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Chemistry of Natural Compounds

, Volume 25, Issue 4, pp 475–484 | Cite as

Synthesis of C-terminal fragments of bombesin and their analogues

  • I. L. Kuranova
  • S. I. Churkina
  • V. L. Dyudmirova
  • E. B. Filonova
  • F. M. Ibatullin
  • F. K. Mutulis
  • I. P. Sekatsis
  • V. D. Grigor'eva
Article
  • 39 Downloads

Abstract

With the aim of structural-functional studies in the bombesin series, a number of bombesin fragments and analogues have been synthesized. The synthesis was performed by the carbodiimide method and by the activated-ester method. Fragments with the sequences 7–14, 8–14, and 9–14 were obtained by 4+4, 3+4, and 2+4 schemes and a pentapeptide with the sequence 9–13 by a 3 + 2 scheme. Acetylation of the octapeptide BN(7–14) was carried out by the action of acetic anhydride in pyridine. Analogues of the C-terminal nonapeptide of bombesin [DPhe7]BN(6–14) and [Pro6, Gly7, DAla11]BN(6–14) were synthesized by fragment condensation using the 5 + 4 scheme. The individuality of the compounds obtained was confirmed by their chromatographic behavior on plates coated with silica gel, and by the results of amino acid analysis, high-voltage electrophoresis, and high-performance liquid chromatography, and their structures were confirmed by the results of high-resolution1H NMR spectroscopy (360 MHz). In experiments on rabbits, in a dose of 1 µg with central administration the full hypothermic effect of bombesin was shown by the preparation [AcGln7]BN(7–14), while the preparation [DPhe7]BN(6–14) and [Pro6,Gly7,DAla11]BN(6–14) possessed only a slight effect (∼1% of the activity of bombesin).

Keywords

Dipeptide Bombesin Preparative HPLC Vasoactive Peptide Main Spot 

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Literature cited

  1. 1.
    M. Broccardo, G. F. Erspamer, P. Melchiorri, L. Negri, and R. Castiglione, Br. J. Pharmacol.,55, No. 2, 221 (1975).CrossRefPubMedCentralGoogle Scholar
  2. 2.
    R. Castiglione, F. Angelucci, V. Erspamer, G. F. Erspamer, and L. Negri, in: Peptides 1972 (eds. H. Hanson and H.-D. Jakubke), North-Holland, Amsterdam (1973), p. 463.Google Scholar
  3. 3.
    V. Erspamer and P. Melchiorri, Pure Appl. Chem.,35, 57 (1973).CrossRefGoogle Scholar
  4. 4.
    I. L. Kuranova, S. I. Churkina, N. G. Kovaleva, V. L. Lyudmirova, E. B. Filonova, A. T. Mar'yanovich, and V. F. Martynov, in: Abstracts of Lectures at the VIth All-Union Symposium on the Chemistry of Proteins and Peptides [in Russian], Zinatne, Riga (1983), p. 347.Google Scholar
  5. 5.
    R. S. Rapaka, R. S. Bhatnagar, and B. E. Nitecki, Biopolymers,15, 317 (1976).CrossRefPubMedCentralGoogle Scholar
  6. 6.
    R. C. Thompson and E. R. Blout, Biochemistry,12, No. 1, 57 (1973).CrossRefPubMedCentralGoogle Scholar
  7. 7.
    Y. Masui, N. Chino, and S. Sakakibara, Bull. Chem. Soc. Jpn,53, No. 2, 464 (1980).CrossRefGoogle Scholar
  8. 8.
    M. Bodanszki, Synthesis, 333 (1981).Google Scholar
  9. 9.
    P. K. Klimov, A. T. Mar'yanovich, E. L. Polyakov, I. L. Kuranova, and S. I. Churkina, Fiziol. Zh. SSSR,71, No. 2, 145 (1985).PubMedPubMedCentralGoogle Scholar
  10. 10.
    G. A. Fletcher and G. A. Jones, Int. J. Peptide Prot. Res.,4, No. 3, 347 (1972).Google Scholar
  11. 11.
    G. A. Fletcher and G. A. Jones, Int. J. Peptide Prot. Res.,7, No. 2, 91 (1975).Google Scholar
  12. 12.
    L. Bernardi, G. Bosisio, R. Castiglione, O. Goffredo, and F. Chillemi, Gazz. Chim. Ital.94, 853 (1964).Google Scholar
  13. 13.
    J. Kovacs, L. Kisfaludi, and M. A. Ceprini, J. Am. Chem. Soc.,89, No. 1, 183 (1967).CrossRefPubMedCentralGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • I. L. Kuranova
  • S. I. Churkina
  • V. L. Dyudmirova
  • E. B. Filonova
  • F. M. Ibatullin
  • F. K. Mutulis
  • I. P. Sekatsis
  • V. D. Grigor'eva

There are no affiliations available

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