Table of Contents Author Guidelines Submit a Manuscript
International Journal of Photoenergy
Volume 2015 (2015), Article ID 148964, 12 pages
http://dx.doi.org/10.1155/2015/148964
Review Article

Water-Solubilization of P(V) and Sb(V) Porphyrins and Their Photobiological Application

1Department of Applied Chemistry, Faculty of Engineering, University of Miyazaki, Gakuen-Kibanadai, Miyazaki 889-2192, Japan
2Department of Applied Chemistry and Biochemical Engineering, Graduate School of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu, Shizuoka 432-8561, Japan

Received 25 September 2014; Revised 25 December 2014; Accepted 8 January 2015

Academic Editor: Maria da Graça P. Neves

Copyright © 2015 Jin Matsumoto 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. P. Haugland, Handbook of Fluorescent Probes and Research Products, Molecular Probes, Eugene, Ore, USA, 9th edition, 2002.
  2. T. Shiragami, J. Matsumoto, H. Inoue, and M. Yasuda, “Antimony porphyrin complexes as visible-light driven photocatalyst,” Journal of Photochemistry and Photobiology C: Photochemistry Reviews, vol. 6, no. 4, pp. 227–248, 2005. View at Publisher · View at Google Scholar · View at Scopus
  3. E. Alves, M. A. F. Faustino, M. G. P. M. S. Neves, Â. Cunha, H. Nadais, and A. Almeida, “Potential applications of porphyrins in photodynamic inactivation beyond the medical scope,” Journal of Photochemistry and Photobiology C: Photochemistry Reviews, vol. 22, pp. 34–57, 2015. View at Publisher · View at Google Scholar
  4. L. B. Josefsen and R. W. Boyle, “Unique diagnostic and therapeutic roles of porphyrins and phthalocyanines in photodynamic therapy, imaging and theranostics,” Theranostics, vol. 2, no. 9, pp. 916–966, 2012. View at Publisher · View at Google Scholar · View at Scopus
  5. N. V. Kudinova and T. T. Berezov, “Photodynamic therapy of cancer: search for ideal photosensitizer,” Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, vol. 4, no. 1, pp. 95–103, 2010. View at Publisher · View at Google Scholar · View at Scopus
  6. E. S. Nyman and P. H. Hynninen, “Research advances in the use of tetrapyrrolic photosensitizers for photodynamic therapy,” Journal of Photochemistry and Photobiology B: Biology, vol. 73, no. 1-2, pp. 1–28, 2004. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Wainwright, “Photodynamic therapy: the development of new photosensitisers,” Anti-Cancer Agents in Medicinal Chemistry, vol. 8, no. 3, pp. 280–291, 2008. View at Publisher · View at Google Scholar · View at Scopus
  8. R. H. Jin, S. Aoki, and K. Shima, “A new route to water soluble porphyrins: phosphonium and ammonium type cationic porphyrins and self-assembly,” Chemical Communications, no. 16, pp. 1939–1940, 1996. View at Google Scholar · View at Scopus
  9. K. Lang, J. Mosinger, and D. M. Wagnerová, “Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules; models for photodynamic therapy,” Coordination Chemistry Reviews, vol. 248, no. 3-4, pp. 321–350, 2004. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Banfi, E. Caruso, L. Buccafurni et al., “Antibacterial activity of tetraaryl-porphyrin photosensitizers: an in vitro study on Gram negative and Gram positive bacteria,” Journal of Photochemistry and Photobiology B: Biology, vol. 85, no. 1, pp. 28–38, 2006. View at Publisher · View at Google Scholar · View at Scopus
  11. I. Batinic-Haberle, I. Spasojevic, H. M. Tse et al., “Design of Mn porphyrins for treating oxidative stress injuries and their redox-based regulation of cellular transcriptional activities,” Amino Acids, vol. 42, no. 1, pp. 95–113, 2012. View at Publisher · View at Google Scholar · View at Scopus
  12. K. Kano, K. Fukuda, H. Wakami, R. Nishiyabu, and R. F. Pasternack, “Factors influencing self-aggregation tendencies of cationic porphyrins in aqueous solution,” Journal of the American Chemical Society, vol. 122, no. 31, pp. 7494–7502, 2000. View at Publisher · View at Google Scholar · View at Scopus
  13. P. Kubát, K. Lang, P. Anzenbacher Jr., K. Jursíková, V. Král, and B. Ehrenberg, “Interaction of novel cationic meso-tetraphenylporphyrins in the ground and excited states with DNA and nucleotides,” Journal of the Chemical Society, Perkin Transactions 1, no. 6, pp. 933–941, 2000. View at Publisher · View at Google Scholar · View at Scopus
  14. Y. Cao, A. F. Gill, and D. W. Dixon, “Synthesis and characterization of a water-soluble porphyrin with a cyclic sulfone,” Tetrahedron Letters, vol. 50, no. 30, pp. 4358–4360, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. J. M. Da̧browski, M. M. Pereira, L. G. Arnaut et al., “Synthesis, photophysical studies and anticancer activity of a new halogenated water-soluble porphyrin,” Photochemistry and Photobiology, vol. 83, no. 4, pp. 897–903, 2007. View at Publisher · View at Google Scholar · View at Scopus
  16. X. Zhang, K. Sasaki, and Y. Kuroda, “Characterization of magnesium porphyrins and aggregation of porphyrins in organic solvent,” Bulletin of the Chemical Society of Japan, vol. 80, no. 3, pp. 536–542, 2007. View at Publisher · View at Google Scholar · View at Scopus
  17. R. H. Jin, S. Aoki, and K. Shima, “Phosphoniumyl cationic porphyrins Self-aggregation origin from π-π and cation-π interactions,” Journal of the Chemical Society—Faraday Transactions, vol. 93, no. 22, pp. 3945–3953, 1997. View at Publisher · View at Google Scholar · View at Scopus
  18. H. Imai, H. Munakata, Y. Uemori, and N. Sakura, “Chiral recognition of amino acids and dipeptides by a water-soluble zinc porphyrin,” Inorganic Chemistry, vol. 43, no. 4, pp. 1211–1213, 2004. View at Publisher · View at Google Scholar · View at Scopus
  19. J. Matsumoto, T. Shiragami, and M. Yasuda, “Water-soluble porphyrin easily derived from tetraphenylporphyrin: alkyloxo(methoxo)porphyrinatoantimony bromides,” Chemistry Letters, vol. 37, no. 8, pp. 886–887, 2008. View at Publisher · View at Google Scholar · View at Scopus
  20. J. Matsumoto, S.-I. Tanimura, T. Shiragami, and M. Yasuda, “Water-solubilization of alkyloxo(methoxo)porphyrinatoantimony bromides,” Physical Chemistry Chemical Physics, vol. 11, no. 42, pp. 9766–9771, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. M. Yasuda, T. Nakahara, T. Matsumoto et al., “Visible light-assisted sterilization activity of water-soluble antimonyporphyrin toward Saccharomyces cerevisiae,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 205, no. 2-3, pp. 210–214, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. J. Matsumoto, S.-I. Tanimura, T. Shiragami, and M. Yasuda, “Concentration-dependent aggregation of water-soluble phosphorus porphyrin in an aqueous solution,” Journal of Porphyrins and Phthalocyanines, vol. 16, no. 2, pp. 210–217, 2012. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Matsumoto, T. Shinbara, S.-I. Tanimura et al., “Water-soluble phosphorus porphyrins with high activity for visible light-assisted inactivation of Saccharomyces cerevisiae,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 218, no. 1, pp. 178–184, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. J. Matsumoto, T. Kubo, T. Shinbara et al., “Spectroscopic analysis of the interaction of human serum albumin with tricationic phosphorus porphyrins bearing axial pyridinio groups,” Bulletin of the Chemical Society of Japan, vol. 86, no. 11, pp. 1240–1247, 2013. View at Publisher · View at Google Scholar · View at Scopus
  25. J. Matsumoto, T. Beppu, T. Shiragami, and M. Yasuda, “Mechanistic analysis of the fluorescence quenching of dodecyloxo(methoxo) tetraphenylporphyrinatoantimony by 9,10-dimethylanthracene in an artificial membrane constructed by a phospholipid liposome,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 249, pp. 47–52, 2012. View at Publisher · View at Google Scholar · View at Scopus
  26. K. Kalyanasundaram, “Photochemistry of water-soluble porphyrins: comparative study of isomeric tetrapyridyl- and tetrakis(N-methylpyridiniumyl)porphyrins,” Inorganic Chemistry, vol. 23, no. 16, pp. 2453–2459, 1984. View at Publisher · View at Google Scholar · View at Scopus
  27. M. Yasuda, T. Shiragami, and J. Matsumoto, “Water-soluble porphyrin and process for production thereof,” JP Patent no. JP20090233246, 2009.
  28. K. Hirakawa, N. Fukunaga, Y. Nishimura, T. Arai, and S. Okazaki, “Photosensitized protein damage by dimethoxyphosphorus(V) tetraphenylporphyrin,” Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 9, pp. 2704–2707, 2013. View at Publisher · View at Google Scholar · View at Scopus
  29. R. Marczak, V. Sgobba, W. Kutner, S. Gadde, F. D'Souza, and D. M. Guldi, “Langmuir-blodgett films of a cationic zinc porphyrin-Imidazole-functionalized fullerene dyad: formation and photoelectrochemical studies,” Langmuir, vol. 23, no. 4, pp. 1917–1923, 2007. View at Publisher · View at Google Scholar · View at Scopus
  30. M. Sirish, V. A. Chertkov, and H.-J. Schneider, “Porphyrin-based peptide receptors: syntheses and NMR analysis,” Chemistry—A European Journal, vol. 8, no. 5, p. 1181, 2002. View at Publisher · View at Google Scholar
  31. O. Yaffe, E. Korin, and A. Bettelheim, “Interaction of Fe(III) tetrakis(4-N-methylpyridinium)porphyrin with sodium dodecyl sulfate at submicellar concentrations,” Langmuir, vol. 24, no. 20, pp. 11514–11517, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. Y. H. Kim, S. D. Jung, M. H. Lee et al., “Photoinduced reduction of manganese(III) meso-tetrakis(1-methylpyridinium- 4-yl)porphyrin at AT and GC base pairs,” The Journal of Physical Chemistry B, vol. 117, no. 33, pp. 9585–9590, 2013. View at Publisher · View at Google Scholar · View at Scopus
  33. R. F. Pasternack, S. Ewen, A. Rao et al., “Interactions of copper(II) porphyrins with DNA,” Inorganica Chimica Acta, vol. 317, no. 1-2, pp. 59–71, 2001. View at Publisher · View at Google Scholar · View at Scopus
  34. J. S. Trommel and L. G. Marzilli, “Synthesis and DNA binding of novel water-soluble cationic methylcobalt porphyrins,” Inorganic Chemistry, vol. 40, no. 17, pp. 4374–4383, 2001. View at Publisher · View at Google Scholar · View at Scopus
  35. M. Haeubl, L. M. Reith, B. Gruber et al., “DNA interactions and photocatalytic strand cleavage by artificial nucleases based on water-soluble gold(III) porphyrins,” Journal of Biological Inorganic Chemistry, vol. 14, no. 7, pp. 1037–1052, 2009. View at Publisher · View at Google Scholar · View at Scopus
  36. S. Naveenraj and S. Anandan, “Binding of serum albumins with bioactive substances—nanoparticles to drugs,” Journal of Photochemistry and Photobiology C: Photochemistry Reviews, vol. 14, no. 1, pp. 53–71, 2013. View at Publisher · View at Google Scholar · View at Scopus
  37. G. Sudlow, D. J. Birkett, and D. N. Wade, “Further characterization of specific drug binding sites on human serum albumin,” Molecular Pharmacology, vol. 12, no. 6, pp. 1052–1061, 1976. View at Google Scholar · View at Scopus
  38. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Springer, New York, NY, USA, 3rd edition, 2006.
  39. S. S. Wong, T. E. Malone, and T. K. Lee, “Use of concanavalin a as a topographical probe for protein-protein interaction application to lactose synthase,” Biochimica et Biophysica Acta, vol. 745, no. 1, pp. 90–96, 1983. View at Publisher · View at Google Scholar
  40. K. D. Hardman and C. F. Ainsworth, “Structure of the concanavalin A-methyl α-D-mannopyranoside complex at 6-Å resolution,” Biochemistry, vol. 15, no. 5, pp. 1120–1128, 1976. View at Publisher · View at Google Scholar · View at Scopus
  41. S. J. Harrop, J. R. Helliwell, T. C. M. Wan, A. J. Kalb, L. Tong, and J. Yariv, “Structure solution of a cubic crystal of concanavalin A complexed with methyl α-D-glucopyranoside,” Acta Crystallographica Section D: Biological Crystallography, vol. 52, no. 1, pp. 143–155, 1996. View at Google Scholar · View at Scopus
  42. K. Hirakawa, T. Hirano, Y. Nishimura, T. Arai, and Y. Nosaka, “Control of singlet oxygen generation photosensitized by meso-anthrylporphyrin through interaction with DNA,” Photochemistry and Photobiology, vol. 87, no. 4, pp. 833–839, 2011. View at Publisher · View at Google Scholar · View at Scopus
  43. K. Hirakawa, M. Harada, S. Okazaki, and Y. Nosaka, “Controlled generation of singlet oxygen by a water-soluble meso-pyrenylporphyrin photosensitizer through interaction with DNA,” Chemical Communications, vol. 48, no. 39, pp. 4770–4772, 2012. View at Publisher · View at Google Scholar · View at Scopus
  44. S. Tada-Oikawa, J. Hirayama, K. Hirakawa, and S. Kawanishi, “DNA damage and apoptosis induced by photosensitization of 5,10,15,20-tetrakis (N-methyl-4-pyridyl)-21H,23H-porphyrin via singlet oxygen generation,” Photochemistry and Photobiology, vol. 85, no. 6, pp. 1391–1399, 2009. View at Publisher · View at Google Scholar · View at Scopus
  45. Y. Fueda, M. Hashimoto, K. Nobuhara et al., “Visible-light bactericidal effect of silica gel-supported porphyrinatoantimony(V) catalyst on Legionella species occurring in the living environmental fields,” Biocontrol Science, vol. 10, no. 1-2, pp. 55–60, 2005. View at Publisher · View at Google Scholar · View at Scopus
  46. K. Hirakawa, S. Kawanishi, J. Matsumoto, T. Shiragami, and M. Yasuda, “Guanine-specific DNA damage photosensitized by the dihydroxo(tetraphenylporphyrinato)antimony(V) complex,” Journal of Photochemistry and Photobiology B: Biology, vol. 82, no. 1, pp. 37–44, 2006. View at Publisher · View at Google Scholar · View at Scopus
  47. K. Hirakawa, M. Yoshida, S. Oikawa, and S. Kawanishi, “Base oxidation at 5′ site of GG sequence in double-stranded DNA induced by UVA in the presence of xanthone analogues: relationship between the DNA-damaging abilities of photosensitizers and their HOMO energies,” Photochemistry and Photobiology, vol. 77, no. 4, pp. 349–355, 2003. View at Publisher · View at Google Scholar
  48. F. D. Lewis and Y. Wu, “Dynamics of superexchange photoinduced electron transfer in duplex DNA,” Journal of Photochemistry and Photobiology C: Photochemistry Reviews, vol. 2, no. 1, pp. 1–16, 2001. View at Publisher · View at Google Scholar · View at Scopus
  49. H. Sugiyama and I. Saito, “Theoretical studies of GG-specific photocleavage of DNA via electron transfer: significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-form DNA,” Journal of the American Chemical Society, vol. 118, no. 30, pp. 7063–7068, 1996. View at Publisher · View at Google Scholar · View at Scopus
  50. Y. Yoshioka, Y. Kitagawa, Y. Takano, K. Yamaguchi, T. Nakamura, and I. Saito, “Experimental and theoretical studies on the selectivity of GGG triplets toward one-electron oxidation in B-form DNA,” Journal of the American Chemical Society, vol. 121, no. 38, pp. 8712–8719, 1999. View at Publisher · View at Google Scholar · View at Scopus
  51. K. Hirakawa, S. Kawanishi, T. Hirano, and H. Segawa, “Guanine-specific DNA oxidation photosensitized by the tetraphenylporphyrin phosphorus(V) complex via singlet oxygen generation and electron transfer,” Journal of Photochemistry and Photobiology B: Biology, vol. 87, no. 3, pp. 209–217, 2007. View at Publisher · View at Google Scholar · View at Scopus
  52. K. Hirakawa, K. Azumi, Y. Nishimura, T. Arai, Y. Nosaka, and S. Okazaki, “Photosensitized damage of protein by fluorinated diethoxyphosphorus(V) porphyrin,” Journal of Porphyrins and Phthalocyanines, vol. 17, no. 1-2, pp. 56–62, 2013. View at Publisher · View at Google Scholar · View at Scopus
  53. H. Yokoi, T. Shiragami, J. Hirose et al., “Bactericidal effect of a silica gel-supported porphyrinatoantimony(V) complex under visible light irradiation,” World Journal of Microbiology and Biotechnology, vol. 19, no. 6, pp. 559–563, 2003. View at Publisher · View at Google Scholar · View at Scopus
  54. Y. Fueda, H. Suzuki, Y. Komiya et al., “Bactericidal effect of silica gel-supported porphyrinatophosphorus(V) catalysts on Escherichia coli under visible-light irradiation,” Bulletin of the Chemical Society of Japan, vol. 79, no. 9, pp. 1420–1425, 2006. View at Publisher · View at Google Scholar · View at Scopus
  55. C. Tanielian and C. Wolff, “Porphyrin-sensitized generation of singlet molecular oxygen: comparison of steady-state and time-resolved methods,” Journal of Physical Chemistry, vol. 99, no. 24, pp. 9825–9830, 1995. View at Publisher · View at Google Scholar · View at Scopus
  56. A. Gomes, E. Fernandes, and J. L. F. C. Lima, “Fluorescence probes used for detection of reactive oxygen species,” Journal of Biochemical and Biophysical Methods, vol. 65, no. 2-3, pp. 45–80, 2005. View at Publisher · View at Google Scholar · View at Scopus
  57. H. Kotani, K. Ohkubo, and S. Fukuzumi, “Photocatalytic oxygenation of anthracenes and olefins with dioxygen via selective radical coupling using 9-mesityl-10-methylacridinium ion as an effective electron-transfer photocatalyst,” Journal of the American Chemical Society, vol. 126, no. 49, pp. 15999–16006, 2004. View at Publisher · View at Google Scholar · View at Scopus
  58. A. D. Bangham, M. M. Standish, and J. C. Watkins, “Diffusion of univalent ions across the lamellae of swollen phospholipids,” Journal of Molecular Biology, vol. 13, no. 1, pp. 238–252, 1965. View at Publisher · View at Google Scholar · View at Scopus
  59. M. R. Hamblin and T. Hasan, “Photodynamic therapy: a new antimicrobial approach to infectious disease?” Photochemical and Photobiological Sciences, vol. 3, no. 5, pp. 436–450, 2004. View at Publisher · View at Google Scholar · View at Scopus
  60. I. J. MacDonald and T. J. Dougherty, “Basic principles of photodynamic therapy,” Journal of Porphyrins and Phthalocyanines, vol. 5, no. 2, pp. 105–129, 2001. View at Publisher · View at Google Scholar · View at Scopus
  61. R. K. Pandey and G. Zheng, “Porphyrins as photosensitizers in photodynamic therapy,” in The Porphyrin Handbook, K. M. Kadish, K. M. Smith, and R. Guilluy, Eds., pp. 157–230, Academic Press, San Diego, Calif, USA, 2000. View at Google Scholar