Presenter Information

Edward Chuang, Colby CollegeFollow

Location

Diamond 145

Start Date

1-5-2014 1:00 PM

End Date

1-5-2014 2:30 PM

Project Type

Presentation

Description

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. An in vitro study was done to react ECH with guanosine to help characterize the mechanism of the cross-linking reaction. Liquid chromatography mass spectrometry was used to determine the intermediates and products of the reaction. It was found that the major monoadduct intermediate formed had a chlorine atom, suggesting that the epoxide of ECH is the first to react. These data support a previous study that showed that the reaction is more efficient in acidic conditions. Further data collection is required to fully characterize the mechanism of cross-linking by epichlorohydrin. However, these preliminary results have helped to understand how epichlorohydrin reacts with DNA.

Faculty Sponsor

Julie Millard

Sponsoring Department

Colby College. Chemistry Dept.

CLAS Field of Study

Natural Sciences

Event Website

http://www.colby.edu/clas

ID

469

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May 1st, 1:00 PM May 1st, 2:30 PM

Structural Characterization of the Major DNA-DNA Cross-Link Formed by Epichlorohydrin

Diamond 145

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. An in vitro study was done to react ECH with guanosine to help characterize the mechanism of the cross-linking reaction. Liquid chromatography mass spectrometry was used to determine the intermediates and products of the reaction. It was found that the major monoadduct intermediate formed had a chlorine atom, suggesting that the epoxide of ECH is the first to react. These data support a previous study that showed that the reaction is more efficient in acidic conditions. Further data collection is required to fully characterize the mechanism of cross-linking by epichlorohydrin. However, these preliminary results have helped to understand how epichlorohydrin reacts with DNA.

http://digitalcommons.colby.edu/clas/2014/program/139