Kinins—II pp 39-50 | Cite as

Preparation of Intrinsically-Labelled Kinins

  • Alfred Chung
  • James W. Ryan
  • Pierre Berryer
  • Ronald Block
Part of the Advances in Experimental Medicine and Biology book series (AEMB)


As part of a program to prepare bradykinin (H-Arg-Pro-ProGly-Phe-Ser-Pro-Phe-Arg-OH) labelled at high specific radioactivities, we have synthesized three analogs for dehalogenation in tritium gas: [4-Br-Phe5]-bradykinin (BK), [4-Br-Phe8]-BK and [4-Br-Phe5,8]-BK. The analogs were synthesized by the Merrifield solid-phase method and were purified by molecular sieve and partition chromatography. The analogs themselves possess biological activity (as assayed for effects on mean arterial blood pressure and isolated rat uterus). [4-Br-Phe8]-BK was 1.5 to 3 times as active as bradykinin. [4-Br-Phe5,8]-BK was approx. 22% as active as BK and [4-Br-Phe5]-BK was approx. 18% as active. [4-Br-Phe5]-BK was submitted to catalytic dehalogenation with 10% Pd/C and 5% Rh/CaCO3 in H2O and DMF (1:1) plus 10 Ci of 3H2. [4-3H-Phe5]-BK was obtained at 6.7 Ci/mmole in an overall yield of 15%. [4-3HPhe8]-BK was prepared similarly to yield an intrinsically-labelled peptide with a specific radioactivity of 21 Ci/mmole.


Angiotensin Converting Enzyme Specific Radioactivity Hydrogen Fluoride Solid Phase Peptide Synthesis Cesium Salt 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Bergman, E.P., 1952, p-Amino-and p-fluoro-ß-phenylalanine, J. Amer. Chem. Soc., 74, 4947.Google Scholar
  2. Brundish, D. and R. Wade, 1976, Tritiated peptides, Part 3, Synthesis of [4–3H-Phe7]-ß-corticotrophin-(1–24)-tetracosapeptide, J. Chem. Soc., Perkin I, 2186.Google Scholar
  3. Chung, A., J.W. Ryan, P. Berryer and A. Day, 1978, Influence of phenylalanine residues on the activity of bradykinin, 176th Nat. Meet. Amer. Chem. Soc., Miami Beach, Sept. 9–15, 1978.Google Scholar
  4. Dornow, A. and G. Winter, 1951, Some chloromycetin-like N-dichloroacetyl derivatives of the “phenylalaninol” series, Chem. Ber. 84, 307.Google Scholar
  5. Eisen, V., Formation and functions of kinins, 1970, in: The Immunochemistry and Biochemistry of Connective Tissue and Its Disease States, Rheumatology, Vol. 3, (Karger Basel), p. 103.Google Scholar
  6. Gisin, B.F., 1973, The preparation of Merrifield-resins through total esterification with cesium salts, Heiv. Chim. Acta, 56, 1476.Google Scholar
  7. Houghten, R.A. and H. Rapoport, 1974, Synthesis of pure p-chlorophenyl-L-alanine from L-phenylalanine, J. Med. Chem., 17, 556.Google Scholar
  8. Irreverre, F., 1965, A modified Sakaguchi spray, Biochim. Biophys. Acta, 111, 551.Google Scholar
  9. Kaiser, LE., R.L. Colescott, C.D. Bossinger and P.I. Cook, 1970, Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides, Anal. Biochem, 34, 595.Google Scholar
  10. Koenig, W. and R. Geiger, 1970, New method for the synthesis of peptides: Activation of the carboxyl group with dicyclohexylcarbodiimide by using 1-hydroxybenzoltriazoles as additives, Chem. Ber., 103, 788.Google Scholar
  11. Roblero, J., J.W. Ryan and J.M. Stewart, 1973, Assay of kinins by their effects on blood pressure, Res. Commun. Chem. Path. Pharmac., 6, 207.Google Scholar
  12. Ryan, J.W. and U.S. Ryan, 1977, Pulmonary endothelial cells, Fed. Proc., 36, 2683.Google Scholar
  13. Ryan, U.S., J.W. Ryan, D. Habliston and G. Pena, Endothelial cells and components of the kallikrein-kinin system, this volume.Google Scholar
  14. Sakakibara, S,, The use of hydrogen fluoride in peptide chemistry, 1971, in: Chemistry and Biochemistry of Amino Acids, ed. C.B. Weinstein ( Marcel Dekker, New York ), p. 51.Google Scholar
  15. Schwyzer, R. and E. Surbeck-Wegmann, 1960, Resolution of D,L-pbromophenylalanine, Hely. Chim. Acta, 63, 1073.Google Scholar
  16. Stewart, J.M. and J.D. Young, 1969, Solid Phase Peptide Synthesis, (W.H. Freeman Co., San Francisco).Google Scholar
  17. Vine, W.H., D.A. Brueckner, P. Needleman, and G.R. Marshall, 1973, Synthesis, biological activity and 19F nuclear magnetic resonance spectra of angiotensin II analogs containing fluorine, Biochemistry, 12, 1630.PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1979

Authors and Affiliations

  • Alfred Chung
    • 1
  • James W. Ryan
    • 1
  • Pierre Berryer
    • 1
  • Ronald Block
    • 2
  1. 1.Department of MedicineUniversity of Miami School of MedicineMiamiUSA
  2. 2.Papanicolaou Cancer Research InstitueMiamiUSA

Personalised recommendations