Table of Contents
Metal-Based Drugs
Volume 2008 (2008), Article ID 391418, 13 pages
http://dx.doi.org/10.1155/2008/391418
Research Article

Synthesis and Biological Analysis of Thiotetra(ethylene glycol) monomethyl Ether-Functionalized Porphyrazines: Cellular Uptake and Toxicity Studies

1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA
2Center for Molecular Biology of Oral Diseases, College of Dentistry, University of Illinois at Chicago, 801 S. Paulina Street, Chicago, IL 60612, USA
3Jesse Brown VAMC, 820 South Damen Avenue, Chicago, IL 60612, USA
4Department of Chemistry, Faculty of Natural Sciences, Imperial College London, Faculty Building, South Kensington Campus, London SW7 2AZ, UK

Received 29 May 2007; Revised 20 July 2007; Accepted 6 August 2007

Academic Editor: Michael J. Cook

Copyright © 2008 Sangwan Lee et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. K. Pandey and G. Zheng, “Porphyrins as photosensitizers in photodynamic therapy,” in The Porphyrin Handbook, K. M. Kadish, K. M. Smith, and R. Guilard, Eds., vol. 6, pp. 157–230, Academic Press, San Diego, Calif, USA, 2000. View at Google Scholar
  2. D. Wöhrle, A. Hirth, T. Bogdahn-Rai, G. Schnurpfeil, and M. Shopova, “Photodynamic therapy of cancer: second and third generations of photosensitizers,” Russian Chemical Bulletin, vol. 47, no. 5, pp. 807–816, 1998. View at Google Scholar
  3. T. J. Dougherty, “Photodynamic therapy (PDT) of malignant tumors,” Critical Reviews in Oncology/Hematology, vol. 2, no. 2, pp. 83–116, 1984. View at Publisher · View at Google Scholar
  4. F. M. Little, C. J. Gomer, S. Hyman, and M. L. J. Apuzzo, “Observations in studies of quantitative kinetics of tritium labelled hematoporphyrin derivatives (HpDI and HpDII) in the normal and neoplastic rat brain model,” Journal of Neuro-Oncology, vol. 2, no. 4, pp. 361–370, 1984. View at Publisher · View at Google Scholar
  5. R. K. Pandoy, “Synthetic strategies in designing porphyrin-based photosensitizers for photodynamic therapy,” in CRC Handbook of Organic Photochemistry and Photobiology, W. Horspool and F. Lenci, Eds., pp. 144-1–144-21, CRC Press, Boca Raton, Fla, USA, 2nd edition, 2004. View at Google Scholar
  6. C. M. Allen, W. M. Sharman, and J. E. Van Lier, “Current status of phthalocyanines in the photodynamic therapy of cancer,” Journal of Porphyrins and Phthalocyanines, vol. 5, no. 2, pp. 161–169, 2001. View at Publisher · View at Google Scholar
  7. R. K. Chowdhary, I. Shariff, and D. Dolphin, “Drug release characteristics of lipid based benzoporphyrin derivative,” Journal of Pharmacy and Pharmaceutical Sciences, vol. 6, no. 1, pp. 13–19, 2003. View at Google Scholar
  8. J. L. Sessler and D. Seidel, “Synthetic expanded porphyrin chemistry,” Angewandte Chemie International Edition, vol. 42, no. 42, pp. 5134–5175, 2003. View at Publisher · View at Google Scholar · View at PubMed
  9. D. Kessel and T. J. Dougherty, “Agents used in photodynamic therapy,” Reviews in Contemporary Pharmacotherapy, vol. 10, no. 1, pp. 19–24, 1999. View at Google Scholar
  10. S. L. J. Michel, B. M. Hoffman, S. M. Baum, and A. G. M. Barrett, “Peripherally functionalized porphyrazines: novel metallomacrocycles with broad, untapped potential,” in Progress in Inorganic Chemistry, vol. 50, pp. 473–590, John Wiley & Sons, New York, NY, USA, 2001. View at Publisher · View at Google Scholar
  11. S. Lee, A. J. P. White, D. J. Williams, A. G. M. Barrett, and B. M. Hoffman, “Synthesis of near-IR absorbing/emitting porphyrazine derivatives with tunable solubility,” Journal of Organic Chemistry, vol. 66, no. 2, pp. 461–465, 2001. View at Publisher · View at Google Scholar
  12. S. Lee, R. Stackow, C. S. Foote, A. G. M. Barrett, and B. M. Hoffman, “Tuning the singlet oxygen quantum yield of near-IR-absorbing porphyrazines,” Photochemistry and Photobiology, vol. 77, no. 1, pp. 18–21, 2003. View at Publisher · View at Google Scholar
  13. E. G. Sakellariou, A. G. Montalban, H. G. Meunier et al., “Peripherally metalated secoporphyrazines: a new generation of photoactive pigments,” Inorganic Chemistry, vol. 41, no. 8, pp. 2182–2187, 2002. View at Publisher · View at Google Scholar
  14. E. G. Sakellariou, A. G. Montalban, S. L. Beall et al., “Novel peripherally functionalized seco-porphyrazines: synthesis, characterization and spectroscopic evaluation,” Tetrahedron, vol. 59, no. 46, pp. 9083–9090, 2003. View at Publisher · View at Google Scholar
  15. N. D. Hammer, S. Lee, B. J. Vesper et al., “Charge dependence of cellular uptake and selective antitumor activity of porphyrazines,” Journal of Medicinal Chemistry, vol. 48, no. 26, pp. 8125–8133, 2005. View at Publisher · View at Google Scholar · View at PubMed
  16. B. J. Vesper, S. Lee, N. D. Hammer et al., “Developing a structure-function relationship for anionic porphyrazines exhibiting selective anti-tumor activity,” Journal of Photochemistry and Photobiology B, vol. 82, no. 3, pp. 180–186, 2006. View at Publisher · View at Google Scholar · View at PubMed
  17. A. Davison, R. H. Holm, R. E. Benson, and W. Mahler, “Metal complexes derived from cis-1,2-dicyano-1,2-ethylenedithiolate and bis(trifluoromethyl)-1,2-dithiete,” in Inorganic Syntheses, vol. 10, pp. 8–26, McGraw-Hill, New York, NY, USA, 1967. View at Publisher · View at Google Scholar
  18. R. P. Linstead and M. J. Whalley, “944. Conjugated macrocycles—part XXII: tetrazaaporphyrin and its metallic derivatives,” Journal of Chemical Society, pp. 4839–4846, 1952. View at Publisher · View at Google Scholar
  19. T. P. Forsyth, D. B. G. Williams, A. G. Montalban, C. L. Stern, A. G. M. Barrett, and B. M. Hoffman, “A facile and regioselective synthesis of trans-heterofunctionalized porphyrazine derivatives,” Journal of Organic Chemistry, vol. 63, no. 2, pp. 331–336, 1998. View at Publisher · View at Google Scholar
  20. C. S. Velázquez, G. A. Fox, W. E. Broderick et al., “Star-porphyrazines: synthetic, structural, and spectral investigation of complexes of the polynucleating porphyrazineoctathiolato ligand,” Journal of the American Chemical Society, vol. 114, no. 19, pp. 7416–7424, 1992. View at Google Scholar
  21. Y. Capetanaki, S. Smith, and J. P. Heath, “Overexpression of the vimentin gene in transgenic mice inhibits normal lens cell differentiation,” The Journal of Cell Biology, vol. 109, no. 4, pp. 1653–1664, 1989. View at Publisher · View at Google Scholar
  22. C. E. Gagna, H.-R. Kuo, E. Florea et al., “Comparison of apoptosis and terminal differentiation: the mammalian aging process,” Journal of Histochemistry and Cytochemistry, vol. 49, no. 7, pp. 929–930, 2001. View at Google Scholar