Citation: Ma Lin, Cai Lingqiao, Jin Qiaomei, Liang Jiajia, Zhang Dongjian, Liu Wei, Ni Yicheng, Yin Zhiqi, Zhang Jian, Pan Ke. Evaluation of necrosis avidity of radioiodinated 5-hydroxytryptophan and its potential applications in myocardial infarction imaging[J]. Chinese Chemical Letters, ;2019, 30(1): 83-86. doi: 10.1016/j.cclet.2018.06.005 shu

Evaluation of necrosis avidity of radioiodinated 5-hydroxytryptophan and its potential applications in myocardial infarction imaging

Ma Lin ^a,b,c ,
Cai Lingqiao ^b,c,d ,
Jin Qiaomei ^b,c ,
Liang Jiajia ^a,b,c ,
Zhang Dongjian ^b,c ,
Liu Wei ^e ,
Ni Yicheng ^f ,
Yin Zhiqi ^a ,
Zhang Jian ^b,c,*,, ,
Pan Ke ^a,,

a.
Department of Natural Medicinal Chemistry & Department of TCMs Pharmaceuticals, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, China
b.
Affliated Hospital of Integrated Traditional Chinese and Western Medicine, Nanjing University of Chinese Medicine, Nanjing 210028, China
c.
Laboratories of Translational Medicine, Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing 210028, China
d.
College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
e.
Department of Nuclear Medicine, The First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, China
f.
Theragnostic Laboratory, Campus Gasthuisberg, KU Leuven, 3000 Leuven, Belgium

Corresponding author: Zhang Jian, zhangjian@jsatcm.com; zjwonderful@hotmail.com; zjwonderful2008@gmail.com Pan Ke, kpan@cpu.edu.cn

Received Date: 24 April 2018
Revised Date: 1 June 2018
Accepted Date: 4 June 2018
Available Online: 6 January 2018

Figures(3)

This study aimed to seek necrosis avid agents with high safety from DNA binding agents. The interaction of 5-hydroxytryptophan (5-HTP) with DNA was investigated by a series of spectroscopic studies. Then, 5-HTP was labeled with iodine-131 ([¹³¹I]5-HTP) and the necrosis avidity of [¹³¹I]5-HTP was evaluated by in vitro cell binding assays, in vivo biodistribution experiments and blocking experiment. Finally, the potential of [¹³¹I]5-HTP to image necrotic myocardium was explored in rat models with myocardial infarction by SPECT/CT imaging. Results showed that 5-HTP bound to DNA in groove binding mode and the binding constant was 1.69×10⁴ L/mol.[¹³¹I]5-HTP showed specific affinity to necrotic A549 cells, which might be related to cell nucleus. Biodistribution and autoradiography results showed preferential accumulation of [¹³¹I]5-HTP in necrotic muscle (necrotic/viable muscle ratio:6.95±0.68 at 3 h postinjection (p.i.)), which could be blocked by 5-HTP with 66.7% decline, indicating that [¹³¹I]5-HTP might share the same necrotic targets with 5-HTP. On SPECT/CT images, a hotspot was clearly observed at 3 h p.i. in the necrotic myocardium while not in the control myocardium. In conclusion, [¹³¹I]5-HTP is a novel necrosis avid agent and can rapidly visualize necrotic myocardium at 3 h p.i. The necrosis avidity mechanism of [¹³¹I]5-HTP may be attributed to its interactions with exposed DNA in the necrotic tissues.
- Radioiodinated 5-hydroxytryptophan,
- Necrosis avidity,
- DNA,
- Groove binding,
- Necrotic myocardium imaging
1. [1]
  T.V. Berghe, S. Grootjans, V. Goossens, et al., Methods 61(2013) 117-129. doi: 10.1016/j.ymeth.2013.02.011
2. [2]
  A.A. Neves, K.M. Brindle, J. Nucl. Med. 55(2014) 1-4. doi: 10.2967/jnumed.112.114264
3. [3]
  Y. Ni, G. Bormans, F. Chen, A. Verbruggen, G. Marchal, Invest. Radiol. 40(2005) 526-535. doi: 10.1097/01.rli.0000171811.48991.5a
4. [4]
  M. Miranda Cona, R. Oyen, Y. Ni, Curr. Med. Chem. 22(2015) 1829-1849. doi: 10.2174/0929867322666150227153550
5. [5]
  M. van de Putte, H. Wang, F. Chen, P.A. de Witte, Y. Ni, Acad. Radiol. 15(2008) 107-113. doi: 10.1016/j.acra.2007.08.008
6. [6]
  H. Fonge, K. Vunckx, H. Wang, et al., Eur. Heart J. 29(2007) 260-269. doi: 10.1093/eurheartj/ehm588
7. [7]
  M. Pietrzak, M. Maciejczyk, M. Szabelski, A. Kasparek, Z. Wieczorek, Chem. Phys. Lett. 601(2014) 39-44. doi: 10.1016/j.cplett.2014.03.076
8. [8]
  Q. Wang, S. Yang, C. Jiang, et al., Sci. Rep. 6(2016) 21341. doi: 10.1038/srep21341
9. [9]
  Q. Luo, Q. Jin, C. Su, et al., Anal. Chem. 89(2017) 1260-1266. doi: 10.1021/acs.analchem.6b03959
10. [10]
  Y. Yuan, J. Zheng, M. Wang, et al., J. Agric. Food Chem. 64(2016) 5742-5750. doi: 10.1021/acs.jafc.6b01872
11. [11]
  M. Dasari, S. Lee, J. Sy, et al., Org. Lett. 12(2010) 3300-3303. doi: 10.1021/ol100923d
12. [12]
  M. Dasari, A.P. Acharya, D. Kim, et al., Bioconjugate Chem. 24(2012) 4-8.
13. [13]
  S. Huang, H.H. Chen, H. Yuan, et al., J. Cardiov. Magn. Reson. 13(2011) O23. doi: 10.1186/1532-429X-13-S1-O23
14. [14]
  X. Duan, Z. Yin, C. Jiang, et al., European J. Pharm. Biop. 117(2017) 151-159. doi: 10.1016/j.ejpb.2017.04.006
15. [15]
  A.Y. Ji, Q.M. Jin, D.J. Zhang, et al., ACS Med. Chem. Lett. 8(2017) 191-195. doi: 10.1021/acsmedchemlett.6b00398
16. [16]
  N.K. Kaushik, N. Kaushik, P. Attri, et al., Molecules 18(2013) 6620-6662. doi: 10.3390/molecules18066620
17. [17]
  Y. Ni, MR contrast agents for cardiac imaging, in: J. Bogaert (Ed.), Clinical Cardiac MRI, Springer, Berlin, Heidelberg, 2011, pp. 31-51.
18. [18]
  E.H. Turner, J.M. Loftis, A.D. Blackwell, Pharmacol. Therapeut. 109(2006) 325-338. doi: 10.1016/j.pharmthera.2005.06.004
19. [19]
  M. Sirajuddin, S. Ali, A. Badshah, J. Photoch. Photobio. B 124(2013) 1-19. doi: 10.1016/j.jphotobiol.2013.03.013
20. [20]
  S. Zhang, H. Yuan, L. Tian, J. Mol. Struct. 1130(2017) 760-764. doi: 10.1016/j.molstruc.2016.11.003
1. [1]
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2. [2]
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4. [4]
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9. [9]
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10. [10]
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12. [12]
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13. [13]
  Yanfei Liu , Yaqin Hu , Yifu Tan , Qiwen Chen , Zhenbao Liu . Tumor acidic microenvironment activatable DNA nanostructure for precise cancer cell targeting and inhibition. Chinese Chemical Letters, 2025, 36(1): 110289-. doi: 10.1016/j.cclet.2024.110289
14. [14]
  Kun Liu , Yulin Cong , Xiongfeng Luo , Meicun Yao , Zhiyong Xie , Hao Li . Utilizing bivalent aptamers as first DNA agonist to activate RTKs heterodimer of different families. Chinese Chemical Letters, 2025, 36(1): 109839-. doi: 10.1016/j.cclet.2024.109839
15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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沈阳化工大学材料科学与工程学院沈阳 110142