Synthesis, characterization and photodynamic activity of phenmethylamino-demethoxy-hypocrellin B.
Two phenmethylamino hypocrellin B derivatives are novel photodynamic agents synthesized by a mild reaction between hypocrellin B and phenmethylamine. The red absorption of the photosensitizers is enlarged distinctly and the peri-hydroxylated perylenequinone structure of the parent HB is preserved. 9,10-diphenyl-anthracene (DPA) bleaching and electron paramagnetic resonance (EPR) spin trapping techniques were used to study the photodynamic activities of the phenmethylamino hypocrellin B derivatives in the presence of oxygen. Singlet oxygen (1O2) and superoxide anion radical (O2*-) generated in the process of illumination of the phenmethylamino hypocrellin B in aerobic solution were observed. The photodamage of PMAHBs to MGC803 cancer cells was investigated in vitro. The results in vitro reveal that the phenmethylamino hypocrellin B derivatives show a much less significant decrease in cytotoxicity than that of their parent HB. It exhibits higher selectivity of light-orientation, which can decrease the damage to normal tissues by irradiating the tumor tissues, and so increases the drug safety.
Xu
Shangjie
S
Center for Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China.
Chen
Shen
S
Zhang
Manhua
M
Shen
Tao
T
D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects / Q000502:physiology / Q000528:radiation effects; D004305:Dose-Response Relationship, Drug; D006801:Humans; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology*; D010775:Photic Stimulation / Q000379:methods; D010778:Photochemotherapy / Q000379:methods; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D011809:Quinones / Q000138:chemical synthesis* / Q000494:pharmacology*
D017319:Photosensitizing Agents; D011809:Quinones; D010569:Perylene; C064522:hypocrellin B