Physicochemical characterization of fullerenol and fullerenol synthesis by-products prepared in alkaline media

Journal of Nanoparticle Research

Volumn 16, Issue 9, 2014, Pages

  Indeglia, Paul A ^a   Georgieva, Angelina ^b   Krishna, Vijay B ^b   Bonzongo, Jean Claude J ^a  

^a J Crayton Pruitt Family Department of Biomedical Engineering   (United States)

^b UNIVERSITY OF FLORIDA   (United States)

Author keywords

Biocompatibility; Environmental effects; Fullerenol; Physicochemical characterization; Surface chemistry; Synthesis; Zeta potential

Indexed keywords

ENVIRONMENTAL IMPACT; SURFACE CHEMISTRY; SYNTHESIS (CHEMICAL); ZETA POTENTIAL;

ALKALINE MEDIA; FULLERENOLS; PHYSICO-CHEMICAL CHARACTERIZATION;

BIOCOMPATIBILITY;

CARBON; FULLERENE DERIVATIVE; FULLERENOL; METHANOL; SODIUM CARBONATE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ARTICLE; CHEMICAL COMPOSITION; ELECTROPHORESIS; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; STATIC ELECTRICITY; SURFACE CHARGE; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRASOUND; X RAY PHOTOELECTRON SPECTROSCOPY; ZETA POTENTIAL;

EID: 84906023218     PISSN: 13880764     EISSN: 1572896X     Source Type: Journal    
DOI: 10.1007/s11051-014-2599-4     Document Type: Article

References (62)

1. 2-atmosphere. J Braz Chem Soc 17(6):1186-1190
2. Aoshima H, Kokubo K, Shirakawa S, Ito M, Wamana S, Oshima T (2009) Antimicrobial activity of fullerenes and their hydroxylated derivatives. Biocontrol Sci 14(2):69-72
3. 24nanoparticles as revealed using flow field-flow fractionation and atomic force microscopy. Langmuir 26(20):16063-16070
4. Birkett PR (1999) Fullerene chemistry. Annual Report of Progressive Chemistry, Section A. 95:431-451
5. 22on doxorubicin-induced cytotoxicity. Toxicol In Vitro 18:629-637
6. )2]10as a MRI contrast agent. J Am Chem Soc 125:5471-5478
7. Bosi S, Da Ros T, Spalluto G, Prato M (2003) Fullerene derivatives: an attractive tool for biological applications. Eur J Med Chem 38:913-923
8. 60) Formed Using Two Procedures. Environ Sci Technol 39(17):6343-6351
9. Brant J, Lecoanet H, Wiesner M (2005b) Aggregation and deposition characteristics of fullerene nanoparticles in aqueous systems. J Nanopart Res 7:545-553
10. Brant JA, Labille J, Bottero J, Wiesner MR (2006) Characterizing the impact of preparation method on fullerene cluster structure and chemistry. Langmuir 22:3878-3885
11. Brant J, Labille J, Robichaud C, Wiesner M (2007) Fullerol cluster formation in aqueous solutions - implication for environmental release. J Colloid Interface Sci 314:281-288
12. Chao T, Song G, Hansmeier N, Westerhoff P, Herckes P, Halden RU (2011) Characterization and LC-MS/MS based quantification of hydroxylated fullerenes. Anal Chem 83(5):1777-1783
13. 60) nanoparticles. Langmuir 22:10994-11001
14. Chiang LY, Upasani RB, Swirczewski JW, Soled S (1993) Evidence of hemiketals incorporated in the structure of fullerols derived from aqueous acid chemistry. J Am Chem Soc 115:563-5457
15. Chiang LY, Wang L, Swirczewski JW, Soled S, Cameron S (1994) Efficient synthesis of polyhydroxylated fullerene derivatives via hydrolysis of polycyclosulfated precursors. J Org Chem 59(14):3960-3968
16. Chiang LY, Bhonsle JB, Wang J, Shu SF, Chang TM, Hwu JR (1996) Efficient one-flask synthesis of water-soluble [60]fullerenols. Tetrahedron 52(14):4963-4972
17. Da Ros T, Prato M (1999) Medicinal chemistry with fullerenes and fullerene derivatives. Chem Commun 8:663-669
18. Dangler M, Burke S, Hering SV, Allen DT (1987) A direct FTIR method for identifying functional groups in size segregated atmospheric aerosols. Atmos Environ 21(4):1001-1004
19. 60colloid formation in aqueous systems: effects of preparation method on size, structure, and surface charge. Environ Sci Technol 42:173-178
20. 24induced tissue factor and ICAM-1 membrane expression and apoptosis in vitro. Int J Nanomed 3(1):59-68
21. Georgieva AT, Pappu V, Krishna V, Georgiev PG, Ghiviriga I, Indeglia P, Fan ZH, Koopman B, Pardalos PM, Moudgil B (2013) Polyhydroxy fullerenes. J Nanopart Res 15:1690-1707
22. 60surface. J Chem Phys 125(154312):1-10
23. Hamley AW (2007) Peptide Fibrillization. Angew Chem Int Ed 46:8128-8147
24. 36and the solvated buckide ion. J Phys Chem 94:8634-8636
25. 70in water. Fullerene Sci Technol 4:543-544
26. 60clusters: wavelength dependency and product characterization. Environ Sci Technol 44:8121-8127
27. Husebo LO, Sitharaman B, Furukawa K, Kato T, Wilson LJ (2004) Fullerenols revisited as stable radical anions. J Am Chem Soc 126:12055-12064
28. 60) in the presence and absence of light. J Nanopart Res 15:2069-2085
29. Isakovic A, Markovic Z, Todorovic-Markovic B, Nikolic N, Vranjes-Djuric S, Mirkovic M, Dramicanin M, Harhaji L, Raicevic N, Nikolic Z, Trajkovic V (2006a) Distinct cytotoxic mechanisms of pristine versus hydroxylated fullerene. Toxicol Sci 91(1):173-183
30. 60cytotoxicity by γ-irradiation. Biomaterials 27:5049-5058
31. Kamaras K, Akselrod L, Roth S, Mittelbach A, Hiinle W, von Schnering HG (1993) The orientational phase transition in C60 films followed by infrared spectroscopy. Chem Phys Lett 214(3,4):338-344
32. Kamat JP, Devasagayam TPA, Priyadarsini KI, Mohan H (2000) Reactive oxygen species mediated membrane damage induced by fullerene derivatives and its possible biological implications. Toxicology 155:55-61
33. Kokubo K, Matsubayashi K, Tategaki H, Takada H, Oshima T (2007) Facile synthesis of highly water-soluble fullerenes more than half-covered by hydroxyl groups. ACSNano. 2(2):327-333
34. Kong L, Tedrow O, Chan YF, Zepp RG (2009) Light-initiated transformations of fullerenol in aqueous Media. Environ Sci Technol 43:9155-9160
35. 60Aggregates toward Mammalian Cells: role of Tetrahydrofuran (THF) Decomposition. Environ Sci Technol 43:6378-6384
36. Krishna K, Noguchi N, Koopman B, Moudgil B (2006) Enhancement of titanium dioxide photocatalysis by water-soluble fullerenes. J Colloid Interface Sci 304:166-171
37. Krishna V, Yanes D, Imaram W, Angerhofer A, Koopman B, Moudgil B (2008) Mechanism of enhanced photocatalysis with polyhydroxy fullerenes. Appl Catal B 79:376-381
38. Lecoanet H, Bottero J, Wiesner M (2004) Laboratory assessment of the mobility of nanomaterials in porous media. Environ Sci Technol 38:5164-5169
39. Lee J, Cho M, Fortner JD, Hughes JB, Kim J (2009) Transformation of aggregated C60 in the aqueous phase by UV irradiation. Environ Sci Technol 43(13):4878-4883
40. 60fullerol formation catalysed by quaternary ammonium hydroxides. Chemical Communications. 23:1784-1785
41. Makarova TL (2001) Electrical and optical properties of pristine and polymerized fullerenes. Semiconductors 35(3):243-278 Translated from Fizika i Tekhnika Poluprovodnikov, 2001, 35 (3), 257-293
42. Markovic Z, Todorovic-Markovica B, Kleuta D, Nikolica N, Vranjes-Djurica S, Misirkicb M, Vucicevicb L, Janjetovicb K, Isakovic A, Harhajib L, Babic-Stojica B, Dramicanina M, Trajkovic V (2007) The mechanism of cell-damaging reactive oxygen generation by colloidal fullerenes. Biomaterials 28:5437-5448
43. Mashino T, Shimotohno K, Ikegami N, Nishikawa D, Okuda K, Takahashi K, Makamura S, Mochizuki M (2005) Human immunodeficiency virus-reverse transcriptase inhibition and hepatitis C virus RNA-dependent RNA polymerase inhibition activities of fullerene derivatives. Bioorg Med Chem Lett 15:1107-1109
44. Nakamura Y, Ueno H, Kokubo K, Ikuma N, Oshima T (2013) Magic number effect on cluster formation of polyhydroxylated fullerenes in water-alcohol binary solution. J Nanopart Res 15:1755-1761
45. Ozawa M, Li J, Kishio K, Tadano A, Aogaki R (1995) Physics and chemistry of fullerenes and derivatives. In: proceedings of the international winterschool on electronic properties of novel materials
46. Podolski IY, Podlubnaya ZA, Kosenkol EA, Mugantseva EA, Makarova EG, Marsagishvili LG, Shpagina MD, Kaminsky GY, Andrievsky GV, Klochkov VK (2007) Effects of hydrated forms of c60 fullerene on amyloid β-peptide fibrillization in vitro and performance of the cognitive task. J Nanosci Nanotechnol 7:1-7
47. Rouse J, Yang J, Ryman-Rasmussen J, Baron A, Monteiro-Riviere N (2007) Effects of mechanical flexion on the penetration of fullerene amino acid-derivatized peptide nanoparticle through skin. Nano Lett 7(1):155-160
48. 60) in a variety of solvents. J Phys Chem 97(13):3379-3383
49. Ryan JJ, Bateman HR, Stover A, Gomez G, Norton SK, Zhao W, Schwartz LB, Lenk R, Kepley CL (2007) Fullerene nanomaterials inhibit the allergic response. J Immunol 179:665-672
50. Sayes CM, Fortner JD, Guo W, Lyon D, Boyd AM, Ausman KD, Tao YJ, Sitharaman B, Wilson LJ, Hughes JB, West JL, Colvin VL (2004) The differential cytotoxicity of water-soluble fullerenes. Nano Lett 4(10):1881-1887
51. 60fullerol. Environ Sci Technol 43:3162-3168
52. Semenov KN, Charykov NA, Keshinov VN (2011) Fullerenol synthesis and identification. Properties of the fullerenol water solutions. J Chem Eng Data 56:230-239
53. Taylor R, Walton D (1993) The chemistry of fullerenes. Nature 363:685-693
54. Tzoupis H, Leonis G, Durdagi S, Mouchlis V, Mavromoustakos T, Papadopolus MG (2011) Binding of novel fullerene inhibitors to HIV-1 protease: insight through molecular dynamics and molecular mechanics Poisson-Boltzmann surface area calculations. J Comput Aided Mol Design 25:959-976
55. 60exposure elicits oxidative stress response in embryonic zebrafish. Appl Pharmacol 229:44-55
56. 60fullerol. Adv Funct Mater 16:120-128
57. Vileno B, Jeney S, Marcoux PR, Miller LM, Forro L (2010) Evidence of lipid peroxidation and protein phosphorylation in cells upon oxidative stress photo-generated by fullerols. Biophys Chem 152:164-169
58. 60. J Chem Soc, Perkin Transmissions 2:1389-1393
59. Xing G, Zhang J, Zhao Y, Tang J, Zhang B, Gao X, Yuan H, Qu L, Cao W, Chai Z, Ibrahim K, Su R (2004) Influences of structural properties on stability of fullerenols. J Phys Chem B 108:11473-11479
60. Xu L, Liu Y, Chen Z, Li W, Liu Y, Wang L, Ma L, Yiming S, Zhao Y, Chen C (2013) Morphologically virus-like fullerenol nanoparticles act as the dual-functional nanoadjuvant for hiv-1 vaccine. Adv Mater 25:5928-5936
61. 24] fullerene phototoxicity towards HaCaT keratinocytes: type I versus type II mechanisms. Chem Res Toxicol 21:1056-1063
62. 60and their cytotoxicity in human keratinocytes. Photochem Photobiol 84:1215-1223