Skip to main content

Intramyocardial fate of 15-p-iodophenyl-β-methylpentadecanoic acid (IMPPA): Is it a good tracer of fatty acid myocardial uptake?

  • Chapter
Lipid Metabolism in Normoxic and Ischemic Heart

Summary

Iodinated fatty acids (FAs) are now used in Nuclear Medicine to assess, by external detection, myocardial metabolism. Methylated FAs have been proposed as tracers of FA myocardial uptake. IMPPA is a new FA analogue in which a methyl group have been introduced in β position to inhibit β-oxidation and a terminal phenyl group prevents a possible omega oxidation. We have compared the intramyocardial behaviour of this FA with the 15-p-iodophenyl-pentadecanoic acid (IPPA), the straight chain analogue, and with the 15-phenyl-β-methylpentadecanoic acid (MPPA), the 3 of them being labelled with C14 on the carboxyl group, in isolated rat hearts perfused in a recirculating system.

When IMPPA is compared to IPPA (influence of the methyl group), we observe 1 — an inhibition of β-oxidation (no significant production of labelled CO2 and very low radioactivity in the aqueous phase) leading to a reduced uptake, 2 — a lower radioactivity in the organic phase due to a hindrance to the esterification process both into TGs and PLs, the free FAs level being higher. When IMPPA is compared to MPPA (influence of the iodine atom), we observe 1 — the same inhibition of β-oxidation, 2 — a higher myocardial radioactivity due to a much higher level of free FAs, the esterification into TGs and PLs being reduced.

This study with IMPPA indicates that it is taken up by the heart and trapped there, as it is not oxydized. This long retention time, apart from giving good scintigraphic images, should make IMPPA useful to study the regional myocardial uptake of FAs.

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

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
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. Bing RJ, Siegel A, Ungar J, Gilbert M: Metabolism of the human heart. II. Studies on fat, ketone and amino acid metabolism. Am J Med 16: 504–528, 1954

    Article  PubMed  CAS  Google Scholar 

  2. Livni E, Elmaleh DR, Levy S, Brownell GL, Strauss WH: Beta-methyl (1–11C) heptadecanoic acid: a new myocardial metabolic tracer for positron emission tomography. J Nucl Med 23: 169–175, 1982

    PubMed  CAS  Google Scholar 

  3. Goodman MM, Kirsch G, Knapp Jr FF: Synthesis of radioiodinated omega-(p-iodophenyl)-substituted methyl-branched long-chain fatty acids. J Lab Compds Radiopharm XIX: 1316–1318, 1982

    Google Scholar 

  4. Goodman MM, Kirsch G, Knapp Jr FF: Synthesis and evaluation of radio-iodinated terminal p-iodophenyl-substited alpha- and β-methyl-branched fatty acids. J Med Chem 25: 390–397, 1984

    Article  Google Scholar 

  5. Livni E, Elmaleh DR, Barlai-Kowach MM, et al Radioiodinated b-methylphenyl fatty acid as potential tracer for myocardial imaging and metabolism. Eur Heart J (suppl B) 6: 85–89, 1985

    PubMed  CAS  Google Scholar 

  6. Otto CA, Brown LE, Wieland DM, Beierwaltes WH: Radioiodinated fatty acids for myocardial imaging: effects of chain length. J Nucl Med 22: 613–618, 1981

    PubMed  CAS  Google Scholar 

  7. Otto CA, Brown LE, Scott AM: Radioiodinated branchedchain fatty acids: substrates for β-oxidation? Concise communication. J Nucl Med 25: 75–80, 1984

    PubMed  CAS  Google Scholar 

  8. Goodmann MM, Callahan AP, Knapp Jr FF: Design, synthesis and evaluation of omega-iodovinyl and omega-iodoalkyl-substituted methyl-branched fatty acids. J Med Chem 28: 807–814, 1985

    Article  Google Scholar 

  9. Yonekura Y, Brill AB, Som P, Yamamoto K, Srivastava SC, Iwai J, Elmaleh DR, Livni E, Strauss HW, Goodmann MM, Knapp Jr FF: Regional myocardial sustrate uptake in hypertensive rats: a quantitative autoradiographic measurement. Science 227: 1494–1496, 1985

    Article  PubMed  CAS  Google Scholar 

  10. Yamamoto K, Som P, Brill AB, Yonekura Y, Srivastava SC, Meinken GE, Iwai J, Goodmann MM, Knapp Jr FF, Elmaleh DR, Livni E, Strauss HW: Dual tracer autoradiographic study of β-methyl-(1–14C) heptadecanoic acid and 15-p-(131I)-iodophenyl-β-methylpentadecanoic acid in normotensive and hypertensive rats. J Nucl Med 27: 1178–1183, 1986

    PubMed  CAS  Google Scholar 

  11. Keriel C, Marti Batlle D, Le Bars D, Mathieu JP, Comet M, Cuchet P: Are iodinated fatty acids good tracers of myocardial metabolism? IHA vs IPPA. A study on rat heart with 14C labeled fatty acids. Nuclear Medicine (in press)

    Google Scholar 

  12. Reske SN, Sauer W, Machulla HJ, Winkler C: 15-p-(123I) iodophenylpentadecanoic acid as tracer of lipids metabolism: comparison with (1–14C) palmitic acid in murine tissues. J Nucl Med 25: 1335–1342, 1984

    Google Scholar 

  13. Le Bars D, Luu-Duc C, Leo PM, Apparu M, Vidal M, Comet M: Synthesis of 15-(p-iodophenyl) pentadecanoic acid labelled with carbon 14. Appl Radiat Isot 37 (3): 256–257, 1986

    Article  Google Scholar 

  14. Humbert T, Luu-Duc C, Marsura A, Le Bars D, Apparu M, Vidal M: Synthesis of 3-methyl 15-phenyl pentadecanoic acid labelled with carbon 14 to study myocardium metabolism. J Lab Compds Radiophar, (in press)

    Google Scholar 

  15. Humbert T, Luu-Duc C, Marsura A, Le Bars D: Synthesis of 3-methyl 15-p-iodophenylpentadecanoic acid labelled with carbon 14 to study uptake in the myocardium. J Lab Compds Radiophar (submitted to publication)

    Google Scholar 

  16. Bligh EG, Dyer WJ: A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37: 911–917, 1959

    Article  PubMed  CAS  Google Scholar 

  17. Vasdev SC, Kako KJ: Metabolism of erucic acid in the isolated perfused rat heart. Biochim Biophys Acta 431: 22–32, 1976

    PubMed  CAS  Google Scholar 

  18. Van der Vusse GJ, Roemen THM, Flameng W, Reneman RS: Serum-myocardium gradients of non-esterified fatty acids in dog, rat, man. Biochim Biophys Acta 572: 361–370, 1983

    Google Scholar 

  19. Ambrose KR, Owen BA, Goodmann MM, Knapp Jr FF: Evaluation of the metabolism in rat hearts of two new radioiodinated 3-methyl-branched fatty acid myocardial imaging agent. Eur J Nucl Med 12: 486–491, 1987

    Article  PubMed  CAS  Google Scholar 

  20. Knapp Jr FF, Goodmann MM, Callahan AP, Kirsh G: Radioiodinated 15-(p-iodophenyl)-3,3-dimethyl pentadecanoic acid: a useful new agent to evaluate myocardial fatty acid uptake. J Nucl Med 27: 521–531, 1986

    PubMed  CAS  Google Scholar 

  21. Fagret D, Wolf JE, Pilichowski P, Mathieu JP, Pernin C, Apparu M, Arvieux Ch, Cuchet P, Comet M, Vidal M: Iodomethylated fatty acid metabolism in mice and dogs. Eur J Nucl Med (in press)

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1989 Kluwer Academic Publishers

About this chapter

Cite this chapter

Humbert, T., Keriel, C., Batlle, D.M., Luu-Duc, C., Comet, M., Cuchet, P. (1989). Intramyocardial fate of 15-p-iodophenyl-β-methylpentadecanoic acid (IMPPA): Is it a good tracer of fatty acid myocardial uptake?. In: Van Der Vusse, G.J. (eds) Lipid Metabolism in Normoxic and Ischemic Heart. Developments in Molecular and Cellular Biochemistry, vol 5. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-1611-4_29

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-1611-4_29

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-8891-6

  • Online ISBN: 978-1-4613-1611-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics