Date of Award


Document Type

Honors Thesis (Colby Access Only)


Colby College. Chemistry Dept.


Julie T. Millard

Second Advisor

Thomas W. Shattuck


Epichlorohydrin (ECH) is a potential human carcinogen that is used in the industrial production of epoxy resin, adhesives, plastics, insecticides, glycerin, and pharmaceuticals. ECH is a bifunctional alkylating agent with the ability to form monoadducts with DNA as well as to cross-link DNA covalently and has been linked to increased risks of cancer due to occupational exposure. In an in vitro study to characterize the mechanism of cross-linking, ECH was reacted with guanosine and liquid chromatography mass spectrometry was used to determine the intermediates and products of the reaction. It was found that the major product formed was a monoadduct with a chlorine atom, suggesting that the epoxide of ECH is the first electrophilic group to react. These data support a previous study that showed that the reaction is more efficient under acidic conditions. The final product with two guanosines cross-linked by ECH was also identified; however, the monoadduct with an epoxide was not found. Therefore, further data collection is required to fully characterize the mechanism of cross-linking by epichlorohydrin. These preliminary results have helped to understand how epichlorohydrin reacts with DNA.


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guanosine, epichlorohydrin, bifunctional alkylating agent, nucleic acid, cross-link, liquid chromatography mass spectrometry

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