10311-012-0387-x     Document Type: Review

References (79)

1. Allouche A (2011) Gabedit-a graphical user interface for computational chemistry softwares. J Comput Chem 32: 174-182.
2. Anctil A, Babbitt C, Raffaelle R, Landi B (2011) Material and energy intensity of fullerene production. Environ Sci Technol 45: 2353-2359.
3. Bakry R, Vallant R, Najam-ul-Haq M et al (2007) Medicinal applications of fullerenes. Int J Nanomed 2: 639.
4. Becke A (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98: 5648-5652.
5. Cagle D, Kenmnel S, Mirzadeh S et al (1999) In vivo studies of materials using endohedral metallofullerene radiotracers. Proc Natl Acad Sci USA 96: 5182-5187.
6. Chen Z, King R (2005) Spherical aromaticity: recent work on fullerenes, polyhedral boranes, and related structures. Chem Rev 105: 3613-3642.
7. Chen Z, Heine T, Jiao H et al (2004) Theoretical studies on the smallest fullerene: from monomer to oligomers and solid States. Chemistry 10: 963-970.
8. Da Ros T (2008) Twenty years of promises: fullerene in medicinal chemistry. Medicinal chemistry and pharmacological potential of fullerenes and carbon nanotubes. Springer, Netherlands, pp 1-21. doi: 10. 1007/978-1-4020-6845-4_1.
9. Dekant W (2009) The role of biotransformation and bioactivation in toxicity. EXS 99: 57-86.
10. Dhawan A, Taurozzi J, Pandey A et al (2006) Stable colloidal dispersions of C60 fullerenes in water: evidence for genotoxicity. Environ Sci Technol 40: 7394-7401.
11. Drug E, Landesman-Milo D, Belgorodsky B et al (2011) Enhanced bioavailability of polyaromatic hydrocarbons in the form of mucin complexes. Chem Res Toxicol 24: 314-320.
12. Eilmes A, Munn R (2004) A test of the method of images at the surface of molecular materials. J Chem Phys 120: 3887-3892.
13. Elliot K (2011) Nanomaterials and the precautionary principle. Environ Health Perspect 119: A240. doi: 10. 1289/ehp. 1103687.
14. Filella M, Rellestab C, Chanudet V, Spaak P (2008) Effect of the filter feeder Daphnia on the particle size distribution of inorganic colloids in freshwaters. Water Res 42: 1919-1924.
15. Fortner J, Lyon D, Sayes C et al (2005) C60 in water: nanocrystal formation and microbial response. Environ Sci Technol 39: 4307-4316.
16. Frisch M, Trucks G, Schlegel H et al (2003) Gaussian 03. Gaussian, Inc., Wallingford.
17. Fujita K, Morimoto Y, Ogami A et al (2009) Gene expression profiles in rat lung after inhalation exposure to C60 fullerene particles. Toxicol 258: 47-55.
18. Gonzalez-Parra E, Gonzalez-Casaus M, Galán A et al (2011) Lanthanum carbonate reduces FGF23 in chronic kidney disease stage 3 patients. Nephrol Dial Transplant 26: 2567-2571.
19. Haddon R, Pasquarello A (1994) Magnetism of carbon clusters. Phys Rev B 50: 16459-16463.
20. Henry T, Menn F, Fleming J et al (2007) Attributing effects of aqueous C60 nano-aggregates to tetrahydrofuran decomposition products in larval zebrafish by assessment of gene expression. Environ Health Perspect 115: 1059-1065.
21. Henry T, Petersen E, Compton R (2011) Aqueous fullerene aggregates (nC60) generate minimal reactive oxygen species and are of low toxicity in fish: a revision of previous reports. Curr Opin Biotechnol 22: 533-537.
22. Hosseini A, Sharifzadeh M, Rezayat S et al (2010) Benefit of magnesium-25 carrying porphyrin-fullerene nanoparticles in experimental diabetic neuropathy. Int J Nanomed 5: 517-523.
23. Hummelen J, Knight B, Pepeq F et al (1995) Preparation and characterization of fulleroid and methanofullerene derivatives. J Org Chem 60: 532-538.
24. Hyung H, Fortner J, Hughes J, Kim J (2007) Natural organic matter stabilizes carbon nanotubes in the aqueous phase. Environ Sci Technol 41: 179-184.
25. Jakubov T, Mainwaring S (2009) Interaction between C60 fullerene and alkali metals demonstrating superconductivity. Procedia Chem 1: 1584-1589.
26. JCrystalSoft (2012) Nanotube modeler. J Crystal Soft. http://www. jcrystal. com/.
27. Jehoulet C, Obeng Y, Kim Y et al (1992) Electrochemistry and langmuir trough studies of fullerene C60 and C70 films. J Am Chem Soc 114: 4237-4247.
28. Jensen A, Wilson S, Schuster D (1996) Biological applications of fullerenes. Bioorg Med Chem 4: 1-20.
29. Jiao F, Qu Y, Zhou G et al (2010) Modulation of oxidative stress by functionalized fullerene materials in the lung tissues of female C57/BL mice with a metastatic Lewis lung carcinoma. J Nanosci Nanotechnol 10: 8632-8637.
30. Jovanović B, Anastasova L, Rowe E, Palić D (2011) Hydroxylated fullerenes inhibit neutrophil function in fathead minnow (Pimephales promelas Rafinesque, 1820). Aquat Toxicol 101: 474-482.
31. Kashiwada S (2006) Distribution of nanoparticles in the see-through medaka (Oryzias latipes). Environ Health Persp 114: 1697-1702.
32. Khairullin I, Chen Y, Hwang L (1997a) Evidence for electron charge transfer in the polyvinylpyrrolidone-c60 system as seen from ESR spectra. Chem Phys Lett 275: 1.
33. Khairullin I, Tsao Z, Hwang L (1997b) Characterization of KC60 obtained via a potassium carbonate route. Fuller Sci Tech 5: 1507.
34. Kim K, Jang M, Kim JY, Kim S (2010) Effect of preparation methods on toxicity of fullerene water suspensions to Japanese medaka embryos. Sci Tot Environ 408: 5606-5612.
35. Knupfer M, Knauff O, Golden M et al (1996) Electronic structure of the two C78 isomers with C2v symmetry. Chem Phys Lett 258: 513.
36. Lee C, Yang W, Parr R (1988) Development of the Colle-Salvetti conelation energy formula into a functional of the electron density. Phys Rev B 37: 785-789.
37. Lee J, Jung J, Emrick T et al (2010) Morphology control of a polythiophene-fullerene bulk heterojunction for enhancement of the high-temperature stability of solar cell performance by a new donor-acceptor diblock copolymer. Nanotechnology 21: 105201.
38. Levin W, Wood A, Chang R et al (1982) Oxidative metabolism of polycyclic aromatic hydrocarbons to ultimate carcinogens. Drug Metab Rev 13: 555-580.
39. Li Q, Xie B, Hwang Y, Xu Y (2009) Kinetics of C60 fullerene dispersion in water enhanced by natural organic matter and sunlight. Environ Sci Technol 43: 3574-3579.
40. Liang C, Xie H, Schwartz V et al (2009) Open-cage fullerene-like graphitic carbons as catalysts for oxidative dehydrogenation of isobutane. J Am Chem Soc 131: 7735-7741.
41. Lin C, Zhang M, Liu S et al (2011) High photoelectric conversion efficiency of metal phthalocyanine/fullerene heterojunction photovoltaic device. Int J Mol Sci 12: 476-505.
42. Lyon D, Fortner J, Sayes C et al (2005) Bacterial cell association and antimicrobial activity of a C60 water suspension. Environ Toxicol Chem 24: 2757-2762.
43. Manzetti S (2011) Quantum toxicology-a potential perspective in toxicology? Toxicology 288: 56-57.
44. Markovic Z, Todorovic-Markovic B, Kleut D et al (2007) The mechanism of cell-damaging reactive oxygen generation by colloidal fullerenes. Biomaterials 28: 5437-5448.
45. Mauter EM (2008) Environmental applications of carbon-based nanomaterials. Environ Sci Technol 42: 5843-5859.
46. Miles R, Hynes K, Forbes I (2005) Photovoltaic solar cells: an overview of state-of-the-art cell development and environmental issues. Progr Cryst Growth Charact Mater 51: 1-42.
47. Mori T et al (2006) Preclinical studies on safety of fullerene upon acute oral administration and evaluation for no mutagenesis. Toxicology 225: 48-54.
48. Nakagawa Y, Suzuki T, Ishii H et al (2011) Cytotoxic effects of hydroxylated fullerenes on isolated rat hepatocytes via mitochondrial dysfunction. Arch Toxicol. doi: 10. 1007/s00204-011-0688-z.
49. Oberdörster E (2004a) Manufactured nanomaterials (fullerenes, C60) induce oxidative stress in the brain of juvenile largemouth bass. Environ Health Perspect 112: 1058-1062.
50. Oberdörster E (2004b) Toxicity of nC60 fullerenes to two aquatic species: Daphnia and largemouth bass [Abstract]. In: 227th American Chemical Society National Meeting, 27 March-1 April 2004, Anaheim, CA.
51. Oberdörster G, Oberdörster E, Oberdörster J (2005) Nanotoxicology: an emerging discipline evolving from 116 studies of ultrafine particles. Environ Health Persp 113: 823-839.
52. Oberdörster E, Zhu S, Blickley T et al (2006) Ecotoxicology of carbon-based engineered nanoparticles: effects of fullerene (C60) on aquatic organisms. Carbon 44: 1112-1120.
53. Park J, Henry T, Menn F et al (2010) No bioavailability of 17α-ethinylestradiol when associated with nC60 aggregates during dietary exposure in adult male zebrafish (Danio rerio). Chemosphere 81: 1227-1232.
54. Qiao R, Roberts A, Mount A et al (2007) Translocation of C60 and its derivatives across a lipid bilayer. Nano Lett 7: 614-619.
55. Raghavachari K, Binkley J, Seeger R, Pople J (1980) Self-consistent molecular orbital methods. 20. Basis set for correlated wave-functions. J Chem Phys 72: 650-654.
56. Rassolov V, Pople J, Ratner M, Windus T (1998) 6-31G* basis set for atoms K through Zn. J Chem Phys 109: 1223-1229. doi: 10. 1063/1. 476673.
57. Rodríguez-Fortea A, Irle S, Poblet J (2011) Fullerenes: formation, stability, and reactivity. Adv Rev. doi: 10. 1002/wcms.
58. Sadauskas E, Wallin H, Stoltenberg M et al (2007) Kupffer cells are central in the removal of nanoparticles from the organism. Part Fibre Toxicol 4: 10.
59. Sayes C et al (2007) Comparative pulmonary toxicity assessments of C60 water suspensions in rats: few differences in fullerene toxicity in vivo in contrast to in vitro profiles. Nano Lett 7: 2399-2406.
60. Shrotriya V, Yao Y, Li G, Yang Y (2006) Effect of self-organization in polymer/fullerene bulk heterojunctions on solar cell performance. Appl Phys Lett 89: 063505.
61. Stephens P, Devlin F, Chabalowski C, Frisch M (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98: 11623-11627.
62. Subach F, Malashkevich V, Zencheck W et al (2009) Photoactivation mechanism of PAmCherry based on crystal structures of the protein in the dark and fluorescent states. Proc Natl Acad Sci USA 106: 21097-21102.
63. Tanaka A (2004) Toxicity of indium arsenide, gallium arsenide, and aluminium gallium arsenide. Toxicol Appl Pharmacol 198: 405-411.
64. Thompson M (2004) ArgusLab. Planaria Software LLC, Seattle.
65. Tokuyama H, Yamago S, Nakamura E et al (1993) Photoinduced biochemical activity of fullerene carboxylic acid. J Am Chem Soc 115: 7918-7919.
66. Tong J, Zimmerman M, Li S et al (2011) Neuronal uptake and intracellular superoxide scavenging of a fullerene (C60)-poly(2-oxazoline)s nanoformulation. Biomaterials 32: 3654-3665.
67. Tsuchiya T, Oguri I, Yamakoshi Y, Miyata N (1996) Novel harmful effects of [60] fullerene on mouse embryos in vitro and in vivo. FEBS Lett 393: 139-145.
68. Voet D, Voet J (2010) Biochemistry, 4th edn. Wiley, New York.
69. Vosko S, Wilk L, Nusair M (1980) Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys 58: 1200-1211.
70. Walsh B (2010) The perils of plastic. Time Magazine, US.
71. Willner I, Willner B (2010) Biomolecule-based nanomaterials and nanostructures. Nano Lett 10: 3805-3815.
72. Yamago S, Tokuyama H, Nakamura E et al (1995) In vivo biological behavior of a water-miscible fullerene: 14C labeling, absorption, distribution, excretion and acute toxicity. Chem Biol 2: 385-389.
73. Yamakoshi Y, Umezawa N, Ryu A et al (2003) Active oxygen species generated from photoexcited fullerene (C60) as potential medicines: O2- versus 1O2. J Am Chem Soc 125: 12803-12809.
74. Yang D, Park C, Min J et al (2009) Fullerene nanohybrid metal oxide ultrathin films. Curr Appl Phys 9: 132-135.
75. Yuan Y, Reece T, Sharma P et al (2011) Efficiency enhancement in organic solar cells with ferroelectric polymer. Nat Mater 10: 296-302.
76. Zhang L, Yang J, Barron A, Monteiro-Riviere N (2009) Endocytic mechanisms and toxicity of a functionalized fullerene in human cells. Toxicol Lett 191: 149-157.
77. Zhang M, Xing G, Yuan H et al (2010) Transmembrane delivery of aggregated [Gd@C82(OH)22]n nanoparticles. J Nanosci Nanotechnol 10: 8556-85661.
78. Zhou Z, Joslin S, Dellinger A et al (2010) A novel class of compounds with cutaneous wound healing properties. J Biomed Nanotechnol 6: 605-611.
79. Zhu X, Zhu L, Lang Y, Chen Y (2008) Oxidative stress and growth inhibition in the freshwater fish Carpassius auratus induced by chronic exposure to sublethal fullerene aggregates. Environ Toxicol 27: 1979-1985.