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RESEARCH ARTICLE
Contents Vol 64(7)

Porphyrin–Phosphoramidate Conjugates: Synthesis, Photostability and Singlet Oxygen Generation

Leandro F. Pedrosa A B , Marcos C. de Souza B , Maria A. F. Faustino A , Maria G. P. M. S. Neves A , Artur M. S. Silva A , Augusto C. Tomé A , Vitor F. Ferreira B and José A. S. Cavaleiro A C
+ Author Affiliations
- Author Affiliations

A Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal.

B Departamento de Química Orgânica, Universidade Federal Fluminense, 24020-141 Niterói, Rio de Janeiro, Brazil.

C Corresponding author. Email: jcavaleiro@ua.pt

Australian Journal of Chemistry 64(7) 939-944 https://doi.org/10.1071/CH11013
Submitted: 7 January 2011  Accepted: 29 March 2011   Published: 19 July 2011

Abstract

meso-Tetrakis(pentafluorophenyl)porphyrin reacts with aminoalkylphosphoramidates to afford porphyrins substituted with one or four phosphoramidate groups in the 4-position of the meso-aryl groups. The new porphyrin derivatives show high photostability and some are better singlet oxygen generators than meso-tetrakis(1-methylpyridinium-4-yl)porphyrin, a well known good singlet oxygen producer.


References

[1]  J. A. S. Cavaleiro, A. C. Tomé, M. G. P. M. S. Neves, in Handbook of Porphyrin Science, (Ed. K. M. Kadish, K. M. Smith, R. Guilard) 2010, Vol 2. Ch. 9, pp. 194–294 (World Scientific: Singapore).

[2]  K. M. Kadish, K. M. Smith, R. Guilard, Eds, The Porphyrin Handbook 2000, Vol. 1–20 (Academic Press: San Diego, CA).

[3]     (a) (a) R. Bonnett, in Chemical Aspects of Photodynamic Therapy 2000, p. 177 (Gordon and Breach Science Publishers: London).
         (b) (b) R. K. Pandey, G. Zheng, in The Porphyrin Handbook (Eds K. M. Kadish, K. M. Smith, R. Guilard), 2000, Vol. 6, Ch. 43 (Academic Press: San Diego, CA).
         (c) (c) J. G. Moser, Photodynamic Tumour Therapy 2nd and 3rd Generation Photosensitizers, 1998 (Harwood Academic: Amsterdam).

[4]  (a) S. R. Rajski, R. M. Williams, Chem. Rev. 1998, 98, 2723.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXntVeru70%3D&md5=b3aa1342876bd9ced77a5e7d026e3fbeCAS |
      (b) E. De Clercq, A. Holý, Nat. Rev. Drug Discov. 2005, 4, 928.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. Fernandes, R. S. Leite, F. M. Lanças, Quim. Nova 2005, 28, 274.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) E. De Clercq, Antiviral Res. 2007, 75, 1.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) E. De Clercq, Biochem. Pharmacol. 2007, 73, 911.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) V. Král, O. Rusin, J. Charvátová, P. Anzenbacher, J. Fogl, Tetrahedron Lett. 2000, 41, 10147.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) J. Charvátová, O. Rusin, V. Král, K. Volka, P. Matejka, Sens. Actuators B Chem. 2001, 76, 366.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) V. Y. Pavlov, M. M. Kabachnik, E. V. Zobnina, V. P. Timofeev, I. O. Konstantinov, B. G. Kimel, G. V. Ponomarev, I. P. Beletskaya, Synlett 2003, 2193.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Habdas, B. Boduszek, Heteroatom Chem. 2008, 19, 107.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. W. Easson, F. R. Fronczek, T. J. Jensen, M. G. H. Vicente, Bioorg. Med. Chem. 2008, 16, 3191.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. Habdas, B. Boduszek, J. Pept. Sci. 2009, 15, 305.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) S. V. Bhosale, M. B. Kalyankar, S. J. Langford, S. V. Bhosale, R. F. Oliver, Eur. J. Org. Chem. 2009, 4128.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) L. Czuchajowski, J. Habdas, H. Niedbala, V. Wandrekar, J. Heterocycl. Chem. 1992, 29, 479.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XkslShs74%3D&md5=d84471856b088553fefcdf0f22b22287CAS |
      (b) B. Boduszek, Phosphorus, Sulfur. Silicon 2001, 176, 119.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. Lauceri, M. De Napoli, A. Mammana, S. Nardis, A. Romeo, R. Purrello, Synth. Met. 2004, 147, 49.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. A. Libera, R. W. Gurney, S. T. Nguyen, J. T. Hupp, C. Liu, R. Conley, M. J. Bedzyk, Langmuir 2004, 20, 8022.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. E. Borbas, V. Chandrashaker, C. Muthiah, H. L. Kee, D. Holten, J. S. Lindsey, J. Org. Chem. 2008, 73, 3145.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. Habdas, B. Boduszek, J. Pept. Sci. 2009, 15, 305.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) C. McGuigan, H. W. Tsang, D. Cahard, K. Turner, S. Velazquez, A. Salgado, L. Bidois, L. Naesens, E. De Clercq, J. Balzarini, Antiviral Res. 1997, 35, 195.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXltl2nt7k%3D&md5=1e1a737752381a8c486c05ad126654c7CAS |
      (b) C. Ballatore, C. McGuigan, E. De Clercq, J. Balzarini, Bioorg. Med. Chem. Lett. 2001, 11, 1053.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) T. S. Torres, W. P. de Macedo, L. F. Pedrosa, M. C. B. V. de Souza, V. F. Ferreira, A. C. Cunha, T. Fogel, F. C. Santos, I. P. Marques, I. C. P. Paixão, M. C. de Souza, Lett. Org. Chem. 2008, 5, 644.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) M. J. Sofia, D. Bao, W. Chang, J. Du, D. Nagarathnam, S. Rachakonda, P. G. Reddy, B. S. Ross, P. Wang, H. Zhang, S. Bansal, C. Espiritu, M. Keilman, A. M. Lam, H. M. M. Steuer, C. Niu, M. J. Otto, P. A. Furman, J. Med. Chem. 2010, 53, 7202.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) Z. Wang, C. Guo, W. Xie, C. Liu, C. Xiao, Z. Tan, Eur. J. Med. Chem. 2010, 45, 890.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhvF2qsLY%3D&md5=9a2dc73a59420bbe2e5c40032609a8f8CAS |
      (b) M. Endo, M. Fujitsuka, T. Majima, J. Org. Chem. 2008, 73, 1106.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  K. Börjesson, J. Wiberg, A. H. El-Sagheer, T. Ljungdahl, J. Martensson, T. Brown, B. Norden, B. Albinsson, ACS Nano 2010, 4, 5037.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  R. De Paula, D. Pinto, M. A. F. Faustino, M. G. P. M. S. Neves, J. A. S. Cavaleiro, J. Heterocycl. Chem. 2008, 45, 453.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjsVWrtL0%3D&md5=1203c140dbb9f6baac4fe88ebf6a0c43CAS |

[11]  M. Costa de Souza, W. P. Macedo, T. S. Torres, L. F. Pedrosa, H. G. Alt, Phosphorus, Sulfur, Silicon 2006, 181, 1885.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XntVCnsrw%3D&md5=99c1bd0891396406d8336eeaf662b3edCAS |

[12]  P. Battioni, O. Brigaud, H. Desvaux, D. Mansuy, T. G. Traylor, Tetrahedron Lett. 1991, 32, 2893.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXltFChsLk%3D&md5=7515a21fb2651afdeeed2a528eb48c2fCAS |

[13]  D. Samaroo, C. E. Soll, L. J. Todaro, C. M. Drain, Org. Lett. 2006, 8, 4985.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVShs7nE&md5=b28d9c204c5d107abcf98c8bd8afd0a0CAS |

[14]  (a) J. P. C. Tomé, M. G. P. M. S. Neves, A. C. Tomé, J. A. S. Cavaleiro, A. F. Mendonça, I. N. Pegado, R. Duarte, M. L. Valdeira, Bioorg. Med. Chem. 2005, 13, 3878.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) F. C. Santos, A. C. Cunha, M. C. B. V. Souza, A. C. Tomé, M. G. P. M. S. Neves, V. F. Ferreira, J. A. S. Cavaleiro, Tetrahedron Lett. 2008, 49, 7268.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. N. Silva, A. M. G. Silva, J. P. Tomé, A. O. Ribeiro, M. R. M. Domingues, J. A. S. Cavaleiro, A. M. S. Silva, M. G. P. M. S. Neves, A. C. Tomé, O. A. Serra, F. Bosca, P. Filipe, R. Santus, P. Morlière, Photochem. Photobiol. Sci. 2008, 7, 834.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) V. V. Serra, F. Camões, S. I. Vieira, M. A. F. Faustino, J. P. C. Tomé, D. C. G. A. Pinto, M. G. P. M. S. Neves, A. C. Tomé, A. M. S. Silva, E. F. C. Silva, J. A. S. Cavaleiro, Acta Chim. Slov. 2009, 56, 603.

[15]  (a) M. Jemli, Z. Alouini, S. Sabbahi, M. Gueddari, J. Environ. Monit. 2002, 4, 511.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xls1anur4%3D&md5=3323722fca8e5a07fa115d0aeb29d848CAS |
      (b) M. Merchat, G. Bertolini, P. Giacomini, A. Villanueva, G. Jori, J. Photochem. Photobiol. B 1996, 32, 153.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Merchat, J. D. Spikes, G. Bertoloni, G. Jori, J. Photochem. Photobiol. B 1996, 35, 149.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  A. J. MacRobert, S. G. Brown, D. Phillips, in Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use (Eds G. Bock, S. Harnett) 1989, p. 4 (Wiley: Chichester).