Non-Toxic Motuporamine Analogues to Target Cancer Metastasis

Technology #30810

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Researchers
Otto Phanstiel, Ph.D.
External Link (med.ucf.edu)
Managed By
Brion Berman
Assistant Director 407.882.0342
Patent Protection
US Patent 7,728,041
Publications
Synthesis and biological evaluation of antimetastatic agents predicated upon dihydromotuporamine C and its carbocyclic derivatives.
J Med Chem, 2014 May 22;57(10):4023-34. doi: 10.1021/jm401906v. Epub 2014 May 2.
Synthesis and bioevaluation of macrocycle-polyamine conjugates as cell migration inhibitors
J Med Chem, 2017 Oct 26;60(20):8606-8619. doi: 10.1021/acs.jmedchem.7b01222. Epub 2017 Oct 4.

Novel motuporamine analogues with high anti-metastatic activity and low toxicity.

UCF researchers have synthesized novel motuporamine analogues that act as anti-metastatic agents with low toxicity and high anti-migration activities. Motuporamines are naturally occurring anti-cancer compounds isolated from the sea sponge Xestospongia exigua. They have unique anti-migration and anti-angiogenic properties. The motuporamine scaffold consists of a macrocycle and an appended polyamine motif. This motif may allow for specific targeting to cancer cells with high polyamine import activity.

Technical Details

The researchers found that incrementally moving the polyamine chain away from the macrocycle structure improved the anti-metastatic activity of the motuporamine analogues while reducing their toxicity, compared to the parent compound. The analogues were shown to reduce the migration ability of metastatic human pancreatic cancer cells in vitro and reduce tumor growth and metastasis in a pancreatic cancer mouse model in vivo. The increased potency of the analogues could lead to a lower required dosage regiment and reduced side effects.

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Benefits

  • Increased anti-metastatic activity
  • Reduced toxicity
  • Ease of synthesis via commercially available 15-membered ketones (eliminates the need for the lengthy synthesis of the motuporamine heterocycle)

Applications

  • Small molecule anti-cancer therapies
  • Anti-metastatic agents

Publications

Synthesis and biological evaluation of antimetastatic agents predicated upon dihydromotuporamine C and its carbocyclic derivatives, J Med Chem. 2014 May 22;57(10):4023-34. doi: 10.1021/jm401906v. Epub 2014 May 2.

Synthesis and bioevaluation of macrocycle-polyamine conjugates as cell migration inhibitors, J Med Chem. 2017 Oct 26;60(20):8606-8619. doi: 10.1021/acs.jmedchem.7b01222. Epub 2017 Oct 4.