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Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins

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Abstract

The association of photosensitisers to peptides and proteins is a recognised and successful method for enhancing the selectivity and efficacy of photodynamic treatment. The covalent attachment of porphyrins and related macrocycles to peptides and proteins can generate new phototoxic species that allow the concentration of the oxidative damage to the target area, thanks to their enhanced cellular uptake, favourable sub-cellular distribution, and ability to target receptors or enzymes over-expressed by a given tissue or cell. The need to exert control over the regioselectivity of the conjugation led to the exploration of a variety of chemistries; in some cases based on bioorthogonal ligations, in others exploring the reactivity of naturally occurring functional groups. In this review we place a major emphasis on the synthetic strategies adopted to generate such conjugates. All such strategies will be surveyed, together with the methods used to introduce or unmask the appropriate reactive functionalities both on the peptide moiety and the photosensitiser.

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References

  1. I. J. MacDonald and T. J. Dougherty, J. Porphyrins Phthalocyanines, 2001, 5, 105–129.

    Article  CAS  Google Scholar 

  2. S. B. Brown, E. A. Brown and I. Walker, Lancet Oncol., 2004, 5, 497–508.

    Article  CAS  PubMed  Google Scholar 

  3. M. R. Hamblin and P. Mroz, Advances in Photodynamic Therapy: Basic, Translational, and Clinical, Artech House, Boston, 2008.

    Google Scholar 

  4. M. Magaraggia and G. Jori, in Advances in Photodynamic Therapy: Basic, Translational, and Clinical, ed. M. R. Hamblin and P. Mroz, Artech House, Boston, 2008, pp. 337–357.

  5. M. R. Hamblin and P. Mroz, in Advances in Photodynamic Therapy: Basic, Translational, and Clinical, ed. M. R. Hamblin and P. Mroz, Artech House, Boston, 2008, pp. 1–12.

  6. J. Fang, H. Nakamura and H. Maeda, Adv. Drug Delivery Rev., 2010, DOI: 10.1016/j.addr.2010.04.009.

    Google Scholar 

  7. A. K. Iyer, G. Khaled, J. Fang and H. Maeda, Drug Discovery Today, 2006, 11, 812–818.

    Article  CAS  PubMed  Google Scholar 

  8. L. B. Josefsen and R. W. Boyle, Br. J. Pharmacol., 2008, 154, 1–3.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. K. Lang, J. Mosinger and D. M. Wagnerová, Coord. Chem. Rev., 2004, 248, 321–350.

    Article  CAS  Google Scholar 

  10. J. Piette, M. Paule, M. Louis and J. Decuyper, Photochem. Photobiol., 1986, 44, 793–802.

    Article  CAS  PubMed  Google Scholar 

  11. M. R. Hamblin, in Advances in Photodynamic Therapy: Basic, Translational, and Clinical, ed. M. R. Hamblin and P. Mroz, Artech House, Boston, 2008, pp. 193–215.

  12. X. Chen and C. M. Drain, Drug Des. Rev.–Online, 2004, 1, 215–234.

    Article  CAS  Google Scholar 

  13. A. A. Aksenova, Y. L. Sebyakin and A. F. Mironov, Russ. J. Bioorg. Chem., 2003, 29, 201–219.

    Article  CAS  Google Scholar 

  14. X. Zheng and R. K. Pandey, Anti-Cancer Agents Med. Chem., 2008, 8, 241–268.

    Article  CAS  Google Scholar 

  15. M. Balaz, J. D. Steinkruger, G. A. Ellestad and N. Berova, Org. Lett., 2005, 7, 5613–5616.

    Article  CAS  PubMed  Google Scholar 

  16. Lorenzo D. Napoli, Stefania D. Luca, Giovanni D. Fabio, A. Messere, D. Montesarchio, G. Morelli, G. Piccialli and D. Tesauro, Eur. J. Org. Chem., 2000, 2000, 1013–1018.

    Article  Google Scholar 

  17. P. Ray and R. R. White, Pharmaceuticals, 2010, 3, 1761–1778.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. J. Zhou, B. Soontornworajit, J. Martin, B. A. Sullenger, E. Gilboa and Y. Wang, Macromol. Biosci., 2009, 9, 831–835.

    Article  CAS  PubMed  Google Scholar 

  19. P. Mallikaratchy, Z. Tang and W. Tan, Chem Med Chem, 2008, 3, 425–428.

    Article  CAS  PubMed  Google Scholar 

  20. R. Schneider, F. Schmitt, C. Frochot, Y. Fort, N. Lourette, F. Guillemin, J.-F. Müller and M. Barberi-Heyob, Bioorg. Med. Chem., 2005, 13, 2799–2808.

    Article  CAS  PubMed  Google Scholar 

  21. E. Girgenti, R. Ricoux and J.-P. Mahy, Tetrahedron, 2004, 60, 10049–10058.

    Article  CAS  Google Scholar 

  22. M. Sibrian-Vazquez, T. J. Jensen and M. G. H. Vicente, Bioconjugate Chem., 2007, 18, 1185–1193.

    Article  CAS  Google Scholar 

  23. M. R. Hamblin, in Advances in Photodynamic Therapy: Basic, Translational, and Clinical, ed. M. R. Hamblin and P. Mroz, Artech House, Boston, 2008, pp. 217–233.

  24. R. Schneider, L. Tirand, C. Frochot, R. Vanderesse, N. Thomas, J. Gravier, F. Guillemin and M. Barberi-Heyob, Anti-Cancer Agents Med. Chem., 2006, 6, 469–488.

    Article  CAS  Google Scholar 

  25. N. Sewald and H.-D. Jakubke, Application of Peptides and Proteins, Wiley-VCH Verlag GmbH & Co. KGaA, Darmstadt, 2009.

    Book  Google Scholar 

  26. T. K. Tiefenbrunn and P. E. Dawson, Peptide Sci., 2010, 94, 95–106.

    Article  CAS  Google Scholar 

  27. R. K. V. Lim and Q. Lin, Chem. Commun., 2010, 46, 1589–1600.

    Article  CAS  Google Scholar 

  28. J. A. Prescher and C. R. Bertozzi, Nat. Chem. Biol., 2005, 1, 13–21.

    Article  CAS  PubMed  Google Scholar 

  29. R. H. Grubbs, Tetrahedron, 2004, 60, 7117–7140.

    Article  CAS  Google Scholar 

  30. R. H. Grubbs, Angew. Chem., Int. Ed., 2006, 45, 3760–3765.

    Article  CAS  Google Scholar 

  31. K. Kirshenbaum and P. S. Arora, Nat. Chem. Biol., 2008, 4, 527–528.

    Article  CAS  PubMed  Google Scholar 

  32. Y. A. Lin, J. M. Chalker and B. G. Davis, ChemBioChem, 2009, 10, 959–969.

    Article  CAS  PubMed  Google Scholar 

  33. V. Sol, V. Chaleix, R. Granet and P. Krausz, Tetrahedron, 2008, 64, 364–371.

    Article  CAS  Google Scholar 

  34. Y. Ikawa, H. Harada, M. Toganoh and H. Furuta, Bioorg. Med. Chem. Lett., 2009, 19, 2448–2452.

    Article  CAS  PubMed  Google Scholar 

  35. N. Umezawa, N. Matsumoto, S. Iwama, N. Kato and T. Higuchi, Bioorg. Med. Chem., 2010, 18, 6340–6350.

    Article  CAS  PubMed  Google Scholar 

  36. E. Saxon, J. I. Armstrong and C. R. Bertozzi, Org. Lett., 2000, 2, 2141–2143.

    Article  CAS  PubMed  Google Scholar 

  37. M. B. Soellner, A. Tam and R. T. Raines, J. Org. Chem., 2006, 71, 9824–9830.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. G. T. Hermanson, Bioconjugate techniques, Academic Press, San Diego, 2008.

    Google Scholar 

  39. S. Asayama, E. Kawamura, S. Nagaoka and H. Kawakami, Mol. Pharmaceutics, 2006, 3, 468–470.

    Article  CAS  Google Scholar 

  40. J. Bernadou, G. Pratviel, F. Bennis, M. Girardet and B. Meunier, Biochemistry, 1989, 28, 7268–7275.

    Article  CAS  PubMed  Google Scholar 

  41. G. Pratviel, M. Pitieè, J. Bernadou and B. Meunier, Nucleic AcidsRes., 1991, 19, 6283–6288.

    Article  CAS  Google Scholar 

  42. L. Chaloin, P. Bigey, C. Loup, M. Marin, N. Galeotti, M. Piechaczyk, F. Heitz and B. Meunier, Bioconjugate Chem., 2001, 12, 691–700.

    Article  CAS  Google Scholar 

  43. G. R. Geier and T. Sasaki, Tetrahedron Lett., 1997, 38, 3821–3824.

    Article  CAS  Google Scholar 

  44. T. Arai, M. Inudo, T. Ishimatsu, C. Akamatsu, Y. Tokusaki, T. Sasaki and N. Nishino, J. Org. Chem., 2003, 68, 5540–5549.

    Article  CAS  PubMed  Google Scholar 

  45. R. Z. Renno, Y. Terada, M. J. Haddadin, N. A. Michaud, E. S. Gragoudas and J. W. Miller, Arch. Ophthalmol., 2004, 122, 1002–1011.

    Article  CAS  PubMed  Google Scholar 

  46. D. Gabriel, M. A. Campo, R. Gurny and N. Lange, Bioconjugate Chem., 2007, 18, 1070–1077.

    Article  CAS  Google Scholar 

  47. D. Gabriel, N. Busso, A. So, H. van den Bergh, R. Gurny and N. Lange, J. Controlled Release, 2009, 138, 225–234.

    Article  CAS  Google Scholar 

  48. M. A. Campo, D. Gabriel, P. Kucera, R. Gurny and N. Lange, Photochem. Photobiol., 2007, 83, 958–965.

    Article  CAS  PubMed  Google Scholar 

  49. C. Dubuc, R. Langlois, F. Bénard, N. Cauchon, K. Klarskov, P. Tone and J. E. van Lier, Bioorg. Med. Chem. Lett., 2008, 18, 2424–2427.

    Article  CAS  PubMed  Google Scholar 

  50. M. Boisbrun, R. Vanderesse, P. Engrand, A. Olié, S. Hupont, J.-B. Regnouf-de-Vains and C. Frochot, Tetrahedron, 2008, 64, 3494–3504.

    Article  CAS  Google Scholar 

  51. J. R. Starkey, A. K. Rebane, M. A. Drobizhev, F. Meng, A. Gong, A. Elliott, K. McInnerney and C. W. Spangler, Clin. Cancer Res., 2008, 14, 6564–6573.

    Article  CAS  PubMed  Google Scholar 

  52. T. Arai, N. Maruo, Y. Sumida, C. Korosue and N. Nishino, Chem. Commun., 1999, 1503–1504.

    Google Scholar 

  53. T. Arai, K. Araki, N. Maruo, Y. Sumida, C. Korosue, K. Fukuma, T. Kato and N. Nishino, New J. Chem., 2004, 28, 1151–1159.

    Article  CAS  Google Scholar 

  54. Y. Choi, J. R. McCarthy, R. Weissleder and C.-H. Tung, ChemMed-Chem, 2006, 1, 458–463.

    Article  CAS  Google Scholar 

  55. S. Rahimipour, N. Ben-Aroya, K. Ziv, A. Chen, M. Fridkin and Y. Koch, J. Med. Chem., 2003, 46, 3965–3974.

    Article  CAS  PubMed  Google Scholar 

  56. S. Rahimipour, N. Ben-Aroya, M. Fridkin and Y. Koch, J. Med. Chem., 2001, 44, 3645–3652.

    Article  CAS  PubMed  Google Scholar 

  57. R. I. Dmitriev, A. V. Zhdanov, G. V. Ponomarev, D. V. Yashunski and D. B. Papkovsky, Anal. Biochem., 2010, 398, 24–33.

    Article  CAS  PubMed  Google Scholar 

  58. R. I. Dmitriev, H. M. Ropiak, D. V. Yashunsky, G. V. Ponomarev, A. V. Zhdanov and D. B. Papkovsky, FEBS J., 2010, 277, 4651–4661.

    Article  CAS  PubMed  Google Scholar 

  59. A. E. Soini, D. V. Yashunsky, N. J. Meltola and G. V. Ponomarev, Luminescence, 2003, 18, 182–192.

    Article  CAS  PubMed  Google Scholar 

  60. L. Qiu and Y. Bae, Pharm. Res., 2006, 23, 1–30.

    Article  CAS  PubMed  Google Scholar 

  61. J. P. C. Tomé, M. G. P. M. S. Neves, A. C. Tomé, J. A. S. Cavaleiro, M. Soncin, M. Magaraggia, S. Ferro and G. Jori, J. Med. Chem., 2004, 47, 6649–6652.

    Article  PubMed  CAS  Google Scholar 

  62. N. S. Soukos, L. A. Ximenez-Fyvie, M. R. Hamblin, S. S. Socransky and T. Hasan, Antimicrob. Agents Chemother., 1998, 42, 2595–2601.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  63. N. S. Soukos, M. R. Hamblin and T. Hasan, Photochem. Photobiol., 1997, 65, 723–729.

    Article  CAS  PubMed  Google Scholar 

  64. L. Polo, A. Segalla, G. Bertoloni, G. Jori, K. Schaffner and E. Reddi, J. Photochem. Photobiol., B, 2000, 59, 152–158.

    Article  CAS  Google Scholar 

  65. C. Frochot, B. D. Stasio, R. Vanderesse, M.-J. Belgy, M. Dodeller, F. Guillemin, M.-L. Viriot and M. Barberi-Heyob, Bioorg. Chem., 2007, 35, 205–220.

    Article  CAS  PubMed  Google Scholar 

  66. F. Nastri, A. Lombardi, G. Morelli, O. Maglio, G. D’Auria, C. Pedone and V. Pavone, Chem.–Eur. J., 1997, 3, 340–349.

    Article  CAS  Google Scholar 

  67. M. Sibrian-Vazquez, T. J. Jensen, F. R. Fronczek, R. P. Hammer and M. G. H. Vicente, Bioconjugate Chem., 2005, 16, 852–863.

    Article  CAS  Google Scholar 

  68. M. Sibrian-Vazquez, I.V. Nesterova, T. J. Jensen and M. G. H. Vicente, Bioconjugate Chem., 2008, 19, 705–713.

    Article  CAS  Google Scholar 

  69. M. Sibrian-Vazquez, E. Hao, T. J. Jensen and M. G. H. Vicente, Bioconjugate Chem., 2006, 17, 928–934.

    Article  CAS  Google Scholar 

  70. M. Sibrian-Vazquez, T. J. Jensen, R. P. Hammer and M. G. H. Vicente, J. Med. Chem., 2006, 49, 1364–1372.

    Article  CAS  PubMed  Google Scholar 

  71. M. Sibrian-Vazquez, T. J. Jensen and M. G. a. H. Vicente, J. Med. Chem., 2008, 51, 2915–2923.

    Article  CAS  PubMed  Google Scholar 

  72. M. Sibrian-Vazquez, J. Ortiz, I. V. Nesterova, F. Fernandez-Lazaro, A. Sastre-Santos, S. A. Soper and M. G. H. Vicente, Bioconjugate Chem., 2007, 18, 410–420.

    Article  CAS  Google Scholar 

  73. P. Dozzo, M.-S. Koo, S. Berger, T. M. Forte and S. B. Kahl, J. Med. Chem., 2005, 48, 357–359.

    Article  CAS  PubMed  Google Scholar 

  74. I. Walker, D. I. Vernon and S. B. Brown, Bioorg. Med. Chem. Lett., 2004, 14, 441–443.

    Article  CAS  PubMed  Google Scholar 

  75. C. L. Conway, I. Walker, A. Bell, D. J. H. Roberts, S. B. Brown and D. I. Vernon, Photochem. Photobiol. Sci., 2008, 7, 290–298.

    Article  CAS  PubMed  Google Scholar 

  76. L. Tirand, C. Frochot, R. Vanderesse, N. Thomas, E. Trinquet, S. Pinel, M.-L. Viriot, F. Guillemin and M. Barberi-Heyob, J. Controlled Release, 2006, 111, 153–164.

    Article  CAS  Google Scholar 

  77. S. De Luca, D. Tesauro, P. Di Lello, R. Fattorusso, M. Saviano, C. Pedone and G. Morelli, J. Pept. Sci., 2001, 7, 386–394.

    Article  PubMed  Google Scholar 

  78. K. Stefflova, H. Li, J. Chen and G. Zheng, Bioconjugate Chem., 2007, 18, 379–388.

    Article  CAS  Google Scholar 

  79. G. Zheng, J. Chen, K. Stefflova, M. Jarvi, H. Li and B. C. Wilson, Proc. Natl. Acad. Sci. U. S. A., 2007, 104, 8989–8994.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  80. P.-C. Lo, J. Chen, K. Stefflova, M. S. Warren, R. Navab, B. Bandarchi, S. Mullins, M. Tsao, J. D. Cheng and G. Zheng, J. Med. Chem., 2009, 52, 358–368.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  81. J. Chen, K. Stefflova, M. J. Niedre, B. C. Wilson, B. Chance, J. D. Glickson and G. Zheng, J. Am. Chem. Soc., 2004, 126, 11450–11451.

    Article  CAS  PubMed  Google Scholar 

  82. J. Chen, T. W. B. Liu, P.-C. Lo, B. C. Wilson and G. Zheng, Bioconjugate Chem., 2009, 20, 1836–1842.

    Article  CAS  Google Scholar 

  83. T. A. Aguilera, E. S. Olson, M. M. Timmers, T. Jiang and R. Y. Tsien, Integr. Biol., 2009, 1, 371–381.

    Article  CAS  Google Scholar 

  84. N. Thomas, M. Pernot, R. Vanderesse, P. Becuwe, E. Kamarulzaman, D. Da Silva, A. François, C. Frochot, F. Guillemin and M. Barberi-Heyob, Biochem. Pharmacol., 2010, 80, 226–235.

    Article  CAS  PubMed  Google Scholar 

  85. L. Tirand, N. Thomas, M. Dodeller, D. Dumas, C. Frochot, B. Maunit, F. Guillemin and M. Barberi-Heyob, Drug Metab. Dispos., 2007, 35, 806–813.

    Article  CAS  PubMed  Google Scholar 

  86. N. Thomas, L. Tirand, E. Chatelut, F. Plenat, C. Frochot, M. Dodeller, F. Guillemin and M. Barberi-Heyob, Photochem. Photobiol. Sci., 2008, 7, 433–441.

    Article  CAS  PubMed  Google Scholar 

  87. V. Chaleix, V. Sol, Y.-M. Huang, M. Guilloton, R. Granet, Jean C. Blais and P. Krausz, Eur. J. Org. Chem., 2003, 2003, 1486–1493.

    Article  Google Scholar 

  88. V. Chaleix, V. Sol, M. Guilloton, R. Granet and P. Krausz, Tetrahedron Lett., 2004, 45, 5295–5299.

    Article  CAS  Google Scholar 

  89. T. Schröder, K. Schmitz, N. Niemeier, T. S. Balaban, H. F. Krug, U. Schepers and S. Bräse, Bioconjugate Chem., 2007, 18, 342–354.

    Article  CAS  Google Scholar 

  90. R. Dosselli, M. Gobbo, E. Bolognini, S. Campestrini and E. Reddi, ACS Med. Chem. Lett., 2010, 1, 35–38.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  91. S. K. Bisland, D. Singh and J. Gariépy, Bioconjugate Chem., 1999, 10, 982–992.

    Article  CAS  Google Scholar 

  92. M. E. Bakleh, V. Sol, K. Estieu-Gionnet, R. Granet, G. Déléris and P. Krausz, Tetrahedron, 2009, 65, 7385–7392.

    Article  CAS  Google Scholar 

  93. I. Sehgal, M. Sibrian-Vazquez and M. G. H. Vicente, J. Med. Chem., 2008, 51, 6014–6020.

    Article  CAS  PubMed  Google Scholar 

  94. M. R. Hamblin, D. A. O’Donnell, N. Murthy, K. Rajagopalan, N. Michaud, M. E. Sherwood and T. Hasan, J. Antimicrob. Chemother., 2002, 49, 941–951.

    Article  CAS  PubMed  Google Scholar 

  95. A. J. Bullous, C. M. A. Alonso and R. W. Boyle, Photochem. Photobiol. Sci., 2011, 10, DOI: 10.1039/c0pp00266f.

  96. M. Endo, M. Fujitsuka and T. Majima, Chem.–Eur. J., 2007, 13, 8660–8666.

    Article  CAS  PubMed  Google Scholar 

  97. Y. Chen, T. Parr, A. E. Holmes and K. Nakanishi, BioconjugateChem., 2008, 19, 5–9.

    Article  CAS  Google Scholar 

  98. A. Gijsens, L. Missiaen, W. Merlevede and P. de Witte, Cancer Res., 2000, 60, 2197–2202.

    CAS  PubMed  Google Scholar 

  99. A. Gijsens and P. de Witte, Int. J. Oncol., 1998, 13, 1171–1177.

    CAS  PubMed  Google Scholar 

  100. J. Khadem, A. A. Veloso, F. Tolentino, T. Hasan and M. R. Hamblin, Invest. Ophthalmol. Vis. Sci., 1999, 40, 3132–3137.

    CAS  PubMed  Google Scholar 

  101. M. R. Hamblin, J. L. Miller and B. Ortel, Photochem. Photobiol., 2000, 72, 533–540.

    Article  CAS  PubMed  Google Scholar 

  102. F. Anatelli, P. Mroz, Q. Liu, C. Yang, A. P. Castano, E. Swietlik and M. R. Hamblin, Mol. Pharmaceutics, 2006, 3, 654–664.

    Article  CAS  Google Scholar 

  103. N. Brasseur, R. Langlois, C. L. Madeleine, R. Ouellet and J. E. van Lier, Photochem. Photobiol., 1999, 69, 345–352.

    Article  CAS  PubMed  Google Scholar 

  104. P. Urizzi, C. M. Allen, R. Langlois, R. Ouellet, C. La Madeleine and J. E. Van Lier, J. Porphyrins Phthalocyanines, 2001, 5, 154–160.

    Article  CAS  Google Scholar 

  105. M. R. Hamblin and E. L. Newman, J. Photochem. Photobiol., B, 1994, 26, 45–56.

    Article  CAS  Google Scholar 

  106. M. R. Hamblin and E. L. Newman, J. Photochem. Photobiol., B, 1994, 26, 147–157.

    Article  CAS  Google Scholar 

  107. R. Laptev, M. Nisnevitch, G. Siboni, Z. Malik and M. A. Firer, Br. J. Cancer, 2006, 95, 189–196.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  108. U. Schmidt-Erfurth, H. Diddens, R. Birngruber and T. Hasan, Br. J. Cancer, 1997, 75, 54–61.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  109. P. G. Cavanaugh, Breast Cancer Res. Treat., 2002, 72, 117–130.

    Article  CAS  PubMed  Google Scholar 

  110. T. V. Akhlynina, A. A. Rosenkranz, D. A. Jans, P. V. Gulak, N. V. Sererryakova and A. S. Sobolev, Photochem. Photobiol., 1993, 58, 45–48.

    Article  CAS  PubMed  Google Scholar 

  111. T. V. Akhlynina, A. A. Rosenkranz, D. A. Jans and A. S. Sobolev, Cancer Res., 1995, 55, 1014–1019.

    CAS  PubMed  Google Scholar 

  112. T. V. Akhlynina, D. A. Jans, A. A. Rosenkranz, N. V. Statsyuk, I. Y. Balashova, G. Toth, I. Pavo, A. B. Rubin and A. S. Sobolev, J. Biol. Chem., 1997, 272, 20328–20331.

    Article  CAS  PubMed  Google Scholar 

  113. Y. Choi, R. Weissleder and C.-H. Tung, ChemMedChem, 2006, 1, 698–701.

    Article  CAS  PubMed  Google Scholar 

  114. Y. Choi, R. Weissleder and C.-H. Tung, Cancer Res., 2006, 66, 7225–7229.

    Article  CAS  PubMed  Google Scholar 

  115. A. A. Rosenkranz, V. G. Lunin, P. V. Gulak, O. V. Sergienko, M. A. Shumiantseva, O. L. Voronina, D. G. Gilyazova, A. P. John, A. A. Kofner, A. F. Mironov, D. A. Jans and A. S. Sobolev, FASEB J., 2003, 1121–1123.

    Google Scholar 

  116. J. M. Sutton, N. Fernandez and R. W. Boyle, J. Porphyrins Phthalocyanines, 2000, 4, 655–658.

    Article  CAS  Google Scholar 

  117. J. M. Sutton, O. J. Clarke, N. Fernandez and R. W. Boyle, Bioconjugate Chem., 2002, 13, 249–263.

    Article  CAS  Google Scholar 

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

    Francesca Giuntini, Cristina M. A. Alonso & Ross W. Boyle

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

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Giuntini, F., Alonso, C.M.A. & Boyle, R.W. Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins. Photochem Photobiol Sci 10, 759–791 (2011). https://doi.org/10.1039/c0pp00366b

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