Synthesis and cytotoxic studies of 5-O-(beta-glucopyranosyl)-2-nitrobenzyl caged L-leucyl-L-leucine methyl ester with increased solubility in PBS containing 1% DMSO.
We report the synthesis of a new type of a caged L-leucyl-L-leucine methyl ester, a sugar derivative 2, and study its photochemical and immunological properties. Compared with those of the previously reported o-nitrobenzyl caged compound, 1, and another new 4, 5-dimethoxy-2-nitorobenzyl caged compound 3, 2 was found to be almost 30 times more soluble in PBS containing 1% DMSO, and released leucyl-leucine methyl ester upon irradiation more efficiently than 1. Efficiency of induction of apoptosis of HL60 cells by irradiation of a solution containing 2 was only slightly lower than that by leucyl-leucine methyl ester itself.
Sakauchi
H
H
Department of Biomolecular Science, Faculty of Science, Toho University, Funabashi, Chiba, Japan.
Furuta
T
T
Kobayashi
Y
Y
Iwamura
M
M
D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D012995:Solubility
C105938:5-O-glucopyranosyl-2-nitrobenzyloxycarbonyl-leucyl-leucine methyl ester; D002219:Carbamates; D004151:Dipeptides; D004121:Dimethyl Sulfoxide