Skip to main content
SpringerLink
Log in

Direct Fluorination of Phenolsulfonphthalein: A Method for Synthesis of Positron-Emitting Indicators for In Vivo pH Measurement

  • Original Paper
  • Published:
Cell Biochemistry and Biophysics Aims and scope Submit manuscript

Abstract

We report a reaction of direct electrophilic fluorination of phenolsulfonphthalein at mild conditions. This reaction affords the synthesis of novel positron-emitting 18F-labeled pH indicators. These compounds are useful for non-invasive in vivo pH measurement in biological objects.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Miller, P. W., Long, N. J., Vilar, R., & Gee, A. D. (2008). Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography. Angewandte Chemie International Edition, 47, 8998–9033.

    Article  CAS  Google Scholar 

  2. Heinrich, T. K., Gottumukkala, V., Snay, E., Dunning, P., Fahey, F. H., Treves, S. T., & Packard, A. B. (2010). Synthesis of fluorine-18 labeled rhodamine B: A potential PET myocardial perfusion imaging agent. Applied Radiation and Isotopes, 68, 96–100.

    Article  CAS  Google Scholar 

  3. Visser, G. W. M., Boele, S., Van Halteren, B. W., Knops, G. H. J. N., Herscheid, J. D. M., Brinkman, G. A., et al. (1986). Mechanism and stereochemistry of the fluorination of uracil and cytosine using fluorine and acetyl hypofluorite. Journal of Organic Chemistry, 51, 1466–1471.

    Article  CAS  Google Scholar 

  4. Visser, G. W. M., Noordhuis, P., Zwaagstra, O., Herscheid, J. D. M., & Hoekstra, A. (1986). A simplified synthesis of 18F-labelled cytosine- and uracil-nucleosides. Applied Radiation and Isotopes, 37, 1074–1076.

    Article  CAS  Google Scholar 

  5. Dolbier, W. R., Li, A.-R., Koch, C. J., Shiue, C.-Y., & Kachur, A. V. (2001). [18F]-EF5—a marker for PET detection of hypoxia: Synthesis of precursor and a new fluorination procedure. Applied Radiation and Isotopes, 53, 73–80.

    Article  Google Scholar 

  6. Mann, J. (1987). Modern methods for the introduction of fluorine into organic molecules: An approach to compounds with altered chemical and biological activities. Chemical Society Reviews, 16, 381–436.

    Article  CAS  Google Scholar 

  7. Rozen, S., & Brand, M. (1986). Direct addition of elemental fluorine to double bonds. Journal of Organic Chemistry, 51, 3607–3611.

    Article  CAS  Google Scholar 

  8. Kachur, A. V., Dolbier, W. R., Xu, W., & Koch, C. J. (2010). Catalysis of fluorine addition to double bond: An improvement of method for synthesis of 18F PET agents. Applied Radiation and Isotopes, 68, 293–296.

    Article  PubMed  CAS  Google Scholar 

  9. Oyelere, A. K., & Strobel, S. A. (2000). Biochemical detection of cytidine protonation within RNA. Journal of American Chemical Society, 122, 10259–10267.

    Article  CAS  Google Scholar 

  10. Tamura, Z., & Maeda, M. (1997). Differences between phthaleins and sulfonphthaleins. Yakugaku Zasshi, 117, 764–770.

    PubMed  CAS  Google Scholar 

  11. Dean, J. A. (Ed.). (1985). Lange’s handbook of chemistry (13th ed.). McGraw-Hill Book Company, New York.

Download references

Acknowledgments

Supported by the Institute for Translational Medicine and Therapeutics (ITMAT) Transdisciplinary Awards Program in Translational Medicine and Therapeutics Translational Biomedical Imaging Core Grant (TAPITMAT-TBIC).

Author information

Authors and Affiliations

  1. Department of Radiology, Perelman School of Medicine, University of Pennsylvania, 195 John Morgan Building, Philadelphia, PA, 19104-6072, USA

    Alexander V. Kachur, Anatoliy V. Popov, Joel S. Karp & E. James Delikatny

Authors
  1. Alexander V. Kachur
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anatoliy V. Popov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Joel S. Karp
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. James Delikatny
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alexander V. Kachur.

Additional information

The manuscript is reserved for publication in the Special Issue of Cell Biochemistry and Biophysics devoted to EPS Montreal International Biochemistry and Biophysics Forum 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kachur, A.V., Popov, A.V., Karp, J.S. et al. Direct Fluorination of Phenolsulfonphthalein: A Method for Synthesis of Positron-Emitting Indicators for In Vivo pH Measurement. Cell Biochem Biophys 66, 1–5 (2013). https://doi.org/10.1007/s12013-012-9390-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12013-012-9390-x

Keywords

Search

Navigation