A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production
- Corresponding author: Zhao Chun-Chang, zhaocchang@ecust.edu.cn Gu Xian-Feng, xfgu@fudan.edu.cn
Citation:
Zhang Li-Li, Zhu Hui-Kun, Zhao Chun-Chang, Gu Xian-Feng. A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production[J]. Chinese Chemical Letters,
;2017, 28(2): 218-221.
doi:
10.1016/j.cclet.2016.07.008
(a) G.D. Yang, L.Y. Wu, B. Jiang, et al., H2S as a physiologic vasorelaxant:hypertension in mice with deletion of cystathionine γ-lyase, Science 322(2008) 587-590;(b) O. Kabil, R. Banerjee, Redox biochemistry of hydrogen sulfide, J. Biol. Chem. 285(2010) 21903-21907;(c) S. Singh, D. Padovani, R.A. Leslie, T. Chiku, R. Banerjee, Relative contributions of cystathionine β-synthase and γ-cystathionase to H2S biogenesis via alternative trans-sulfuration reactions, J. Biol. Chem. 284(2009) 22457-22466.
(a) V.S. Lin, W. Chen, M. Xian, C.J. Chang, Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems, Chem. Soc. Rev. 44(2015) 4596-4618;(b) X. Zhou, S. Lee, Z.C. Xu, J. Yoon, Recent progress on the development of chemosensors for gases, Chem. Rev. 115(2015) 7944-8000.
(a) A.R. Lippert, E.J. New, C.J. Chang, Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells, J. Am. Chem. Soc. 133(2011) 10078-10080;(b) H.J. Peng, Y.F. Cheng, C.F. Dai, et al., A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood, Angew. Chem. Int. Ed. 50(2011) 9672-9675;(c) J.Y. Zhang, W. Guo, A new fluorescent probe for gasotransmitter H2S:high sensitivity, excellent selectivity, and a significant fluorescence off-on response, Chem. Commun. 50(2014) 4214-4217;(d) B.F. Chen, C. Lv, X.J. Tang, Chemoselective reduction-based fluorescence probe for detection of hydrogen sulfide in living cells, Anal. Bioanal. Chem. 404(2012) 1919-1923;(e) H.A. Henthorn, M.D. Pluth, Mechanistic insights into the H2S-mediated reduction of aryl azides commonly used in H2S detection, J. Am. Chem. Soc. 137(2015) 15330-15336;(f) W. Sun, J.L. Fan, C. Hu, et al., A two-photon fluorescent probe with nearinfrared emission for hydrogen sulfide imaging in Biosystems, Chem. Commun. 49(2013) 3890-3892;(g) F.B. Yu, P. Li, P. Song, et al., An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells, Chem. Commun. 48(2012) 2852-2854;(h) S. Chen, Z.J. Chen, W. Ren, H.W. Ai, Reaction-based genetically encoded fluorescent hydrogen sulfide sensors, J. Am. Chem. Soc. 134(2012) 9589-9592;(i) S.K. Bae, C.H. Heo, D.J. Choi, et al., A ratiometric two-photon fluorescent probe reveals reduction in mitochondrial H2S production in Parkinson's disease gene knockout astrocytes, J. Am. Chem. Soc. 135(2013) 9915-9923;(j) H.Y. Liu, M. Zhao, Q.L. Qiao, et al., Fluorescein-derived fluorescent probe for cellular hydrogen sulfide imaging, Chin. Chem. Lett. 25(2014) 1060-1064.
(a) Y.C. Chen, C.C. Zhu, Z.H. Yang, et al., A ratiometric fluorescent probe for rapid detection of hydrogen sulfide in mitochondria, Angew. Chem. Int. Ed. 52(2013) 1688-1691;(b) Y. Qian, L. Zhang, S.T. Ding, et al., A fluorescent probe for rapid detection of hydrogen sulfide in blood plasma and brain tissues in mice, Chem. Sci. 3(2012) 2920-2923;(c) C.R. Liu, J. Pan, S. Li, et al., Capture and visualization of hydrogen sulfide by a fluorescent probe, Angew. Chem. Int. Ed. 50(2011) 10327-10329;(d) Y. Qian, J. Karpus, O. Kabil, et al., Selective fluorescent probes for live-cell monitoring of sulphide, Nat. Commun. 2(2011) 495;(e) X. Wang, J. Sun, W.H. Zhang, et al., A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells, Chem. Sci. 4(2013) 2551-2556;(f) W. Zhang, J.Q. Kang, P. Li, H. Wang, B. Tang, Dual signaling molecule sensor for rapid detection of hydrogen sulfide based on modified tetraphenylethylene, Anal. Chem. 87(2015) 8964-8969;(g) C.C. Zhao, X.L. Zhang, K.B. Li, et al., Forster resonance energy transfer switchable self-assembled micellar nanoprobe:ratiometric fluorescent trapping of endogenous H2S generation via fluvastatin-stimulated upregulation, J. Am. Chem. Soc. 137(2015) 8490-8498.
(a) K. Sasakura, K. Hanaoka, N. Shibuya, et al., Development of a highly selective fluorescence probe for hydrogen sulfide, J. Am. Chem. Soc. 133(2011) 18003-18005;(b) X.F. Gu, C.H. Liu, Y.C. Zhu, Y.Z. Zhu, Development of a boron-dipyrrometheneCu2+ ensemble based colorimetric probe toward hydrogen sulfide in aqueous media, Tetrahedron Lett. 52(2011) 5000-5003.
(a) L.Y. Niu, Y.Z. Chen, H.R. Zheng, et al., Design strategies of fluorescent probes for selective detection among biothiols, Chem. Soc. Rev. 44(2015) 6143-6160;(b) K.Z. Gu, Y.S. Xu, H. Li, et al., Real-time tracking and in vivo visualization of β-galactosidase activity in colorectal tumor with a ratiometric near-infrared fluorescent probe, J. Am. Chem. Soc. 138(2016) 5334-5340;(c) C.C. Zhao, X.A. Li, F.Y. Wang, Target-triggered NIR emission with a large stokes shift for the detection and imaging of cysteine in living cells, Chem. Asian J. 9(2014) 1777-1781.
(a) C.C. Zhao, Y. Zhang, S.L. Pan, L. Rothberg, M.K. Ng, Synthesis, characterization, and properties of homopolymers functionalized with oligothiophene derivatives in the side chain, Macromolecules 40(2007) 1816-1823;(b) C.C. Zhao, P. Feng, J. Cao, et al., Borondipyrromethene-derived Cu2+ sensing chemodosimeter for fast and selective detection, Org. Biomol. Chem. 10(2012) 3104-3109.
X.M. Wu, X.R. Sun, Z.Q. Guo. In vivo and in situ tracking cancer chemotherapy by highly photostable NIR fluorescent theranostic prodrug[J]. J. Am. Chem. Soc., 2014,136:3579-3588. doi: 10.1021/ja412380j
(a) L.L. Zhang, H.K. Zhu, M.M. Li, X.F. Gu, A novel fluorescent probe for imaging endogenous hydrogen sulphide via the CSE enzymatic pathway, Chem. Commun. 51(2015) 13135-13137;(b) X.F. Gu, H.K. Zhu, S.N. Yang, Y.C. Zhu, Y.Z. Zhu, Development of a highly selective H2S fluorescent probe and its application to evaluate CSE inhibitors, RSC Adv. 4(2014) 50097-50101;(c) F.Y. Wang, L. Zhou, C.C. Zhao, et al., A dual-response BODIPY-based fluorescent probe for the discrimination of glutathione from cystein and homocystein, Chem. Sci. 6(2015) 2584-2589;(d) F.Y. Wang, Y. Zhu, L. Zhou, et al., Fluorescent in situ targeting probes for rapid imaging of ovarian-cancer-specific γ-glutamyltranspeptidase, Angew. Chem. Int. Ed. 54(2015) 7349-7353.
Y. Xu, H.P. Du, J.J. Li. Statins upregulate cystathionine γ-lyase transcription and H2S generation via activating Akt signaling in macrophage[J]. Pharmacol. Res., 2014,87:18-25. doi: 10.1016/j.phrs.2014.06.006
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