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Metabolic Stability of [18F]Fluoroalkylbiphenyls

  • Lee, Kyo-Chul (Korea Institute of Radiological & Medical Sciences) ;
  • Lee, Sang-Yoon (Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine, Division of Radiological Sciences, Department of Radiology, Washington University School of Medicine) ;
  • Choe, Yearn-Seong (Department of Nuclear Medicine, Samsung Medical Center, Sungkyunkwan University School of Medicine) ;
  • Chi, Dae-Yoon (Department of Chemistry, Inha University)
  • Published : 2004.08.20

Abstract

The stability of fluoroalkyl groups as a pendent on the phenyl ring was measured in vitro using rat hepatic microsomes and human serum to predict their in vivo stabilities. We have prepared three [$^{18}F$]fluoroalkyl-biphenyls as the model compounds of fluoroalkyl aromatic compounds to compare the in vitro stabilities. In addition, in vitro stabilities were measured separately using rat hepatic microsomes and human serum at $37^{\circ}C$. Fluoroethylbiphenyl had similar or slightly superior stability to fluoropropylbiphenyl and these two compounds were much more stable than fluoromethylbiphenyl in vitro.

Keywords

References

  1. Raichle, M. E. Ann. Rev. Neurosci. 1983, 6, 249. https://doi.org/10.1146/annurev.ne.06.030183.001341
  2. Lee, K. C.; Chi, D. Y. J. Org. Chem. 1999, 64, 8576. https://doi.org/10.1021/jo990994f
  3. Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124,10278. https://doi.org/10.1021/ja026242b
  4. Kim, D. W.; Choe, Y. S.; Chi, D. Y. Nucl. Med. Biol. 2003, 30,345. https://doi.org/10.1016/S0969-8051(03)00017-9
  5. Chi, D. Y.; Kilbourn, M. R.; Katzenellenbogen, J. A.; Brodack, J.W.; Welch, M. J. Appl. Radiat. Isot. 1986, 37, 1173. https://doi.org/10.1016/0883-2889(86)90002-X
  6. Yu, K. H.; Park, J. H.; Yang, S. D. Bull. Korean Chem. Soc. 2004,25, 506. https://doi.org/10.5012/bkcs.2004.25.4.506
  7. Oh, S. J.; Choe, Y. S.; Kim, S. E.; Choi, Y.; Lee, K. H.; Kim, B.-T.Bull. Korean Chem. Soc. 2000, 21, 1162.
  8. Mach, R. H.; Scripko, J. G.; Ehrenkaufer, R. L.; Morton, T. E. J.Labelled Compd. Radiopharm. 1991, 30, 154.
  9. Haroutounian, S. A.; DiZio, J. P.; Katzenellenbogen, J. A. J. Org.Chem. 1991, 56, 4993. https://doi.org/10.1021/jo00016a040
  10. Ng, J. S.; Katzenellenbogen, J. A.; Kilbourn, M. R. J. Org. Chem.1981, 46, 2520. https://doi.org/10.1021/jo00325a017
  11. Barrio, J. R.; Satyamurthy, N.; Ku, H.; Phelps, M. E. J. Chem.Soc., Chem. Commun. 1983, 443.
  12. Choe, Y. S.; Song, D. H.; Lee, K.-J.; Kim, S. E.; Choi, Y.; Lee, K.H.; Kim, B.-T.; Oh, S. J.; Chi, D. Y. Appl. Radiat. Isot. 1998, 49,73. https://doi.org/10.1016/S0969-8043(97)00224-8
  13. Petric, A.; Barrio, J. R.; Namavari, M.; Huang, S. C.; Satyamurthy,N. Nucl. Med. Biol. 1999, 26, 529. https://doi.org/10.1016/S0969-8051(99)00023-2
  14. Gerdes, J. M.; Keil, R. N.; Shulgin, A. T.; Mathis, C. A. J.Fluorine Chem. 1996, 78, 121. https://doi.org/10.1016/0022-1139(96)03417-3
  15. Lee, K. C.; Moon, B. S.; Lee, J. H.; Chung, K.-H.; Katzenellenbogen,J. A.; Chi, D. Y. Bioorg. Med. Chem. 2003, 11, 3649. https://doi.org/10.1016/S0968-0896(03)00362-6
  16. Lee, B. C.; Paik, J.-Y.; Chi, D. Y.; Lee, K.-H.; Choe, Y. S.Bioconjugate Chem. 2004, 15, 104. https://doi.org/10.1021/bc034115e
  17. Kim, H. W.; Jeong, J. M.; Lee, Y.-S.; Chi, D. Y.; Chung, K.-H.;Lee, D. S.; Chung, J.-K.; Lee, M. C. Appl. Radiat. Isot. 2004, 61,in web.
  18. Oh, S. J.; Moszidanowski, C.; Chi, D. Y.; Kim, J. Y.; Kang, S. H.;Ryu, J. S.; Yeo, J. S.; Moon, D. H. Nucl. Med. Biol. 2004, 30, inprint.
  19. de Paulis, T.; Kumar, Y.; Johansson, L.; Ramsby, S.; Florvall, L.;Hall, H.; Ängeby-Möller, K.; Ögren, S. J. Med. Chem. 1985, 28,1263. https://doi.org/10.1021/jm00147a025
  20. de Paulis, T. Curr. Pharm. Design 2003, 9, 673. https://doi.org/10.2174/1381612033391135
  21. Mukherjee, J.; Yang, Z.-y.; Das, M. K.; Brown, T. Nucl. Med.Biol. 1995, 22, 283. https://doi.org/10.1016/0969-8051(94)00117-3
  22. Schmidt, D. E.; Votaw, J. R.; Kessler, R. M.; de Paulis, T. J.Pharm. Sci. 1994, 83, 305. https://doi.org/10.1002/jps.2600830309
  23. Lee, B. S.; Chu, S.; Lee, K. C.; Lee, B.-S.; Chi, D. Y.; Kim, S. E.;Choe, Y. S.; Song, Y. S.; Jin, C. Bioorg. Med. Chem. 2003, 11,4949. https://doi.org/10.1016/j.bmc.2003.09.009
  24. Lee, S.-Y.; Choe, Y. S.; Kim, D. H.; Park, B.-N.; Kim, S. E.;Choi, Y.; Lee, K.-H.; Lee, J.; Kim, B.-T. Nucl. Med. Biol. 2001,28, 391. https://doi.org/10.1016/S0969-8051(01)00203-7
  25. Chen, P.; Kilts, C. D.; Camp, V. M.; Ely, T. D.; Malveaux, E.;Votaw, J.; Hoffman, J. M.; Goodman, M. M. J. Labelled Compd. Radiopharm. 1999, 42, S324.
  26. Welch, M. J.; Katzenellenbogen, J. A.; Mathias, C. J.; Brodack, J.W.; Carlson, K. E.; Chi, D. Y.; Dence, C. S.; Kilbourn, M. R.;Perlmutter, J. S.; Raichle, M. E.; Ter-Pogossian, M. M. Nucl. Med. Biol. 1988, 15, 83.
  27. Williams, D. A. Drug Metabolism in Principle of Medicinal Chemistry; Foye, W. O., Ed.; Lea & Febiger: Philadelphia, 1981;pp 95-103.

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