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New betulinic acid derivatives as potent proteasome inhibitors.

Publication ,  Journal Article
Qian, K; Kim, S-Y; Hung, H-Y; Huang, L; Chen, C-H; Lee, K-H
Published in: Bioorg Med Chem Lett
October 1, 2011

In this study, 22 new betulinic acid (BA) derivatives were synthesized and tested for their inhibition of the chymotrypsin-like activity of 20S proteasome. From the SAR study, we concluded that the C-3 and C-30 positions are the pharmacophores for increasing the proteasome inhibition effects, and larger lipophilic or aromatic side chains are favored at these positions. Among the BA derivatives tested, compounds 13, 20, and 21 showed the best proteasome inhibition activity with IC(50) values of 1.42, 1.56, and 1.80 μM, respectively, which are three to fourfold more potent than the proteasome inhibition controls LLM-F and lactacystin.

Duke Scholars

Published In

Bioorg Med Chem Lett

DOI

EISSN

1464-3405

Publication Date

October 1, 2011

Volume

21

Issue

19

Start / End Page

5944 / 5947

Location

England

Related Subject Headings

  • Triterpenes
  • Structure-Activity Relationship
  • Signal Transduction
  • Proteasome Inhibitors
  • Pentacyclic Triterpenes
  • Neoplasms
  • Molecular Targeted Therapy
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Inflammation
 

Citation

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Qian, K., Kim, S.-Y., Hung, H.-Y., Huang, L., Chen, C.-H., & Lee, K.-H. (2011). New betulinic acid derivatives as potent proteasome inhibitors. Bioorg Med Chem Lett, 21(19), 5944–5947. https://doi.org/10.1016/j.bmcl.2011.07.072
Qian, Keduo, Sang-Yong Kim, Hsin-Yi Hung, Li Huang, Chin-Ho Chen, and Kuo-Hsiung Lee. “New betulinic acid derivatives as potent proteasome inhibitors.Bioorg Med Chem Lett 21, no. 19 (October 1, 2011): 5944–47. https://doi.org/10.1016/j.bmcl.2011.07.072.
Qian K, Kim S-Y, Hung H-Y, Huang L, Chen C-H, Lee K-H. New betulinic acid derivatives as potent proteasome inhibitors. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5944–7.
Qian, Keduo, et al. “New betulinic acid derivatives as potent proteasome inhibitors.Bioorg Med Chem Lett, vol. 21, no. 19, Oct. 2011, pp. 5944–47. Pubmed, doi:10.1016/j.bmcl.2011.07.072.
Qian K, Kim S-Y, Hung H-Y, Huang L, Chen C-H, Lee K-H. New betulinic acid derivatives as potent proteasome inhibitors. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5944–5947.
Journal cover image

Published In

Bioorg Med Chem Lett

DOI

EISSN

1464-3405

Publication Date

October 1, 2011

Volume

21

Issue

19

Start / End Page

5944 / 5947

Location

England

Related Subject Headings

  • Triterpenes
  • Structure-Activity Relationship
  • Signal Transduction
  • Proteasome Inhibitors
  • Pentacyclic Triterpenes
  • Neoplasms
  • Molecular Targeted Therapy
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Inflammation