WU Hong-mei, GUO Yu,. Synthesis of Ratiometric Fluorescent Probe for The Recognition of Glutathione[J]. Chinese Journal of Luminescence, 2017,38(12): 1561-1566
WU Hong-mei, GUO Yu,. Synthesis of Ratiometric Fluorescent Probe for The Recognition of Glutathione[J]. Chinese Journal of Luminescence, 2017,38(12): 1561-1566 DOI: 10.3788/fgxb20173812.1561.
Synthesis of Ratiometric Fluorescent Probe for The Recognition of Glutathione
Two fluorescent groups of quinoline and dansylamide were introduced into ligand L1 together
and a trinuclear zinc metal-organic compound H-1 as a ratiometric fluorescent probe was self-assembled by L1 and zinc ion
and the sensitive recognition of
-glutamyl-cysteinyl-glycine (GSH) was realized by H-1. The recognition process was studied by UV-Vis
fluorescence spectra
1
H NMR and ESI-MS. UV-Vis adsorption titration results show that the addition of GSH to the solution of H-1 causes a significant absorbance decrease at 425 nm and an obvious absorbance increase at 320 nm. The isobestic point is 355 nm. The equilibrium constant lg
K
of 4.03 0.11 is obtained with the absorbance value at 320 nm. This indicates that 1:1 stoichiometric host-guest complexation of H-1 for GSH is formed. The fluorescence spectra show that the addition of GSH to the solution of H-1 causes an obvious dansyl-based fluorescence decrease at 513 nm upon excitation at 340 nm with a significant red-shift
and an increase of quinoline-based fluorescence at 396 nm. The ratio of dansyl-based fluorescence to quinoline-based fluorescence can be used to detect GSH and the detection limit is up to 2.510
-6
molL
-1
.
关键词
Keywords
references
LU S C. Regulation of hepatic glutathione synthesis:current concepts and controversies[J]. FASEB J., 1999, 13(10):1169-1183.
PASTORE A, FEDERICIA G, BERTINI E, et al.. Analysis of glutathione:implication in redox and detoxification[J]. Clinica Chim. Acta, 2003, 333(1):19-39.
GUO Y S, WANG H, SUN Y S, et al.. A disulfide bound-molecular beacon as a fluorescent probe for the detection of reduced glutathione and its application in cells[J]. Chem. Commun., 2012, 48:3221-3223.
ZHANG W, WAN F, ZHU W, et al.. Determination of glutathione and glutathione disulfide in hepatocytes by liquid chromatography with an electrode modified with functionalized carbon nanotubes[J]. J. Chromatog. B, 2005, 818(2):227-232.
LIU J, BAO C, ZHONG X, et al.. Highly selective detection of glutathione using a quantum-dot-based OFF-ON fluorescent probe[J]. Chem. Commun., 2010, 46:2971-2973.
NARANG J, CHAUHAN N, JAIN P, et al.. Silver nanoparticles/multiwalled carbon nanotube/polyaniline film for amperometric glutathione biosensor[J]. Int. J. Biolog. Macromol., 2012, 50(3):672-678.
SHAO N, JIN J, WANG H, et al.. Design of bis-spiropyran ligands as dipolar molecule receptors and application to in vivo glutathione fluorescent probes[J]. J. Am. Chem. Soc., 2010, 132(2):725-736.
LI Y, LIU W M, ZHANG P P, et al.. A fluorescent probe for the efficient discrimination of Cys, Hcy and GSH based on different cascade reactions[J]. Biosens. Bioelectron., 2017, 90:117-124.
ZHANG L L, LI M M, ZHAO C C, et al.. A novel fluorescent probe for discrimination of Cys from GSH:inspiration from chemical ligation[J]. Tetrahedron Lett., 2016, 57(5):578-581.
JHONG Y, HSIEH W H, CHIR J L, et al.. A highly selective and turn-on fluorescence sensor for detection of cyanide[J]. J. Fluoresc., 2014, 24:1723-1726.
LIU X, LI T Z, WU Q H, et al.. Carbon nanodots as a fluorescence sensor for rapid and sensitive detection of Cr(Ⅵ) and their multifunctional applications[J]. Talanta, 2017, 165:216-222.
刘静, 李东伟, 武小强, 等. 萘酰亚胺铁离子荧光探针的合成及识别性能[J]. 发光学报, 2017, 38(2):226-231. LIU J, LI D W, WU X Q, et al.. Synthesis and recognition performance of naphthalene imide-iron ion fluorescent probe[J]. Chin. J. Lumin., 2017, 38(2):226-231. (in Chinese)
高勇, 汪军, 付妹, 等. 水溶性罗丹明基Fe3+荧光探针及其在细胞成像中的应用[J]. 有机化学, 2017, 37:617-623. GAO Y, WANG J, FU M, et al.. A water-soluble rhodamine-based fluorescent probe for Fe3+ and its application in live cell imaging[J]. Chin. J. Org. Chem., 2017, 37:617-623. (in Chinese)
FRISCIC T. Supramolecular concepts and new techniques in mechanochemistry:cocrystals, cages, rotaxanes, open metal-organic frameworks[J]. Chem. Soc. Rev., 2012, 41:3493-3510.
KOBERL M, COKOJA M, HERRMANN W A. From molecules to materials:molecularpaddle-wheel synthons of macromolecules, cage compounds and metal-organic frameworks[J]. Dalton Trans., 2011, 40:6834-6859.
BUNZEN J, IWASA J, BONAKDARZADEH P, et al.. Self-assembly of M24L48 polyhedra based on empirical prediction[J]. Angew. Chem. Int. Ed., 2012, 51(13):3161-3163.
SUN Q F, SATO S, FUJITA M. An M18L24 stellated cuboctahedron through post-stellation of an M12L24 core[J]. Nat. Chem., 2012, 4:330-333.
JIN M, MOU Z L, ZHANG R L, et al.. An efficient ratiometric fluorescence sensor based on metal-organic frameworks and quantum dots for highly selective detection of 6-mercaptopurine[J]. Biosens. Bioelectron., 2017, 91:162-168.
LV Y Y, GU W, WANG J B, et al.. A ratiometric fluorescence chemodosimeter for detecting Hg2+ in aqueous solutions and living cells[J]. Sens. Actuators B:Chem., 2017, 246:1017-1024.