Synthesis of caged compounds of L-leucyl-L-leucine methyl ester, an apoptosis inducer, and their cytotoxic activity.
In this study, we newly synthesized caged compounds of L-leucyl-L-leucine methyl ester and examined their photochemical and immunological properties. From the viewpoints of solubility in phosphate-buffered saline containing 1% dimethyl sulfoxide as well as photoreactivity, we chose two caged compounds, 1 and 2, for study. Upon irradiation, L-leucyl-L-leucine methyl ester with a trans-o-hydroxycinnamoyl group (1) releases L-leucyl-L-leucine methyl ester quite slowly, whereas L-leucyl-L-leucine methyl ester with an o-nitrobenzyl group (2) releases L-leucyl-L-leucine methyl ester quickly. Both irradiated compounds induced apoptosis of U937 cells, as evidenced by a decrease in cell size, although 1 itself caused necrosis (cell swelling) of these cells.
Odaka
M
M
Department of Biomolecular Science, Faculty of Science, Toho University, Chiba, Japan.
Furuta
T
T
Kobayashi
Y
Y
Iwamura
M
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000138:chemical synthesis* / Q000494:pharmacology; D003602:Cytotoxicity, Immunologic; D004121:Dimethyl Sulfoxide; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D005434:Flow Cytometry; D006801:Humans; D007166:Immunosuppressive Agents; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000494:pharmacology; D010782:Photolysis; D012995:Solubility; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D002934:Cinnamates; D004151:Dipeptides; D007166:Immunosuppressive Agents; D009578:Nitrobenzenes; C095196:hydroxycinnamoyl caged Leu-Leu-OMe; C095197:nitrobenzyl caged Leu-Leu-OMe; C045139:leucyl-leucine-methyl ester; D004121:Dimethyl Sulfoxide