Date of Award


Document Type

Honors Thesis (Open Access)


Colby College. Chemistry Dept.


Julie T. Millard

Second Advisor

James K. Zimmerman


Diepoxybutane (DEB), epichlorohydrin (ECH), and 1-(chloroethenyl)oxirane (COX) are small molecules that can form DNA interstrand cross-links. All three of these compounds are, or are metabolites of, industrial chemicals linked to cancer. Additionally, DEB is a metabolite of treosulfan, an anti-cancer drug. We are trying to determine why some of these compounds cause cancer and some can also cure cancer. To do so, we are attempting to link cytotoxicity, cross-linking efficiency, and apoptotic potential of the three compounds to see if any correlations exist. The purpose of this project was to quantify apoptotic potential of DEB, ECH and COX. This was done first by determining caspase activity. These studies showed that in terms of apoptotic potential, DEB>ECH>COX. Later studies quantified apoptosis using flow cytometry with Annexin V/propidium iodide staining. It was determined from these studies that DEB has the strongest apoptotic potential, and while it seems COX>ECH, more work must be done to be sure. If it is determined that DEB>COX>ECH, this would correlate directly to crosslinking efficiency as determined in other studies. Future work may use this correlation to mechanistically explain how some compounds cure cancer while others cause cancer.


Diepoxybutane (DEB), epichlorohydrin (ECH), 1-(chloroethenyl)oxirane (COX), DNA, cancer

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Chemistry Commons