Reductive amination of 6-deoxy-6-formyl-beta -cyclodextrin with 5-(p-aminophenyl)-10,15,20-tris(p-sulfonatophenyl)porphyrin in the presence of an excess of sodium cyanoborohydride affords the hydrophilic cyclodextrin-porphyrin conjugate 3 in 23% yield. The structure of 3 was confirmed by NMR spectroscopy and mass spectrometry techniques. Compound 3 showed a marked tendency to dimerize in aqueous conditions via the formation of intermolecular porphyrin-cyclodextrin inclusion complexes and/or through electrostatic interactions. Information on the structure of these aggregates has been obtained by the use of circular dichroism and UV-vis spectroscopy. Aggregation can be avoided by the use of heptakis(2,3,6-tri-O-methyl)-beta -cyclodextrin (TM beta CD) that forms a 1:1 inclusion complex with compound 3.

Synthesis, characterization, and supramolecular properties of a hydrophilic porphyrin-beta-cyclodextrin conjugate

CAROFIGLIO, TOMMASO;FORNASIER, ROBERTO;TONELLATO, UMBERTO
2000

Abstract

Reductive amination of 6-deoxy-6-formyl-beta -cyclodextrin with 5-(p-aminophenyl)-10,15,20-tris(p-sulfonatophenyl)porphyrin in the presence of an excess of sodium cyanoborohydride affords the hydrophilic cyclodextrin-porphyrin conjugate 3 in 23% yield. The structure of 3 was confirmed by NMR spectroscopy and mass spectrometry techniques. Compound 3 showed a marked tendency to dimerize in aqueous conditions via the formation of intermolecular porphyrin-cyclodextrin inclusion complexes and/or through electrostatic interactions. Information on the structure of these aggregates has been obtained by the use of circular dichroism and UV-vis spectroscopy. Aggregation can be avoided by the use of heptakis(2,3,6-tri-O-methyl)-beta -cyclodextrin (TM beta CD) that forms a 1:1 inclusion complex with compound 3.
2000
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11577/2433094
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