HEMATOPORPHYRIN

The Uses of HEMATOPORPHYRIN

Hematoporphyrin (Photodyn, Sensibion) is a porphyrin prepared from hemin. It is a derivative of protoporphyrin IX, where the two vinyl groups have been hydrated (coverted to alcohols). It is used as a photosensitizer in photodynamic therapy. Acetylation of hematoporphyrin followed by hydrolysis of the product of that reaction affords a mixture called hematoporphyrin derivative (HPD), which is also used in photodynamic therapy. Hematoporphyrin has also been used as an antidepressant and antipsychotic since the 1920s.

The Uses of HEMATOPORPHYRIN

antidepressant, antineoplastic

Definition

ChEBI: A dicarboxylic acid that is protoporphyrin in which the vinyl groups at positions 7 and 12 are replaced by 1-hydroxyethyl groups.

Hazard

Toxic. Reported to be preferentially absorbed by cancerous tissues, making them fluoresce under UV light.

Purification Methods

Purify it by dissolving it in EtOH Hematoporphyrin and adding H2O or Et2O to give deep red crystals. It has also been recrystallised from MeOH. UV has max at 615.5, 565, 534.4 and 499.5nm in 0.1N NaOH, and 597, 619, 634, 653, 683 and 701nm in 2N HCl [Falk Porphyrins and Metalloporphyrins Elsevier, NY, p 175 1964, LCCCNo 63-19821.] It is used in the affinity chromatographic purification of Heme proteins [Olsen Methods Enzymol 123 324 1986]. The O-methyl-dimethyl ester has m 203-206o (from CHCl3/MeOH), and the O,O'-dimethyl-dimethyl ester has m 145o (from CHCl3/MeOH). [Paul Acta Chem Scand 5 389 1951, Beilstein 26 III/IV 3157, and 3158 for the HCl.]