%0 Journal Article %T Design and Synthesis of a 4-Nitrobromobenzene Derivative Bearing an Ethylene Glycol Tetraacetic Acid Unit for a New Generation of Caged Calcium Compounds with Two-Photon Absorption Properties in the Near-IR Region and Their Application in Vivo %+ JST-CREST %+ Department of Chemistry, Graduate School of Science, Hiroshima University (HIRODAI) %+ Niigata University %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Laboratory of Structural Physiology, Graduate School of Medicine (CDBIM) %+ Laboratory of Structural Physiology (CDBIM) %A Jakkampudi,, Satish %A Abe, Manabu %A Komori, Naomitsu %A Tagaki, Ryukichi %A Furukawa, Ko %A Katan, Claudine %A Sawada, Wakako %A Takahashi, Noriko %A Kasai, Haruo %Z 24109008, Japan Society for the Promotion of Science %< avec comité de lecture %@ 2470-1343 %J ACS Omega %I ACS Publications %V 1 %N 2 %P 193–201 %8 2016-08-09 %D 2016 %R 10.1021/acsomega.6b00119 %M 31457124 %Z Chemical Sciences/Theoretical and/or physical chemistry %Z Chemical Sciences %Z Chemical Sciences/Inorganic chemistry %Z Chemical Sciences/Medicinal Chemistry %Z Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC]Journal articles %X Among biologically active compounds, calcium ions (Ca2+) are one of the most important species in cell physiological functions. Development of new calcium chelators with two-photon absorption (TPA) properties is a state-of-the-art challenge for chemists. In this study, we report the first and efficient synthesis of 5-bromo-2-nitrobenzyl-substituted ethylene glycol tetraacetic acid (EGTA) as a platform for a new generation of calcium chelators with TPA properties in the near-infrared region. New calcium chelators with high TPA properties, that is, a two-photon (TP) fragmentation efficiency of δu = 20.7 GM at 740 nm for 2-(4-nitrophenyl)benzofuran (NPBF)-substituted EGTA (NPBF-EGTA, Kd = 272 nM) and δu = 7.8 GM at 800 nm for 4-amino-4′-nitro-1,1′-biphenyl (BP)-substituted EGTA (BP-EGTA, Kd = 440 nM) derivatives, were synthesized using Suzuki–Miyaura coupling reactions of the bromide with benzofuran-2-boronic acid and 4-(dimethylamino)phenyl boronic acid, respectively. The corresponding acetoxymethyl (AM) esters were prepared and successfully applied to the Ca2+-uncaging reaction triggered by TP photolysis in vivo. %G English %2 https://univ-rennes.hal.science/hal-01395864/document %2 https://univ-rennes.hal.science/hal-01395864/file/acsomega_2016_1_193.pdf %L hal-01395864 %U https://univ-rennes.hal.science/hal-01395864 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ ISCR %~ ISCR-CTI %~ UR1-SPM %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ UR1-SDLM %~ TEST-UNIV-RENNES %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ UR1-MMS %~ TEST2-HALCNRS