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Enhanced Drug Photosafety by Interchromophoric Interaction Owing to Intramolecular Charge Separation

Ming-De Li1, Zhiping Yan2, Ruixue Zhu2

  • 1Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Guangdong, 515063, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 15, 2018
PubMed

Insights

Imatinib, a cancer drug, shows low phototoxicity due to intramolecular charge separation. Its pyridylpyrimidine fragment is phototoxic, highlighting the role of interchromophoric interactions in drug photosafety.

Area of Science:

  • Photochemistry
  • Medicinal Chemistry
  • Molecular Biophysics

Background:

  • Imatinib is a cancer therapeutic with low DNA phototoxicity.
  • The pyridylpyrimidine fragment of imatinib exhibits significant phototoxicity.
  • The mechanism behind imatinib's enhanced photosafety is not well understood.

Purpose of the Study:

  • To investigate the excited state properties and interchromophoric interactions of imatinib.
  • To elucidate the mechanism of imatinib's photosafety.
  • To understand the phototoxicity of the pyridylpyrimidine fragment.

Main Methods:

  • Ultrafast laser flash photolysis.
  • Agarose electrophoresis.
  • Time-resolved resonance Raman spectroscopy.
  • Quenching studies.

Main Results:

  • Direct observation of intramolecular charge separation in irradiated imatinib, facilitating excited state relaxation.
  • Identification of an anionic form of the pyridylpyrimidine fragment.
  • Pyridylpyrimidine efficiently forms long-lived triplet excited states, correlating with its phototoxicity.

Conclusions:

  • Intramolecular charge separation contributes to imatinib's photosafety.
  • Interchromophoric interactions are crucial for modulating drug phototoxicity.
  • This study offers insights for designing safer or more photostable drugs.
Keywords:
absorptioncharge separationchromophoreselectronic structureraman spectroscopy

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