Date of Submission

Spring 2018

Academic Programs and Concentrations


Project Advisor 1

Emily McLaughlin

Abstract/Artist's Statement

Violacein is an intensely purple microbial pigment with an arsenal of biological activity. A structural analog to the better-known bis-indole alkaloids staurosporine and rebeccamycin, violacein has been touted as an antimicrobial and anticancer therapeutic. It is most frequently obtained as a biosynthetic secondary metabolite from bacterial cell cultures. However, we have developed an efficient, environmentally benign methodology for synthesizing the natural product via a 3-component condensation in polyethylene glycol. Violacein, along with a series of analogs have been prepared in our laboratory. The deoxyviolacein analog has been investigated for its effects against cancer cell migration in HeLa. This initial screening has served as the impetus to study deoxyviolacein’s specific interactions in cancer cells via proteomics. In this project, the synthesis of the deoxyviolacein scaffold for solid support is designed, in preparation for SILAC (Stable Isotope Labeling by Amino acids in Cell culture) analysis. The synthesis requires preparation of 5-hydroxymethyl-1H-indole, reported here. The main objective of this project is to design and synthesize a functional analog that can be used to determine the protein interactions responsible for the biological activity of violacein.

Open Access Agreement

On-Campus only

Creative Commons License

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