Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS charac...

• Author(s): Monteiro, Carlos J. P. ; 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.
• Date: 2008
• Persistent ID: http://hdl.handle.net/10316/5012
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): Amphiphilic porphyrins synthesis; 1-Octanol/water partition coefficients; MALDI-TOFMS
• Document Type: Article
• Language: English

Description

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. http://www.sciencedirect.com/science/article/B6THR-4S3S2CR-3/1/354752ab2cc5e753ede41d0a4595c5a6