Master of Science (M.Sc.)
Robert J Hinkle
William R McNamara
Randolph A Coleman
Polyynes represent a class of naturally occurring products that have been linked to a variety of forms of cytotoxicity, including antibacterial and anti-cancer activity. Because these molecules could represent an advancement in modern medical treatments of a variety of ailments, they have been studied much more frequently in the last decade as the need for new antimicrobial treatments has increased. By investigating the structure-activity relationship of the biologically active polyyne, dodeca-2,4-diyn-1-ol, we determined that key structural features such as polyyne conjugation and hydroxyl presence are necessary for the compounds to be biologically active. Using this known molecule as a scaffold and varying chain length, and placement of the conjugation in the chain, we found that diynes around 10-12 carbons showed cytotoxic activity with E. coli while P. fluorescens was only affected by specific molecules that showed no noticeable trend. Further investigation into the trend of molecules that affect E. coli found that increasing the number of alkynes in the conjugation tended to make the molecules more effective than their diyne analogs in most cases.
© The Author
Green, Lauren Cheyenne, "Synthesis And Structure-Activity-Relationships Of Differentially Substituted Diynes And Triynes" (2022). Dissertations, Theses, and Masters Projects. William & Mary. Paper 1697552716.
Available for download on Monday, August 25, 2025