Citation: ZHAO Zi-Jian, HOU Ming-Xuan, WANG Kang-Nan, LIU Liu-Yi, MAO Zong-Wan. Mitochondria-Targeted Iridium(Ⅲ) Complex Used as a Two-Photon Phosphorescent Probe for SO₂ Derivatives Detection in Vitro and in Vivo[J]. Chinese Journal of Inorganic Chemistry, ;2020, 36(6): 1113-1122. doi: 10.11862/CJIC.2020.124 shu

Mitochondria-Targeted Iridium(Ⅲ) Complex Used as a Two-Photon Phosphorescent Probe for SO₂ Derivatives Detection in Vitro and in Vivo

MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China

Corresponding author: WANG Kang-Nan, wangkn3@mail2.sysu.edu.cn MAO Zong-Wan, cesmzw@mail.sysu.eddu.cn
Received Date: 5 February 2020
Revised Date: 23 March 2020

Figures(6)

Exposure to high doses of sulfur dioxide (SO₂) derivatives (SO₃^2-and HSO₃^-) are associated with many cardiovascular diseases and lung cancer. Benefiting from the advantages of two-photon phosphorescence imaging microscopy (TPPIM) even two-photon phosphorescence lifetime imaging microscopy (TPPLIM), including excellent spatial and temporal resolutions, anti-photobleaching, anti-autofluorescence, and strong penetration, could be promising features for real-time detection of biological bisulfite derivatives in living tissues. Herein, we firstly report the probe (named as Ir-EA) for SO₂ derivatives based on TPPLIM technology. Ir-EA was developed with an iridium complex according to its long phosphorescence lifetime (~110 ns) and the mitochondrial targeting properties. More importantly, Ir-EA displayed a significant luminescence enhancement (69-fold, 10 eq.) and a low detection limit (65 nmol·L^-1) for bisulfite in an aqueous solution. Additionally, Ir-EA can selectively lighting-up mitochondria bisulfite derivatives in living cells as well as zebrafish.
- biological bisulfite,
- two-photon phosphorescence lifetime imaging microscopy,
- iridium(Ⅲ) complex,
- mitochondria-targeted,
- zebrafish
1. [1]
  Chen T M, Kuschner W G, Gokhale J, et al. Am. J. Med. Sci., 2007, 333:249-256 doi: 10.1097/MAJ.0b013e31803b900f
2. [2]
  Rich D Q, Schwartz J, Mittleman M A, et al. Am. J. Epidemiol., 2005, 161:1123-1132 doi: 10.1093/aje/kwi143
3. [3]
  Singh A, Agrawal M. J. Environ. Biol., 2007, 29:15-24
4. [4]
  Sang N, Yun Y, Li H, et al. Toxicol. Sci., 2010, 114:226-236 doi: 10.1093/toxsci/kfq010
5. [5]
  Lee W J, Teschke K, Kauppinen T, et al. Environ. Health Perspect., 2002, 110:991-995 doi: 10.1289/ehp.02110991
6. [6]
  Shapiro R. Mutat. Res.:Rev. Genet. Toxicol., 1977, 39:149-175 doi: 10.1016/0165-1110(77)90020-3
7. [7]
  Ji A J, Savon S R, Jacobsen D W. Clin. Chem., 1995, 41:897-903 doi: 10.1093/clinchem/41.6.897
8. [8]
  Mitsuhashi H, Ikeuchi H, Yamashita S, et al. Shock, 2004, 21:99-102
9. [9]
  Tsuzuki T, Obaru K, Setoyama C, et al. J. Mol. Biol., 1987, 198:21-31 doi: 10.1016/0022-2836(87)90454-2
10. [10]
  Mitsuhashi H, Yamashita S, Ikeuchi H, et al. Shock, 2005, 24:529-534 doi: 10.1097/01.shk.0000183393.83272.de
11. [11]
  Liang Y, Liu D, Ochs T, et al. Lab. Invest., 2011, 91:12-23 doi: 10.1038/labinvest.2010.156
12. [12]
  Wang X B, Jin H F, Tang C S, et al. Eur. J. Pharmacol., 2011, 670:1-6 doi: 10.1016/j.ejphar.2011.08.031
13. [13]
  Wang X B, Jin H F, Tang C S, et al. Clin. Exp. Pharmacol. Physiol., 2010, 37:745-752
14. [14]
  Li X, Bazer F W, Gao H, et al. Amino Acids, 2009, 37:65-78 doi: 10.1007/s00726-009-0264-5
15. [15]
  Kajiyama H, Nojima Y, Mitsuhashi H, et al. J. Am. Soc. Nephrol., 2000, 11:923-927
16. [16]
  Wang K N, Cao Q, Liu L Y, et al. Chem. Sci., 2019, 10:10053-10064 doi: 10.1039/C9SC03594J
17. [17]
  Theisen S, Hansch R, Kothe L, et al. Biosens. Bioelectron., 2010, 26:175-181 doi: 10.1016/j.bios.2010.06.009
18. [18]
  Zeng L, Gupta P, Chen Y, et al. Chem. Soc. Rev., 2017, 46:5771-5804 doi: 10.1039/C7CS00195A
19. [19]
  Sun M, Dai W, Liu D Q. J. Mass Spectrom., 2008, 43:383-393 doi: 10.1002/jms.1335
20. [20]
  Daunoravicius Z, Padarauskas A. Electrophoresis, 2002, 23:2439-2444 doi: 10.1002/1522-2683(200208)23:15<2439::AID-ELPS2439>3.0.CO;2-Z
21. [21]
  Liang X, Zhong T, Quan B, et al. Sens. Actuators B, 2008, 134:25-30 doi: 10.1016/j.snb.2008.04.003
22. [22]
  Yin J, Hu Y, Yoon J. Chem. Soc. Rev., 2015, 44:4619-4644 doi: 10.1039/C4CS00275J
23. [23]
  Vendrell M, Zhai D, Er J C, et al. Chem. Rev., 2012, 112:4391-4420 doi: 10.1021/cr200355j
24. [24]
  ZHAO Zhen-Sheng, GUO Xu-Dong, LI Sha-Yu, et al. Acta Chim. Sinica, 2016, 74:593-596
25. [25]
  Yang Y, Zhao Q, Feng W, et al. Chem. Rev., 2013, 113:192-270 doi: 10.1021/cr2004103
26. [26]
  Tang Y, Kong X, Xu A, et al. Angew. Chem. Int. Ed., 2016, 55:3356-3359 doi: 10.1002/anie.201510373
27. [27]
  Wang J W, Wong A M, Flores J, et al. Cell, 2003, 112:271-282 doi: 10.1016/S0092-8674(03)00004-7
28. [28]
  Gissibl T, Thiele S, Herkommer A, et al. Nat. Photonics, 2016, 10:554-560 doi: 10.1038/nphoton.2016.121
29. [29]
  Cao D, Liu Z, Verwilst P, et al. Chem. Rev., 2019, 119:10403-10519 doi: 10.1021/acs.chemrev.9b00145
30. [30]
  Zhao Q, Huang C, Li F. Chem. Soc. Rev., 2011, 40:2508-2524 doi: 10.1039/c0cs00114g
31. [31]
  Ma D L, He H Z, Leung K H, et al. Angew. Chem. Int. Ed., 2013, 52:7666-7682 doi: 10.1002/anie.201208414
32. [32]
  He L, Tan C P, Ye R R, et al. Angew. Chem. Int. Ed., 2014, 53:12137-12141 doi: 10.1002/anie.201407468
33. [33]
  Li Y, Tan C P, Zhang W, et al. Biomaterials, 2015, 39:95-104 doi: 10.1016/j.biomaterials.2014.10.070
34. [34]
  Li J, Pu K. Chem. Soc. Rev., 2019, 48:38-71 doi: 10.1039/C8CS00001H
35. [35]
  Guo Z, Park S, Yoon J, et al. Chem. Soc. Rev., 2014, 43:16-29 doi: 10.1039/C3CS60271K
36. [36]
  Zhang K Y, Gao P, Sun G, et al. J. Am. Chem. Soc., 2018, 140:7827-7834 doi: 10.1021/jacs.8b02492
37. [37]
  Hao L, Li Z W, Zhang D Y, et al. Chem. Sci., 2019, 10:1285-1293 doi: 10.1039/C8SC04242J
38. [38]
  Zhao Q, Cao T, Li F, et al. Organometallics, 2007, 26:2077-2081 doi: 10.1021/om061031r
39. [39]
  Li G, Chen Y, Wang J, et al. Chem. Sci., 2013, 4:4426-4433 doi: 10.1039/c3sc52301b
40. [40]
  Li G, Chen Y, Wang J, et al. Biomaterials, 2015, 63:128-136 doi: 10.1016/j.biomaterials.2015.06.014
41. [41]
  Wang K N, Zhu Y, Xing M, et al. Sens. Actuators B, 2019, 295:215-222 doi: 10.1016/j.snb.2019.05.077
42. [42]
  Liu J B, Yang C, Ko C N, et al. Sens. Actuators B, 2017, 243:971-976 doi: 10.1016/j.snb.2016.12.083
43. [43]
  Li X, Zeng R, Xie C, et al. Dyes Pigm., 2019, 165:128-136 doi: 10.1016/j.dyepig.2019.02.018
44. [44]
  Gao H, Qi H, Peng Y, et al. Analyst, 2018, 143:3670-3676 doi: 10.1039/C8AN00640G
45. [45]
  Liu Z, Guo S, Piao J, et al. RSC Adv., 2014, 4:54554-54557 doi: 10.1039/C4RA10137E
46. [46]
  Zhang Y, Guan L, Yu H, et al. Anal. Chem., 2016, 88:4426-4431 doi: 10.1021/acs.analchem.6b00061
47. [47]
  Zhang W, Liu T, Huo F, et al. Anal. Chem., 2017, 89:8079-8083 doi: 10.1021/acs.analchem.7b01580
48. [48]
  Li C, Yu M, Sun Y, et al. J. Am. Chem. Soc., 2011, 133:11231-11239 doi: 10.1021/ja202344c
49. [49]
  Liu Z, Zhou X, Miao Y, et al. Angew. Chem. Int. Ed., 2017, 56:5812-5816 doi: 10.1002/anie.201702114
50. [50]
  Sheldrick G M. SHELX-97, Program for the Solution and the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
51. [51]
  Zhang F, Liang X, Zhang W, et al. Biosens. Bioelectron., 2017, 87:1005-1011 doi: 10.1016/j.bios.2016.09.067
52. [52]
  He L, Qiao J, Duan L, et al. Adv. Funct. Mater., 2009, 19:2950-2960 doi: 10.1002/adfm.200900723
53. [53]
  Jiao X, Li Y, Niu J, et al. Anal. Chem., 2018, 90:533-555 doi: 10.1021/acs.analchem.7b04234
54. [54]
  Lin V S, Chen W, Xian M, et al. Chem. Soc. Rev., 2015, 44:4596-4618 doi: 10.1039/C4CS00298A
55. [55]
  Wu J, Pan J, Ye Z, et al. Sens. Actuators B, 2018, 274:274-284 doi: 10.1016/j.snb.2018.07.161
56. [56]
  Hou J T, Ren W X, Li K, et al. Chem. Soc. Rev., 2017, 46:2076-2090 doi: 10.1039/C6CS00719H
57. [57]
  Cipollone R, Ascenzi P, Tomao P, et al. J. Mol. Microbiol. Biotechnol., 2008, 15:199-211 doi: 10.1159/000121331
58. [58]
  Ploegman J H, Drent G, Kalk K H, et al. Nature, 1978, 273:120-124 doi: 10.1038/273120a0
59. [59]
  Ramasamy S, Singh S, Taniere P, et al. Am. J. Physiol.:Gastrointest. Liver Physiol., 2006, 291:288-296 doi: 10.1152/ajpgi.00324.2005
60. [60]
  Malliopoulou V, Rakitzis E, Malliopoulou T. Anticancer Res., 1989, 9:1133-1136
61. [61]
  Zhang K Y, Yu Q, Wei H, et al. Chem. Rev., 2018, 118:1770-1839 doi: 10.1021/acs.chemrev.7b00425
62. [62]
  Nasevicius A, Ekker S C. Nat. Genet., 2000, 26:216-220 doi: 10.1038/79951
63. [63]
  Zon L I, Peterson R T. Nat. Rev. Drug Discovery, 2005, 4:35-44 doi: 10.1038/nrd1606
64. [64]
  Lieschke G J, Currie P D. Nat. Rev. Genet., 2007, 8:353-367 doi: 10.1038/nrg2091
1. [1]
  Yue WANG , Zhizhi GU , Jingyi DONG , Jie ZHU , Cunguang LIU , Guohan LI , Meichen LU , Jian HAN , Shengnan CAO , Wei WANG . Effects of kelp-derived carbon dots on embryonic development of zebrafish. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1209-1217. doi: 10.11862/CJIC.20230423
2. [2]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
3. [3]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
4. [4]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
5. [5]
  Zhiyu Yu , Xiang Luo , Cheng Zhang , Xin Lu , Xiaohui Li , Pan Liao , Zhongqiu Liu , Rong Zhang , Shengtao Wang , Zhiqiang Yu , Guochao Liao . Mitochondria-targeted carrier-free nanoparticles based on dihydroartemisinin against hepatocellular carcinoma. Chinese Chemical Letters, 2024, 35(10): 109519-. doi: 10.1016/j.cclet.2024.109519
6. [6]
  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
7. [7]
  Ke Gong , Jinghan Liao , Jiangtao Lin , Quan Wang , Zhihua Wu , Liting Wang , Jiali Zhang , Yi Dong , Yourong Duan , Jianhua Chen . Mitochondria-targeted nanoparticles overcome chemoresistance via downregulating BACH1/CD47 axis in ovarian carcinoma. Chinese Chemical Letters, 2024, 35(5): 108888-. doi: 10.1016/j.cclet.2023.108888
8. [8]
  Pengyu Chen , Beibei Chen , Man He , Yuxi Zhou , Lei Lei , Jian Han , Bingsheng Zhou , Ligang Hu , Bin Hu . Nanoplastics and nano-ZnO facilitate Cd accumulation in zebrafish larvae via a distinct pathway: Revelation by LA-ICP-MS imaging. Chinese Chemical Letters, 2025, 36(2): 109908-. doi: 10.1016/j.cclet.2024.109908
9. [9]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
10. [10]
  Feng-Qing Huang , Yu Wang , Ji-Wen Wang , Dai Yang , Shi-Lei Wang , Yuan-Ming Fan , Raphael N. Alolga , Lian-Wen Qi . Chemical isotope labeling-assisted liquid chromatography-mass spectrometry enables sensitive and accurate determination of dipeptides and tripeptides in complex biological samples. Chinese Chemical Letters, 2024, 35(11): 109670-. doi: 10.1016/j.cclet.2024.109670
11. [11]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
12. [12]
  Zekun Gao , Xiuli Zheng , Weimin Liu , Jie Sha , Shuaishuai Bian , Haohui Ren , Jiasheng Wu , Wenjun Zhang , Chun-Sing Lee , Pengfei Wang . GSH-activatable copper-elsinochrome off-on photosensitizer for combined specific NIR-Ⅱ two-photon photodynamic/chemodynamic therapy. Chinese Chemical Letters, 2025, 36(3): 109874-. doi: 10.1016/j.cclet.2024.109874
13. [13]
  Jiawei Li , Cheng Chen , Mingyan Wu . Donor-acceptor type organic cocrystals for deep-red circularly polarized luminescence and two-photon excited emission. Chinese Journal of Structural Chemistry, 2025, 44(3): 100513-100513. doi: 10.1016/j.cjsc.2025.100513
14. [14]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
15. [15]
  Shuaige Bai , Shuai Huang , Ting Luo , Bin Feng , Yanpeng Fang , Feiyi Chu , Jie Dong , Wenbin Zeng . Debut of a responsive chemiluminescent probe for butyrylcholinesterase: Application in biological imaging and pesticide residue detection. Chinese Chemical Letters, 2025, 36(3): 110054-. doi: 10.1016/j.cclet.2024.110054
16. [16]
  Hualei Xu , Manman Han , Haiqiang Liu , Liang Qin , Lulu Chen , Hao Hu , Ran Wu , Chenyu Yang , Hua Guo , Jinrong Li , Jinxiang Fu , Qichen Hao , Yijun Zhou , Jinchao Feng , Xiaodong Wang . 4-Nitrocatechol as a novel matrix for low-molecular-weight compounds in situ detection and imaging in biological tissues by MALDI-MSI. Chinese Chemical Letters, 2024, 35(6): 109095-. doi: 10.1016/j.cclet.2023.109095
17. [17]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
18. [18]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
19. [19]
  Botao QU , Qian WANG , Xiaogang NING , Yuxin ZHOU , Ruiping ZHANG . Deeply penetrating photoacoustic imaging in tumor tissues based on dual-targeted melanin nanoparticle. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1025-1032. doi: 10.11862/CJIC.20230416
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1759)
HTML views(55)

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

Mitochondria-Targeted Iridium(Ⅲ) Complex Used as a Two-Photon Phosphorescent Probe for SO2 Derivatives Detection in Vitro and in Vivo

Metrics

通讯作者: 陈斌, bchen63@163.com

Mitochondria-Targeted Iridium(Ⅲ) Complex Used as a Two-Photon Phosphorescent Probe for SO₂ Derivatives Detection in Vitro and in Vivo