Skip to main content

Syntheses of PET-Tracers for the Determination of Hypoxia

  • Chapter
Imaging of Hypoxia

Part of the book series: Developments in Nuclear Medicine ((DNUM,volume 33))

Abstract

1-(2-Nitro-1-imidazolyl)-3-fluoro-2-propanol, FMISO (1), was suggested as a tracer for the determination of hypoxic tissue in vivo with PET in 19841. Since then, several synthetic approaches to FMISO have been undertaken with the aim of serving clinical applications. Though the focus has been on FMISO production, the development of other alternative hypoxia tracers has merit, based on pursuit of simpler synthetic methods or the long range goal of discovering new tracers that act biologically under less severe hypoxic conditions.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Jerabek, P.A.; Dischino, D.D.; Kilbourn, M.R.; Welch, M.J.; Synthesis of Fluorine-18 Labeled 1-(2-Nitro-1-imidazolyl)-3-fluoro-2-propanol, A Hypoxic Cell Radiosensitizer; J. Labelled Compd. Radiopharm. 21: 1234 (1984)

    Google Scholar 

  2. Jerabek, P.A.; Patrick, T.B.; Kilbourn, M.R.; Dischino, D.D.; Welch, M.J.; Synthesis and Biodistribution of 18F-Labeled Fluoronitroimidazoles: Potential in vivo Markers of Hypoxic Tissue; Appl. Rad. Isot. 37 (7): 599–605 (1986)

    Article  CAS  Google Scholar 

  3. Lim, J.L.; Berridge, M.S.; Efficient Radiosynthesis of [18F]-Fluoromisonidazole Suitable For Routine PET; J. Labelled Compd. Radiopharm. 32: 541 (1993)

    Google Scholar 

  4. Lim, J -L; Berridge, M.S.; An Efficient Radiosynthesis of [18F]Fluoromisonidazole; Appl. Radiat. Isot. 44 (8): 1085–1091 (1993)

    Article  CAS  Google Scholar 

  5. Cherif, A.; Yang, D.J.; Tansey, W.; Kim, E.E.; Wallace, S.; Rapid Synthesis of 3-[18F]Fluoro-1-(2’-Nitro-l’-Imidazolyl)-2-Propanol ([18F]Fluoromisonidazole); Pharmaceutical Research 11 (3): 466–469 (1994)

    CAS  Google Scholar 

  6. Wallace, S.;Yang, D.J.; Cherif, A.; Rapid Synthesis and Use of 18F-Fluoromisonidazole and Analogs, US Patent WO 95 /09844, 1995

    Google Scholar 

  7. Hwang, D.-R.; Dence, C.S.; Bonasera, T.A.; Welch, M.J.; No-carrier-added Synthesis of 3-[18F]Fluoro-1-(2-nitro-l-imidazolyl)-2-propanol. A Potential PET Agent for Detecting Hypoxic but Viable Tissues. Appl. Radiat. Isot. 40 (2): 117–126 (1989)

    Article  CAS  Google Scholar 

  8. Grierson, J.; Mathis, C.; Shankland, E.; Link, J.; Grunbaum, Z.; Rasey, J.; Krohn, K.; A Radiosynthesis of F-18-Fluoromisonidazole; J. Nucl. Med. 28: 1081 (1987)

    Google Scholar 

  9. Grierson, J.R.; Link, J.M.; Mathis, C.A.; Rasey, J.S.; Krohn, K.A.; A Radiosynthesis of Fluorine-18 Fluoromisonidazole; J. Nucl. Med. 30: 343–350 (1989)

    PubMed  CAS  Google Scholar 

  10. Grierson, J.R., unpublished data

    Google Scholar 

  11. Hwang, D.-R.; Dence, C.S.; Welch, M.J.; Shelton, M.E.; Bergmann, S.R.; An Improved Synthesis of No-Carrier-Added 3-[18F]-Fluoro-1-(2-nitro-l-imidazolyl)-2-propanol; J. Labelled Compd. Radiopharm. 29: 442 (1989)

    Article  Google Scholar 

  12. Solbach, M.; Machulla, H.-J.; J. Labelled Compd. Radiopharm. 37: 199 (1995)

    Google Scholar 

  13. McCarthy, T.J.; Dence, C.S.; Welch, M.J.; Application of Microwave Heating to the Synthesis of [18F]FluoromisonidazoleL; Appl. Radiat. Isot. 44 (8): 1129–1132 (1993)

    Article  CAS  Google Scholar 

  14. Tada, M.; Iwata, R.; Sugiyama, H.; Sato, K.; Kubota, K.; Kubota, R.; Takahashi, H.; Fukuda, H.; Ido, T.; A Concise One-pot Synthesis of [18F]Fluoromisonidazole from (2R)-(-)-Glycidyl Tosylate; J. Labelled Compd. Radiopharm. 38 (8): 771–774 (1996)

    Article  CAS  Google Scholar 

  15. Lim, J -L; Berridge, M.S.; Synthesis of [F-18]Fluoroetanidazole for Hypoxia Imaging Evaluation; J. Nucl. Med. 35 (5): 6 P (1994)

    Google Scholar 

  16. T.J Tewson; Synthesis of [F-18]-Fluoroetanidazole - A New Nitroimidazole Tracer of Hypoxia, abstract presented at the XIIth International Symposium on Radiopharmaceutical Chemistry in Uppsala, Sweden 1997

    Google Scholar 

  17. Zheng, L.; Ma, C.; McCarthy, T.J.; Welch, M.J.; Synthesis of 1-(2-Nitro-l-imidazolyl)-3-(2-[F-18]fluoromethyl- 1-aziridinyl)-2-propanol, A Potential Hypoxic Radiosensitizer for PET; J. Nucl. Med. 35 (5): 73 P (1994)

    Google Scholar 

  18. Krohn, K.A.; personal communication

    Google Scholar 

  19. Krohn, K.A.; unpublished results

    Google Scholar 

  20. Biskupiak, J.E.; Grierson, J.R.; Rasey, J.S.; Martin, G.V.; Krohn, K.A.: Synthesis of an (Iodovinyl)misonidazole Derivative for Hypoxia Imaging; J. Med. Chem. 34 (7): 2165 (1991)

    Article  PubMed  CAS  Google Scholar 

  21. Martin, G.V.; Biskupiak, J.E.; Caldwell, J.H.; Rasey, J.S.; Krohn, K.A.; Characterization of Iodovinylmisonidazole as a Marker for Myocardial Hypoxia; J. Nucl. Med. 34 (6): 918 (1993)

    PubMed  CAS  Google Scholar 

  22. Kumar, P.; Stypinski, D.; Xia, H.; Mcewan, A.J.B.; Machulla, H.J.; Wiebe, L.I.; Fluoroazomycin arabinoside (FAZA): Synthesis, 2H and 3H-Labelling and preliminary biological evaluation of a novel 2-nitroimidazole marker of tissue hypoxia. Nucl. Med. Biol. (submitted)

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Grierson, J., Patt, M. (1999). Syntheses of PET-Tracers for the Determination of Hypoxia. In: Machulla, HJ. (eds) Imaging of Hypoxia. Developments in Nuclear Medicine, vol 33. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-1828-8_5

Download citation

  • DOI: https://doi.org/10.1007/978-94-017-1828-8_5

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-90-481-5157-8

  • Online ISBN: 978-94-017-1828-8

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics