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Chemistry

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Also known as: 99685-96-8, Fullerene, Fullerene c60, C60 fullerene, Fullerene-c60, Buckyball
Molecular Formula
C60
Molecular Weight
720.6  g/mol
InChI Key
XMWRBQBLMFGWIX-UHFFFAOYSA-N
FDA UNII
NP9U26B839

Fullerene C60
A polyhedral CARBON structure composed of around 60-80 carbon atoms in pentagon and hexagon configuration. They are named after Buckminster Fuller because of structural resemblance to geodesic domes. Fullerenes can be made in high temperature such as arc discharge in an inert atmosphere.
1 2D Structure

Fullerene C60

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(C60-Ih)[5,6]fullerene
2.1.2 InChI
InChI=1S/C60/c1-2-5-6-3(1)8-12-10-4(1)9-11-7(2)17-21-13(5)23-24-14(6)22-18(8)28-20(12)30-26-16(10)15(9)25-29-19(11)27(17)37-41-31(21)33(23)43-44-34(24)32(22)42-38(28)48-40(30)46-36(26)35(25)45-39(29)47(37)55-49(41)51(43)57-52(44)50(42)56(48)59-54(46)53(45)58(55)60(57)59
2.1.3 InChI Key
XMWRBQBLMFGWIX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C12=C3C4=C5C6=C1C7=C8C9=C1C%10=C%11C(=C29)C3=C2C3=C4C4=C5C5=C9C6=C7C6=C7C8=C1C1=C8C%10=C%10C%11=C2C2=C3C3=C4C4=C5C5=C%11C%12=C(C6=C95)C7=C1C1=C%12C5=C%11C4=C3C3=C5C(=C81)C%10=C23
2.2 Other Identifiers
2.2.1 UNII
NP9U26B839
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Buckminsterfullerenes

2. Buckyball

3. Buckyballs

4. Fullerene

5. Fullerenes

2.3.2 Depositor-Supplied Synonyms

1. 99685-96-8

2. Fullerene

3. Fullerene C60

4. C60 Fullerene

5. Fullerene-c60

6. Buckyball

7. Footballene

8. (c60-ih)[5,6]fullerene

9. Fullerene 60

10. Fullerite

11. [5,6]fullerene-c60-ih

12. 131159-39-2

13. Soccerballene

14. Fullerene Powder

15. C60

16. Fullerene C60 (pure)

17. Buckminsterfullerene C60

18. (5,6)fullerene-c60-ih

19. Np9u26b839

20. Fullerene - C60

21. Mfcd00151408

22. Mfcd00282904

23. [60]fullerene

24. (c_{60}-i_{h})[5,6]fullerene

25. C60 Compound

26. Fullerenes

27. Fullerene C60(purity: 99.95wt%)

28. Unii-np9u26b839

29. Ccris 9349

30. Fullerene Mixture

31. Fullerenes - C60/c70 Mixture

32. Buckminsterfulereno

33. Fullerenes C76

34. Fullerenes C78

35. Fullerenes C84

36. Buckminsterfulleren

37. Polyhydroxy C60

38. Polyhydroxy-c60

39. Carboxyl Fullerene

40. Fullerenes C60

41. 60c

42. [60-ih]fullerene

43. Fullerene Powder, Mixed

44. Icosahedral C60

45. N-ethyl-polyamino-c60

46. Fullerene Extract, C60

47. Polyhydroxylated Fullerene

48. Fullerenes [inci]

49. Fullerene C60, (pure)

50. Follene-60

51. Fullerene Powder, Sublimed

52. Footballene (c60)

53. Graphitized Carbon Nanofibers

54. Fullerene-c60 (buckeyballs)

55. Fullerene C60 Cluster

56. Dtxsid4031772

57. Buckminsterfullerene [mi]

58. Chebi:33128

59. Fullerene Nanotubes, Multi-walled

60. Fullerene Nanotubes, Single-walled

61. Giant Fullerene(purity: 95.0wt%)

62. Fullerene C60(purity: 99.5wt%)

63. Fullerene C60(purity: 99.9wt%)

64. Fullerene C70(purity: 98.0wt%)

65. Fullerene C70(purity: 99.0wt%)

66. Fullerene C70(purity: 99.5wt%)

67. Fullerenes C76(purity: 95.0wt%)

68. Fullerenes C76(purity: 98.0wt%)

69. Fullerenes C78(purity: 95.0wt%)

70. Fullerenes C78(purity: 98.0wt%)

71. Fullerenes C84(purity: 95.0wt%)

72. Fullerenes C84(purity: 98.0wt%)

73. Fullerenes C84(purity: 99.0wt%)

74. Zinc85548520

75. Fullerenes C60(purity: 99.5wt%)

76. Fullerene Powder, 99.9+% C{60}

77. Fullerenes C60(purity: 99.9 Wt%)

78. Fullerenes Mixtures(purity: 98.0wt%)

79. Ls-15519

80. F1232

81. Ft-0623278

82. Ft-0626559

83. Fullerene Powder, Sublimed, 99.9+% C{60}

84. N-ethyl-polyamino-c60(purity: 98-99.5%)

85. D81921

86. 685f968

87. Fullerene - C60, 99.9+% (buckminsterfullerene)

88. Fullerene Extract, C60 (contains Ca. 20% C70)

89. Fullerene - C60, Min. 99% (buckminsterfullerene)

90. Q1075376

91. W-204191

92. Fullerite(a Synthetic Mixture Of C60 And C70 Fullerenes)

93. Fullerene Powder, Mixed, Typically 98% C{60}, 2% C{70}

94. Fullerene C60 (purified By Sublimation) [for Organic Electronics]

95. Fullerene Carbon Soot (contains 5-8wt% C60/c70 And Higher Fullerenes)

96. Fullerene Powder, Mixed Refined, Typically 70% C{60}, 28% C{70}, Higher 2%

97. Fullerene Powder, Mixed Refined, Typically 77% C{60}, 22% C{70}, <2% Higher

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 720.6 g/mol
Molecular Formula C60
XLogP316.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass720 g/mol
Monoisotopic Mass720 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count60
Formal Charge0
Complexity2030
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/Experimental Therapy:/ Fullerene (C60), a third carbon allotrope, is a classical engineered material with the potential application in biomedicine. One of the biologically most relevant features of C60 is the ability to quench various free radicals, behaving as a "free radical sponge". Conversely, photosensitization of C60 leads to its transition to a long-lived triplet excited state and the subsequent energy or electron transfer to molecular oxygen, yielding highly reactive singlet oxygen (1O2) or superoxide anion (O2-), respectively. These reactive oxygen species (ROS) react with a wide range of biological targets and are known to be involved in both cellular signaling and cell damage. Therefore, the dual property of fullerenes to either quench or generate cell-damaging ROS could be potentially exploited for their development as cytoprotective or cytotoxic anticancer/antimicrobial agents. However, the attempts to that effect have been hampered by the extremely low water solubility of C60, and by the fact that solubilization procedures profoundly influence the ROS-generating/quenching properties of C60, either through chemical modification or through formation of complex nanoscale particles with different photophysical properties...

PMID:18534675 Markovica Z, Trajkobicb; Biomaterials 29 (26): 3561-73 (2008)


/Experimental Therapy: Gadolinium metallofullerenol nanoparticles [Gd@C82(OH)22]n particles (22 nm in a saline solution) of a dose level as low as 10-7 mol/kg exhibit a very high antineoplastic efficiency ( approximately 60%) in mice. A dose increment of 1 x 10-7 mol/kg increases the tumor inhibition rate 26%. [Gd@C82(OH)22]n particles have a strong capacity to improve immunity and interfere with tumor invasion in normal muscle cells, nearly without toxicity in vivo and in vitro. Unlike conventional antineoplastic chemicals, the high antitumor efficiency of nanoparticles is not due to toxic effects to cells because they do not kill the tumor cells directly and only about 0.05% of the used dose is found in the tumor tissues. Results suggest that fullerene derivatives with proper surface modifications and sizes may /be developed as/ tumor chemotherapeutics of high-efficacy and low-toxicity. /Gadolinium metallofullerenol nanoparticles/

PMID:16218736 Chen C et al; Nano Lett 5 (10): 2050-7 (2005)


/Experimental Therapy:/ This is the first report on the targeted delivery of fullerene-based low toxic nanocationite particles (porphyrin adducts of cyclohexyl fullerene-C(60)) to treat hypoxia-induced mitochondrial dysfunction in mammalian heart muscle. ... The magnetic isotope effect generated by the release of paramagnetic (25)Mg(2+) from these nanoparticles selectively stimulates the ATP overproduction in the oxygen-depleted cell. ... Because nanoparticles are membranotropic cationites, they will only release the overactivating paramagnetic cations in response to hypoxia-induced acidic shift. The resulting changes in the heart cell energy metabolism result in approximately 80% recovery of the affected myocardium in <24 hr after a single injection (0.03-0.1 LD(50)).... Pharmacokinetics and pharmacodynamics of the nanoparticles suggest their suitability for safe and efficient administration in either single or multi-injection (acute or chronic) therapeutic schemes for the prevention and treatment of clinical conditions involving myocardial hypoxia.

PMID:18662585 Amirshahi N et al; Arch Medical Res 39 (6): 549-59 (2008)


/Experimental Therapy:/ Oxidative stress plays a major role in acne formation, suggesting that oxygen radical scavengers are potential therapeutic agents. Fullerene is a spherical carbon molecule with strong radical sponge activity; therefore, the effectiveness of fullerene gel in treating acne vulgaris /was studied/. /Investigators/ performed an open trial using a fullerene gel twice a day; at 4 and 8 weeks, the mean number of inflammatory lesions (erythematous papules and pustules) significantly (P < 0.05) decreased from 16.09 +/- 9.08 to 12.36 +/- 7.03 (reduction rate 23.2%) and 10.0 +/- 5.62 (reduction rate 37.8%), respectively. The number of pustules, consisting of accumulation of neutrophils, was significantly (P < 0.05) decreased from 1.45 +/- 1.13 to 0.18 +/- 0.60 (reduction rate 87.6%), and further in vitro assays of sebum production in hamster sebocytes revealed that 75 uM polyvinylpyrrolidone-fullerene inhibits sebum production, suggesting that fullerene suppresses acne through decreasing neutrophil infiltration and sebum production. After treatment for 8 weeks, the water content of the skin significantly (P < 0.05) increased from 51.7 +/- 7.9 to 60.4 +/- 10.3 instrumental units. Therefore, the fullerene gel may help in controlling acne vulgaris with skin care benefit. ...

PMID:20887812 Inui S et al; Nanomedicine 7 (2): 238-41 (2011)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

This study was conducted to determine the distribution of (14)C-C60 in the pregnant rat and fetus, and in the lactating rat and off-spring. Four dams were dosed via tail vein injection on gestational day (gd) 15 with 0.28 mg/kg body weight (14)C-C60 (~ 3 uCi per rat) prepared in 5% polyvinylpyrrolidone in saline (PVP), and four dams were dosed with PVP alone. Urine (0-24 hr) and tissues (24 hr) were collected from the dams. Eight lactating rats were dosed on postnatal day (pnd) 8 with 0.36 mg/kg (14)C-C 60 prepared in PVP, and sacrificed at 24 hr or 48 hr after exposure. In the pregnant dams, radioactivity was distributed to the placenta (approximately 2% of the dose), to the fetus (1.0%), and to the female reproductive tract (3.0%). Radioactivity was distributed to the milk (< 1%) and mammary tissue (<1%) in the lactating rats, and to the GI tract (<1%) and liver of the pup (< 1%). For the pregnant dam, radioactivity was distributed to the urine (<2%), feces (2%), blood (0.9% per mL) and plasma (1.7% per mL), brain (< 1%), lung (<1%), heart (<1%), liver (~43%), spleen (4%). In comparison to the pregnant dam, lactating rats had a similar radioactivity distribution to the blood and plasma at 24 hr after exposure (with a 50% decrease by 48 hr), a higher distribution to the lung, and a decreased distribution to the liver. Metabolomics analysis of urine indicated that dams exposed to C60 had a decrease in metabolites derived from the Krebs cycle and an increase in metabolites derived from the urea cycle or glycolysis; with alterations in the levels of some sulfur-containing amino acids and purine/pyrimidine metabolites. This study indicated that C60 can cross the placenta and can be transmitted from mother to offspring via milk.

Snyder R et al; Abstract No. 234. 48th Annual Meeting and ToxExpo, Society of Toxicology, Baltimore, MD (March 15-19, 2009


Dermatomed porcine skin was fixed to a flexing device and topically dosed with 33.5 mg/mL of an aqueous solution of a fullerene-substituted phenylalanine (Baa) derivative of a nuclear localization peptide sequence (Baa-Lys(FITC)-NLS). Skin was flexed for 60 or 90 min or left unflexed (control). Confocal microscopy depicted dermal penetration of the nanoparticles at 8 hr in skin flexed for 60 and 90 min, whereas Baa-Lys(FITC)-NLS did not penetrate into the dermis of unflexed skin until 24 hr. TEM analysis revealed fullerene-peptide localization within the intercellular spaces of the stratum granulosum.

PMID:17212456 Rouse JG et al; Nano Lett 7 (1): 155-60 (2007)


...Both microscopic imaging and biological techniques /were used/ to explore the processes of [C60(C(COOH)2)2]n nanoparticles across cellular membranes and their intracellular translocation in 3T3 L1 and RH-35 living cells. The fullerene nanoparticles are quickly internalized by the cells and then routed to the cytoplasm with punctate localization. Upon entering the cell, they are synchronized to lysosome-like vesicles. The [C60(C(COOH)2)2]n nanoparticles entering cells are mainly via endocytosis with time-, temperature- and energy-dependent manners. The cellular uptake of [C60(C(COOH)2)2]n nanoparticles was found to be clathrin-mediated but not caveolae-mediated endocytosis...

Wei L et al; Nanotechnology 19: 145102 (12 pp) (2008)


... An overview of the nanostructure and the physical and chemical characteristics of fullerene-drug derivatives is given. The biological behavior of fullerene derivatives shows their potential to medical application fields because C(60) is rapidly absorbed by tissues and is excreted through urinary tract and enterons, which reveals low toxicity in vitro and in vivo studies. Nanomedicine has become one of the most promising areas of nanotechnology, while many have claimed its therapeutic use against cancer, human immunodeficiency virus (HIV), and neurodegenerative disorders. Water-soluble C(60) fullerene derivatives that come from chemical modification largely enhance the biological efficacy. The blood-brain barrier (BBB) is a physical barrier composed of endothelial tight junctions that restrict the paracellular permeability. A major challenge facing neuropharmacology is to find compounds that can be delivered into the brain through the bloodstream. Fullerene C(60) was demonstratively able to cross the BBB by hybridizing a biologically active moiety dyad, which provides a promising clue as a pharmacological therapy of neural disorders. /C(60) Fullerene derivatives/

Lin CM, Lu TY; Recent Pat Nanotechnol 6 (2): 105-13 (2012)


Pristine fullerenes (C60) in different solvents will be used in many industrial and pharmaceutical manufacturing and derivatizing processes. This report explores the impact of solvents on skin penetration of C60 from different types of industrial solvents (toluene, cyclohexane, chloroform and mineral oil). Yorkshire weanling pigs (n=3) were topically dosed with 500 uL of 200 ug/mL C60 in a given solvent for 24 hr and re-dosed daily for 4 days to simulate the worst scenario in occupational exposures. The dose sites were tape-stripped and skin biopsies were taken after 26 tape-strips for quantitative analysis. When dosed in toluene, cyclohexane or chloroform, pristine fullerenes penetrated deeply into the stratum corneum, the primary barrier of skin. More C60 was detected in the stratum corneum when dosed in chloroform compared to toluene or cyclohexane. Fullerenes were not detected in the skin when dosed in mineral oil. This is the first direct evidence of solvent effects on the skin penetration of pristine fullerenes. The penetration of C60 into the stratum corneum was verified using isolated stratum corneum in vitro; the solvent effects on the stratum corneum absorption of C60 were consistent with those observed in vivo. In vitro flow-through diffusion cell experiments were conducted in pig skin and fullerenes were not detected in the receptor solutions by 24 hr. The limit of detection was 0.001 ug/mL of fullerenes in 2 mL of the receptor solutions.

PMID:19796651 Xia XR et al; Toxicol Appl Pharmacol 242 (1): 29-37 (2010)


5.2 Biological Half-Life

Fullerenes ... are spherical molecules consisting entirely of carbon atoms (C(x)) to which side chains can be added, furnishing compounds with widely different properties. ... Absorption, distribution and excretion strongly depend on the properties of the side chains. The pristine C(60) has a very long biological half-life, whereas the most water-soluble derivatives are eliminated from the exposed animals within weeks.

PMID:18684229 Nielsen G et al; Basic Clin Pharmacol TOxicol 103 (3): 197-208 (2008)


... Male rats /were exposed/ to C60 fullerene nanoparticles (2.22 mg/cu m, 55 nm diameter) and microparticles (2.35 mg/cu m, 0.93 um diameter) for 3 hr a day, for 10 consecutive days using a nose-only exposure system. Nanoparticles were created utilizing an aerosol vaporization and condensation process. Nanoparticles and microparticles were subjected to high-pressure liquid chromatography (HPLC), XRD, and scanning laser Raman spectroscopy, which cumulatively indicated no chemical modification of the C60 fullerenes occurred during the aerosol generation. ... Lung half-lives for C60 fullerene nanoparticles and microparticles were 26 and 29 days, respectively...

PMID:17878152 Baker GL et al; Toxicol Sci 101 (1): 122-31 (2008)


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