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Related Experiment Videos

Solution conformations of amphidinolide H.

Kazutaka Shimbo1, Kohei Nozawa, Masashi Tsuda

  • 1Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

Bioorganic & Medicinal Chemistry
|May 5, 2005
PubMed
Summary

Amphidinolide H (1) shows potent antitumor activity. Its solution conformations differ between chloroform and DMSO-d6, with the latter deviating from the X-ray structure.

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Area of Science:

  • Natural Product Chemistry
  • Structural Biology
  • Medicinal Chemistry

Background:

  • Amphidinolide H (1) is a 26-membered macrolide with demonstrated cytotoxic and antitumor properties.
  • Understanding the three-dimensional structure of bioactive molecules in solution is crucial for drug design and mechanism of action studies.

Purpose of the Study:

  • To elucidate the solution conformations of amphidinolide H (1) in different solvent environments (CDCl3 and DMSO-d6).
  • To compare the solution structures with the known X-ray crystal structure.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy was employed to gather structural data.
  • Distance geometry calculations and restrained energy minimization were used to model the three-dimensional conformations.

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Main Results:

  • In CDCl3, the determined conformations of amphidinolide H (1) closely resemble its established X-ray crystal structure.
  • In DMSO-d6, the solution conformations of amphidinolide H (1) were found to be distinct from both its CDCl3 conformation and its X-ray structure.

Conclusions:

  • Solvent significantly influences the conformational landscape of amphidinolide H (1).
  • The conformational flexibility in DMSO-d6 may have implications for its biological activity and interaction with cellular targets.