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Project TitleNovel Biaryl Compounds as Antimicrobial Agents
Track Code2016-015
Short Description
Abstract
 
Tagsantibiotic, antibiotic resistance, therapeutic
 
Posted DateMay 20, 2016 4:35 PM

Challenge

The threatening emergence of bacterial resistance to several antibiotics presents a serious hurdle for their clinical use. The biaryl natural product, bromophene, originally isolated from a marine bacterium is associated with potent antimicrobial activity. Chemical synthesis of bromophene and related biaryls, however, is challenging, involving arduous purification that makes the overall process expensive and less scalable. In addition, lack of an efficient synthetic method limits creation of a library of functionalized derivatives that is a crucial requirement for modern drug discovery.

Solution

Rice researchers have invented a simplified one-pot approach to synthesize bromophene-based biaryls. This process involves a unique set of reactions and catalysts that enable the generation of structurally diverse biaryl compounds. Furthermore, lead molecules with enhanced antimicrobial activities against Gram-positive multidrug resistant bacteria, including methicillin resistant Staphylococcus aureus (MRSA), have been developed.

Benefits and Features

  • Natural product inspired derivatives that are easy to synthesize 
  • Superior antibacterial activity compared to clinically used antibiotics
  • Active against multidrug resistant bacteria
  • Good safety profile/large therapeutic window
  • Comprehensive in vitro screening studies conducted

Market Potential / Applications

These molecules are potential lead candidates for further development into antibacterial drugs. They could be useful in treating patients infected with bacteria including multidrug resistant bacteria either alone or in combination with other antibiotics.

Development and Licensing Status

Synthetic feasibility of these molecules has been demonstrated on the laboratory scale. Their antimicrobial evaluation against various Gram-positive bacteria and extensive cell toxicity studies have been conducted. The synthetic methods and biologically active compounds are available for licensing from Rice University.

Rice Researcher

Laszlo Kurti is Associate Professor in the Department of Chemistry at Rice University. Carolyn L. Cannon is Associate Professor in the College of Medicine at Texas A&M University.

Technology Relevant Papers and Web Links

  • Gao H, Xu QL, Keene C, Yousufuddin M, Ess DH, K├╝rti L, Practical Organocatalytic Synthesis of Functionalized Non-C2 -Symmetrical Atropisomeric Biaryls. Angew Chem Int Ed Engl. 2016, 55(2), 566-71.
  • US provisional patent application claiming the synthetic methods, compositions and biological activity of the molecules and their potential uses has been filed.
  • Researcher web site:  
https://chemistry.rice.edu/FacultyDetail.aspx?p=6F84F7BD8729F155
https://research.tamhsc.edu/cannonlab/

Case #

2016-015

Inquiries to:

Neha Malik, neha.malik@rice.edu, (713) 348-4106