Skip to main content
Log in

(S)-2-((S)-2-(4-(3-[18F]fluoropropyl)benzamido)-3-phenylpropanamido)pentanedioic acid labeled with 18F

Journal of Radioanalytical and Nuclear Chemistry Aims and scope Submit manuscript

Abstract

As degradation product of Antineoplaston A10 in vivo, phenylacetyl glutamine showed antitumor activities. According to literatures, we designed and radiosynthesized a phenylacetyl glutamine derivative, which was achieved under a mild reaction condition. Evaluations in vitro and in vivo were performed on tumor bearing mice. Excitingly, the radiochemical purity of (S)-2-((S)-2-(4-(3-fluoropropyl)benzamido)-3-phenylpropanamido)pentanedioic acid ([18F]FBPPA) was 98%, and besides the best radiochemical yield was up to 46%. T/Bl (Tumor/Blood) and T/M (Tumor/Muscle) ratios of [18F]FBPPA at 60 min post injection were 2.33 and 3.51. Meanwhile, it showed satisfied stability in vitro and in vivo, compared with 2-[18F]fluorodeoxyglucose ([18F]FDG). Although [18F]FBPPA deserved further studies to make optimizations on its structure, the results revealed it might become a potential PET imaging agent for detecting tumors.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Abbreviations

[18F]FBPPA:

(S)-2-((S)-2-(4-(3-fluoropropyl)benzamido)-3-phenylpropanamido)pentanedioic acid

References

  1. Thomas B, Christopher JRF, Andrew KJ (2008) Label Compd Radiopharm 51:369

    Article  Google Scholar 

  2. Tetsuhiro H, Nobuyuki K, Yoshihiro N (2008) Eur J Nucl Med Mol Imaging 35:2009

    Article  Google Scholar 

  3. Weiping Y, Larry W, Mark MG (2009) Bioorg Med Chem 17:1982

    Article  Google Scholar 

  4. Patt M, Schildan A, Habermann B, Mishchenko O, Patt JT, Sabri O (2010) J Radioanal Nucl Chem 283:487

    Article  CAS  Google Scholar 

  5. Burzynski SR (1983) Abstracts of papers Eur 13th Int Cong chemother[C]. Vienna, p 11

  6. Khalid M (1987) Drugs Exptl Clin Res 13(Supp 1):57

    CAS  Google Scholar 

  7. Qu X, Cui S, Tiani Z (2007) Anticancer Res 27(4B):2427

    CAS  Google Scholar 

  8. Revelle LK, Avignon DAD, Wilson JA (1996) J Pharm Sci 85(10):1049

    Article  CAS  Google Scholar 

  9. Eagel H (1957) Arch Bilphys 67:432

    Article  Google Scholar 

  10. Furst P, Pogan K, Stehle P (1997) Nutrition 13(7–8):731

    Article  CAS  Google Scholar 

  11. Curthoys NP, Watford M (1995) Ann Rev Nutr 15:133

    Article  CAS  Google Scholar 

  12. Segura JA, Donadio AC, Lobo C (2005) Cancer Lett 218(1):91

    Article  CAS  Google Scholar 

  13. Medina MA (2001) J Nutr 131(9 Suppl):2539S

    CAS  Google Scholar 

  14. Deberardinis RJ, Cheng T (2010) Oncogene 29(3):313

    Article  CAS  Google Scholar 

  15. Byrne TA, Persinger RL, Young LS (1995) Ann Surg 222(3):243

    Article  CAS  Google Scholar 

  16. Lohmann R, Souba WW, Zakrzewski (1998) Metab Clin Exp 47:608

    CAS  Google Scholar 

  17. Kung HF, Zhu L, Ploessl K (2009) Abstracts of papers 238th ACS national meeting, Wahington DC, USA, August 16–20. ACS, Wahington, DC, p 641

  18. Dinkelborg L, Friebe M, Krasikowa R. WO Patent. 2008052788, 2008

  19. Guan MY, Shi N, Sun JZ (2003) J Chin Clin Med Imaging 14(2):112

    Google Scholar 

  20. Chu TW, Xie JL, Wang XY (2002) Nucl Tech 25(5):361

    CAS  Google Scholar 

  21. Wang MW, Yin DZ, Zhang L (2006) Nucl Sci Tech 17(3):148

    Article  CAS  Google Scholar 

  22. Zhao YL, Zhang CL, Qi CM (2007) J Radioanal Nucl Chem 273:9

    Article  CAS  Google Scholar 

  23. Jinming Zhang, Yungang Li, Jian Liu (2010) J Radioanal Nucl Chem 283:565

    Article  Google Scholar 

  24. Nandy SK, Krishnamurthy NV, Rajan MGR (2010) J Radioanal Nucl Chem 283:245

    Article  CAS  Google Scholar 

  25. Coleman RE (2000) Imaging Nucl Med Bio 27:689

    Article  CAS  Google Scholar 

  26. Li RF, Wu SC, Wang SC (2010) Appl Radiat Isot 68:303

    Article  CAS  Google Scholar 

  27. Hoh CK (2007) Nucl Med & Bio 34:737

    Article  CAS  Google Scholar 

  28. Qiao YL, He Y, Zhang S (2009) Bioorg Med Chem Lett 19:4873

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We acknowledged with thanks for financial supports from the National Natural Science Foundation of China (No.20371009 and No.20671014), Key laboratory of Radioactive Medicine of Ministry Education and Beijing Municipal Commission of Education.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chuan-Min Qi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

He, Y., Ding, R., Liu, H. et al. (S)-2-((S)-2-(4-(3-[18F]fluoropropyl)benzamido)-3-phenylpropanamido)pentanedioic acid labeled with 18F. J Radioanal Nucl Chem 286, 135–140 (2010). https://doi.org/10.1007/s10967-010-0633-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10967-010-0633-2

Keywords

Navigation