The α,5-dicarboxy-2-nitrobenzyl caging group, a tool for biophysical applications with improved hydrophilicity: synthesis, photochemical properties and biological characterization.
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.
Schaper
Klaus
K
Group for Organic Photochemistry, Institute for Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Düsseldorf, Düsseldorf, Germany. schaper@klaus-schaper.de
Madani Mobarekeh
Sayed Abdollah
SA
Doro
Peter
P
Maydt
Daniela
D
D055592:Biophysical Phenomena; D002460:Cell Line; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes
D009578:Nitrobenzenes