Enhanced Doubly Activated Dual Emission Fluorescent Probes for Selective Imaging of Glutathione or Cysteine in Living Systems.

Autor: Mulay SV; Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea.; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Kim Y; Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea.; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Choi M; Department of Biological Sciences, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Lee DY; Graduate School of Medical Science and Engineering, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Choi J; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Lee Y; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Jon S; Department of Biological Sciences, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea.; Graduate School of Medical Science and Engineering, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea., Churchill DG; Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea.; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Republic of Korea.
Jazyk: angličtina
Zdroj: Analytical chemistry [Anal Chem] 2018 Feb 20; Vol. 90 (4), pp. 2648-2654. Date of Electronic Publication: 2018 Feb 06.
DOI: 10.1021/acs.analchem.7b04375
Abstrakt: The development of novel fluorescent probes for monitoring the concentration of various biomolecules in living systems has great potential for eventual early diagnosis and disease intervention. Selective detection of competitive species in biological systems is a great challenge for the design and development of fluorescent probes. To improve on the design of fluorescent coumarin-based biothiol sensing technologies, we have developed herein an enhanced dual emission doubly activated system (DACP-1 and the closely related DACP-2) for the selective detection of glutathione (GSH) through the use of one optical channel and the detection of cysteine (Cys) by another channel. A phenylselenium group present at the 4-position completely quenches the fluorescence of the probe via photoinduced electron transfer to give a nonfluorescent species. Probes are selective for glutathione (GSH) in the red region and for cysteine/homocysteine (Cys/Hcy) in the green region. When they were treated with GSH, DACP-1 and DACP-2 showed strong fluorescence enhancement in comparison to that for closely related species such as amino acids, including Cys/Hcy. Fluorescence quantum yields (Φ F ) increased for the red channel (<0.001 to 0.52 (DACP-1) and 0.48 (DACP-2)) and green channel (Cys) (<0.001 to 0.030 (DACP-1) and 0.026 (DACP-2)), respectively. Competing fluorescent enhancements upon addition of closely related species were negligible. Fast responses, improved water solubility, and good cell membrane permeability were all properly established with the use of DACP-1 and DACP-2. Live human lung cancer cells and fibroblasts imaged by confocal microscopy, as well as live mice tumor model imaging, confirmed selective detection.
Databáze: MEDLINE
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