New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds
作者： Benoît Roubinet , Pierre-Yves Renard , Anthony Romieu
DOI: 10.1016/J.DYEPIG.2014.02.004
关键词:
摘要: Abstract The synthesis and photophysical properties of novel water-soluble phenol-based fluorophores derived from 3-benzothiazolyl-7-hydroxycoumarin emitting in the range 485–631 nm are described. Further conversion into thiol-sensitive fluorogenic probes through chemical modification their hydroxyl group was next investigated. Depending on type thiol-reactive quenching moiety used (2,4-dinitrobenzenesulfonyl ester, 2,4-dinitrophenyl ether or benzoquinone-type Michael acceptors) water-solubilizing group(s) pre-introduced coumarin core, dramatic differences thiol-induced fluorescence activation these pro-fluorophores under physiological conditions were observed. Results for this comparative study provide valuable informations selection most suitable structural features designing 7-hydroxycoumarin-based long-wavelength fluorescent thiol bioimaging.
sci-hub.se 参考文章(61)
Hongqi Li, Li Cai, Zhen Chen, None, Coumarin-Derived Fluorescent Chemosensors InTech. ,(2012) , 10.5772/33157
Kathrin-Maria Roy, Thiols and Organic Sulfides Ullmann's Encyclopedia of Industrial Chemistry. ,(2000) , 10.1002/14356007.A26_767
Todor Deligeorgiev, Teodora Tsvetkova, Stanislav Stanimirov, Synthesis of novel water-soluble fluorescent coumarins bearing sulphonic and hydroxyl groups Coloration Technology. ,vol. 127, pp. 434- 439 ,(2011) , 10.1111/J.1478-4408.2011.00340.X
Robert M Strongin, Lovemore Hakuna, Hanjing Peng, Weixuan Chen, Yunfeng Cheng, Binghe Wang, None, Thiol Reactive Probes and Chemosensors Sensors. ,vol. 12, pp. 15907- 15946 ,(2012) , 10.3390/S121115907
Lin Yuan, Weiying Lin, Kaibo Zheng, Longwei He, Weimin Huang, Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging Chemical Society Reviews. ,vol. 42, pp. 622- 661 ,(2013) , 10.1039/C2CS35313J
Qian Huang, Xiao-Feng Yang, Hua Li, A ratiometric fluorescent probe for hydrogen sulfide based on an excited-state intramolecular proton transfer mechanism Dyes and Pigments. ,vol. 99, pp. 871- 877 ,(2013) , 10.1016/J.DYEPIG.2013.07.033
Jean-Alexandre Richard, Marc Massonneau, Pierre-Yves Renard, Anthony Romieu, 7-Hydroxycoumarin−Hemicyanine Hybrids: A New Class of Far-Red Emitting Fluorogenic Dyes Organic Letters. ,vol. 10, pp. 4175- 4178 ,(2008) , 10.1021/OL801582W
Jun Li, Chun-Fang Zhang, Ze-Zhong Ming, Wen-Chao Yang, Guang-Fu Yang, Novel coumarin-based sensitive and selective fluorescent probes for biothiols in aqueous solution and in living cells RSC Advances. ,vol. 3, pp. 26059- 26065 ,(2013) , 10.1039/C3RA45002C
Zhenghao Yang, Zhipeng Liu, Yuncong Chen, Xiaoqing Wang, Weijiang He, Yi Lu, None, A new ratiometric and colorimetric chemosensor for cyanide anion based on Coumarin-hemicyanine hybrid Organic and Biomolecular Chemistry. ,vol. 10, pp. 5073- 5076 ,(2012) , 10.1039/C2OB25516B
Ludivine Louise-Leriche, Emilia Pǎunescu, Géraldine Saint-André, Rachid Baati, Anthony Romieu, Alain Wagner, Pierre-Yves Renard, A HTS assay for the detection of organophosphorus nerve agent scavengers. Chemistry: A European Journal. ,vol. 16, pp. 3510- 3523 ,(2010) , 10.1002/CHEM.200902986