Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

• Main Author: Monteiro, Carlos J. P.
• Publication Date: 2008
• Other Authors: Pereira, Mariette M., Pinto, Sara M. A., Simões, Ana V. C., Sá, Gonçalo F. F., Arnaut, Luís G., Formosinho, Sebastião J., Simões, Sérgio, Wyatt, Mark F.
• Format: Article
• Language: eng
• Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
• Download full: https://hdl.handle.net/10316/5012; https://doi.org/10.1016/j.tet.2008.03.055
• topic: Amphiphilic porphyrins synthesis; 1-Octanol/water partition coefficients; MALDI-TOFMS

Porphyrins are key precursors for development of photosensitizers for photodynamic therapy. A new series of ortho-halogenated tetraarylporphyrins with sulfonamide substituents have been synthesized via chlorosulfonation reaction and characterized by MALDI-TOFMS. To predict their partition properties, log KOW of a selected range of the synthesized halogenated amphiphilic porphyrins is described. A significant effect of the number and type of halogen group as well as on the number of sulfonamide side chain was observed. The determined 1-octanol/water partition coefficients showed that it is possible to obtain compounds with a wide range of lipophilicities, from log KOW=-2.71 till log KOW>4, which are suitable to optimize the biological efficacy of this class of sensitizers.