Date Awarded
2022
Document Type
Thesis
Degree Name
Master of Science (M.Sc.)
Department
Chemistry
Advisor
Robert J Hinkle
Committee Member
William R McNamara
Committee Member
Randolph A Coleman
Abstract
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.
DOI
https://dx.doi.org/10.21220/s2-0rc6-7z32
Rights
© The Author
Recommended Citation
Green, Lauren Cheyenne, "Synthesis And Structure-Activity-Relationships Of Differentially Substituted Diynes And Triynes" (2022). Dissertations, Theses, and Masters Projects. William & Mary. Paper 1697552716.
https://dx.doi.org/10.21220/s2-0rc6-7z32
