A novel photosensitizer, 2-butylamino-2-demethoxy-hypocrellin B (2-BA-2-DMHB) - its photodynamic effects on HeLa cells: efficacy and apoptosis.
A novel hypocrellin congener, 2-butylamino-2-demethoxy-hypocrellin B (2-BA-2-DMHB) was found to be an effective photosensitizer. Compared with its parent compound hypocrellin B (HB), its absorption bands extended toward longer wavelength and the extinction coefficients raised to some degree (lambda(max) (nm) (log(epsilon)): 463 (4.06), 583 (4.09), 621 (4.10) for 2-BA-2-DMHB and 466 (4.06), 548 (3.70), 580 (3.52) for HB). And it also had a much higher photopotentiation factor than HB (i.e., more than 250 versus 10 at a dose of 24 J cm(-2) of red light on HeLa cells). This might be correlated to the higher ability of superoxide anion generation and the higher cellular uptake of 2-BA-2-DMHB. Meanwhile, the examinations of Hoechst 33342-labeled nuclei, DNA fragmentation on agarose gel and flow cytometry showed that 2-BA-2-DMHB induces apoptosis in photosensitized HeLa cells more quickly than HB, which might be correlated to the higher cellular uptake of 2-BA-2-DMHB and the difference of their cellular localization. The study suggested that 2-BA-2-DMHB was a well-suited candidate for a new generation of photodynamic therapy photosensitizer.
Yang
H
H
Institute of Biophysics, Academia Sinica, Beijing, PRChina. yanghy@moon.ibp.ac.cn
Wu
T
T
Zhang
M
M
Zhang
Z
Z
D017209:Apoptosis; D001562:Benzimidazoles; D002467:Cell Nucleus / Q000378:metabolism / Q000473:pathology; D002470:Cell Survival; D053938:DNA Fragmentation; D004305:Dose-Response Relationship, Drug; D004587:Electrophoresis, Agar Gel; D005434:Flow Cytometry; D005456:Fluorescent Dyes; D006367:HeLa Cells / Q000187:drug effects* / Q000378:metabolism / Q000473:pathology; D006801:Humans; D008027:Light; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000494:pharmacology*; D011809:Quinones / Q000138:chemical synthesis / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism; D013053:Spectrophotometry; D019097:Spin Trapping
C437043:2-butylamino-2-demethoxy-hypocrellin B; D001562:Benzimidazoles; D005456:Fluorescent Dyes; D017319:Photosensitizing Agents; D011809:Quinones; D017382:Reactive Oxygen Species; D010569:Perylene; C017807:bisbenzimide ethoxide trihydrochloride; C064522:hypocrellin B