Date of Completion


Embargo Period



Dr. Amy R. Howell, Dr. Alfredo Angeles-Boza

Field of Study



Master of Science

Open Access

Open Access


Nitropolycyclic aromatic hydrocarbons are ubiquitous in the environment, and many compounds of this family are carcinogenic. 6-Nitrochrysene, a representative member of this group, is a suspected human carcinogen that has been shown to cause lung, breast, and other forms of cancer in rodents. It is believed that this derivative of chrysene causes cancer by forming DNA adducts, which, in turn, induce mutations in critical gene sequences. The goal of my research is to synthesize one or more of the major DNA adducts formed by 6-nitrochrysene, which will be introduced in DNA in order to study their biological effects.

The initiation step of the multi-step process that leads to cancer involves mutations in DNA via erroneous replication, which occurs when the body is unable to repair certain DNA damages. Accumulation of these mutations in critical genes triggers a series of biological events, ultimately making the cell an outlaw. Usually, there are specific processes the cell employs to repair DNA damages. Cancer-causing agents, such as 6-nitrochrysene, are metabolically activated in a cell to electrophilic species, which induce specific DNA damages resulting in a high frequency of mutations.

Understanding exactly how 6-nitrochrysene causes mutations will provide insight into how cancer by this chemical is initiated. In order to accomplish this, one must synthesize the damaged nucleoside and incorporate it into a DNA fragment. In this thesis, two new schemes are presented to prepare the 6-nitrochrysene-damaged DNA fragments.

Major Advisor

Dr. Ashis K. Basu