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Mitochondria-localized iridium(III) complexes with anthraquinone groups as effective photosensitizers for photodynamic therapy under hypoxia

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Abstract

Photodynamic therapy (PDT) is a potential way for the tumor treatment. However, it notably suffers the limitation of hypoxia in solid tumors. Thus, it is significant to develop effective photosensitizers which can exhibit excellent therapeutic performance under both normoxia and hypoxia. Herein, we reported four ionic iridium(III) complexes (Ir1Ir4) with anthraquinone groups which can regulate their excited state energy levels effectively. Among them, the energy gap of Ir1 was between 1.63 and 2.21 eV, which can match well with that of O2, and the HOMO energy of Ir1 is less than −5.51 eV. Compared with Ir2Ir4, the luminescent quantum efficiency of Ir1 was the highest. Particularly, Ir1 can specifically target the mitochondria of the tumor cells. Meanwhile, Ir1 showed high singlet oxygen quantum yields (ΦΔ) in both solutions and living cells with low cytotoxicity. The results of PDT experiments revealed that Ir1, as a photosensitizer, exhibited excellent therapeutic effect not only in normoxia but also in hypoxia condition. We believe that this work is meaningful for developing excellent PDT agents based on cyclometalated Ir(III) complexes via rational ligand modification.

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References

  1. Tan Y, Xu CS, Xia XS, Yu HP, Bai DQ, He Y, Xu J, Wang P, Wang XN, Leung AWN. Laser Phys, 2009, 19: 1045–1049

    CAS  Google Scholar 

  2. Dougherty TJ, Gomer CJ, Henderson BW, Jori G, Kessel D, Korbelik M, Moan J, Peng Q. J Natl Cancer Inst, 1998, 90: 889–905

    CAS  PubMed  PubMed Central  Google Scholar 

  3. Dolmans DEJGJ, Fukumura D, Jain RK. Nat Rev Cancer, 2003, 3: 380–387

    CAS  PubMed  Google Scholar 

  4. Fan W, Huang P, Chen X. Chem Soc Rev, 2016, 45: 6488–6519

    CAS  PubMed  Google Scholar 

  5. Kelly JF, Snell ME. J Urology, 1976, 115: 150–151

    CAS  Google Scholar 

  6. Mistry P, Kelland LR, Abel G, Sidhar S, Harrap KR. Br J Cancer, 1991, 64: 215–220

    CAS  PubMed  PubMed Central  Google Scholar 

  7. Holford J, Beale PJ, Boxall FE, Sharp SY, Kelland LR. Eur J Cancer, 2000, 36: 1984–1990

    CAS  PubMed  Google Scholar 

  8. Li M, Luo Z, Zhao Y. Sci China Chem, 2018, 61: 1214–1226

    CAS  Google Scholar 

  9. Guo Z, Ma Y, Liu Y, Yan C, Shi P, Tian H, Zhu WH. Sci China Chem, 2018, 61: 1293–1300

    CAS  Google Scholar 

  10. Li Z, Yu L, Yang T, Chen Y. Sci China Chem, 2018, 61: 1243–1260

    CAS  Google Scholar 

  11. Ge J, Jia Q, Liu W, Lan M, Zhou B, Guo L, Zhou H, Zhang H, Wang Y, Gu Y, Meng X, Wang P. Adv Healthcare Mater, 2016, 5: 665–675

    CAS  Google Scholar 

  12. Jia Q, Ge J, Liu W, Liu S, Niu G, Guo L, Zhang H, Wang P. Nanoscale, 2016, 8: 13067–13077

    CAS  PubMed  Google Scholar 

  13. Dai Y, Xu C, Sun X, Chen X. Chem Soc Rev, 2017, 46: 3830–3852

    CAS  PubMed  PubMed Central  Google Scholar 

  14. Song G, Liang C, Yi X, Zhao Q, Cheng L, Yang K, Liu Z. Adv Mater, 2016, 28: 2716–2723

    CAS  PubMed  Google Scholar 

  15. Liu CP, Wu TH, Liu CY, Chen KC, Chen YX, Chen GS, Lin SY. Small, 2017, 13: 1700278

    Google Scholar 

  16. Zhao M, Xu Y, Xie M, Zou L, Wang Z, Liu S, Zhao Q. Adv Healthcare Mater, 2018, 7: 1800606

    Google Scholar 

  17. Jiang J, Qian Y, Xu Z, Lv Z, Tao P, Xie M, Liu S, Huang W, Zhao Q. Chem Sci, 2019, 10: 5085–5094

    CAS  PubMed  PubMed Central  Google Scholar 

  18. Tao P, Li WL, Zhang J, Guo S, Zhao Q, Wang H, Wei B, Liu SJ, Zhou XH, Yu Q, Xu BS, Huang W. Adv Funct Mater, 2016, 26: 881–894

    CAS  Google Scholar 

  19. Feng Z, Tao P, Zou L, Gao P, Liu Y, Liu X, Wang H, Liu S, Dong Q, Li J, Xu B, Huang W, Wong WY, Zhao Q. ACS Appl Mater Interfaces, 2017, 9: 28319–28330

    CAS  PubMed  Google Scholar 

  20. Guo S, Ma Y, Liu S, Yu Q, Xu A, Han J, Wei L, Zhao Q, Huang W. J Mater Chem C, 2016, 4: 6110–6116

    CAS  Google Scholar 

  21. Guo S, Huang T, Liu S, Zhang KY, Yang H, Han J, Zhao Q, Huang W. Chem Sci, 2017, 8: 348–360

    CAS  PubMed  Google Scholar 

  22. Han J, Guo S, Lu H, Liu S, Zhao Q, Huang W. Adv Optical Mater, 2018, 6: 1800538

    Google Scholar 

  23. Han J, Guo S, Wang J, Wei L, Zhuang Y, Liu S, Zhao Q, Zhang X, Huang W. Adv Optical Mater, 2017, 5: 1700359

    Google Scholar 

  24. Lv W, Xia H, Zhang KY, Chen Z, Liu S, Huang W, Zhao Q. Mater Horiz, 2017, 4: 1185–1189

    CAS  Google Scholar 

  25. Lv W, Zhang Z, Zhang KY, Yang H, Liu S, Xu A, Guo S, Zhao Q, Huang W. Angew Chem Int Ed, 2016, 55: 9947–9951

    CAS  Google Scholar 

  26. Nam JS, Kang MG, Kang J, Park SY, Lee SJC, Kim HT, Seo JK, Kwon OH, Lim MH, Rhee HW, Kwon TH. J Am Chem Soc, 2016, 138: 10968–10977

    CAS  PubMed  Google Scholar 

  27. Tao P, Miao Y, Zhang Y, Wang K, Li H, Li L, Li X, Yang T, Zhao Q, Wang H, Liu S, Zhou X, Xu B, Huang W. Org Electron, 2017, 45: 293–301

    CAS  Google Scholar 

  28. Miao Y, Tao P, Wang K, Li H, Zhao B, Gao L, Wang H, Xu B, Zhao Q. ACS Appl Mater Interfaces, 2017, 9: 37873–37882

    CAS  PubMed  Google Scholar 

  29. Tao P, Zhang Y, Wang J, Wei L, Li H, Li X, Zhao Q, Zhang X, Liu S, Wang H, Huang W. J Mater Chem C, 2017, 5: 9306–9314

    CAS  Google Scholar 

  30. Tao P, Miao Y, Wang H, Xu B, Zhao Q. Chem Rec, 2019, 19: 1531–1561

    CAS  PubMed  Google Scholar 

  31. Zhao Q, Jiang CY, Shi M, Li FY, Yi T, Cao Y, Huang CH. Organometallics, 2006, 25: 3631–3638

    CAS  Google Scholar 

  32. Liu Z, Deeth RJ, Butler JS, Habtemariam A, Newton ME, Sadler PJ. Angew Chem Int Ed, 2013, 52: 4194–4197

    CAS  Google Scholar 

  33. Sun L, Chen Y, Kuang S, Li G, Guan R, Liu J, Ji L, Chao H. Chem Eur J, 2016, 22: 8955–8965

    CAS  PubMed  Google Scholar 

  34. Zhang KY, Gao P, Sun G, Zhang T, Li X, Liu S, Zhao Q, Lo KKW, Huang W. J Am Chem Soc, 2018, 140: 7827–7834

    CAS  PubMed  Google Scholar 

  35. Liu B, Monro S, Lystrom L, Cameron CG, Colón K, Yin H, Kilina S, McFarland SA, Sun W. Inorg Chem, 2018, 57: 9859–9872

    CAS  PubMed  PubMed Central  Google Scholar 

  36. DeRosa M. Coord Chem Rev, 2002, 233–234: 351–371

    Google Scholar 

  37. Schweitzer C, Schmidt R. Chem Rev, 2003, 103: 1685–1758

    CAS  PubMed  Google Scholar 

  38. Hao L, Li ZW, Zhang DY, He L, Liu W, Yang J, Tan CP, Ji LN, Mao ZW. Chem Sci, 2019, 10: 1285–1293

    CAS  PubMed  Google Scholar 

  39. James AM, Cochemé HM, Smith RAJ, Murphy MP. J Biol Chem, 2005, 280: 21295–21312

    CAS  PubMed  Google Scholar 

  40. Chen Y, Zhu C, Cen J, Bai Y, He W, Guo Z. Chem Sci, 2015, 6: 3187–3194

    CAS  PubMed  PubMed Central  Google Scholar 

  41. Cao JJ, Zheng Y, Wu XW, Tan CP, Chen MH, Wu N, Ji LN, Mao ZW. J Med Chem, 2019, 62: 3311–3322

    CAS  PubMed  Google Scholar 

  42. Zhou X, Liang H, Jiang P, Zhang KY, Liu S, Yang T, Zhao Q, Yang L, Lv W, Yu Q, Huang W. Adv Sci, 2016, 3: 1500155

    Google Scholar 

  43. Jia Q, Ge J, Liu W, Zheng X, Chen S, Wen Y, Zhang H, Wang P. Adv Mater, 2018, 30: 1706090

    Google Scholar 

Download references

Acknowledgements

This work was supported by the National Funds for Distinguished Young Scientists (61825503), the National Program for Support of Top-Notch Young Professionals, the Priority Academic Program Development of Jiangsu Higher Education Institutions (YX03001), China Postdoctoral Science Foundation Funded Project (2018M642282), Natural Science Foundation of Jiangsu Province of China (BK20180760) and Jiangsu Planned Projects for Postdoctoral Research Funds (2018K155C).

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Correspondence to Qiang Zhao.

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The authors declare that they have no conflict of interest.

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The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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11426_2019_9583_MOESM1_ESM.pdf

Mitochondria-localized iridium(III) complexes with anthraquinone groups as effective photosensitizers for photodynamic therapy under hypoxia

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Guo, S., Han, M., Chen, R. et al. Mitochondria-localized iridium(III) complexes with anthraquinone groups as effective photosensitizers for photodynamic therapy under hypoxia. Sci. China Chem. 62, 1639–1648 (2019). https://doi.org/10.1007/s11426-019-9583-4

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