2,2'-Bithiophene-5,5'-dicarbaldehyde: Synthesis and mechanistic evaluation of generating guanine adducts

CHED 1354

Danae R. Quirk Dorr, danae.quirk-dorr@mnsu.edu, Department of Chemistry and Geology, Minnesota State University - Mankato, Trafton North 242, Mankato, MN 56001 and Jeffrey P. Freund, Department of Chemistry and Geology, Minnesota State University, Mankato, Trafton North 242, Mankato, MN 56001.
Thiophene derivative NSC 652287 has been found to possess anti-tumor properties. This cytotoxicity has been correlated with the oxidized dialdehyde of NSC 652287. It has been proposed that this dialdehyde interacts irreversibly with cellular DNA and/or proteins. Other linear conjugated thiophene containing compounds have been shown to demonstrate cytotoxicity toward bacteria and viruses. In this research, 2,2'-bithiophene-5,5'-dicarbaldehyde, the oxidized form of 2,2'-bithiophene, has been synthesized and evaluated for selectivity in interacting with nucleosides and DNA. Guanine adducts of 2,2'-bithiophene were also prepared as standards and utilized in the mechanistic studies of this compound.
 

Undergraduate Research Poster Session: Medicinal
2:00 PM-4:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Chemical Education

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007