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An efficient method to produce high yield analogs of Hemi-Phorboxazole A with anticancer and antifungal activities

Description:

A two-step, high yield, method for synthesizing naturally derived, Hemi-Phorboxazole A analogs

 

Problem: 

(+)-Phorboxazole A and B, extracted from the sponge Phorbas sp., display extraordinary anti-proliferative activity against National Cancer Institute’s (NCI) panel of 60 human tumor cell lines. Due to their complex structures, the reported syntheses of Phorboxazole A and B analogues consist of 100 total steps with an average yield of 4%. The limited availability of these compounds has precluded the evaluation of their biological activity. As such, there is a need for improved syntheses of these compounds, featuring fewer steps while providing higher yield and selectivity.

 

Solution: 

Researchers in the Smith Lab have developed a two-step, high yield (85%) method for preparing Hemi-Phorboxazole A from a known precursor. Two analogues of Hemi-Phorboxazole were designed and synthesized in this manner. One analogue exhibits anti-proliferation activities of human cancer cell lines HCT-116 (colon) and SPKB-3 (breast). Another analogue shows antifungal activity against Candida albicans.

 

 

Synthesis of completely synthetic (+)-hemi-phorboxazole A.  From Smith AB et al, 2009. 

 

Advantages: 

  • Efficient two-step method to synthesize complex and scarce molecules, compared to previously-reported syntheses having 100 steps
  • Improved synthetic yield (~85%) over other reported procedures (average 4%)
  • Less expensive process than other known procedures

 

Applications: 

  • Antitumor activities for colon and breast cancer cell lines
  • Antifungal activity against Candida albicans


Stage of Development: 

In vitro testing in human cell lines

 

Intellectual Property: 

USSN 8,957,097 

 

Reference Media: 

  • Smith AB et al.  Org. Lett., 2009, 11(16), p. 3766-3769.
  • Dalisay DS et al.  Org. Lett., 2009, 11(9), p. 1967-1970.

Desired Partnerships:

License

 

Docket # W5271

 

 

Download PDF

 


Patent Information:
For Information, Contact:
Joshua Jeanson
Associate Director, SEAS/SAS Licensing Group
University of Pennsylvania
jeanson@upenn.edu
Inventors:
Amos Smith
Keywords: