Synthesis and characterization of three novel amphiphilic aminated hypocrellins as photodynamic therapeutic agents.
To improve the amphiphilicities and red absorption of the hypocrellins, three novel 2-amino-2-demethoxy-hypocrellins were synthesized by the mild reactions of hypocrellin B with 4-(2-amino-ethyl)morpholine, N,N-dimethylethylenediamine and 1-(2-amino-ethyl)piperazine, respectively. The structures of these derivatives were characterized with proton nuclear magnetic resonance, infrared and mass spectra (MS). The ultraviolet-visible absorption and fluorescence spectra of the derivatives were measured and the new amino-substituted hypocrellins showed strong absorption in the domain of the phototherapeutic window (600-900 nm). Their amphiphilicities evaluated via the partition coefficients between n-octanol and phosphate-buffered saline buffer improved remarkably. Electron paramagnetic resonance spin-trapping measurements were used to investigate the photodynamic action of the three compounds in the presence of oxygen. Singlet oxygen (1O2) and superoxide anion radical (O2.-) generated by illuminating the hypocrellin derivatives in aerobic solution were observed.
Xu
Shangjie
S
Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, Peoples' Republic of China.
Chen
Shen
S
Zhang
Manhua
M
Shen
Tao
T
Zhang
Xiaoxing
X
Wang
Zhengping
Z
D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D019800:Phenol; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D017382:Reactive Oxygen Species; D013050:Spectrometry, Fluorescence
D017319:Photosensitizing Agents; D011809:Quinones; D017382:Reactive Oxygen Species; D019800:Phenol; D010569:Perylene; C048388:hypocrellin A