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Does Cysteine Rule (CysR) Complete the CendR Principle? Increase in Affinity of Peptide Ligands for NRP-1 Through the Presence of N-Terminal Cysteine.


ABSTRACT: The structure-activity relationship of branched H-Lys(hArg)-Dab-Dhp-Arg-OH sequence analogues, modified with Cys-Asp or Cys at N-terminal amino acids (Lys, hArg), in VEGF-A165/Neuropilin-1 complex inhibition is presented. The addition of Cys residue led to a 100-fold decrease in the IC50 value, compared to the parent peptide. The change occurred regardless of coupling Cys to the free N-terminal amino group present in the main or the side chain. A few analogues extended by the attachment of Cys at the N-terminus of several potent NRP-1 peptide ligands documented in the literature are also presented. In all studied cases, the enhancement of inhibitory properties after the addition of Cys at the N-terminus is observed. It is particularly evident for the tetrapeptide derived from the C-terminus of VEGF-A165 (KPRR), suggesting that extending the K/RXXK/R motif (CendR) with the Cys moiety can significantly improve affinity to NRP-1 of CendR peptides.

SUBMITTER: Puszko AK 

PROVIDER: S-EPMC7175122 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Does Cysteine Rule (CysR) Complete the CendR Principle? Increase in Affinity of Peptide Ligands for NRP-1 Through the Presence of N-Terminal Cysteine.

Puszko Anna K AK   Sosnowski Piotr P   Raynaud Françoise F   Hermine Olivier O   Hopfgartner Gérard G   Lepelletier Yves Y   Misicka Aleksandra A  

Biomolecules 20200313 3


The structure-activity relationship of branched H-Lys(<i>h</i>Arg)-Dab-Dhp-Arg-OH sequence analogues, modified with Cys-Asp or Cys at N-terminal amino acids (Lys, <i>h</i>Arg), in VEGF-A<sub>165</sub>/Neuropilin-1 complex inhibition is presented. The addition of Cys residue led to a 100-fold decrease in the IC<sub>50</sub> value, compared to the parent peptide. The change occurred regardless of coupling Cys to the free N-terminal amino group present in the main or the side chain. A few analogues  ...[more]

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