4.4 Article

Magnetic Resonance Signal Amplification by Reversible Exchange of Selective PyFALGEA Oligopeptide Ligands Towards Epidermal Growth Factor Receptors

期刊

CHEMBIOCHEM
卷 22, 期 5, 页码 855-860

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.202000711

关键词

epidermal growth factor receptors; hyperpolarization; NMR spectroscopy; SABRE; tyrosine kinases

资金

  1. Alexander von Humboldt Foundation
  2. National Science Centre of Poland [2018/02/X/ST5/01252]
  3. Deutsche Forschungsgemeinschaft [Bu 911-22-2]

向作者/读者索取更多资源

The biorelevant PyFALGEA oligopeptide ligand has been successfully utilized in SABRE experiments for signal amplification, with its interaction with the iridium catalyst influencing the efficiency of hyperpolarization. Steric hindrance caused by the bulky phenylalanine in the PyFALGEA oligopeptide can hinder hyperpolarization, highlighting the importance of optimizing the molecular structures for efficient hyperpolarization. Additionally, a unique NMR pattern in the hydride region observed during SABRE experiments with PyFALGEA and IMesBn can serve as a fingerprint for this oligopeptide.
The biorelevant PyFALGEA oligopeptide ligand, which is selective towards the epidermal growth factor receptor (EGFR), has been successfully employed as a substrate in magnetic resonance signal amplification by reversible exchange (SABRE) experiments. It is demonstrated that PyFALGEA and the iridium catalyst IMes form a PyFALGEA:IMes molecular complex. The interaction between PyFALGEA:IMes and H-2 results in a ternary SABRE complex. Selective 1D EXSY experiments reveal that this complex is labile, which is an essential condition for successful hyperpolarization by SABRE. Polarization transfer from parahydrogen to PyFALGEA is observed leading to significant enhancement of the H-1 NMR signals of PyFALGEA. Different iridium catalysts and peptides are inspected to discuss the influence of their molecular structures on the efficiency of hyperpolarization. It is observed that PyFALGEA oligopeptide hyperpolarization is more efficient when an iridium catalyst with a sterically less demanding NHC ligand system such as IMesBn is employed. Experiments with shorter analogues of PyFALGEA, that is, PyLGEA and PyEA, show that the bulky phenylalanine from the PyFALGEA oligopeptide causes steric hindrance in the SABRE complex, which hampers hyperpolarization with IMes. Finally, a single-scan H-1 NMR SABRE experiment of PyFALGEA with IMesBn revealed a unique pattern of NMR lines in the hydride region, which can be treated as a fingerprint of this important oligopeptide.

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