Target-activated and ratiometric photochromic probe for “double-check” detection of toxic thiols in live cells
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摘要
Photochromic molecules can achieve reversible isomerization upon alternate light irradiations, which offers a great opportunity to improve the precision of analytes detection and imaging in complicated biological environments. Previous reported photochromic probe exhibited only mono-color switching and an initially fluorescence-ON state that may cause high background signal and impose an adverse impact on the desired sensing precision. To overcome this set-back, we developed a novel photochromic probe with an analyte-activation mode for ratiometric sensing of toxic thiols in both real water samples and live cells. The dynamic dual-fluorescence signal is released only after the fast and selective cleavage of the 2,4-dinitrophenyl sulfonate by the targeted thiophenol derivatives. Consequently, a "double-check" with synchronized dual-fluorescence blinking for analyte detection is successfully employed upon alternate light triggers with rapid response(k=7.2×10~(-2) s~(-1)), high sensitivity(LOD=6.1 nM) as well as selectivity of thiophenol derivatives over other common thiol species(e.g., GSH, Cys and Hcy). The photochromic probe was successfully introduced to the fast and on-site detection of highly toxic thiophenols in real waste water samples. Moreover, by using confocal laser-scanning microscopy(CLSM) and flow cytometric analysis, the potential applications of this ratiometric photochromic probe for trace toxic thiol sensing in live cells are examined.
Photochromic molecules can achieve reversible isomerization upon alternate light irradiations, which offers a great opportunity to improve the precision of analytes detection and imaging in complicated biological environments. Previous reported photochromic probe exhibited only mono-color switching and an initially fluorescence-ON state that may cause high background signal and impose an adverse impact on the desired sensing precision. To overcome this set-back, we developed a novel photochromic probe with an analyte-activation mode for ratiometric sensing of toxic thiols in both real water samples and live cells. The dynamic dual-fluorescence signal is released only after the fast and selective cleavage of the 2,4-dinitrophenyl sulfonate by the targeted thiophenol derivatives. Consequently, a "double-check" with synchronized dual-fluorescence blinking for analyte detection is successfully employed upon alternate light triggers with rapid response(k=7.2×10~(-2) s~(-1)), high sensitivity(LOD=6.1 nM) as well as selectivity of thiophenol derivatives over other common thiol species(e.g., GSH, Cys and Hcy). The photochromic probe was successfully introduced to the fast and on-site detection of highly toxic thiophenols in real waste water samples. Moreover, by using confocal laser-scanning microscopy(CLSM) and flow cytometric analysis, the potential applications of this ratiometric photochromic probe for trace toxic thiol sensing in live cells are examined.
Photochromic molecules can achieve reversible isomerization upon alternate light irradiations, which offers a great opportunity to improve the precision of analytes detection and imaging in complicated biological environments. Previous reported photochromic probe exhibited only mono-color switching and an initially fluorescence-ON state that may cause high background signal and impose an adverse impact on the desired sensing precision. To overcome this set-back, we developed a novel photochromic probe with an analyte-activation mode for ratiometric sensing of toxic thiols in both real water samples and live cells. The dynamic dual-fluorescence signal is released only after the fast and selective cleavage of the 2,4-dinitrophenyl sulfonate by the targeted thiophenol derivatives. Consequently, a "double-check" with synchronized dual-fluorescence blinking for analyte detection is successfully employed upon alternate light triggers with rapid response(k=7.2×10~(-2) s~(-1)), high sensitivity(LOD=6.1 nM) as well as selectivity of thiophenol derivatives over other common thiol species(e.g., GSH, Cys and Hcy). The photochromic probe was successfully introduced to the fast and on-site detection of highly toxic thiophenols in real waste water samples. Moreover, by using confocal laser-scanning microscopy(CLSM) and flow cytometric analysis, the potential applications of this ratiometric photochromic probe for trace toxic thiol sensing in live cells are examined.
引文
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36 Bai Y,Liu D,Han Z,Chen Y,Chen Z,Jiao Y,He W,Guo Z.Sci China Chem,2018,61:1413-1422
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39 Liu HW,Zhang XB,Zhang J,Wang QQ,Hu XX,Wang P,Tan W.Anal Chem,2015,87:8896-8903
40 Li X,Qian S,He Q,Yang B,Li J,Hu Y.Org Biomol Chem,2010,8:3627-3630
41 Yang J,Li M,Kang L,Zhu W.Sci China Chem,2017,60:607-613
42 Yang GY,Li C,Fischer M,Cairo CW,Feng Y,Withers SG.Angew Chem Int Ed,2015,54:5389-5393
43 Wu D,Sedgwick AC,Gunnlaugsson T,Akkaya EU,Yoon J,James TD.Chem Soc Rev,2017,46:7105-7123
44 Mo S,Tan L,Fang B,Wu Z,Su Z,Zhang Y,Yin M.Sci China Chem,2018,61:1587-1593
45 Yu D,Huang F,Ding S,Feng G.Anal Chem,2014,86:8835-8841
46 Ma Q,Xu J,Zhang X,Zhou L,Liu H,Zhang J.Sens Actuat B-Chem,2016,229:434-440
47 Li KB,Zhou D,He XP,Chen GR.Dyes Pigments,2015,116:52-57
48 Zhou L,Lin Q,Liu S,Tan Y,Sun H.Sens Actuat B-Chem,2017,244:958-964
49 Sheng X,Ye Z,Liu S,He W,Ren J,Yin J.Dyes Pigments,2016,131:84-90
50 Yang L,Su Y,Geng Y,Zhang Y,Ren X,He L,Song X.ACS Sens,2018,3:1863-1869
2 Zhang J,Zou Q,Tian H.Adv Mater,2013,25:378-399
3 Minkin VI.Chem Rev,2004,104:2751-2776
4 Ankenbruck N,Courtney T,Naro Y,Deiters A.Angew Chem Int Ed,2018,57:2768-2798
5 Zhang J,Tian H.Adv Opt Mater,2018,6:1701278
6 Velema WA,Szymanski W,Feringa BL.J Am Chem Soc,2014,136:2178-2191
7 Lerch MM,Hansen MJ,van Dam GM,Szymanski W,Feringa BL.Angew Chem Int Ed,2016,55:10978-10999
8 Hüll K,Morstein J,Trauner D.Chem Rev,2018,118:10710-10747
9 Simeth NA,Kneuttinger AC,Sterner R,K?nig B.Chem Sci,2017,8:6474-6483
10 Vomasta D,H?gner C,Branda NR,K?nig B.Angew Chem Int Ed,2008,47:7644-7647
11 Reisinger B,Kuzmanovic N,L?ffler P,Merkl R,K?nig B,Sterner R.Angew Chem Int Ed,2014,53:595-598
12 Falenczyk C,Schiedel M,Karaman B,Rumpf T,Kuzmanovic N,Gr?tli M,Sippl W,Jung M,K?nig B.Chem Sci,2014,5:4794-4799
13 Xiao W,Chen WH,Xu XD,Li C,Zhang J,Zhuo RX,Zhang XZ.Adv Mater,2011,23:3526-3530
14 Ruskowitz ER,Deforest CA.Nat Rev Mater,2018,3:17087
15 Jia S,Fong WK,Graham B,Boyd BJ.Chem Mater,2018,30:2873-2887
16 Zou Y,Yi T,Xiao S,Li F,Li C,Gao X,Wu J,Yu M,Huang C.J Am Chem Soc,2008,130:15750-15751
17 Roubinet B,Weber M,Shojaei H,Bates M,Bossi ML,Belov VN,Irie M,Hell SW.J Am Chem Soc,2017,139:6611-6620
18 Roubinet B,Bossi ML,Alt P,Leutenegger M,Shojaei H,Schnorrenberg S,Nizamov S,Irie M,Belov VN,Hell SW.Angew Chem Int Ed,2016,55:15429-15433
19 Cheng H,Yoon J,Tian H.Coordin Chem Rev,2018,372:66-84
20 Qi Q,Chi W,Li Y,Qiao Q,Chen J,Miao L,Zhang Y,Li J,Ji W,Xu T,Liu X,Yoon J,Xu Z.Chem Sci,2019,316:4914-4922
21 Xiong Y,Vargas Jentzsch A,Osterrieth JWM,Sezgin E,Sazanovich IV,Reglinski K,Galiani S,Parker AW,Eggeling C,Anderson HL.Chem Sci,2018,9:3029-3040
22 Zhang H,Wang C,Jiang T,Guo H,Wang G,Cai X,Yang L,Zhang Y,Yu H,Wang H,Jiang K.Anal Chem,2015,87:5216-5222
23 Xie X,Mistlberger G,Bakker E.J Am Chem Soc,2012,134:16929-16932
24 Valderrey V,Bonasera A,Fredrich S,Hecht S.Angew Chem Int Ed,2017,56:1914-1918
25 Zhang J,Fu Y,Han HH,Zang Y,Li J,He XP,Feringa BL,Tian H.Nat Commun,2017,8:987
26 Fu Y,Han HH,Zhang J,He XP,Feringa BL,Tian H.J Am Chem Soc,2018,140:8671-8674
27 Zhang C,Pu S,Sun Z,Fan C,Liu G.J Phys Chem B,2015,119:4673-4682
28 Goldberg JM,Wang F,Sessler CD,Vogler NW,Zhang DY,Loucks WH,Tzounopoulos T,Lippard SJ.J Am Chem Soc,2018,140:2020-2023
29 Zhang J,Ma W,He XP,Tian H.ACS Appl Mater Interfaces,2017,9:8498-8507
30 Zhang Y,Song KH,Tang S,Ravelo L,Cusido J,Sun C,Zhang HF,Raymo FM.J Am Chem Soc,2018,140:12741-12745
31 Lee MH,Kim JS,Sessler JL.Chem Soc Rev,2015,44:4185-4191
32 Wan Q,Chen S,Shi W,Li L,Ma H.Angew Chem Int Ed,2014,53:10916-10920
33 Wang J,Xu W,Yang Z,Yan Y,Xie X,Qu N,Wang Y,Wang C,Hua J.ACS Appl Mater Interfaces,2018,10:31088-31095
34 Cheng D,Pan Y,Wang L,Zeng Z,Yuan L,Zhang X,Chang YT.J Am Chem Soc,2017,139:285-292
35 Cao C,Liu X,Qiao Q,Zhao M,Yin W,Mao D,Zhang H,Xu Z.Chem Commun,2014,50:15811-15814
36 Bai Y,Liu D,Han Z,Chen Y,Chen Z,Jiao Y,He W,Guo Z.Sci China Chem,2018,61:1413-1422
37 Jing T,Yan L.Sci China Chem,2018,61:863-870
38 Shao X,Kang R,Zhang Y,Huang Z,Peng F,Zhang J,Wang Y,Pan F,Zhang W,Zhao W.Anal Chem,2014,87:399-405
39 Liu HW,Zhang XB,Zhang J,Wang QQ,Hu XX,Wang P,Tan W.Anal Chem,2015,87:8896-8903
40 Li X,Qian S,He Q,Yang B,Li J,Hu Y.Org Biomol Chem,2010,8:3627-3630
41 Yang J,Li M,Kang L,Zhu W.Sci China Chem,2017,60:607-613
42 Yang GY,Li C,Fischer M,Cairo CW,Feng Y,Withers SG.Angew Chem Int Ed,2015,54:5389-5393
43 Wu D,Sedgwick AC,Gunnlaugsson T,Akkaya EU,Yoon J,James TD.Chem Soc Rev,2017,46:7105-7123
44 Mo S,Tan L,Fang B,Wu Z,Su Z,Zhang Y,Yin M.Sci China Chem,2018,61:1587-1593
45 Yu D,Huang F,Ding S,Feng G.Anal Chem,2014,86:8835-8841
46 Ma Q,Xu J,Zhang X,Zhou L,Liu H,Zhang J.Sens Actuat B-Chem,2016,229:434-440
47 Li KB,Zhou D,He XP,Chen GR.Dyes Pigments,2015,116:52-57
48 Zhou L,Lin Q,Liu S,Tan Y,Sun H.Sens Actuat B-Chem,2017,244:958-964
49 Sheng X,Ye Z,Liu S,He W,Ren J,Yin J.Dyes Pigments,2016,131:84-90
50 Yang L,Su Y,Geng Y,Zhang Y,Ren X,He L,Song X.ACS Sens,2018,3:1863-1869