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Title: Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients
Authors: 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. 
Keywords: Amphiphilic porphyrins synthesis; 1-Octanol/water partition coefficients; MALDI-TOFMS
Issue Date: 2008
Citation: Tetrahedron. 64:22 (2008) 5132-5138
Abstract: 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.
DOI: 10.1016/j.tet.2008.03.055
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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