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 shu

A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H₂S production

a.
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, China
b.
Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China

Corresponding author: Zhao Chun-Chang, zhaocchang@ecust.edu.cn Gu Xian-Feng, xfgu@fudan.edu.cn
Received Date: 3 June 2016
Revised Date: 17 June 2016
Accepted Date: 29 June 2016
Available Online: 16 February 2016

Figures(4)

Most reported fluorescent probes have limitations in practical applications in living systems due to the strong autofluorescence background, construction of probes with near-infrared (NIR) fluorescence emission is an accessible approach for addressing this challenge. We here designed a NIR fluorescent probe for monitoring the endogenous production of H₂S in living cells. The designed probe showed significant NIR fluorescence turn-on response to H₂S with high selectivity, enabling the sensitive detection H₂S. Importantly, the probe could be applied in monitoring the endogenous production of H₂S in raw264.7 macrophages. This study showed that fluvastatin can promote the activity of cystathionine γ-lyase (CSE) for generation H₂S.
- Fluorescent probe,
- Near-infrared fluorescence emission,
- Endogenous H₂S detection,
- Fluvastatin
1. [1]
  (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.
2. [2]
  (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.
3. [3]
  (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.
4. [4]
  (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.
5. [5]
  (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.
6. [6]
  (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.
7. [7]
  (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.
8. [8]
  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
9. [9]
  (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.
10. [10]
  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
1. [1]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
2. [2]
  Xianzhu Luo , Feifei Yu , Rui Wang , Tian Su , Pan Luo , Pengfei Wen , Fabiao Yu . A near-infrared two-photon fluorescent probe for the detection of HClO in inflammatory and tumor-bearing mice. Chinese Chemical Letters, 2025, 36(7): 110531-. doi: 10.1016/j.cclet.2024.110531
3. [3]
  Wenping Dong , Mo Ma , Jingkang Li , Lanlan Xu , Dejiang Gao , Pinyi Ma , Daqian Song . Near-infrared fluorescent probe with large Stokes shift and long emission wavelength for rapid diagnosis of lung cancer via aerosol inhalation delivery. Chinese Chemical Letters, 2025, 36(5): 110147-. doi: 10.1016/j.cclet.2024.110147
4. [4]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
5. [5]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
6. [6]
  Meitong Wu , Ke Wu , Shumin Feng , Li Xu , Mi Lei , Jianmei Chen , Shuang Li , Mian Qin , Dahui Liu , Guoqiang Feng . A NIR and ratiometric fluorescent probe for quantitative detection of SO₂ derivatives in Chinese medicinal materials and bioimaging in vivo. Chinese Chemical Letters, 2026, 37(1): 110979-. doi: 10.1016/j.cclet.2025.110979
7. [7]
  Mengyu Cao , Yiyan Yin , Jingyi Qin , Jin Ouyang , Na Na . Unconventional application of a fluorescent probe for MS-based detection of multiple sulfur species in ferroptosis. Chinese Chemical Letters, 2026, 37(1): 111260-. doi: 10.1016/j.cclet.2025.111260
8. [8]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
9. [9]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
10. [10]
  Yi-Xin Zhang , Fang-Qi Zhang , Ao-Pei Peng , Tao Jiang , Ya-Xi Meng , Yang Li , Shuang-Xi Gu , Yuan-Yuan Zhu . Enantioselective recognition of amino acids in water using emission-tunable chiral fluorescent probes. Chinese Chemical Letters, 2026, 37(1): 111500-. doi: 10.1016/j.cclet.2025.111500
11. [11]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
12. [12]
  Qian Pang , Fangjun Huo , Yongkang Yue , Caixia Yin . ONOO⁻ and viscosity dual-response fluorescent probe for arthritis imaging in vivo. Chinese Chemical Letters, 2025, 36(9): 110713-. doi: 10.1016/j.cclet.2024.110713
13. [13]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
14. [14]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
15. [15]
  Zhixiao Xiong , Shanni Qiu , Yuyu Wang , Houna Duan , Yi Xiao , Yufang Xu , Weiping Zhu , Xuhong Qian . Photocalibrated NO release from the zinc ion fluorescent probe based on naphthalimide and its application in living cells. Chinese Chemical Letters, 2025, 36(4): 110002-. doi: 10.1016/j.cclet.2024.110002
16. [16]
  Jiayu Zeng , Minhui Liu , Ting Yang , Jia Huang , Songjiao Li , Wanting Zhang , Dan Cheng , Longwei He , Jia Zhou . Two-dimensional design strategy to construct smart dual-responsive fluorescent probe for the precise tracking of ischemic stroke. Chinese Chemical Letters, 2025, 36(5): 110166-. doi: 10.1016/j.cclet.2024.110166
17. [17]
  Xinyi Zhao , Yuai Duan , Zihan Liu , Hua Geng , Yaping Li , Zhongfeng Li , Tianyu Han . Mapping sweat pores for biometric identification based on a donor-acceptor hydrophilic fluorescent probe. Chinese Chemical Letters, 2025, 36(8): 110617-. doi: 10.1016/j.cclet.2024.110617
18. [18]
  Chengcheng Zhang , Zhe Wu , Ningning Jiang , Yi Song , Weina Geng , Hongmei Liu , Ming Jin , Shuxiang Wang , Jinchao Zhang , Yutao Yang . A fluorescent probe regulated by trifluoromethyl and nitrogen-containing heterocycles for monitoring biothiol fluctuations in the brains of mice with schizophrenia. Chinese Chemical Letters, 2026, 37(1): 111476-. doi: 10.1016/j.cclet.2025.111476
19. [19]
  Hui Zhang , Rong Feng , Wanyi Yu , Hongbei Wei , Tianhong Wu , Peng Zhang , Wenhai Bian , Xin Li , Di Gao , Guojun Weng , Zhe Yang , Tony D. James , Xiaolong Sun . Evaluating the global thiols redox state in living cells using a reducing sulfur species responsive fluorescence switching platform. Chinese Chemical Letters, 2025, 36(4): 110528-. doi: 10.1016/j.cclet.2024.110528
20. [20]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1468)
HTML views(84)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production

Metrics

通讯作者: 陈斌, bchen63@163.com

A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H₂S production