Abstract
Hypocrellin A (HA), a perylenoquinone derivative, is an efficient phototherapeutic agent. The reaction of HA with Na 2SO 3 in alkaline solution under reflux led to the formation of the sodium salt of 14-dehydroxy-15-deacetyl-hypocrellin A-13-sulfonate (13-SO 3Na-DDHA). ESR studies in combination with chemical methods showed that 13-SO 3Na-DDHA was an active photosensitizer. An ESR spectrum, assigned to the semiquinone radical anion of 13-SO 3Na-DDHA was generated by illumination of a DMF buffer (1:1 by volume) solution of 13-SO 3Na-DDHA in the presence of a series of reductive biomaterials. Using 13-SO 3Na-DDHA as photosensitizer and 5,5-dimethyl-1-pyrroline- N-oxide (DMPO) as a spin trap, the ESR spectra of DMPO/S̊O 3 − radical adduct, ascorbyl radical and DMPO/O 2 ·− radical adduct were obtained. Singlet oxygen formed from 13-SO 3Na-DDHA photosensitization was detected by means of the 13-SO 3Na-DDHA photosensitized oxidation of anthracene and ESR spectroscopy. It was therefore concluded that the photodynamic actions of 13-SO 3Na-DDHA proceeded via both Type 1 and Type 2 reactions.
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