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Synthesis and in vitro/vivo Evaluation of Iodine-123/124 Labelled Hypericin Derivatives

  • Kim, Sang-Wook (Radiation Research Division for Industry & Environment, Korea Atomic Energy Research Institute) ;
  • Park, Jeong-Hoon (Radiation Research Division for Industry & Environment, Korea Atomic Energy Research Institute) ;
  • Yang, Seung-Dae (Radiation Research Division for Industry & Environment, Korea Atomic Energy Research Institute) ;
  • Hur, Min-Goo (Radiation Research Division for Industry & Environment, Korea Atomic Energy Research Institute) ;
  • Choi, Chang-Woon (Department of Nuclear Medicine, Korea Institute of Radiological and Medical Sciences) ;
  • Yu, Kook-Hyun (Department of Chemistry, Dongguk University)
  • Published : 2008.10.20

Abstract

To evaluate the potential of radioiodine labelled hypericin as a malignant glioma imaging agent, U-251 MG, U-373 MG, C6 glioma and fibroblast were treated with a I-123 labelled hypericin derivative and C6 glioma transplanted nude mouse were injected with a I-124 labelled hypericin derivative for a micro PET imaging. 2- Iodohypericin was prepared as a reference compound. In this paper, we describe the syntheses of 2- iodohypericin and 2-[$^{123}I/^{124}I$]iodohypericin and the results of a corresponding biological evaluation. In all glioma cell lines, 2-[$^{123}I$]iodohypericin uptake was increased in a time dependant manner and an accumulation of 2-[$^{124}I$]iodohypericin was observed in C6 glioma bearing nude mouse. These results suggest that radioiodine labelled hypericin can visualize a PKC overexpressed malignant glioma.

Keywords

References

  1. Gruszecka-Kowalik, E.; Zalkow, L. H. Org. Prep. Proc. Int. 2000, 32, 57 https://doi.org/10.1080/00304940009356746
  2. Muruelo, D.; Lavie, G.; Lavie, D. Proc. Natl. Sci. USA 1988, 85, 5230 https://doi.org/10.1073/pnas.85.14.5230
  3. Lavie, G.; Valentine, F.; Levin, B.; Mazur, Y.; Gallo, G.; Lavie, D.; Weiner, D.; Muruelo, D. Proc. Natl. Acad. Sci. 1989, 86, 5963 https://doi.org/10.1073/pnas.86.15.5963
  4. Lavie, G.; Mazur, Y.; Valentine, F.; Lavie, D.; Levin, B.; Itta, Y.; Muruelo, D. Therapies and Vaccines of the Annals of the New York Academy of Sciences 1995, 616, 556
  5. Kraus, G. A.; Pratt, D.; Tossberg, J.; Carpenter, S. Biochem. Biophys. Res. Commun. 1990, 172, 149 https://doi.org/10.1016/S0006-291X(05)80185-8
  6. Lavie, G.; Kaplinsky, C.; Toren, A.; Aizman, I.; Meruelo, D.; Manden, M. Br. J. Cancer 1999, 79, 423 https://doi.org/10.1038/sj.bjc.6690066
  7. Colasanti, A.; Kisslinger, A.; Liuzzi, R.; Quarto, M.; Riccio, P.; Roberti, G.; Tramontano, D.; Villani, F. J. Photochem. Photobiol. B: Biol. 2000, 54, 103 https://doi.org/10.1016/S1011-1344(99)00149-9
  8. Hoepfner, M.; Maaser, K.; Theiss, A.; Lenz, M.; Sutter, A. P.; Kashtan, H.; von Lampe, B.; Riecken, E. O.; Zeitz, M.; Scheruebl, H. Int. J. Colorectal. Dis. 2003, 18, 239
  9. Kamuhabwa, A. A. R.; Cosserat-Geradin, I.; Didelon, J.; Notter, D.; Guillemin, F.; Roskams, T.; D'Hallewin, M.-A.; Baert, L.; de Witte, P. A. M. Int. J. Cancer 2002, 97, 253 https://doi.org/10.1002/ijc.1594
  10. Chen, B.; Roskams, T.; de Witte, P. A. M. Lasers in Surgery and Medicine 2002, 31, 158 https://doi.org/10.1002/lsm.10089
  11. Takahashi, I.; Nakanishi, S.; Kobayashi, E.; Nakano, H.; Suzuki, K.; Tamaoki, T. Biochem. Biophys. Res. Commun. 1989, 165, 1207 https://doi.org/10.1016/0006-291X(89)92730-7
  12. Couldwell, W. T.; Uhm, J. H.; Antel, J. P.; Yong, V. W. Neurosurgery 1991, 29, 880 https://doi.org/10.1227/00006123-199112000-00013
  13. Nishizuka, Y. JAMA. 1989, 262, 1826 https://doi.org/10.1001/jama.262.13.1826
  14. Tysnes, O. B.; Laerum, O. D. Anticancer Res. 1993, 13, 1325
  15. Baltuch, G. H.; Couldwell, W. T.; Villemure, J. G.; Yong, V. W. Neurosurgery 1993, 33, 495 https://doi.org/10.1227/00006123-199309000-00021
  16. Couldwell, W. T.; Hinton, D. R.; He, S.; Chen, T. C.; Sebat, I.; Weiss, M. H.; Law, R. E. FEBS Lett. 1994, 345, 43 https://doi.org/10.1016/0014-5793(94)00415-3
  17. Vanbilloen, H.; Bormans, G.; Chen, P.; de Witte, P. A. M.; Verbruggen, A.; Verbeke, K. J. Labelled Cpd. Radiopharm. 2001, 44(Supp. 1), S965 https://doi.org/10.1002/jlcr.25804401339
  18. Bormans, G.; Huygye, D.; Christiaen, A.; Verbeke, K.; de Groot, T.; Vanvilloen, H.; de Witte, P. A. M.; Verbruggen, A. J. Labelled Cpd. Radiopharm. 2004, 47, 191 https://doi.org/10.1002/jlcr.812
  19. Brockmann, H.; Kluge, F.; Muxfeldt, H. Chem. Ber. 1957, 90, 2302 https://doi.org/10.1002/cber.19570901027
  20. Falk, H.; Schoppel, G. Monatsh. Chem. 1992, 123, 931 https://doi.org/10.1007/BF00811548
  21. Kim, S. W.; Park, J. H.; Yang, S. D.; Hur, M. G.; Kim, Y.-S.; Chai, J.-S.; Kim, Y. S.; Yu, K. H. Bull. Korean Chem. Soc. 2004, 25, 1147 https://doi.org/10.5012/bkcs.2004.25.8.1147
  22. Chen, B.; Roskams, T.; de Witte, P. A. M. Photochem. Photobiol. 2002, 76, 509 https://doi.org/10.1562/0031-8655(2002)076<0509:ATEBHM>2.0.CO;2
  23. Daniel, C. Hippokrates 1949, 19, 526
  24. Vandenbogaerde, A. L.; Delaey, E. M.; Vantieghem, A. M.; Himpens, B. E.; Merlevede, W. J.; de Witte, P. A. M. J. Photochem. Photobiol. B: Biol. 1998, 45, 87 https://doi.org/10.1016/S1011-1344(98)00163-8
  25. Kamuhabwa, A. A. R.; Agostinis, P.; D'Hallewin, M.-A.; Kasran, A.; de Witte, P. A. M. Anticancer. Res. 2000, 20, 2579

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