Date of Submission

Spring 2018

Academic Programs and Concentrations

Chemistry

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

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 4.0 License.

Download

This work is protected by a Creative Commons license. Any use not permitted under that license is prohibited.

Bard Off-campus Download

Bard College faculty, staff, and students can login from off-campus by clicking on the Off-campus Download button and entering their Bard username and password.

Share

COinS