2,6,8-Trisubstituted 3-Hydroxychromone Derivatives as Fluorophores for Live-Cell Imaging

被引:28
作者
Dyrager, Christine [1 ]
Friberg, Annika [1 ]
Dahlen, Kristian [1 ]
Friden-Saxin, Maria [1 ]
Borjesson, Karl [2 ]
Wilhelmsson, L. Marcus [2 ]
Smedh, Maria [3 ]
Grotli, Morten [1 ]
Luthman, Kristina [1 ]
机构
[1] Univ Gothenburg, Dept Chem Med Chem, S-41296 Gothenburg, Sweden
[2] Chalmers, Dept Chem & Biol Engn Phys Chem, S-41296 Gothenburg, Sweden
[3] Univ Gothenburg, Sahlgrenska Acad, Ctr Cellular Imaging, S-40530 Gothenburg, Sweden
基金
瑞典研究理事会;
关键词
cellular imaging; excited-state intramolecular proton transfer (ESIPT); fluorescence; fluorophores; hydroxychromones; STATE PROTON-TRANSFER; INTRAMOLECULAR EXCITED-STATE; PHOSPHOLIPID-MEMBRANES; FLUORESCENCE PROBES; SURFACE-CHARGE; DUAL EMISSION; 3-HYDROXYFLAVONE; DYES; PERTURBATION; HYDRATION;
D O I
10.1002/chem.200900279
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We present the synthesis and photophysical characterisation of a series of structurally diverse, fluorescent 2,6,8-trisubstituted 3-hydroxychromone derivatives with high fluorescence quantum yields and molar extinction coefficients. Two of these derivatives (9 and 10a) have been studied as fluorophores for cellular imaging in HeLa cells and show excellent permeability and promising fluorescence properties in a cellular environment. In addition, we have demonstrated by photophysical characterisation of 3-isobutyroxychromone derivatives that esterification of the 3-hydroxyl group results in acceptable and useful fluorescence properties.
引用
收藏
页码:9417 / 9423
页数:7
相关论文
共 35 条
[1]   Heat perturbation of bovine eye lens α-crystallin probed by covalently attached ratiometric fluorescent dye 4′-diethylamino-3-hydroxyflavone [J].
Avilov, SV ;
Bode, C ;
Tolgyesi, FG ;
Klymchenko, AS ;
Fidy, J ;
Demchenko, AR .
BIOPOLYMERS, 2005, 78 (06) :340-348
[2]   REVERSAL OF EXCITATION BEHAVIOR OF PROTON-TRANSFER VS CHARGE-TRANSFER BY DIELECTRIC PERTURBATION OF ELECTRONIC MANIFOLDS [J].
CHOU, PT ;
MARTINEZ, ML ;
CLEMENTS, JH .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (11) :2618-2622
[3]   A scaffold approach to 3,6,8-trisubstituted flavones [J].
Dahlén, K ;
Grotli, M ;
Luthman, K .
SYNLETT, 2006, (06) :897-900
[4]   Synthesis of 2,3,6,8-tetrasubstituted chromone scaffolds [J].
Dahlen, Kristian ;
Wallen, Erik A. A. ;
Grotli, Morten ;
Luthman, Kristina .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :6863-6871
[5]   TITRIMETRIC AND EQUILIBRIUM STUDIES USING INDICATORS RELATED TO NILE BLUE A [J].
DAVIS, MM ;
HETZER, HB .
ANALYTICAL CHEMISTRY, 1966, 38 (03) :451-&
[6]   Synthesis and anti-rhinovirus activity of 2-styrylchromones [J].
Desideri, N ;
Conti, C ;
Mastromarino, P ;
Mastropaolo, F .
ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 2000, 11 (06) :373-381
[7]   Neutral fluorescence probe with strong ratiometric response to surface charge of phospholipid membranes [J].
Duportail, G ;
Klymchenko, A ;
Mely, Y ;
Demchenko, A .
FEBS LETTERS, 2001, 508 (02) :196-200
[8]   On the coupling between surface charge and hydration in biomembranes:: Experiments with 3-hydroxyflavone probes [J].
Duportail, G ;
Klymchenko, A ;
Mély, Y ;
Demchenko, AP .
JOURNAL OF FLUORESCENCE, 2002, 12 (02) :181-185
[9]   A peptide-based, ratiometric biosensor construct for direct fluorescence detection of a protein analyte [J].
Enander, Karin ;
Choulier, Laurence ;
Olsson, A. Linnea ;
Yushchenko, Dmytro A. ;
Kanmert, Daniel ;
Klymchenko, Andrey S. ;
Demchenko, Alexander P. ;
Mely, Yves ;
Altschuh, Daniele .
BIOCONJUGATE CHEMISTRY, 2008, 19 (09) :1864-1870
[10]   Novel two-color fluorescence probe with extreme specificity to bovine serum albumin [J].
Ercelen, S ;
Klymchenko, AS ;
Demchenko, AP .
FEBS LETTERS, 2003, 538 (1-3) :25-28