Structural Chemistry

, Volume 28, Issue 2, pp 527–535

Synthesis, conformation and cytotoxicity of new, branched polymeric polypeptides containing hydrophobic amino acid or arginine moiety

  • Mónika Sebestyén
  • Rita Szabó
  • László Kőhidai
  • Éva Pállinger
  • Gábor Mező
  • György Kóczán
  • Ferenc Hudecz
Original Research

DOI: 10.1007/s11224-016-0901-z

Cite this article as:
Sebestyén, M., Szabó, R., Kőhidai, L. et al. Struct Chem (2017) 28: 527. doi:10.1007/s11224-016-0901-z
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Abstract

In this paper we report on the synthesis and solution conformation of a new set of structurally related polycationic branched chain polypeptides (poly[Lys(Xi-dl-Alam)]) with hydrophobic (Ile, Nle, Val) or cationic (Arg) amino acids at the N-terminal end of the side chains as well as their cytotoxic effect on murine bone marrow derived macrophages. Solution conformation of the polypeptides was studied with circular dichroism spectroscopy under different conditions (pH, ionic strength). The results of these comparative studies indicate that a) polypeptides could adopt an ordered (mainly helical) conformation at physiological pH and salt concentration (pH 7.4, 0.2 M NaCl); b) the nature of side chain terminal amino acid (X) could determine under which conditions the ordered structure was formed. Thus, the solution conformation of branched polypeptides could be modulated by the selection of amino acid X under physiological conditions. All polypeptides with hydrophobic amino acid at the terminal position were essentially non-toxic on macrophages, whereas the polypeptide with terminal Arg proved to be markedly cytotoxic.

Keywords

polylysine based polypeptides hydrophobic side chain solution conformation in vitro cytotoxicity 

Funding information

Funder NameGrant NumberFunding Note
Hungarian National Research Fund
  • OTKA K104385

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Mónika Sebestyén
    • 1
  • Rita Szabó
    • 1
  • László Kőhidai
    • 2
  • Éva Pállinger
    • 2
  • Gábor Mező
    • 1
  • György Kóczán
    • 1
  • Ferenc Hudecz
    • 1
    • 3
  1. 1.MTA-ELTE Research Group of Peptide ChemistryBudapestHungary
  2. 2.Department of Genetics, Cell- and ImmunobiologySemmelweis UniversityBudapestHungary
  3. 3.ELTE Department of Organic ChemistryBudapestHungary

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