129618-96-8Relevant articles and documents
Synthesis, self-assembling properties and incorporation of carbohydrate-substituted porphyrins into cell membrane models
Schell, Christian,Hombrecher, Hermann K.
, p. 587 - 598 (2007/10/03)
A general and very efficient synthesis of new carbohydrate-substituted porphyrins is described. Reaction of porphyrin 6 with different glycosyl imidates 7a-g leads to the formation of carbohydrate-substituted porphyrins 9a-g in good yield. Subsequent demetallation and removal of the carbohydrate protection groups leads to the metal-free compounds 11a-g. In aqueous solution, compounds 11a-g tend to form defined water-soluble aggregates in a self-assembling process. In methanol/water mixtures the aggregation process depends upon the configuration of the anomeric carbon in the carbohydrate moiety. The porphyrinic aggregates are characterized by strong exciton splitting in the Soret absorption spectrum and a red shift for all absorption bands. Interaction of the porphyrinic aggregates with phosphatidylethanolamine and DMPC liposomes leads to very efficient incorporation of mainly monomeric porphyrins 11a-g into the liposomes, as was indicated by very large binding constants. At low liposome concentrations noncovalent porphyrin dimers were detected.
A novel approach to the synthesis of symmetrical and unsymmetrical porphyrin dimers
Pandey,Forsyth,Gerzevske,Lin,Smith
, p. 5315 - 5318 (2007/10/02)
Methodology for synthesis of symmetrical or unsymmetrical porphyrin dimers linked at the meso positions with phenyl or stilbene functionalities is reported; 5-porphyrinyl-dipyrromethanes are key intermediates in this approach.
