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The α ,5‐Dicarboxy‐2‐nitrobenzyl Caging Group, a Tool for Biophysical Applications with Improved Hydrophilicity: Synthesis, Photochemical Properties and Biological Characterization
Author(s) -
Schaper Klaus,
Madani Mobarekeh Sayed Abdollah,
Doro Peter,
Maydt Daniela
Publication year - 2010
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2010.00803.x
Subject(s) - moiety , chemistry , functional group , derivative (finance) , photochemistry , group (periodic table) , combinatorial chemistry , characterization (materials science) , stereochemistry , organic chemistry , nanotechnology , materials science , financial economics , economics , polymer
Earlier we reported on the synthesis of α ,4‐dicarboxy‐2‐nitrobenyzl caged compounds (Schaper, K. et al. [2002] Eur. J. Org. Chem., 1037–1046). These compounds have the advantage of an increased hydrophilicity compared with the well‐established α ‐carboxy‐2‐nitrobenzyl caged compounds; however, the release of the active compound becomes slower due to the introduction of the additional carboxy group. Based upon theoretical calculations we predicted that the release would become faster when the additional carboxy group is moved to the 5‐position. Here we describe the synthesis and the photochemical and biological characterization of an α ,5‐dicarboxy‐2‐nitrobenyzl caged compound. The high hydrophilicity of the new caging group is maintained due to the fact that the additional carboxy moiety is preserved, while the release of the active species from the new derivative is even faster than for the reference, an α ‐CNB caged compound.