Chemistry on Boranils: An Entry to Functionalized Fluorescent Dyes

被引:88
作者
Frath, Denis [1 ]
Azizi, Sebastien [1 ]
Ulrich, Gilles [1 ]
Ziessel, Raymond [1 ]
机构
[1] CNRS, Ecole Chim Polymeres Mat Strasbourg ECPM, UMR 7515, Lab Chim Organ & Spect Avancees LCOSA, F-67087 Strasbourg 02, France
关键词
ISOTHIOCYANATE;
D O I
10.1021/ol3020573
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Boranil fluorophore bearing a nitro-phenyl group has been selectively reduced to its anilino form and then successfully converted to amide, imine, urea, and thiourea derivatives which are fluorescent dyes. Its isolated isothiocyanate intermediate derivative was used in a model labeling experiment with Bovine Serum Albumin (BSA). The purified labeled-BSA exhibits strong luminescence (Phi(f) = 47%) in a phosphate buffer at pH = 7.4.
引用
收藏
页码:4774 / 4777
页数:4
相关论文
共 27 条
  • [1] High Stokes Shift Anilido-Pyridine Boron Difluoride Dyes
    Araneda, Juan F.
    Piers, Warren E.
    Heyne, Belinda
    Parvez, Masood
    McDonald, Robert
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) : 12214 - 12217
  • [2] Addition of boranes to N-aryl-salicylaldimines: Intramolecular hydrogenation of imines
    Barnes, Stephanie S.
    Vogels, Christopher M.
    Decken, Andreas
    Westcott, Stephen A.
    [J]. DALTON TRANSACTIONS, 2011, 40 (17) : 4707 - 4714
  • [3] Synthesis and applications of Rhodamine derivatives as fluorescent probes
    Beija, Mariana
    Afonso, Carlos A. M.
    Martinho, Jose M. G.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2410 - 2433
  • [4] Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications
    Beverina, Luca
    Salice, Patrizio
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (07) : 1207 - 1225
  • [5] Fluorescent indicators based on BODIPY
    Boens, Noel
    Leen, Volker
    Dehaen, Wim
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) : 1130 - 1172
  • [6] Briand JP, 1988, LAB TECHNIQUES BIOCH, V19
  • [7] Evidence for hapten recognition in receptor-mediated intracellular uptake of a hapten-protein conjugate by murine macrophage
    Cherkuri, A
    Durack, G
    Voss, EW
    [J]. MOLECULAR IMMUNOLOGY, 1997, 34 (01) : 21 - 32
  • [8] Selective NIR chromophores: Bis(Pyrrolopyrrole) Cyanines
    Fischer, Georg M.
    Daltrozzo, Ewald
    Zumbusch, Andreas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) : 1406 - 1409
  • [9] Facile Synthesis of Highly Fluorescent Boranil Complexes
    Frath, Denis
    Azizi, Sebastien
    Ulrich, Gilles
    Retailleau, Pascal
    Ziessel, Raymond
    [J]. ORGANIC LETTERS, 2011, 13 (13) : 3414 - 3417
  • [10] Design and Synthesis of a New Class of Membrane-Permeable Triazaborolopyridinium Fluorescent Probes
    Hapuarachchige, Sudath
    Montano, Gilbert
    Ramesh, Chinnasamy
    Rodriguez, Delany
    Henson, Lauren H.
    Williams, Casey C.
    Kadavakkollu, Samuel
    Johnson, Dennis L.
    Shuster, Charles B.
    Arterburn, Jeffrey B.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (17) : 6780 - 6790