Quinoline-Derived Two-Photon-Sensitive Octupolar Probes

被引：7
|
作者：
Dunkel, Petra [1 ]
Petit, Morgane [1 ]
Dhinnane, Hamid [1 ]
Blanchard-Desce, Mireille [2 ]
Ogden, David [3 ]
Dalko, Peter I. [1 ]
机构：
[1] Univ Paris 05, Lab Chim & Biochim Pharmacol & Toxicol, 45 Rue St Peres, F-75270 Paris 06, France
[2] Univ Bordeaux, ISM CNRS UMR5255, Batiment A72,357 Cours Liberat, F-33405 Talence, France
[3] Univ Paris 05, Lab Physiol Cerebrale, 45 Rue St Peres, F-75270 Paris 06, France
来源：
CHEMISTRYOPEN | 2017年 / 6卷 / 05期
关键词：
caged compounds; nonlinear optics; photolysis; protecting groups; reactive intermediates; ENHANCED RAMAN-SCATTERING; UP-CONVERSION EMISSION; OPAL PHOTONIC CRYSTALS; PHOTOCATALYTIC ACTIVITY; GOLD NANOPARTICLE; SILICA SPHERES; POLYSTYRENE; AG; FABRICATION; SUBSTRATE;
D O I：
10.1002/open.201700097
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A systematic study on quinoline-derived light sensitive probes, having third-order rotational symmetry is presented. The electronically linked octupolar structures show considerably improved linear and nonlinear photophysical properties under one- and two-photon irradiation conditions compared to the corresponding monomers. Photolysis of the three acetate derivatives shows strong structure dependency: whereas irradiation of the 6- and 7-aminoquinoline derivatives resulted in fast intramolecular cyclization and only trace amounts of fragmentation products, the 8-aminoquinoline derivative afforded clean and selective photolysis, with a sequential release of their acetate groups (delta(730J)(0) = 0.67 GM).
引用
收藏
页码：660 / 667
页数：8
相关论文
共 50 条
  • [41] Two-Photon Polarity Probes Built from Octupolar Fluorophores: Synthesis, Structure-Properties Relationships, and Use in Cellular Imaging
    Le Droumaguet, Celine
    Sourdon, Aude
    Genin, Emilie
    Mongin, Olivier
    Blanchard-Desce, Mireille
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (12) : 2984 - 3001
  • [42] Two quinoline-based two-photon fluorescent probes for imaging of viscosity in subcellular organelles of living HeLa cells
    Yu, Feng-Tao
    Huang, Ze
    Yang, Jia-Xiang
    Yang, Long-Mei
    Xu, Xian-Yun
    Huang, Jian-Yan
    Kong, Lin
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2022, 283
  • [43] One/two-photon-sensitive photoacid generators based on benzene oligomer-containing D-π-A-type aryl dialkylsulfonium salts
    Jin, Ming
    Wu, Xingyu
    Xie, Jianchao
    Malval, Jean Pierre
    Wan, Decheng
    RSC ADVANCES, 2015, 5 (68): : 55340 - 55347
  • [44] Thermal and Photoinduced Radical Cascade Annulation using Aryl Isonitriles: An Approach to Quinoline-Derived Benzophosphole Oxides
    Banjare, Shyam Kumar
    Lezius, Lena
    Horst, Elena S.
    Leifert, Dirk
    Daniliuc, Constantin G.
    Alasmary, Fatmah A.
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (30)
  • [45] Development of Quinoline-Derived Chiral Diaminocarbene Ligands and Their Transition Metal Complexes: Synthesis, Structural Characterization, and Catalytic Properties
    Xu, Cong
    Feng, Yu
    Wang, Li-Ren
    Ma, Wen-Peng
    He, Yan-Mei
    Fan, Qing-Hua
    ORGANOMETALLICS, 2020, 39 (10) : 1945 - 1960
  • [46] Novel quinoline-derived mTOR inhibitors with remarkable enzymatic and cellular activities: design, synthesis and biological evaluation
    Ma, Xiao-Dong
    Qiu, Ni
    Yang, Bo
    He, Qiao-Jun
    Hu, Yong-Zhou
    MEDCHEMCOMM, 2016, 7 (02) : 297 - 310
  • [47] Discovery of quinoline-derived trifluoromethyl alcohols, and determining their in vivo toxicity and anticancer activity in zebrafish embryo model
    Lnu, Mohammed
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [48] Taming Janus-Faced Quinoline-Derived Fluorescent Probes for Dual-Channel Distinguishable Visualization of HSO3-° and HClO in Dried Foods and Living Cells
    Xu, Zi Yi
    Wang, Rong
    Xiao, Qi
    Luo, Hong Qun
    Li, Nian Bing
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (17) : 10097 - 10105
  • [49] Discovery of Quinoline-Derived Trifluoromethyl Alcohols, Determination of Their in vivo Toxicity and Anticancer Activity in a Zebrafish Embryo Model
    Sittaramane, Vinoth
    Padgett, Jihan
    Salter, Philip
    Williams, Ashley
    Luke, Shauntelle
    McCall, Rebecca
    Arambula, Jonathan F.
    Graves, Vincent B.
    Blocker, Mark
    Van Leuven, David
    Bowe, Keturah
    Heimberger, Julia
    Cade, Hannah C.
    Immaneni, Supriya
    Shaikh, Abid
    CHEMMEDCHEM, 2015, 10 (11) : 1802 - 1807
  • [50] Chemogenomic profiling of the cellular effects associated with histone H3 acetylation impairment by a quinoline-derived compound
    Ruotolo, Roberta
    Tosi, Federica
    Vernarecci, Stefano
    Ballario, Paola
    Mai, Antonello
    Filetici, Patrizia
    Ottonello, Simone
    GENOMICS, 2010, 96 (05) : 272 - 280
12345