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Implication of the disulfide bridge in trypsin inhibitor SFTI-1 in its interaction with serine proteinases

Abstract

Fourteen monocyclic analogues of trypsin inhibitor SFTI-1 isolated from sunflower seeds were synthesized by the solid-phase method. The purpose of this work was to establish the role of a disulfide bridge present in inhibitor's side chains of Cys3 and Cys11 in association with serine proteinases. This cyclic fragment was replaced by the disulfide bridges formed by L-pencillamine (Pen), homo-L-cysteine (Hcy), N-sulfanylethylglycine (Nhcy) or combination of the three with Cys. As in the substrate specificity the P(1) position of the synthesized analogues Lys, Nlys [N-(4-aminobutyl) glycine], Phe or Nphe (N-benzylglycine) were present, and they were checked for trypsin and chymotrypsin inhibitory activity. The results clearly indicated that Pen and Nhcy were not acceptable at the position 3, yielding inactive analogues, whereas another residue (Cys11) could be substituted without any significant impact on the affinity towards proteinase. On the other hand, elongation of the Cys3 side chain by introduction of Hcy did not affect inhibitory activity, and an analogue with the Hcy-Hcy disulfide bridge was more than twice as effective as the reference compound ([Phe(5)] SFTI-1) in inhibition of bovine alpha-chymotrypsin. (C) 2010 Elsevier Ltd. All rights reserved.

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Authors (7)

  • Photo of  Anna Łęgowska

    Anna Łęgowska

    • Wydział Chemii UG Katedra Chemii Bioorganicznej
  • Photo of  Dawid Dębowski

    Dawid Dębowski

    • Wydział Chemii UG Katedra Chemii Bioorganicznej
  • Photo of  Łukajtis Rafał

    Łukajtis Rafał

    • Wydział Chemii UG Katedra Chemii Bioorganicznej
  • Photo of  Magdalena Wysocka

    Magdalena Wysocka

    • Wydział Chemii UG Katedra Chemii Bioorganicznej
  • Photo of Dr hab. Cezary Czaplewski

    Cezary Czaplewski Dr hab.

    • Wydział Chemii UG Katedra Chemii Teoretycznej
  • Photo of  Krzysztof Rolka

    Krzysztof Rolka

    • Wydział Chemii UG Katedra Chemii Bioorganicznej

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Details

Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
BIOORGANIC & MEDICINAL CHEMISTRY no. 18, edition 23, pages 8188 - 8193,
ISSN: 0968-0896
Language:
English
Publication year:
2010
Bibliographic description:
Łęgowska A., Dębowski D., Rafał Ł., Wysocka M., Czaplewski C., Lesner A., Rolka K.: Implication of the disulfide bridge in trypsin inhibitor SFTI-1 in its interaction with serine proteinases// BIOORGANIC & MEDICINAL CHEMISTRY. -Vol. 18, iss. 23 (2010), s.8188-8193
DOI:
Digital Object Identifier (open in new tab) 10.1016/j.bmc.2010.10.014
Verified by:
Gdańsk University of Technology

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