A disintegrin derivative as a case study for PHIP labeling of disulfide bridged biomolecules.


Journal

Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288

Informations de publication

Date de publication:
11 02 2022
Historique:
received: 01 11 2021
accepted: 25 01 2022
entrez: 12 2 2022
pubmed: 13 2 2022
medline: 13 2 2022
Statut: epublish

Résumé

A specific labeling strategy for bioactive molecules is presented for eptifibatide (integrilin) an antiplatelet aggregation inhibitor, which derives from the disintegrin protein barbourin in the venom of certain rattlesnakes. By specifically labeling the disulfide bridge this molecule becomes accessible for the nuclear spin hyperpolarization method of parahydrogen induced polarization (PHIP). The PHIP-label was synthesized and inserted into the disulfide bridge of eptifibatide via reduction of the peptide and insertion by a double Michael addition under physiological conditions. This procedure is universally applicable for disulfide-containing biomolecules and preserves their tertiary structure with a minimum of change. HPLC and MS spectra prove the successful insertion of the label.

Identifiants

pubmed: 35149768
doi: 10.1038/s41598-022-06327-z
pii: 10.1038/s41598-022-06327-z
pmc: PMC8837631
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

2337

Informations de copyright

© 2022. The Author(s).

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Auteurs

Max Fleckenstein (M)

Institute of Organic Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 4, 64287, Darmstadt, Germany.

Kevin Herr (K)

Institute of Physical Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 8, 64287, Darmstadt, Germany.

Franziska Theiß (F)

Institute of Physical Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 8, 64287, Darmstadt, Germany.

Stephan Knecht (S)

Institute of Physical Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 8, 64287, Darmstadt, Germany.

Laura Wienands (L)

Institute of Physical Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 8, 64287, Darmstadt, Germany.

Martin Brodrecht (M)

Institute of Physical Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 8, 64287, Darmstadt, Germany.

Michael Reggelin (M)

Institute of Organic Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 4, 64287, Darmstadt, Germany. re@chemie.tu-darmstadt.de.

Gerd Buntkowsky (G)

Institute of Physical Chemistry, Technical University Darmstadt, Alarich-Weiss-Straße 8, 64287, Darmstadt, Germany. gerd.buntkowsky@chemie.tu-darmstadt.de.

Classifications MeSH