Citation: Danghui Ma, Shumin Hou, Chaeeon Bae, Thanh Chung Pham, Songyi Lee, Xin Zhou. Aza-BODIPY based probe for photoacoustic imaging of ONOO⁻ in vivo[J]. Chinese Chemical Letters, ;2021, 32(12): 3886-3889. doi: 10.1016/j.cclet.2021.05.048 shu

Aza-BODIPY based probe for photoacoustic imaging of ONOO⁻ in vivo

Danghui Ma ^a ,
Shumin Hou ^a ,
Chaeeon Bae ^d ,
Thanh Chung Pham ^d ,
Songyi Lee ^{c, d, *,} ,
Xin Zhou ^{a, b, **,}

a.
Department of Chemistry, College of Chemistry and Chemical Engineering, Qingdao 266071, China
b.
Qingdao Cancer Institute, Qingdao University, Qingdao 266071, China
c.
Department of Chemistry, Pukyong National University, Busan 48513, Korea
d.
Industry 4.0 Convergence Bionics Engineering, Pukyong National University, Busan 48513, Korea

slee@pknu.ac.kr

zhouxin@qdu.edu.cn

Received Date: 16 March 2021
Revised Date: 18 May 2021
Accepted Date: 24 May 2021
Available Online: 1 June 2021

Figures(5)

The effective detecting ONOO⁻ variations in vivo is of great importance to well understand the complex pathophysiological processes. We reported here a photoacoustic (PA) probe AZB-1 for imaging ONOO⁻ in vivo. AZB-1 showed an originally strong photoacoustic signal at 660 nm. And its PA signal can be turned off by shutting the ICT effect caused by the conjugated electron withdrawing group at 2-position of the aza-BODIPY core. Moreover, the probe was successfully employed to imaging ONOO⁻ variations in inflammatory mice models. Wisely utilized this strategy may serve as powerful platforms for the preparation of novel PA chemosensors.
- Photoacoustic,
- ONOO⁻,
- Imaging,
- Aza-BODIPY,
- In vivo
1. [1]
  F.J. Corpas, J.B. Barroso, Ann. Bot. 113(2014) 87-96. doi: 10.1093/aob/mct260
2. [2]
  H. Li, X. Li, X. Wu, W. Shi, H. Ma, Anal. Chem. 89(2017) 5519-5525. doi: 10.1021/acs.analchem.7b00503
3. [3]
  J. Liu, Y. Dong, Y. Ma, et al., Nanoscale 10(2018) 13589-13598. doi: 10.1039/C8NR04596H
4. [4]
  Y. Deng, G. Feng, Anal. Chem. 92(2020) 14667-14675. doi: 10.1021/acs.analchem.0c03199
5. [5]
  J.H.M. Tsai, J.G. Harrison, J.C. Martin, et al., J. Am. Chem. Soc. 116(1994) 4115-4116. doi: 10.1021/ja00088a072
6. [6]
  G. Ferrer-Sueta, R. Radi, ACS Chem. Biol. 4(2009) 161-177. doi: 10.1021/cb800279q
7. [7]
  C. Ducrocq, B. Blanchard, B. Pignatellib, H. Ohshima, Cell. Mol. Life Sci. 55(1999) 1068-1077. doi: 10.1007/s000180050357
8. [8]
  Y. Li, X. Xie, X. Yang, et al., Chem. Sci. 8(2017) 4006-4011. doi: 10.1039/C7SC00303J
9. [9]
  P. Pacher, J.S. Beckman, L. Liaudet, Physiol. Rev. 87(2007) 315-424. doi: 10.1152/physrev.00029.2006
10. [10]
  T. Sawa, M.H. Zaki, T. Okamoto, et al., Nat. Chem. Biol. 3(2007) 727-735. doi: 10.1038/nchembio.2007.33
11. [11]
  T. Koppal, J. Drake, S. Yatin, et al., J. Neurochem. 72(1999) 310-317. doi: 10.1046/j.1471-4159.1999.0720310.x
12. [12]
  D. Lee, C.S. Lim, G. Ko, et al., Anal. Chem. 90(2018) 9347-9352. doi: 10.1021/acs.analchem.8b01960
13. [13]
  V.L. Dawson, T.M. Dawson, J. Chem. Neuroanat. 10(1996) 179-190. doi: 10.1016/0891-0618(96)00148-2
14. [14]
  T. Franc, S. Salman-Tabcheh, M.C. Guérin, J. Torreilles, Res. Rev. 30(1999) 153-163. doi: 10.1016/S0165-0173(99)00014-4
15. [15]
  S. Wang, L. Chen, P. Jangili, et al., Coord. Chem. Rev. 374(2018) 36-54. doi: 10.1016/j.ccr.2018.06.013
16. [16]
  B. Li, Z. He, H. Zhou, H. Zhang, T. Cheng, Chin. Chem. Lett. 28(2017) 1929-1934. doi: 10.1016/j.cclet.2017.08.055
17. [17]
  X. Li, X. Gao, W. Shi, H. Ma, Chem. Rev. 114(2014) 590-659. doi: 10.1021/cr300508p
18. [18]
  J.F. Zhang, Y. Zhou, J. Yoon, J.S. Kim, Chem. Soc. Rev. 40(2011) 3416-3429. doi: 10.1039/c1cs15028f
19. [19]
  X. Chen, X. Tian, I. Shin, J. Yoon, Chem. Soc. Rev. 40(2011) 4783-4804. doi: 10.1039/c1cs15037e
20. [20]
  J. Lu, Y. Song, W. Shi, X. Li, H. Ma, Sens. Actuators B: Chem. 161(2012) 615-620. doi: 10.1016/j.snb.2011.11.009
21. [21]
  H. Maeda, H. Matsuno, M. Ushida, et al., Angew. Chem. Int. Ed. 44(2005) 2922-2925. doi: 10.1002/anie.200500114
22. [22]
  C. Yin, F. Huo, J. Zhang, et al., Chem. Soc. Rev. 42(2013) 6032-6059. doi: 10.1039/c3cs60055f
23. [23]
  M. Xu, L.V. Wang, Rev. Sci. Instrum. 77(2006) 041101. doi: 10.1063/1.2195024
24. [24]
  Q. Fu, R. Zhu, J. Song, H. Yang, X. Chen, Adv. Mater. 31(2019) 1805875.
25. [25]
  L.V. Wang, Nat. Photonics 3(2009) 503-509. doi: 10.1038/nphoton.2009.157
26. [26]
  J. Weber, P.C. Beard, S.E. Bohndiek, Nat. Methods 13(2016) 639-650. doi: 10.1038/nmeth.3929
27. [27]
  K.J. Cash, C. Li, J. Xia, L.V. Wang, H.A. Clark, ACS Nano 9(2015) 1692-1698. doi: 10.1021/nn5064858
28. [28]
  P. Beard, Interface Focus 1(2011) 602-631. doi: 10.1098/rsfs.2011.0028
29. [29]
  S. Mallidi, G.P. Luke, S. Emelianov, Trends Biotechnol. 29(2011) 213-221. doi: 10.1016/j.tibtech.2011.01.006
30. [30]
  J. Jo, C. Tian, G. Xu, et al., Photoacoustics 12(2018) 82-89. doi: 10.1016/j.pacs.2018.07.004
31. [31]
  H. Li, P. Zhang, L.P. Smaga, R.A. Hoffman, J. Chan, J. Am. Chem. Soc. 137(2015) 15628-15631. doi: 10.1021/jacs.5b10504
32. [32]
  Y. Liu, S. Wang, Y. Ma, et al., Adv. Mater. 29(2017) 1606129. doi: 10.1002/adma.201606129
33. [33]
  X. Li, Y. Tang, J. Li, et al., Chem. Commun. 55(2019) 5934-5937. doi: 10.1039/C9CC02224D
34. [34]
  J. Zheng, Q. Zeng, R. Zhang, D. Xing, T. Zhang, J. Am. Chem. Soc. 141(2019) 19226-19230. doi: 10.1021/jacs.9b10353
35. [35]
  C.J. Reinhardt, E.Y. Zhou, M.D. Jorgensen, G. Partipilo, J. Chan, J. Am. Chem. Soc. 140(2018) 1011-1018. doi: 10.1021/jacs.7b10783
36. [36]
  J. Zhang, X. Zhen, J. Zeng, K. Pu, Anal. Chem. 90(2018) 9301-9307. doi: 10.1021/acs.analchem.8b01879
37. [37]
  X. Qin, F. Li, Y. Zhang, et al., Anal. Chem. 90(2018) 9381-9385. doi: 10.1021/acs.analchem.8b01992
38. [38]
  W. Zhao, E.M. Carreira, Angew. Chem. Int. Ed. 44(2005) 1677-1679. doi: 10.1002/anie.200461868
39. [39]
  A.H. Panchal, N.J. Patel, N.G. Patel, et al., Pharma. Sci. Monit. 1(2010) 79-94.
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Aza-BODIPY based probe for photoacoustic imaging of ONOO− in vivo

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通讯作者: 陈斌, bchen63@163.com

Aza-BODIPY based probe for photoacoustic imaging of ONOO⁻ in vivo