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Chemistry and Biologic Activity of Peptides Related to Bradykinin

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Bradykinin, Kallidin and Kallikrein

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 25 / 1))

Abstract

The great physiologic importance of the kinin system has prompted much investigation, during the last decade, of the chemistry, pharmacology and physiology of the peptides which constitute and affect this system. Since the earlier tabulation of bradykinin analogs in this work (Schröder, 1970), nearly 150 peptides related in structure to bradykinin have been synthesized and described. These new kinin analogs are tabulated in this chapter and the information gained from the study of these peptides is discussed. The attempts to make good peptide inhibitors of bradykinin will also be discussed.

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References

  • Aarsen, P.N.: Sensitization of guinea pig ileum to the action of bradykinin by trypsin hydrolysate of ox and rabbit plasma. Br. J. Pharmacol. 32,453–465 (1968)

    CAS  Google Scholar 

  • Abiko, T.: Syntheses of 4-nitrophenylalanine5, O-methyltyrosine8-, and O-methyltyrosine5, 4-nitrophenylalanine8-BK. Chem. Pharm. Bull. (Tokyo) 22,2191–2196 (1974)

    CAS  Google Scholar 

  • Abramson, F.B., Elliott, D.F., Lindsay, D.G., Wade, R.: Synthesis of peptides related to bradykinin. J. Chem. Soc. (C), 1042–1048 (1970)

    Google Scholar 

  • Ali, A., Guidicci, M.A., Stevenson, D.: Synthesis of bradykinin-potentiating peptide BPP5a. Experientia 32,1503–1504(1976)

    PubMed  CAS  Google Scholar 

  • Anastasi, A., Bertaccini, G., Erspamer, V.: Pharmacological data on phyllokinin and bradykininisoleucine-tyrosine. Br. J. Pharmacol. 27,479–485 (1966)

    CAS  Google Scholar 

  • Arkhipova, S.F., Sevastyanova, N.N., Lipkind, G.M., Popov, E.M.: Theoretical conformational analysis of BPP9a. Bioorganicheskaya Khimiya 3, 335–347 (1977)

    CAS  Google Scholar 

  • Armstrong, D.: Pain. In: Handbook experimental pharmacology. Vol. XXV: Bradykinin, kallidin, and kallikrein. Erdös, E.G. (ed.), p. 434. Berlin, Heidelberg, New York: Springer 1970

    Google Scholar 

  • Atherton, E., Law, H.D., Moore, S., Elliott, D.F., Wade, R.: Synthesis of peptides containing N-2-aminoethyl glycine — Reduction analogues. J. Chem. Soc. (C) 3393–3396 (1971)

    Google Scholar 

  • Bakhle, Y. S.: Conversion of angiotensin I to angiotensin II by cell-free extracts of dog lung. Nature 220,919–921 (1968)

    PubMed  CAS  Google Scholar 

  • Balaspiri, L., Penke, B., Papp, G., Dombi, G., Kovacs, K.: Rational synthesis of α-l-homoproline and its derivatives. Production of 7-α-l-homoproline bradykinin. Helv. Chim. Acta 58, 969–973 (1975)

    PubMed  CAS  Google Scholar 

  • Bisset, G.W., Lewis, G.P.: A spectrum of pharmacological activity in some biologically active peptides. Br. J. Pharmacol. 19,168–182 (1962)

    CAS  Google Scholar 

  • Bodanszky, A., Bodanszky, M., Jorpes, E.J., Mutt, V., Ondetti, M.A.: Molecular architecture of peptide hormones. Optical rotatory dispersion of cholecystokinin, bradykinin, and 6-glycine bradykinin. Experientia 26,948–950 (1970)

    PubMed  CAS  Google Scholar 

  • Bodanszky, A., Ondetti, M.A., Ralofsky, C.A., Bodanszky, M.: Optical rotatory dispersion of proline-rich peptides from the venom of Bothrops jararaca. Experientia 27, 1269–1270 (1971)

    PubMed  CAS  Google Scholar 

  • Brady, A.H., Ryan, J.W., Stewart, J.M.: Circular dichroism of bradykinin and related peptides. Biochem. J. 121,179–184 (1971)

    PubMed  CAS  Google Scholar 

  • Burgus, R., Rivier, J.: Use of high pressure liquid chromatography in the purification of peptides. In: Peptides 1976. Loffet, A. (ed.), p. 85. Brussels: Editions de l’Université de Bruxelles 1976

    Google Scholar 

  • Cann, J.R., Stewart, J.M., Matsueda, G.R.: A circular dichroism study of the secondary structure of bradykinin. Biochemistry 12,3780–3788 (1973)

    PubMed  CAS  Google Scholar 

  • Cann, J.R., Stewart, J. M., London, R. E., Matwiyoff, N.: On the solution conformation of bradykinin and certain fragments. Biochemistry 15,498–504 (1976)

    PubMed  CAS  Google Scholar 

  • Corley, L., Sachs, D. H., Anfinsen, C. B.: Rapid solid-phase synthesis of bradykinin. Biochem. Biophys. Res. Commun. 47,1353–1359 (1972)

    PubMed  CAS  Google Scholar 

  • Cushman, D.W, Pluscec, J, Williams, N. J., Weaver, E.R., Sabo, E.F., Kocy, O., Cheung, H.S, Ondetti, M.A.: Inhibition of angiotensin-converting enzyme by analogs of peptides from Bothrops jararaca venom. Experientia 29,1032–1035 (1973)

    PubMed  CAS  Google Scholar 

  • Cushman, D.W., Cheung, H.S., Sabo, E.F., Ondetti, M. A.: Design of potent competitive inhibitors of angiotensin-converting enzyme. Biochemistry 16, 5484–5491 (1977)

    PubMed  CAS  Google Scholar 

  • Damas, J., Cession-Fossion, A.: Are the smooth muscle and adrenal medulla receptors for BK different? C. R. Soc. Biol. (Paris) 167,1478–1482 (1973)

    CAS  Google Scholar 

  • Donaldson, V. H., Ratnoff, O. D.: Effect of some analogs of bradykinin on vascular permeability. Proc. Soc. Exp. Biol. Med. 125,145–148 (1967)

    PubMed  CAS  Google Scholar 

  • Dorer, F.E., Skeggs, L.T., Kahn, J.R., Lentz, K.E., Levine, M.: Angiotensin converting enzyme: method of assay and partial purification. Anal. Biochem. 33,102–113 (1970)

    PubMed  CAS  Google Scholar 

  • Dorer, F.E., Ryan, J.W., Stewart, J.M.: Hydrolysis of bradykinin and its higher homologues by angiotensin-converting enzyme. Biochem. J. 141,915–917 (1974)

    PubMed  CAS  Google Scholar 

  • Dunn, F.W., Stewart, J.M.: Analogs of bradykinin containing β-2-thienyl-l-alanine. J. Med. Chem. 14,779–781(1971)

    PubMed  CAS  Google Scholar 

  • Edery, H.: Further studies of the sensitization of smooth muscle to the action of plasma kinins by proteolytic enzymes. Br. J. Pharmacol. 24,485–496 (1965)

    CAS  Google Scholar 

  • Efremov, E.S., Filatova, M.P., Reutova, T.O., Stepanova, L.N., Reissmann, S., Ivanov, V.T.: Conformational states of bradykinin and its analogs in solution. II. Fluorescence spectra. Bioorganicheskaya Khimiya 3,1169–1180 (1977)

    CAS  Google Scholar 

  • El-Maghraby, M.A.: New synthetic analogue of bradykinin. Journal of the Indian Chemical Society 53,65–67(1976)

    CAS  Google Scholar 

  • Engel, S.L., Schaeffer, T.R., Gold, B.L, Rubin, B.: Inhibition of pressor effects of angiotensin I and augmentation of depressor effects of bradykinin by synthetic peptides. Proc. Soc. Exp. Biol. Med. 140,240–244 (1972)

    PubMed  CAS  Google Scholar 

  • Erdös, E.G., Yang, H.Y.T.: Kininases. In: Handbook of experimental pharmacology. Vol. XXV: Bradykinin, kallidin, and kallikrein. Erdös, E.G. (ed.), p. 289. Berlin, Heidelberg, New York: Springer 1970

    Google Scholar 

  • Erickson, B.W., Merrifield, R.B.: Solid phase peptide synthesis. In: The proteins, 3rd ed. Neurath, H., Hill, R.L. (eds.), Vol. II, p. 257. London, New York: Academic Press 1976

    Google Scholar 

  • Faber, D.B.: Pharmacology of peptides which enhance the action of bradykinin. Acta Physiologica et Pharmacologica Neerlandica 15,101–102 (1969)

    Google Scholar 

  • Felix, A.M., Jiminez, M.H., Vergona, R., Cohen, M.R.: Synthesis and biological studies of novel bradykinin analogues. Int. J. Pept. Protein Res. 5,201–206 (1973)

    PubMed  CAS  Google Scholar 

  • Ferreira, S. H.: Bradykinin potentiating factor (BPF) present in venom of Bothrops jararaca. Br. J. Pharmacol. 24,163–169 (1965)

    CAS  Google Scholar 

  • Ferreira, S. H.: Bradykinin-potentiating factor. In: Hypotensive peptides. Erdös, E. G., Back, N., Sicuteri, F. (eds.), p. 356. Berlin, Heidelberg, New York: Springer 1966

    Google Scholar 

  • Ferreira, S.H., Bartelt, D.C., Greene, L.J.: Isolation of bradykinin-potentiating peptides from Bothrops jararaca venom. Biochemistry 9,2583–2593 (1970)

    PubMed  CAS  Google Scholar 

  • Filatova, M.P., Reissmann, S., Ravdel, G.A., Ivanov, V.T., Grigoryan, G.L., Shapiro, A.B.: Konformationsuntersuchungen an Bradykinin und Bradykininanaloga mit Hilfe von CD-, NMR und ESR-Messungen. In: Peptides 1972. Hanson, H, Jakubke, H.-D. (eds.), p. 333. New York: American Elsevier 1973

    Google Scholar 

  • Filatova, M.P., Krit, N.A., Suchkova, G.S., Ravdel, G.A., Ivanov, V.T.: New synthesis of bradykinin and its analogs. Bioorganicheskaya Khimiya 1,437–446 (1975)

    CAS  Google Scholar 

  • Filatova, M.P., Reissmann, S., Reutova, T.O., Ivanov, V.T., Grigoryan, G.L., Shapiro, A.M., Rozantsev, E.G.: Conformational states of bradykinin and its analogs in solution. III. ESR spectra of spin-labeled analogs. Bioorganicheskaya Khimiya 3,1181–1189 (1977)

    CAS  Google Scholar 

  • Finn, F.M., Hofmann, K.: The synthesis of peptides by solution methods. In: The proteins, 3rd ed. Neurath, H., Hill, R.L. (eds.), Vol. II, p. 106. London, New York: Academic Press 1976

    Google Scholar 

  • Fisher, G.H., Chung, A., Ryan, J.W.: Para-Halogenated phenylaline analogs of bradykinin: Effects on blood pressure. Circulation 55 and 56 (Suppl III), 241 (1977)

    Google Scholar 

  • Fisher, G.H., Marlborough, D.I., Ryan, J.W., Felix, A.M.: L-3,4-Dehydroproline analogs of bradykinin: synthesis, biological activity, and solution conformation. Arch. Biochem. Biophys. 189, 81–85 (1978)

    PubMed  CAS  Google Scholar 

  • Fisher, G.H., Ryan, J.W., Martin, L.C., Peña, G.: Strucutre-activity relationships for kininase II inhibition by lower homologs of the bradykinin potentiating peptide BPP9a. In: Proceedings, International Symposium on Kinins (Kinin 78 Tokyo). Moriya, H. (ed.). New York, London: Plenum Press 1979 (in press)

    Google Scholar 

  • Fletcher, G.A., Young, G.T.: Amino acids and peptides. The synthesis of analogues of bradykinin by the picolyl ester method. J. Chem. Soc. (Perkin I) 1867–1874 (1972)

    Google Scholar 

  • Fredrickson, R. C. A.: Enkephalin pentapeptides — a review. Life Sci. 21,23–42 (1977)

    Google Scholar 

  • Freer, R. J., Stewart, J. M.: Synthetic bradykinin potentiating peptides related to those isolated from snake venoms. Ciencia e Cultura 23, 539–542 (1971)

    CAS  Google Scholar 

  • Freer, R. J., Stewart, J. M.: Alkylating analogs of peptide hormones. Synthesis and properties of p-[N,N-Bis(2-chloroethyl)amino]phenylbutyryl derivatives of bradykinin and bradykinin potentiating factor. J. Med. Chem. 15,1–5 (1972)

    PubMed  CAS  Google Scholar 

  • Freer, R. J., Stewart, J. M.: In vivo pulmonary metabolism of bradykinin, angiotensin I, and 5-hydroxytryptamine in the rat. Arch. Int. Pharmacodyn. Ther. 217,97–109 (1975)

    PubMed  CAS  Google Scholar 

  • Gabbiani, G., Baddonel, M.C., Majno, G.: Vascular leakage induced by intra-arterial histamine, serotonin or bradykinin. Proc. Soc. Exp. Biol. Med. 135,447–452 (1970)

    PubMed  CAS  Google Scholar 

  • Galaktionov, S.G., Sherman, S.A., Shenderovich, M.D., Nikiforovich, G.V., Leonova, V.I.: Conformational states of bradykinin in solution. Calculation of stable conformations. Bioorganicheskaya Khimiya 3,1190–1197 (1977)

    CAS  Google Scholar 

  • Gaponyuk, P. Y, Oivin, V.I.: Comparative study of the effect of BK, kallidin, methionyl-lysyl-BK, and eledoisin on the permeability of skin vessels and the mechanism of their action. In: Histo-hematic barriers. Rosin, Y. A. (ed.), p. 115. Moscow: Nauka 1971

    Google Scholar 

  • Geese, A., Zsilinszky, E., Szekeres, L.: Bradykinin antagonism. In: Advances in experimental medicine and biology. Vol. 70: Kinins. Sicuteri, F., Back, N., Haberland, G. (eds.), pp. 5–13. New York, London: Plenum Press 1976

    Google Scholar 

  • Gisin, B.F., Merrifield, R.B.: Carboxyl-catalyzed intramolecular aminolysis. A side reaction in solid-phase peptide synthesis. J. Am. Chem. Soc. 94,3102–3106 (1972)

    PubMed  CAS  Google Scholar 

  • Gladner, J. A.: Potentiation of the effect of bradykinin. In: Hypotensive peptides. Erdös, E.G., Back, N., Sicuteri, F. (eds.), p. 344. Berlin, Heidelberg, New York: Springer 1966

    Google Scholar 

  • Greene, L.J., Camargo, A.CM., Krieger, E.M., Stewart, J.M., Ferreira, S.H.: Inhibition of the conversion of angiotensin I to II and potentiation of bradykinin by small peptides present in Bothrops jararaca venom. Circ. Res. 30II, 62–71 (1972)

    Google Scholar 

  • GrÜber, K.A., Stein, S., Brink, L., Radhakrishnan, A., Udenfriend, S.: Fluorimetric assay of vasopressin and oxytocin: A general approach to the assay of peptides in tissues. Proc. Nat. Acad. Sci. USA 73,1314–1318 (1976)

    PubMed  Google Scholar 

  • Hamberg, U., Elg, P., Stellwagen, P.: On the mechanism of bradykinin potentiation. In: Pharmacology of hormonal polypeptides and proteins. Back, N., Martini, L., Paoletti, R. (eds.), pp. 626–631. New York, London: Plenum Press 1968

    Google Scholar 

  • Han, Y.N., Kato, H., Iwanaga, S.: Identification of Ser-Leu-Met-Lys-bradykinin isolated from chemically modified high-molecular-weight bovine kininogen. FEBS Lett. 71,45–48 (1976)

    CAS  Google Scholar 

  • Hirschmann, R. F., Denkewalter, R. G.: Controlled stepwise synthesis of polypeptides. US Pat. 3,846,399 (1974)

    Google Scholar 

  • Hochstrasser, K., Werle, E.: Kinin-yielding peptides from pepsin-treated bovine plasma proteins. Hoppe Seylers Z. Physiol. Chem. 348,177–182 (1967)

    PubMed  CAS  Google Scholar 

  • Ishikawa, O., Yasuhara, T., Nakajima, T., Tachibana, S.: Ranakinin N, a new bradykinin analog from Rana nigromaculata. 12 th Peptide Symp., Tokyo 1974

    Google Scholar 

  • Ivanov, V.T., Filatova, M.P., Reissmann, S., Reutova, T.O., Efremov, E.S., Pashkov, U.S., Galaktionov, S.G., Grigoryan, G.L., Ovchinnikov, Y.A.: The solution conformation of bradykinin. In: Peptides: Chemistry, structure, and biology. Walter, R., Meienhofer, J. (eds.), pp. 151–157. Ann Arbor: Ann Arbor Science Publishers 1975a

    Google Scholar 

  • Ivanov, V.T., Filatova, M.P., Reissmann, S., Reutova, T.O., Kogan, G.A., Efremov, E.S., Pashkov, V. S., Galaktionov, S. G., Grigoryan, G. L., Bystrov, V. F.: Conformational state of bradykinin in solution. Bioorganicheskaya Khimiya 1,1241–1244 (1975b)

    CAS  Google Scholar 

  • Ivanov, V.T., Filatova, M.P., Reissmann, S., Reutova, T.O., Chekhlyaeva, N.M.: Conformational states of bradykinin and its analogs in solution. I. Circular dichroism spectra. Bioorganicheskaya Khimiya 3,1157–1168 (1977)

    CAS  Google Scholar 

  • Kameyama, T., Sasaki, K.: Comparison of hypotensive activities of synthetic bradykinin and bradykinin analogs in rats. Nippon Yakubutsugaku Zasshi 66,503–510 (1970)

    CAS  Google Scholar 

  • Kameyama, T., Sasaki, K., Suzuki, K.: Interaction between contractile action of low-molecular kininogen-like peptides on guinea pig ileum and trypsin. Nippon Yakubutsugaku Zasshi 91, 1–5 (1971); Chem. Abstr. 74,10754p (1971)

    CAS  Google Scholar 

  • Kato, H., Suzuki, T.: Bradykinin potentiating peptides from the venom of Agkistrodon halys blomhoffii. Biochemistry 10,972–980 (1971)

    PubMed  CAS  Google Scholar 

  • Kato, H., Suzuki, T.: Bradykinin-potentiating peptides from the venom of Agkistrodon halys blomhoffii: Their amino acid sequence and the inhibitory activity on angiotensin I-converting enzyme from rabbit lung. In: Chemistry and biology of the kallikrein-kinin system in health and disease. Pisano, J. J., Austen, K.F. (eds.), pp. 299–303. Fogarty Internat. Center Proc. No. 27. Washington: U.S. Gov. Printing Office 1977

    Google Scholar 

  • Kato, H., Suzuki, T., Okada, K., Kimura, T., Sakakibara, S.: Structure of potentiator A, one of the five bradykinin potentiating peptides from the venom of Agkistrodon halys blomhoffii. Experientia 29, 574–575 (1973)

    PubMed  CAS  Google Scholar 

  • Kier, L.B., George, J.M.: Molecular orbital consideration of amino acid conformation. In: Molecular orbital studies in chemical pharmacology. Kier, L.B. (ed.), pp. 82–104. Berlin, Heidelberg, New York: Springer 1970

    Google Scholar 

  • Kishimura, H., Yasuhara, T., Yoshida, H., Nakajima, T.: Vespakinin-M, a novel bradykinin analogue containing hydroxyproline, in the venom of Vespa mandarinia Smith. Chem. Pharm. Bull. (Tokyo) 24,2896–2897 (1976)

    CAS  Google Scholar 

  • Krit, N. A, Ravdel, G.A., Ivanov, V.T.: Synthesis of bradykinin analogs modified in position 8. Bioorganicheskaya Khimiya 2,1455–1463 (1976)

    CAS  Google Scholar 

  • Lalka, D., Back, N.: The high voltage paper electrophoresis of kinin peptides K9, K10, and K11. Biochim. Biophys. Acta 236,47–51 (1971)

    PubMed  CAS  Google Scholar 

  • Law, H.D., Johnson, W.H., Studer, R.D.: Synthesis and properties of bradykinin analogs: 1-deamino-, 9-decarboxy-, and l-deamino-9-decarboxy-bradykinin. J. Chem. Soc. (C) 748–753 (1971)

    Google Scholar 

  • London, R.E., Stewart, J. M, Cann, J.R., Matwiyoff, N. A.: 13C and 1H NMR studies of bradykinin and selected peptide fragments. Biochemistry 17,2270–2277 (1978)

    PubMed  CAS  Google Scholar 

  • Marlborough, D.I., Ryan, J.W.: Circular dichroism spectra of bradykinin analogs containing jS-homoamino acids. Biochem. Biophys. Res. Commun. 75,757–765 (1977)

    PubMed  CAS  Google Scholar 

  • Marlborough, D.I., Ryan, J.W., Felix, A.M.: Conformative response of bradykinin and analogs to solvent variation. Arch. Biochem. Biophys. 176,582–590 (1976)

    PubMed  CAS  Google Scholar 

  • Mazur, R.H., Plume, G.: Improved synthesis of bradykinin. Experientia 24,661 (1968)

    PubMed  CAS  Google Scholar 

  • Mc Gee, J. O., Jimenez, M. H., Felix, A. M., Cardinale, G. J., Udenfriend, S.: Inhibition of prolyl hydroxylase activity by bradykinin analogs containing a prolyl-like residue. Arch. Biochem. Biophys. 154,483–487 (1973)

    PubMed  CAS  Google Scholar 

  • Melrose, G.J.H., Muller, H.K., Vagg, W. J.: Capillary permeability activity of alanine analogs of bradykinin. Nature 225, 547–548 (1970)

    PubMed  CAS  Google Scholar 

  • Merrifield, R. B.: New approaches to the chemical synthesis of peptides. Recent Prog. Horm. Res. 23,451–482(1967)

    PubMed  CAS  Google Scholar 

  • Montgomery, E.H., Kroeger, D.C.: Bradykinin relaxation of duodenum. Fed. Proc. 26, 465 (1967)

    Google Scholar 

  • Moore, S., Law, H. D., Brundish, D. E., Elliott, D. F., Wade, R.: Synthesis of analogs of bradykinin with replacement of arginine residues by 4-guanidinophenylalanine. J. Chem. Soc. (Perkin I)2025–2030(1977)

    Google Scholar 

  • Najjar, V. A., Merrifield, R. B.: The use of the o-nitrophenylsulfenyl group in the synthesis of the octadecapeptide bradykinylbradykinin. Biochemistry 5, 3765–3770 (1966)

    CAS  Google Scholar 

  • NeÜbert, K., Balaspiri, L., Losse, G.: Solid phase synthesis of 2-l-and 2-d-pipecolic acidbradykinin. Monatshefte für Chemie 103,1575–1584 (1972)

    Google Scholar 

  • Ng, K.K.F., Vane, J.R.: Some properties of angiotensin converting enzyme in the lung in vivo. Nature 225,1142–1144 (1970)

    PubMed  CAS  Google Scholar 

  • Nicolaides, E.D., McCarthy, D.A., Potter, D.E.: Bradykinin: configuration of the arginine moieties and biological activity. Biochemistry 4,190–195 (1965)

    CAS  Google Scholar 

  • Odya, C.E., Levin, Y., Erdös, E.G., Robinson, C.J.G.: Soluble dextran complexes of kallikrein, bradykinin, and enzyme inhibitors. Biochem. Pharmacol. 27,173–179 (1978)

    PubMed  CAS  Google Scholar 

  • Ondetti, M.A., Engel, S.L.: Bradykinin analogs containing β-homoamino acids. J. Med. Chem. 18,761–763(1975)

    PubMed  CAS  Google Scholar 

  • Ondetti, M.A., Williams, N.J., Sabo, E.F., Pluscec, J., Weaver, E.R., Kocy, O.: Angiotensinconverting enzyme inhibitors from the venom of Bothrops jararaca. Biochemistry 10, 4033–4039(1971)

    PubMed  CAS  Google Scholar 

  • Ondetti, M.A., Pluscec, J., Weaver, E.R., Williams, N., Sabo, E.F., Kocy, O.: Mode of action of peptide inhibitors of angiotensin converting enzyme. In: Chemistry and biology of peptides. Meienhofer, J. (ed.), pp. 525–531. Ann Arbor: Ann Arbor Science Publishers 1972

    Google Scholar 

  • Ondetti, M.A., Rubin, B., Cushman, D.W.: Design of specific inhibitors of angiotensin converting enzyme. Science 196,441–443 (1977)

    PubMed  CAS  Google Scholar 

  • Paiva, T.B., Paiva, A.CM., Freer, R.J., Stewart, J.M.: Alkylating analogs of peptide hormones. 2. Synthesis and properties of p-[N,N-Bis(2-chloroethyl)amino]phenylbutyryl derivatives of angiotensin II. J. Med. Chem. 15,6–8 (1972)

    PubMed  CAS  Google Scholar 

  • Park, W.K., St-Pierre, S.A., Barabe, J., Regoli, D.: Synthesis of peptides by the solid phase method. III. Bradykinin: fragments and analogs. Canad. J. Biochem. 56, 92–100 (1978)

    CAS  Google Scholar 

  • Peña, C, Stewart, J.M., Goodfriend, T.C.: A new class of angiotensin inhibitors: N-Methylphenylalanine analogs. Life Sci. 14,1331–1336 (1974)

    PubMed  Google Scholar 

  • Pinker, T.G., Young, G.T., Elliott, D.F., Wade, R.: Synthesis of analogs of bradykinin with modifications in positions 1,6, and 9. J. Chem. Soc. (Perkin I), 220–228 (1976)

    Google Scholar 

  • Piper, P. J., Vane, J. R.: Release of additional factors in anaphylaxis and its antagonism by antiinflammatory drugs. Nature 223,29–35 (1969)

    PubMed  CAS  Google Scholar 

  • Pisano, J. J.: Availability of labeled bradykinin. Science 163,494 (1969)

    PubMed  CAS  Google Scholar 

  • Popkova, G.A., Astapova, M.V., Lisunkin, Y. Y., Ravdel, G. A., Krit, N.A.: A comparative study of biological activity and resistance to tissue kininases of bradykinin analogs modified in position 8. Bioorganicheskaya Khimiya 2,1606–1612 (1976)

    CAS  Google Scholar 

  • Ragnarsson, U., Karlsson, S. M., Hamberg, U.: Synthesis of peptides by fragment condensation on a solid support. Int. J. Pept. Protein Res. 7,307–312 (1975)

    PubMed  CAS  Google Scholar 

  • Regoli, D., Barabe, J.: Receptors for peptide hormones. In: Proc. 5th American Peptide Symposium. Goodman, M. (ed.), pp. 157–160. New York: Wiley & Sons 1977

    Google Scholar 

  • Reissmann, S., Pagelow, I., Arold, H.: Relationship between structure and activity of new bradykinin analogs. Acta Biol. Med. Ger. 33,77–88 (1974)

    PubMed  CAS  Google Scholar 

  • Reissmann, S., Arold, H., Filatova, M.P., Reutova, T.O., Ivanov, V.T.: Activated esters of spin labels and their use for substituting functional groups on the nonapeptide bradykinin. Z. Chem. 15, 399–400 (1975a)

    CAS  Google Scholar 

  • Reissmann, S., Pagelow, I., Leisner, H., Arold, H.: Bradykinin-binding cell fractions. Stability of some bradykinin analogs against kininase II. Experientia 31,1395–1396 (1975b)

    CAS  Google Scholar 

  • Reissmann, S., Filatova, M.P., Reutova, T.O., Arold, H., Ivanov, V.T.: Synthesis of bradykinin analogs and partial sequences with tyrosine for electron spin resonance and fluorescence studies. Journal für praktische Chemie 318,429–440 (1976)

    CAS  Google Scholar 

  • Ribeiro, S.A., Rocha e Silva, M.: Antinociceptive action of bradykinin and related kinins of larger molecular weight by the intraventricular route. Br. J. Pharmacol. 47, 517–528 (1973)

    PubMed  CAS  Google Scholar 

  • Roblero, J., Ryan, J.W., Stewart, J.M.: Assay of kinins by their effects on blood pressure. Res. Commun. Chem. Pathol. Pharmacol. 6,207–212 (1973)

    CAS  Google Scholar 

  • Rocha e Silva, M.: Kinin hormones. Springfield: Thomas 1970

    Google Scholar 

  • Rudinger, J.: The design of peptide hormone analogs. In: Drug design. Ariens, E.J. (ed.), pp. 319–419. London, New York: Academic Press 1971

    Google Scholar 

  • Ryan, J.W., Roblero, J., Stewart, J.M.: Inactivation of bradykinin in the pulmonary circulation. Biochem. J. 110,795–797 (1968)

    PubMed  CAS  Google Scholar 

  • Ryan, J. W., Roblero, J., Stewart, J.M.: Inactivation of bradykinin in rat lung. In: Bradykinin and related kinins. Sicuteri, F., Rocha e Silva, M., Back, N. (eds.), pp. 263–271. New York, London: Plenum Press 1970

    Google Scholar 

  • Sabia, E. B., Tominaga, M., Paiva, A. C. M., Paiva, T. B.: Bradykinin potentiating and sensitizing activities of new synthetic analogues of snake venom peptides. J. Med. Chem. 20, 1679–1681 (1977)

    PubMed  CAS  Google Scholar 

  • Safdy, M.E., Lyons, P.A.: Synthesis and pharmacology of homoarginine bradykinin analogs. J. Med. Chem. 17,1227–1228 (1974)

    PubMed  CAS  Google Scholar 

  • Sakakibara, S., Naruse, M.: Bradykinin-like peptides. Japan Pat 7,503,306 (1975); Chemical Abstracts 83,10889 (1975)

    Google Scholar 

  • Sandberg, B.E.B., Ragnarsson, U.: Preparation of some 2-phenylisopropyloxycarbonyl amino acids. Evaluation of their properties with particular reference to application in solid phase peptide synthesis. Int. J. Pept. Protein Res. 6,111–119 (1974)

    PubMed  CAS  Google Scholar 

  • Sander, G.E., West, D.W., Huggins, C.G.: Inhibitors of the pulmonary angiotensin I-converting enzyme. Biochim. Biophys. Acta 289,392–400 (1972)

    PubMed  CAS  Google Scholar 

  • Schafer, D. J., Young, G.T., Elliott, D. F., Wade, R.: A simplified synthesis of bradykinin by use of the picolyl ester method. J. Chem. Soc. (C) 46–49 (1971)

    Google Scholar 

  • Scholtz, H.W., Biron, P.: Non-identity between pulmonary bradykininase and converting enzyme activity. Rev. Can. Biol. 28,197–198 (1969)

    Google Scholar 

  • Schröder, E.: Synthesis of kinin-liberating kininogens. Experientia 25,1126–1127 (1969)

    PubMed  Google Scholar 

  • Schröder, E.: Structure-activity relationships of kinins. In: Handbook of experimental pharmacology. Vol. XXV: Bradykinin, kallidin, and kallikrein. Erdös, E.G. (ed.), pp. 324–350. Berlin, Heidelberg, New York: Springer 1970

    Google Scholar 

  • Shemyakin, M., Shchukina, L.A., Vinogradova, E.I., Ravdel, G.A., Ovchinnikov, Y.A.: Mutual replaceability of amide and ester groups in biologically active peptides and depsipeptides. Experientia 22,535–536 (1966)

    PubMed  CAS  Google Scholar 

  • Southard, G.L.: Comments. In: Peptides 1969. Scoffone, E. (ed.), pp. 168–170. Amsterdam: North-Holland 1971

    Google Scholar 

  • Stewart, J.M.: Effects of bradykinin analogs on capillary permeability. Abstract 1-66, 7 th Intl. Cong. Biochem., Tokyo 1967

    Google Scholar 

  • Stewart, J.M.: Structure-activity relationships in bradykinin analogs. Fed. Proc. 27, 63–66 (1968a)

    CAS  Google Scholar 

  • Stewart, J.M.: Synthesis and pharmacology of polisteskinin, a bradykinin homolog. Fed. Proc. 27,534 (1968b)

    Google Scholar 

  • Stewart, J.M.: The kinins: Methods of chemical synthesis. In: Handbook of experimental pharmacology. Vol. XXV: Bradykinin, kallidin, and kallikrein. Erdös, E.G. (ed.), pp. 14–20. Berlin, Heidelberg, New York: Springer 1970

    Google Scholar 

  • Stewart, J. M.: Structure-activity relationships among the kinins. In: Structure-activity relationships of protein and polypeptide hormones. Margoulies, M., Greenwood, F. C. (eds.), pp. 23–30. Amsterdam: Excerpta Medica 1971

    Google Scholar 

  • Stewart, J.M.: Solid phase peptide synthesis. Journal of Macromolecular Science-Chemistry A10,259–288 (1976)

    CAS  Google Scholar 

  • Stewart, J.M.: Modifiers of the response to kinins and their interactions with other systems. In: Chemistry and biology of the kallikrein-kinin system in health and disease. Pisano, J. J., Austen, K.F. (eds.), pp. 287–294. Fogarty Internat. Center Proc. No. 27. Washington: U.S. Gov. Printing Office 1977

    Google Scholar 

  • Stewart, J.M., Woolley, D. W.: Importance of the carboxyl end of bradykinin and other peptides. Nature (Lond.) 207,1160–1161 (1965a)

    CAS  Google Scholar 

  • Stewart, J.M., Woolley, D. W.: Effect of proline configuration on pro and anti activity of bradykinin peptides. In: Abstracts, p. 81c. 150th Meeting of the American Chemical Society, Atlantic City, N. J. 1965 b

    Google Scholar 

  • Stewart, J.M., Woolley, D.W.: The search for peptides with specific antibradykinin activity. In: Hypotensive peptides. Erdös, E.G., Back, N., Sicuteri, F. (eds.)., pp. 23–33. Berlin, Heidelberg, New York: Springer 1966

    Google Scholar 

  • Stewart, J.M., Ferreira, S.H., Greene, L.J.: Bradykinin potentiating peptide PCA-Lys-Trp-Ala-Pro. Biochem. Pharmacol. 20,1557–1567 (1971)

    CAS  Google Scholar 

  • Stewart, J.M., Freer, R.J., Ferreira, S.H.: Two mechanisms for potentiation of the response of smooth muscle to bradykinin. Fed. Proc. 32,846 (Abstract) (1973)

    Google Scholar 

  • Stewart, J.M., Ryan, J.W., Brady, A.H.: Hydroxyproline analogs of bradykinin. J. Med. Chem. 17,537–539(1974)

    PubMed  CAS  Google Scholar 

  • Stewart, J.M., Peña, C, Matsueda, G.R., Harris, K.: Some improvements in the solid phase synthesis of large peptides. In: Peptides 1976. Loffet, A. (ed.), pp. 285–290. Brussels: Editions de l’Université de Bruxelles 1976

    Google Scholar 

  • Suzuki, K., Asaka, M., Abiko, T.: Synthesis of 6-leucine-, 6-O-acetyl threonine-, and 6-threoninebradykinin. Chem. Pharm. Bull. (Tokyo) 14,211–216 (1966)

    CAS  Google Scholar 

  • Suzuki, K., Abiko, T., Endo, N.: Synthesis of every kind of peptide fragments of bradykinin. Chem. Pharm. Bull. (Tokyo) 17,1671–1678 (1969)

    CAS  Google Scholar 

  • Takahashi, S., Shimonishi, Y.: Solid phase peptide synthesis using ultrasonic waves. Chem. Lett. 1, 51–56 (1974)

    Google Scholar 

  • Tewksbury, D.A.: Studies on bradykinin-potentiating peptides. In: Chemistry and biology of peptides. Meienhofer, J. (ed.), pp. 461–463. Ann Arbor: Ann Arbor Science Publishers 1972

    Google Scholar 

  • Tomatis, R., Ferroni, R., Guarneri, M., Benassi, C.A.: Synthesis of bradykinin via oximinopyrazoline active esters. J. Med. Chem. 16,1053–1054 (1973)

    PubMed  CAS  Google Scholar 

  • Tominaga, M., Stewart, J.M., Paiva, T.B., Paiva, A.CM.: Synthesis and properties of new bradykinin potentiating peptides. J. Med. Chem. 18,130–133 (1975)

    PubMed  CAS  Google Scholar 

  • Toniolo, C: Relations between primary structures, conformations, and biological activities of polypeptide hormones. Il Farmaco (Pavia), Edizione Scientifica 27,156–178 (1972)

    CAS  Google Scholar 

  • Turk, J., Needleman, P., Marshall, G.R.: Alkylating analogs of bradykinin. J. Med. Chem. 18, 1135–1139 (1975a)

    CAS  Google Scholar 

  • Turk, J., Needleman, P., Marshall, G.R.: Analogs of bradykinin with restricted conformational freedom. J. Med. Chem. 18,1139–1142 (1975b)

    CAS  Google Scholar 

  • Vardel, G.A., Monapova, N.N., Krit, N.A., Filatova, M.P., Lisunken, V.I., Ivanova, V.T.: Synthesis and biological properties of bradykinin-potentiating peptides from snake venom. Khimiya Prirodnych Soedinenii 11,47–56 (1975)

    CAS  Google Scholar 

  • Watanabe, M., Yasuhara, T., Nakajima, T.: Occurrence of Thr6-bradykinin and its analogous peptide in the venom of Polistes rothneyi iwatai. In: Proc. 4th Int. Symp. Toxins, Tokyo 1974.

    Google Scholar 

  • Ohsaka, A., Hayashi, K., Sawai, Y. (eds.), pp. 105–112. New York, London: Plenum Press 1976

    Google Scholar 

  • Weyers, R., Hagel, D., Das, B.C., Van der Meer, C: Tryptic peptides from rabbit albumin enhancing the effect of bradykinin. Biochim. Biophys. Acta 279,331–355 (1972)

    PubMed  CAS  Google Scholar 

  • Yanaihara, N., Yanaihara, C, Sakagami, M., Nakajima, T., Nakayama, T., Matsumoto, K.: Chem. Pharm. Bull. (Tokyo) 21,616–621 (1973)

    CAS  Google Scholar 

  • Yasuhara, T., Hira, M., Nakajima, T., Yanaihara, N., Yanaihara, C, Hashimoto, T., Sakura, N., Tachibana, S., Abaki, K., Besho, M., Yamanaka, T.: Active peptides on smooth muscle in the skin of Bombina orientalis Boulenger and characterization of a new bradykinin analogue. Chem. Pharm. Bull. (Tokyo) 21,1388–1391 (1973)

    CAS  Google Scholar 

  • Yasuhara, T., Nakajima, T.: The structure of granuliberin-R, a potent mastocytolytic peptide obtained from the skin of Rana rugosa. In: Peptide chemistry 1976. Nakajima, T. (ed.), p. 159. Osaka: Protein Research Foundation 1977; Chem. Pharm. Bull. 25,936–941 (1977)

    Google Scholar 

  • Yasuhara, T., Yoshida, H., Nakajima, T.: The structure of a new bradykinin analogue “Vespakinin-X”. Chem. Pharm. Bull. (Tokyo) 25,936–941 (1977)

    CAS  Google Scholar 

  • Yoshida, H., Geller, R.G., Pisano, J. J.: Vespulakinins: New carbohydrate-containing bradykinin derivatives. Biochemistry 15,61–64 (1976)

    PubMed  CAS  Google Scholar 

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Stewart, J.M. (1979). Chemistry and Biologic Activity of Peptides Related to Bradykinin. In: Erdös, E.G. (eds) Bradykinin, Kallidin and Kallikrein. Handbook of Experimental Pharmacology, vol 25 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-67301-6_5

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