title: The composition of Photofrin II.
abstract: The compositions of Photofrin II and haematoporphyrin derivative (HPD) were examined. Dihaematoporphyrin ester was unambiguously synthesized and shown by high performance liquid chromatography (HPLC) not to be a significant component of Photofrin II. Hydrolysis studies showed the presence of an acid-stable oligomer in Photofrin II which comprised about 40% of of an acid-stable oligomer in Photofrin II which comprised about 40% of the total sample. A dimer derivative was isolated from this oligomeric material by fully dehydrating the methyl-esterified acidic hydrolysis product of Photofrin II. The structure of this dimer, in which two porphyrin units are linked by a three-carbon bridge containing a double bond and a methyl group, was determined by nuclear magnetic resonance (NMR) and fast atom bombardment (FAB) mass spectrometry. An analogous trimer was also isolated and identified. Structures for the hydroxyl-containing precursors to the dimer and trimer, and for the acid-stable oligomeric material in Photofrin II, are suggested. The acid-stable oligomeric material is produced in the sodium hydroxide polymerization step of the preparation of Photofrin II.
authors: Department of Organic Chemistry, University of Adelaide, Australia.
authors: C J
authors: CJ
authors: Byrne
authors: L V
authors: LV
authors: Marshallsay
authors: A D
authors: AD
authors: Ward
mesh_terms: D017323:Dihematoporphyrin Ether; D006415:Hematoporphyrins / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
chemical_list: D006415:Hematoporphyrins; D017323:Dihematoporphyrin Ether