Skip to main content
SpringerLink
Log in

Photosensitiser—antibody conjugates for photodynamic therapy

  • Perspective
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Research into targeting of photodynamic sensitisers to specific biological tissue has been an area of increasing interest over the last twenty years. A significant number of these investigations have involved the use of antibodies or antibody fragments, and the field of photosensitiser bioconjugation is now an established area in its own right. This review seeks to bring together the diverse range of methodology now available for the efficient attachment of photodynamic agents to antibodies. The chemistry involved to obtain the complementary functionality required, on both photosensitiser and antibody, for successful conjugation is also discussed.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. C. Alonso, and R. W. Boyle, Bioconjugates of porphyrins and related molecules for photodynamic therapy, in Handbook of porphyrin science, ed. K. M. Kadish, K. M. Smith and R. Guilard, World Scientific, 2010, vol. 4, pp. 121–190.

    Article  CAS  Google Scholar 

  2. Y. N. Konan, R. Gurney and E. Allémann, State of the art in the delivery of photosensitizers for photodynamic therapy, J. Photochem. Photobiol., B, 2002, 66, 89–106.

    Article  CAS  Google Scholar 

  3. H. Hudson and R. W. Boyle, Strategies for selective delivery of photodynamic sensitisers to biological targets, J. Porphyrins Phthalocyanines, 2004, 8, 954–975.

    Article  CAS  Google Scholar 

  4. W. M. Sharman, J. E. van Lier and C. M. Allen, Targeted photodynamic therapy via receptor mediated delivery systems, Adv. Drug DeliveryRev., 2004, 56, 53–76.

    Article  CAS  Google Scholar 

  5. J. F. Hainfeld and R. D. Powell, New Frontiers in Gold Labeling, J. Histochem. Cytochem., 2000, 48, 471–480.

    Article  CAS  PubMed  Google Scholar 

  6. G. Köhler and C. Meilstein, Continuous cultures of fused cells secreting antibody of predefined specificity, Nature, 1975, 256, 495–497.

    Article  PubMed  Google Scholar 

  7. T. Kretzschmar and T. von Rüden, Antibody discovery: phage display, Curr. Opin. Biotechnol., 2002, 13, 598–602.

    Article  CAS  PubMed  Google Scholar 

  8. G. A. M. S. van Dongen, G. W. M. Visser and M. B. Vrouenraets, Photosensitizer-antibody conjugates for detection and therapy of cancer, Adv. Drug Delivery Rev., 2004, 56, 31–52.

    Article  CAS  Google Scholar 

  9. N. E. Weisser and J. C. Hall, Applications of single-chain variable fragment antibodies in therapeutics and diagnostics, Biotechnol. Adv., 2009, 27, 502–520.

    Article  CAS  PubMed  Google Scholar 

  10. S. K. Batra, M. Jain, U. A. Wittel, S. C. Chauhan and D. Colcher, Pharmacokinetics and biodistribution of genetically engineered antibodies, Curr. Opin. Biotechnol., 2002, 13, 603–608.

    Article  CAS  PubMed  Google Scholar 

  11. R. de Bree, J. C. Roos, J. J. Quak, W. den Hollander, A. J. Wilhelm, A. van Lingen, G. B. Snow and G. A. M. S. van Dongen, Biodistribution of radiolabeled monoclonal antibody E48 IgG and F(ab)2 in patients with head and neck cancer, Clin. Cancer Res., 1995, 1, 277–286.

    PubMed  Google Scholar 

  12. L. Borsi, E. Balza, M. Bestagno, P. Castellani, B. Carnemolla, A. Biro, A. Leprini, J. Sepulveda, O. Burrone, D. Neri and L. Zardi, Selective targeting of the tumoural vasculature: comparison of different formats of an antibody (L19) to the ED-B domain of fibronectin, Int. J. Cancer, 2002, 102, 75–85.

    Article  CAS  PubMed  Google Scholar 

  13. R. K. Jain, Physiological barriers to delivery of monoclonal antibodies and other macromolecules in tumours, Cancer Res., 1990, 50, 814–819.

    Google Scholar 

  14. M. B. Vrouenraets, G. W. M. Visser, F. A. Stewart, M. Stigter, H. Oppelaar, P. E. Postmus, G. B. Snow and G. A. M. S. van Dongen, Development of meta-tetrahydroxyphenylchlorin-monoclonal antibody conjugates for photoimmunotherapy, Cancer Res., 1999, 59, 1505–1513.

    CAS  PubMed  Google Scholar 

  15. G. Walsh, Second-generation biopharmaceuticals, Eur. J. Pharm. Biopharm., 2004, 58, 185–196.

    Article  CAS  PubMed  Google Scholar 

  16. E. D. Sternberg, D. Dolphin and C. Brückner, Porphyrin-based Photosensitizers for use in Photodynamic Therapy, Tetrahedron, 1998, 54, 4151–4202.

    Article  CAS  Google Scholar 

  17. R. R. Allison, G. H. Downie, R. Cuenca, X-H. Hu, C. J. H. Childs and C. H. Sibata, Photosensitizers in clinical PDT, Photodiagn. Photodyn. Ther., 2004, 1, 27–42.

    Article  CAS  Google Scholar 

  18. A. E. O’Connor, W. M. Gallagher and A. T. Byrne, Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy, Photochem. Photobiol., 2009, 85, 1053–1074.

    Article  CAS  PubMed  Google Scholar 

  19. M. D. Governatore, M. R. Hamblin, E. E. Piccinini, G. Ugolini and T. Hasan, Targeted photodestruction of human colon cancer cells using charged 17.1A chlorin e6 immunoconjugates, Br. J. Cancer, 2000, 82, 56–64.

    Article  PubMed  Google Scholar 

  20. I. J. Macdonald and T. J. Dougherty, Basic principles of photodynamic therapy, J. Porphyrins Phthalocyanines, 2001, 5, 105–129.

    Article  CAS  Google Scholar 

  21. D. Mew, C-K. Wat, G. H. N. Towers and J. G. Levy, Photoimmunotherapy: treatment of animal tumours with tumour-specific monoclonal antibody-hematoporphyrin conjugates, J. Immunol., 1983, 130, 1473–1477.

    CAS  PubMed  Google Scholar 

  22. D. Mew, V. Lum, C-K. Wat, G. H. N. Towers, C-H. C. Sun, R. J. Walter, W. Wright, M. W. Berns and J. G. Levy, Ability of specific monoclonal antibodies and conventional antisera conjugated to hematoporphyrin to label and kill selected cell lines subsequent to light activation, Cancer Res., 1985, 45, 4380–4386.

    CAS  PubMed  Google Scholar 

  23. J. K. Steele, D. Liu, A. T. Stammers, S. Whitney and J. G. Levy, Suppressor deletion therapy: selective elimination of T suppressor cells in vivo using a hematoporphyrin conjugated monoclonal antibody permits animals to reject syngeneic tumour cells, Cancer Immunol. Immunother., 1988, 26, 125–131.

    Article  CAS  PubMed  Google Scholar 

  24. H. W. Pogrebniak, W. Matthews, C. Black, A. Russo, J. B. Mitchell, P. Smith, J.A. Roth and H. I. Pass, Targeted phototherapywith sensitizermonoclonal antibody conjugate and light, Surg. Oncol., 1993, 2, 31–42.

    Article  CAS  PubMed  Google Scholar 

  25. T. Berki and P. Németh, Photo-immunotargeting with haematoporphyrin conjugates activated by a low-power He-Ne laser, Cancer Immunol. Immunother., 1992, 35, 69–74.

    Article  CAS  PubMed  Google Scholar 

  26. T. Berki and P. Németh, Novel method for in vitro depletion of T cells by a monoclonal antibody-targeted photosensitization, J. Immunol. Methods, 1998, 211, 139–146.

    Article  CAS  PubMed  Google Scholar 

  27. R. Linares, J. R. Pacheco and T. A. Good, Efficacy of different targeting agents in the photolysis of interleukin-2 receptor bearing cells, J. Photochem. Photobiol., B, 2004, 77, 17–26.

    Article  CAS  Google Scholar 

  28. K. A. Colon and M. Berrios, Site-directed photoproteolysis of 8-oxoguanine DNA glycosylase 1 (OGG1) by specific porphyrin-protein probe conjugates: a strategy to improve the effectiveness of photodynamic therapy for cancer, J. Photochem. Photobiol., B, 2007, 87, 9–17.

    Article  CAS  Google Scholar 

  29. G. L. Mayo, R. F. Melendez, N. Kumar, S. J. McKinnon and R. D. Glickman, Antibody-targeted photodynamic therapy, Am. J. Ophthalmol., 2003, 136, 1151–1152.

    Article  CAS  PubMed  Google Scholar 

  30. S. P. Martsez, V. A. Preygerzon, Y. I. Mel’nikova, Z. I. Kravchuk, G. V. Ponomarev, V. E. Lunev and A. P. Savitsky, Modification of monoclonal and polyclonal IgG with palladium (II) coporphyrin I: stimulatory and inhibitory functional effects induced by two different methods, J. Immunol. Methods, 1995, 186, 293–304.

    Article  Google Scholar 

  31. K. E. Borbas, P. Mroz, M. R. Hamblin and J. S. Lindsey, Bioconjugatable porphyrins bearing a compact swallowtail motif for water solubility, Bioconjugate Chem., 2006, 17, 638–653.

    Article  CAS  Google Scholar 

  32. A. Z. Muresan and J. S. Lindsey, Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins, Tetrahedron, 2008, 64, 11440–11448.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. K. E. Borbas, H. L. Kee, D. Holton and J. S. Lindsey, Acompact watersoluble porphyrin bearing an iodoacetamido bioconjugatable site, Org. Biomol. Chem., 2008, 6, 187–194.

    Article  CAS  PubMed  Google Scholar 

  34. O. J. Clarke and R. W. Boyle, Isothiocyanatoporphyrins, useful intermediates for the conjugation of porphyrins with biomolecules and solid supports, Chem. Commun., 1999, 2231–2232.

    Google Scholar 

  35. N. S. Soukos, M. R. Hamblin, S. Keel, R. L. Fabian, T. F. Deutsch and T. Hasan, Epidermal growth factor receptor-targeted immunophotodiagnosis and photoimmunotherapy of oral precancer in vivo, Cancer Res., 2001, 61, 4490–4496.

    CAS  PubMed  PubMed Central  Google Scholar 

  36. S-I. Ogura, Y. Fujita, T. Kamachi and I. Okura, Preparation of chlorin e6-monoclonal antibody conjugate and its effect for photodynamic therapy, J. Porphyrins Phthalocyanines, 2001, 5, 486–489.

    Article  CAS  Google Scholar 

  37. M. L. Embleton, S. P. Nair, B. D. Cookson and M. Wilson, Selective lethal photosensitization of methicillin-resistant Staphylococcus aureus using an IgG-tin (IV) chlorin e6 conjugate, J. Antimicrob. Chemother., 2002, 50, 857–864.

    Article  CAS  PubMed  Google Scholar 

  38. M. L. Embleton, S. P. Nair, B. D. Cookson and M. Wilson, Antibodydirected photodynamic therapy of methicillin-resistant Staphylococcus aureus, Microb. Drug Res., 2004, 10, 92–97.

    Article  CAS  Google Scholar 

  39. M. Fabbrini, E. Trachsel, P. Soldani, S. Bindi, P. Alessi, L. Bracci, H. Kosmehl, L. Zardi, D. Neri and P. Neri, Selective occlusion of tumour blood vessels by targeted delivery of an antibody-photosensitizer conjugate, Int. J. Cancer, 2006, 118, 1805–1813.

    Article  CAS  PubMed  Google Scholar 

  40. M. D. Savellano and T. Hasan, Targeting cells that overexpress the epidermal growth factor receptor with polyethylene glycolated BPD verteporfin photosensitizer immunoconjugates, Photochem. Photobiol., 2003, 77, 431–439.

    Article  CAS  PubMed  Google Scholar 

  41. M. D. Savellano and T. Hasan, Photochemical targeting of epidermal growth factor receptor: a mechanistic study, Clin. Cancer Res., 2005, 11, 1658–1668.

    Article  CAS  PubMed  Google Scholar 

  42. M. D. Savellano, B. W. Pogue, P. J. Hoopes, E. S. Vitette and K. D. Paulsen, Multiepitope HER2 targeting enhances photoimmunotherapy of HER2-overexpressing cancer cells with pyropheophorbide-a immunoconjugates, Cancer Res., 2005, 65, 6371–6379.

    Article  CAS  PubMed  Google Scholar 

  43. M. K. Kuimova, M. Bhatti, M. Deonarain, G. Yahioglu, J. A. Levitt, I. Stamati, K. Suhling and D. Phillips, Fluorescence characterisation of multiply-loaded anti-HER2 single chain Fv-photosensitizer conjugates suitable for photodynamic therapy, Photochem. Photobiol. Sci., 2007, 6, 933–939.

    Article  CAS  PubMed  Google Scholar 

  44. M. Bhatti, G. Yahioglu, L. R. Milgrom, M. Garcia-Maya, K. A. Chester and M. P. Deonarian, Targeted photodynamic therapy with multiply-loaded recombinant antibody fragments, Int. J. Cancer, 2008, 122, 1155–1163.

    Article  CAS  PubMed  Google Scholar 

  45. H. Abe, M. Kuroki, K. Tachibana, T. Li, A. Awasthi, A. Ueno, H. Matsumoto, T. Imakiire, Y. Yamauchi, H. Yamada, A. Ariyoshi and M. Kuroki, Targeted sonodynamic therapy of cancer using a photosensitizer conjugated with antibody against carcinoembryonic antigen, Anticancer Res., 2002, 22, 1575–1580.

    CAS  PubMed  Google Scholar 

  46. S. Gross, A. Brandis, L. Chen, V. Rosenbach-Belkin, S. Roehrs, A. Scherz and Y. Salomon, Protein-A-mediated targeting of bacteriochlorophyll-IgG to Staphylococcus aureus: a model for enhanced site-specific photocytotoxicity, Photochem. Photobiol., 1997, 66, 872–878.

    Article  CAS  PubMed  Google Scholar 

  47. K. A. Conlon and M. Berrios, Light-induced proteolysis of myosin heavy chain by rose bengal-conjugated antibody complexes, J. Photochem. Photobiol., B, 2001, 65, 22–28.

    Article  CAS  Google Scholar 

  48. M. Carcenac, C. Larroque, R. Langlosis, J. E. van Lier, J-C. Artus and A. Pèlegrin, Preparation, phototoxicity and biodistribution studies of anti-carcinoembryonic antigen monoclonal antibody-phthalocyanine conjugates, Photochem. Photobiol., 1999, 70, 930–936.

    CAS  PubMed  Google Scholar 

  49. M. Carcenac, M. Dorvillius, V. Gamambois, F. Glaussel, Ch. Larroque, R. Langlosis, N. E. Hynes, J. E. van Lier and A. Pèlegrin, Internalisation enhances photo-induced cytotoxicity of monoclonal antibodyphthalocyanine conjugates, Br. J. Cancer, 2001, 85, 1787–1793.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. N. Brasseur, R. Langlois, C. La Madeleine, R. Ouellet and J. E. van Lier, Receptor-mediated targeting of phthalocyanines to macrophages via covalent coupling to native or maleylated bovine serum albumin, Photochem. Photobiol., 1999, 69, 345–352.

    Article  CAS  PubMed  Google Scholar 

  51. Z. Halime, L. Michaudet, M. Lachkar, P. Brossier and B. Boitrel, Influence of pendant arms bearing ligating groups on the structure of bismuth porphyrins: implications for labeling immunoglobins used in medical applications, Bioconjugate Chem., 2004, 15, 1193–1200.

    Article  CAS  Google Scholar 

  52. J. P. Collman, M. Bröring, L. Fu, M. Rapta, R. Schwenninger and A. Straumanis, Novel protecting strategy for the synthesis of porphyrins with different distal and proximal superstructures, J. Org. Chem., 1998, 63, 8082–8083.

    Article  CAS  Google Scholar 

  53. M. B. Vrouenraets, G. W. M. Visser, M. Stigter, H. Oppelaar, G. B. Snow and G. A. M. S. van Dongen, Targeting of aluminium (III) phthalocyanine tetrasulfonate by use of internalizing monoclonal antibodies: improved efficacy in photodynamic therapy, Cancer Res., 2001, 61, 1970–1975.

    CAS  PubMed  Google Scholar 

  54. M. B. Vrouenraets, G. W. M. Visser, M. Stigter, H. Oppelaar, G. B. Snow and G. A. M. S. van Dongen, Comparison of aluminium (III) phthalocyanine tetrasulfonate-and meta-tetrahydroxyphenylchlorinmonoclonal antibody conjugates for their efficacy in photodynamic therapy in vitro, Int. J. Cancer, 2002, 98, 793–798.

    Article  CAS  PubMed  Google Scholar 

  55. M. B. Vrouenraets, G. W. M. Visser, C. Loup, B. Meunier, M. Stigter, H. Oppelaar, F. A. Stewart, G. B. Snow and G. A. M. S. van Dongen, Targeting of a hydrophilic photosensitizer by use of internalizing monoclonal antibodies: a new possibility for use in photodynamic therapy, Int. J. Cancer, 2000, 88, 108–114.

    Article  CAS  PubMed  Google Scholar 

  56. C. Casas, B. Saint-Jalmes, C. Loup, C. J. Lacey and B. Meunier, Synthesis of cationic metalloporphyrin precursors related to the design of DNA cleavers, J. Org. Chem., 1993, 58, 2913–2917.

    Article  CAS  Google Scholar 

  57. X-M. Lu, A. J. Fischman, E. Stevens, T. T. Lee, L. Strong, R. G. Tompkins and M. L. Yarmush, Sn-chlorin e6 antibacterial immunoconjugates: An in vitro and in vivo analysis, J. Immunol.Methods, 1992, 156, 85–99.

    Article  CAS  PubMed  Google Scholar 

  58. W. P. Thorpe, M. Toner, R. M. Ezzell, R. G. Tompkins and M. L. Yarmush, Dynamics of photoinduced cell plasma membrane injury, Biophys. J., 1995, 68, 2198–2206.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  59. S. F. Wolfort, S. R. Reiken, F. Berthiaume, R. G. Tompkins and M. L. Yarmush, Control of hypertrophic scar growth using antibody-targeted photolysis, J. Surg. Res., 1996, 62, 17–22.

    Article  CAS  PubMed  Google Scholar 

  60. L. H. Strong, F. Berthiaume and M. L. Yarmush, Control of fibroblast populated collagen lattice contraction by antibody targeted photolysis of fibroblasts, Lasers Surg. Med., 1997, 21, 235–247.

    Article  CAS  PubMed  Google Scholar 

  61. J. M. Sutton, O. J. Clarke, N. Fernandez and R. W. Boyle, Porphyrin, chlorin and bacteriochlorin isothiocyanates: useful reagents for the synthesis of photoactive bioconjugates, Bioconjugate Chem., 2002, 13, 249–263.

    Article  CAS  Google Scholar 

  62. N. Malatesti, K. Smith, H. Savoie, J. Greenman and R. W. Boyle, Synthesis and in vitro investigation of cationic 5, 15-diphenyl porphyrinmonoclonal antibody conjugates as targeted photodynamic sensitisers, Int. J. Oncol., 2006, 28, 1561–1569.

    CAS  PubMed  Google Scholar 

  63. R. Hudson, M. Carcenac, K. Smith, L. Madden, O. J. Clarke, A. Pèlegrin, J. Greenman and R. W. Boyle, The development and characterisation of porphyrin isothiocyanate-monoclonal antibody conjugates for photoimmunotherapy, Br. J. Cancer, 2005, 92, 1442–1449.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  64. C. Staneloudi, K. A. Smith, R. Hudson, N. Malatesti, H. Savoie, R.W. Boyle and J. Greenman, Development and characterization of novel photosensitizer: scFv conjugates for the use in photodynamic therapy of cancer, Immunology, 2007, 120, 512–517.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. L. R. Milgrom and F. O’Neill, Towards syntheticporphyrin/monoclonal antibody conjugates, Tetrahedron, 1995, 51, 2137–2144.

    Article  CAS  Google Scholar 

  66. C. M. A. Alonso, A. Palumbo, A. J. Bullous, F. Pretto, D. Neri and R. W. Boyle, Site-specific and stoichiometric conjugation of cationic porphyrins to antiangiogenic monoclonal antibodies, Bioconjugate Chem., 2010, 21, 302–313.

    Article  CAS  Google Scholar 

  67. A. R. Oseroff, D. Ohuoha, T. Hasan, J. C. Bommer and M. L. Yarmush, Antibody-targeted photolysis: selective photodestruction of human Tcell leukaemia cells using monoclonal antibody-chlorin e6 conjugates, Proc. Natl. Acad. Sci. U. S. A., 1986, 83, 8744–8748.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. A. R. Oseroff, G. Ara, D. Ohuoha, J. Aprille, J. C. Bommer, M. L. Yarmush, J. Foley and L. Cincotta, Strategies for selective cancer photochemotherapy: antibody-targeted and selective carcinoma cell photolysis, Photochem. Photobiol., 1987, 46, 83–96.

    Article  CAS  PubMed  Google Scholar 

  69. S. L. Rakestraw, R. G. Tompkins and M. L. Yarmush, Preparation and characterization of immunoconjugates for antibody-targeted photolysis, Bioconjugate Chem., 1990, 1, 212–221.

    Article  CAS  Google Scholar 

  70. S. L. Rakestraw, R. G. Tompkins and M. L. Yarmush, Antibodytargeted photolysis: in vitro studies with Sn(IV) chlorin e6 covalently bound to monoclonal antibodies using a modified dextran carrier, Proc. Natl. Acad. Sci. U. S. A., 1990, 87, 4217–4221.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. S. L. Rakestraw, W. E. Ford, R. G. Tompkins, M. A. J. Rodgers, W. P. Thorpe and M. L. Yarmush, Antibody-targeted photolysis: in vitro immunological, photophysical, and cytotoxic properties of monoclonal antibody-dextran-Sn(IV) chlorin e6 immunoconjugate, Biotechnol. Prog., 1992, 8, 30–39.

    Article  CAS  PubMed  Google Scholar 

  72. T. Hasan, A. Lin, D. Yarmush, A. Oseroff and M. Yarmush, Monoclonal antibody-chromophore conjugates as selective phototoxins, J. Controlled Release, 1989, 10, 107–117.

    Article  CAS  Google Scholar 

  73. B. A. Goff, M. Bamberg and T. Hasan, Photoimmunotherapy of human ovarian carcinoma cells ex vivo, Cancer Res., 1991, 51, 4762–4767.

    CAS  PubMed  Google Scholar 

  74. B. A. Goff, U. Hermanto, J. Rumbaugh, J. Blake, M. Bamberg and T. Hasan, Photoimmunotherapy and biodistribution with an OC125-chlorin immunoconjugate in an in vivo murine ovarian cancer model, Br. J. Cancer, 1994, 70, 474–480.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  75. B. A. Goff, J. Blake, M. P. Bamberg and T. Hasan, Treatment of ovarian cancer with photodynamic therapy and immunoconjugates in murine ovarian cancer model, Br. J. Cancer, 1996, 74, 1194–1198.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  76. L. K. Hu, T. Hasan, E. S. Gragoudas and L. H. Y. Young, Photoimmunotherapy of human uveal melanoma cells, Exp. Eye Res., 1995, 61, 385–391.

    Article  CAS  PubMed  Google Scholar 

  77. F. N. Jiang, S. Jiang, D. Liu, A. Richter and J. G. Levy, Development of technology for linking photosensitizers to a model monoclonal antibody, J. Immunol. Methods, 1990, 134, 139–149.

    Article  CAS  PubMed  Google Scholar 

  78. F. N. Jiang, D. Liu, A. Richter, H. Neyndorff, M. Chester, S. Jiang and J. G. Levy, Photodynamic killing of human squamous cell carcinoma cells using a monoclonal antibody-photosensitizer conjugate, J. Natl. Cancer Inst., 1991, 83, 1218–1225.

    Article  CAS  PubMed  Google Scholar 

  79. F.N. Jiang, B. Allison, D. Liu and J.G. Levy, Enhanced photodynamic killing of target cells by either monoclonal antibody or low density lipoprotein mediated delivery systems, J. Controlled Release, 1992, 19, 41–58.

    Article  CAS  Google Scholar 

  80. F.N. Jiang, D. Liu, A. M. Richter, A. K. Jain, J.G. Levy and C. Smits, Biodistribution of a benzoporphyrin derivative-monoclonal antibody conjugate in A549-tumour-bearing nude mice, Biotechnol. Ther., 1993, 4, 43–61.

    CAS  PubMed  Google Scholar 

  81. A. W. Hemming, N. L. Davis, B. Dubois, N. F. Quenville and R. J. Finley, Photodynamic therapy of squamous cell carcinoma: An evaluation of a new photosensitizing agent, benzoporphyrin derivative and new photoimmunoconjugate, Surg. Oncol., 1993, 2, 187–196.

    Article  CAS  PubMed  Google Scholar 

  82. M. R. Hamblin, J. L. Miller and T. Hasan, Effect of charge on the interaction of site-specific photoimmunoconjugates with human ovarian cancer cells, Cancer Res., 1996, 56, 5205–5210.

    CAS  PubMed  Google Scholar 

  83. L. R. Duska, M. R. Hamblin, M. P. Bamberg and T. Hasan, Biodistribution of charged F(ab’)2 photoimmunoconjugates in a xenograft model of ovarian cancer, Br. J. Cancer, 1997, 75, 837–844.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  84. L. R. Duska, M. R. Hamblin, J. L. Miller and T. Hasan, Combination photoimmunotherapy and cisplatin: effects on human ovarian cancer ex vivo, J. Natl. Cancer Inst., 1999, 91, 1557–1563.

    Article  CAS  PubMed  Google Scholar 

  85. K. L. Molpus, M. R. Hamblin, I. Rizvi and T. Hasan, Intraperitoneal photoimmunotherapy of ovarian carcinoma xenografts in nude mice using charged photoimmunoconjugates, Gynecol. Oncol., 2000, 76, 397–404.

    Article  CAS  PubMed  Google Scholar 

  86. M. R. Hamblin, M. D. Governatore, I. Rizvi and T. Hasan, Biodistribution of charged 17.1A photoimmunoconjugates in a murine model of hepaticmetastasis of colorectal cancer, Br. J. Cancer, 2000, 83, 1544–1551.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  87. M. D. Governatore, M. R. Hamblin, C. R. Shea, I. Rizvi, K. G. Molpus, K. K. Tanabe and T. Hasan, Experimental photoimmunotherapy of hepatic metastases of colorectal cancer with a 17.1A chlorin e6 immunoconjugate, Cancer Res., 60, 4200–4205.

  88. F. Rancan, M. Helmreich, A. Mölich, E. A. Ermilov, N. Jux, B. Röder, A. Hirsch and F. Böhm, Synthesis and in vitro testing of a pyropheophorbide-a-fullerene hexakis adduct immunoconjugate for photodynamic therapy, Bioconjugate Chem., 2007, 18, 1078–1086.

    Article  CAS  Google Scholar 

  89. J. Kopeček, P. Kopečková, T. Minko and Z-R. Lu, HPMA copolymeranticancer drug conjugates: design, activity, and mechanism of action, Eur. J. Pharm. Biopharm., 2000, 50, 61–81.

    Article  PubMed  Google Scholar 

  90. V. Omelyanenko, P. Kopečková, C. Gentry, J-G. Shiah and J. Kopeček, HPMA co-polymer-anticancer drug-OV-TL16 antibody conjugates. 1. influence of themethod of synthesis on the binding affinity toOVCAR-3 ovarian carcinoma cells in vitro, J. Drug Targeting, 1996, 3, 357–373.

    Article  CAS  Google Scholar 

  91. V. Omelyanenko, C. Gentry, P. Kopečková and J. Kopeček, HPMA copolymer-anticancer drug-OV-TL16 antibody conjugates. II. processing in epithelial ovarian carcinoma cells in vitro, Int. J. Cancer, 1998, 75, 600–608.

    Article  CAS  PubMed  Google Scholar 

  92. J-G. Shiah, Y. Sun, P. Kopečková, C. M. Peterson, R. C. Straight and J. Kopeček, Combination chemotherapy and photodynamic therapy of targetable N-(2-hyroxypropyl)methacrylamide copolymerdoxorubicin(mesochlorin e(6)-OV-TL 16 antibody immunoconjugates, J. Controlled Release, 2001, 74, 249–253.

    Article  CAS  Google Scholar 

  93. J-G. Shiah, Y. Sun, C. M. Peterson and J. Kopeček, Biodistribution of free and N-(2-hydroxypropyl)methacrylamide copolymer-bound mesochlorin e6 and adriamycin in nude mice bearing human ovarian carcinoma OVCAR-3 xenografts, J. Controlled Release, 1999, 61, 145–157.

    Article  CAS  Google Scholar 

  94. Z-R. Lu, P. Kopečková and J. Kopeček, Polymerizable antibody Fab’ antibody fragments for targeting of anticancer drugs, Nat. Biotechnol., 1999, 17, 1101–1104.

    Article  CAS  PubMed  Google Scholar 

  95. Z-R. Lu, J-G. Shiah, P. Kopečková and J. Kopeček, Preparation and biological evaluation of polymerizable antibody Fab’ fragment targeted polymeric drug delivery system, J. Controlled Release, 2001, 74, 263–268.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Hull, Cottingham Road, Kingstonupon-Hull, HU6 7RX, UK

    Aaron J. Bullous, Cristina M. A. Alonso & Ross W. Boyle

Authors
  1. Aaron J. Bullous
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cristina M. A. Alonso
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ross W. Boyle
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ross W. Boyle.

Additional information

This article is published as part of a themed issue on immunological aspects and drug delivery technologies in PDT.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bullous, A.J., Alonso, C.M.A. & Boyle, R.W. Photosensitiser—antibody conjugates for photodynamic therapy. Photochem Photobiol Sci 10, 721–750 (2011). https://doi.org/10.1039/c0pp00266f

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c0pp00266f

Search

Navigation