Skip to main content
SpringerLink
Log in

Free Radical Scavenging and Photodynamic Functions of Micelle-like Hydrophilic Hexa(sulfobutyl)fullerene (FC4S)

  • Chapter
Perspectives of Fullerene Nanotechnology

Abstract

Biological applications of water-soluble hexa(sulfobutyl)fullerene (FC4S) are reviewed. It was synthesized in a yield of 80–85% by the treatment of C60 in dimethoxyethane (DME) with sodium naphthalide (10 equiv.) at 25 °C, followed by reacting the resulting hexaanionic fullerene intermediates with an excess of 1,4-butane sultone (15 equiv.). FC4S showed an enhanced superoxide radical (O − ·2 ) scavenging activity and suppression efficiency against the superoxide-induced ferricytochrome c reduction under physiologic conditions, as compared with those of fullerenols at a dose level of 100 μm. For example, a profound suppression efficiency of 60 and 96% was detected at a dose level of 50 and 10011m, respectively. Aggregation behaviors of FC4S molecules in aqueous solution were investigated using SAXS (small-angle X-ray scattering) and SANS (small-angle neutron scattering) techniques. We concluded that the aggregation size and shape of FC4S nanoparticles with the radius of gyration, R g, of 18.9–19.1 Å remain relatively unchanged with the variation of concentration in the concentration range of 0.35–26.0 mM. The phenomena were correlated to a high total surface area of nanoparticles and interfacial accessability of fullerene cages to reactive oxygen radical species.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  1. A. W. Jensen, S. R. Wilson and D. I. Schuster, Bioorg. Med. Chem. 4 (1996) 767.

    Article  CAS  Google Scholar 

  2. For reviews: H. Esterbauer, J. Gebicki, H. Puhl and G. Jurgens, Free Rad. Biol. Med. 13 (1992) 341; J. A. Imlay and S. Linn. Science 240 (1988) 1302.

    Google Scholar 

  3. D. Steinberg. Circulation 84 (1991) 1420.

    CAS  Google Scholar 

  4. H. B. Stahelin, K. F. Gey, M. Eichholzer, E. Ludin, F. Bernasconi, J. Thurneysen and G. Brubacher, Am. J. Epidemiol. 133 (1991) 766.

    CAS  Google Scholar 

  5. L. Y. Chiang, F. J. Lu and J. T. Lin, J. Chem. Soc., Chem. Commun. (1995) 1283.

    Google Scholar 

  6. J. B. Bhonsle, Y. Chi, J. P. Huang, J. Shiea, B. J. Chen and L. Y. Chiang, Chem. Lett. (1998) 465.

    Google Scholar 

  7. M. C. Tsai, Y. H. Chen and L. Y. Chiang, J. Pharm. Pharmacol. 49 (1997) 438.

    Article  CAS  Google Scholar 

  8. Y. L. Lai and L. Y. Chiang, J. Autonomic Pharmacol. 17 (1997) 229.

    Article  CAS  Google Scholar 

  9. Y. L. Lai, W. Y. Chiou, F. J. Lu and L. Y. Chiang, Br. J. Pharmacol. 126 (1999) 778.

    Article  CAS  Google Scholar 

  10. L. H. Lu, Y. T. Lee, H. W. Chen, L. Y. Chiang and H. C. Huang, ibid. 123 (1998) 1097.

    Google Scholar 

  11. H. S. Lai, W. J. Chen and L. Y. Chiang. World J. Surg. 24 (2000) 450.

    Article  CAS  Google Scholar 

  12. H. C. Hsu, L. Y. Chiang, W. J. Chen and Y. T. Lee, J. Cardiovascular Pharmacol. 36 (2000) 423.

    Article  CAS  Google Scholar 

  13. H. M. Huang, H. C. Ou, S. J. Hsieh and L. Y. Chiang, Life Sciences 66 (2000) 1525.

    Article  CAS  Google Scholar 

  14. H. S. Lai, Y. Chen, W. J. Chen, K. J. Chang and L. Y. Chiang, Transplantation Proc. 32 (2000) 1272.

    Article  CAS  Google Scholar 

  15. T. H. Ueng, J. J. Kang, H. W. Wang, Y. W. Cheng and L. Y. Chiang, Toxicol. Lett. 93 (1997) 29.

    Article  CAS  Google Scholar 

  16. L. Y. Chiang, R. B. Upasani and J. W. Swirczewski, J. Am. Chem. Soc. 114 (1992) 10154.

    Article  CAS  Google Scholar 

  17. L. Y. Chiang, R. B. Upasani, J. W. Swirczewski and S. J. Soled, ibid. 115 (1993) 5453.

    CAS  Google Scholar 

  18. For review: T. J. Dougherty, Photochem. Photobiol. 58 (1993) 895.

    Google Scholar 

  19. T. J. Dougherty, G. B. Grindey, R. Fiel, K. R. Weishaupt and D. G. Boyle, J. Natl. Cancer Inst. 55 (1975) 115.

    CAS  Google Scholar 

  20. S. G. Bown, C. J. Tralau, P. D. Coleridge Smith, D. Akdemis and T. J. Wieman, Br. J. Cancer 54 (1986) 43.

    Article  CAS  Google Scholar 

  21. E. Ben-Hur and I. Rosenthal. Int. J. Radiat. Biol. 47 (1985) 135.

    Article  Google Scholar 

  22. W. S. Chan, R. Svensen, D. Phillips and I. R. Hart, Br. J. Cancer 53 (1986) 255.

    Article  CAS  Google Scholar 

  23. N. Brasseur, H. Ali, D. Autenrieth, R. Langlois and J. E. van Lier, Photochem. Photobiol. 42 (1985) 515.

    Article  CAS  Google Scholar 

  24. For Review: C. J. Gomer, N. Rucker, A. Ferrario and S. Wong, Radiat. Res. 120 (1989) 1.

    Google Scholar 

  25. D. Kessel, Photochem. Photobiol. 44 (1986) 489.

    Article  CAS  Google Scholar 

  26. B. W. Henderson, S. M. Waldow, T. S. Mang, W. R. Potter, P. B. Malone and T. J. Dougherty, Cancer Res. 45 (1985) 572.

    CAS  Google Scholar 

  27. J. Moan, E. O. Pettersen and T. Christensen, Br. J. Cancer 39 (1979) 398.

    Article  CAS  Google Scholar 

  28. B. W. Henderson and T. J. Dougherty, Photochem. Photobiol. 55 (1992) 145.

    Article  CAS  Google Scholar 

  29. H. Tokuyama, S. Yamago and E. Nakamura, J. Am. Chem. Soc. 115 (1993) 7918.

    Article  CAS  Google Scholar 

  30. Y. Tabata, Y. Murakami and Y. Ikada, Jpn. J. Cancer Res. 88 (1997) 1108.

    Article  CAS  Google Scholar 

  31. R. C. Dunn, J. L. Anderson, C. S. Foote and J. D. Simon, J. Am. Chem. Soc. 115 (1993) 5307.

    Article  CAS  Google Scholar 

  32. C. Taliani, G. Ruani, R. Zamboni, R. Danieli, S. Rossini, V. N. Denisov, V. M. Buriakov, F. Negri, G. Oriandi and F. Zerbetto. J. Chem. Soc., Chem. Commun. (1993) 220.

    Google Scholar 

  33. J. L. Anderson, Y. Z. An, Y. Rubin and C. S. Foote, J. Am. Chem. Soc. 116 (1994) 9763.

    Article  CAS  Google Scholar 

  34. M. Orfanopoulos and S. Kambourakis, Tetrahedron Lett. 35 (1994) 1945.

    Article  CAS  Google Scholar 

  35. J. Piette, J. Photochem. Photobiol. B4 (1990) 335.

    Article  CAS  Google Scholar 

  36. R. A. Floyd, M. S. West, K. L. Eneff and J. E. Schneider, Arch. Biochem. Biophys. 273 (1989) 106.

    Article  CAS  Google Scholar 

  37. Y. Z. An, C. B. Chen, J. L. Anderson, D. S. Sigman, C. S. Foote and Y. Rubin, Tetrahedron 52 (1996) 5179.

    Article  CAS  Google Scholar 

  38. J. P. Kamat, T. A. Devasagayam, H. Mohan, L. Y. Chiang and J. R. Mittal, Fullerene Sci. Technol. 6 (1998) 663.

    Article  CAS  Google Scholar 

  39. Y. Yamakoshi, S. Sueyoshi, K. Fukuhara and N. Miyata, J. Am. Chem. Soc. 120 (1998) 12363.

    Article  CAS  Google Scholar 

  40. Y. Murata, K. Komatsu and T. S. M. Wan, Tetrahedron Lett. 39 (1996) 7061.

    Article  Google Scholar 

  41. L. Y. Chiang, J. B. Bhonsle, L. Y. Wang, S. F. Shu, T. M. Chang and J. R. Hwu, Tetrahedron 52 (1996) 4963.

    Article  CAS  Google Scholar 

  42. S. H. Chen, Ann. Rev. Phys. Chem. 37 (1986) 351.

    Article  CAS  Google Scholar 

  43. K. Linliu, S. A. Chen, T. L. Yu, T. L. Lin, C. H. Lee, J. J. Kai, S. L. Chang and J. S. Lin J. Polym. Res. 2 (1995) 63.

    Google Scholar 

  44. U. Jeng, T. L. Lin, C. S. Tsao, C. H. Lee, T. Canteenwala, L. Y. Wang, L. Y. Chiang and C. C. Han J Phys. Chem. B 103 (1999) 1059.

    Google Scholar 

  45. S. H. Chen Ann. Rev. Phys. Chem. 37 (1986) 351.

    Article  CAS  Google Scholar 

  46. H. H. C. Chen, C. Yu, T. H. Ueng, S. Chen, B. J. Chen, K. J. Huang and L. Y. Chiang Toxicol. Pathol. 26 (1998) 143.

    Article  CAS  Google Scholar 

  47. H. H. C. Chen, C. Yu, T. H. Ueng, C. T. Liang, B. J. Chen, C. C. Hong and L. Y. Chiang, Fullerene Sci. Technol. 5 (1997) 1387.

    Article  CAS  Google Scholar 

Download references

Author information

Author notes

  1. Long Y. Chiang

    Present address: Department of Chemistry, University of Massachusetts Lowell, One University avenue, Lowell, MA, 01854, USA

Authors and Affiliations

  1. Center for Condensed Matter Sciences, National Taiwan University, Taiwan, China

    Yu Chi, Taizoon Canteenwala & Long Y. Chiang

  2. National Laboratory of Animal Breeding and Research Center, National Science Council, Taiwan, China

    Hans H. C. Chen

  3. Department of Engineering and System Science, National Tsing Hua University, Taiwan, China

    U-Ser Jeng & Tsang-Lang Lin

Authors
  1. Yu Chi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Taizoon Canteenwala
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hans H. C. Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. U-Ser Jeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tsang-Lang Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Long Y. Chiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Nanocarbon Research Institute, Chiba, Japan

    Eiji Ōsawa

Rights and permissions

Reprints and permissions

Copyright information

© 2002 Kluwer Academic Publishers

About this chapter

Cite this chapter

Chi, Y., Canteenwala, T., Chen, H.H.C., Jeng, US., Lin, TL., Chiang, L.Y. (2002). Free Radical Scavenging and Photodynamic Functions of Micelle-like Hydrophilic Hexa(sulfobutyl)fullerene (FC4S). In: Ōsawa, E. (eds) Perspectives of Fullerene Nanotechnology. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-9598-3_15

Download citation

  • DOI: https://doi.org/10.1007/978-94-010-9598-3_15

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-9600-3

  • Online ISBN: 978-94-010-9598-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation