Volume 4 Supplement 2

Abstracts of the 16th International Charles Heidelberger Symposium on Cancer Research

Open Access

A nonconjugated naphthalene derivative of meso-tetra-(3-hydroxy)-phenyl-porphyrin as a sensitizer for photodynamic therapy

  • Abílio JFN Sobral1Email author,
  • Ana M Urbano2,
  • Pedro Silva1,
  • Sofia M Fonseca1,
  • Cláudia T Arranja1 and
  • Hugh D Burrows1
BMC Proceedings20104(Suppl 2):P25

DOI: 10.1186/1753-6561-4-S2-P25

Published: 24 September 2010

Photodynamic Therapy (PDT) is a clinical procedure that is showing promising results in the treatment of certain types of cancer, including melanomas, oesophageal and retinal cancers [14]. The search for molecules suitable for use in PDT is a field of continuing interest. These molecules need to possess certain characteristics, including high affinity for tumour tissues and intense absorption in a region where biological tissues are relatively transparent. Porphyrin derivatives have become prime targets as sensitizers with potential to become good PDT agents, and have already been in use for over a decade in clinical PDT (ex: Foscan®). We report the synthesis and characterization of a meso-tetra-(3-hydroxy)-phenyl-porphyrin (T(OH)PP) derivative to which a naphthyl isocyanate group was attached, giving the meso-tetra-(phenoxy-3-carbonyl-1-amino-naphthyl)-porphyrin (T(NAF)PP (Figure 1).

Figure 1

The synthesized compound showed considerably enhanced photostability compared with the parent T(OH)PP (photodegradation quantum yield 4.65 × 10-4). The photosensitizer triplet state is normally considered to be essential for PDT, and to lead to the formation of cytotoxic oxygen species [5, 6]. The lifetimes and quantum yields of the triplet state of T(NAF)PP were evaluated and presented typical values for this type of compounds. The quenching rate constant by molecular oxygen and singlet oxygen yield were also determined. The photodynamic effect in human carcinoma HT-29 cells was evaluated, and this novel porphyrin showed good properties as a sensitizer in photodynamic therapy with an in vitro cytotoxicity IC50 value of 6.80 μg mL-1 for 24 h incubation.

Authors’ Affiliations

Departmento de Química, Faculdade de Ciências e Tecnologia da Universidade de Coimbra (FCTUC)
Unidade de Química Física Molecular and Departamento de Ciências da Vida, Faculdade de Ciências e Tecnologia da Universidade de Coimbra (FCTUC)


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© Sobral et al; licensee BioMed Central Ltd. 2010

This article is published under license to BioMed Central Ltd.