Analogues of Arginine Vasopressin (AVP) Modified in the N-terminal Part of the Molecule with Stereoisomers of 4-Aminopyroglutamic Acid

• Autorzy: Sobolewski D. , Kowalczyk W. , Derdowska I. , Slaninova J. , Kaczmarek K. , Zabrocki J. , Lammek B.
• Języki publikacji: EN

Abstrakty

EN

The present work is a part of our studies aimed at clarifying the influence of sterical constraints in N-terminal part of AVP analogues on the pharmacological activity of the resulting peptides. In this study we described the synthesis of four new analogues of AVP substituted at positions 2 and 3 or 3 and 4 with two diastereoisomers of 4-aminopyroglutamic acid and four peptides in which we combined the above modification with the placement of 3-mercaptopropionic acid at position 1. All new peptides were not active in bioassays for pressor, antidiuretic and uterotonic activity.

Słowa kluczowe

EN

analogues; arginine vasopressin (AVP); conformational constraints; V1a-agonists; V2-agonists

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 4
• Strony: 731--737
• Opis fizyczny: Bibliogr. 21 poz., rys.

Twórcy

autor

Sobolewski D.

• Department of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland

autor

Kowalczyk W.

• Department of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland

autor

Derdowska I.

• Department of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland

autor

Slaninova J.

• Department of Biological Chemistry, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, Prague 6, CZ-16610, Czech Republic

autor

Kaczmarek K.

• Institute of Organic Chemistry, Technical University, 90-924 Łódź, Poland

autor

Zabrocki J.

• Institute of Organic Chemistry, Technical University, 90-924 Łódź, Poland

autor

Lammek B.

• Department of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland

Bibliografia

• 1.Mannig M., Barikowski, K. and Sawyer W.H., in Vasopressin (Eds. Gash D.M. and Boyer G.J.), pp. 335-368, Plenum Publishing Corporation, New York 1987.
• 2.Manning M. and Sawyer W.H., J. Receptor Res.,13, 195 (1993).
• 3.Hlavacek J., in Handbook of Neurohypophyseal Hormone Analogs (Eds. JoSt K., LeblM. and Brtm'k R), Vol. I, Part 2, pp. 109-129, CRC Press Inc., Boca Raton, Florida 1987.
• 4.Lammek B.,Czaja M.,DerdowskaI.,Łempicka E., Sikora P., Szkrobka W. and Trzeciak H. l., J. Peptide Res., 51, 149(1998).
• 5.Lebl M., JoSt K. and Brtnik R, in Handbook of Neurohypophyseal Hormone Analogs, (Eds. JoSt K., Lebl M. and Brtnik R), Vol. II, Part 2, pp. 127-267, CRC Press Inc., Boca Raton, Florida 1987.
• 6.Lammek B., Czaja M., Derdowska I., Rekowski P., TrzeciakH.I., Sikora P., Szkrobka W., Stojko R. and Kupryszewski G., J. Pepl. Res., 49,261 (1987).
• 7.Stoev S., Cheng L.L., Olma A., Klis W.A., Manning M., Sawyer W.H., WoN.C. and Chan W.Y,,J. Pept. Set, 5, 141 (1999).
• 8.Paul P.K., Burney P.A., Campbell M.M. and Osguthorpe D.J., Bioorg. Med. Chem. Lett., 2, 141 (1992).
• 9.Bodanszky M.and Bad A., in Practice of peptide synthesis, p. 83, Springer-Verlag Berlin, Germany 1984.
• 10.KaczmarekK., Zabrocki J., tachwa M. and Lipkowski A., in Peptides 1998, Procedings of the25lhEuropean Peptide Symposium, (Eds. Bajusz S. and Hudecz F.), p. 668, Akademiai Kiado, Budapeszt, Hungary 1999.
• 11.Kaczmarek K., Kaleta M., Chung N.N., Schiller P. W. and Zabrocki I., Acta Biochim. Pol., 48,1159 (2001).
• 12.KaczmarekK., ChungN.N., Schiller P. W. and Zabrocki J., in Peptides 2002, Procedings of the 2Th European Peptide Symposium, (Eds. Benedetti E. and Pedone C.), p. 158, Edizioni Ziino, Napoli, Italy 2002.
• 13.Kaiser E., Colescott R.I., Bossinger C.D. and Cook P., Anal Biochem., 34, 595 (1970).
• 14.Christensen T.C., in Peptides - Structure and Biological Function, (Eds. Gross E. and Meienhofer J.), p. 385, Pierce Chemical Company, Rockford, Illinois 1979.
• 15.Holton P., Br. J. Pharmacol., 3, 328 (1948).
• 16.Munsick R.A., Endocrinology, 66, 451 (I960).
• 17.Dekański J„ Br. J. Pharmacol, 7, 567 (1952).
• 18.Bum H.J., Finney D.J. and Goodwin L.G., in Biological Standardization (2nd ed), p. 187, Oxford University Press, London 1950.
• 19.Vavra I., Machova A. and KrejCi 1., J. Pharmacol Exp. Ther., 188, 241 (1974).
• 20.Slaninova J., in Handbook of Neurohypophyseal Hormone Analogs, (Eds. Jost K., Lebl M. and Brtnik F.), Vol. I, Part 2, pp. 83-107, CRC Press Inc., Boca Raton, Florida 1987.
• 21.Gramberg D., Webe C., Beeli R., Inglis J., Bruns C. and Robinson J., Helv. Chim. Acta, 78,1588 (1995).