Presentation Title

Cyclic Voltammograms of Estrogen Quinones

Advisor Information

Douglas Stack

Location

Milo Bail Student Center Ballroom

Presentation Type

Poster

Start Date

8-3-2013 9:00 AM

End Date

8-3-2013 12:00 PM

Abstract

Estrogen is considered the strongest risk factor for breast and other human cancers. Oxidative metabolism of estrogen (Figure 1) generates o-quinones (Qs) that can damage DNA. The most genotoxic oquinone is E2-3,4-Q. Cyclic voltammetry (CV) was done on E2-2,3-Q, E2-3,4-Q, and 1-n-butyl- E2-3,4,Q in order to gain insight into their possible role as redox cycling metabolites. The first reduction potential of E2-2,3-Q, E2-3,4-Q, and 1-n-butyl- E2-3,4,Q was measured at -0.275, -0.495, and -0.965 V, respectively versus a silver/silver chloride reference electrode. The second reduction potential of E2-2,3-Q, E2- 3,4-Q, and 1-n-butyl-E2-3,4,Q was measured at -0.930, -0.935, and -1.440 V, respectively. All reduction potentials became more positive (more easily reduced) at lower pH. 1-n-butyl- E2-3,4,Q reduction potential was significantly made more positive when converted to its conjugate acid (-0.965V vs. +0.275 V). These results indicate that E2-2,3-Q is more easily reduced than E2-3,4-Q. While E2-3,4-Q has more a reversible CV profile indicating it a more likely candidate for redox cycling.

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Mar 8th, 9:00 AM Mar 8th, 12:00 PM

Cyclic Voltammograms of Estrogen Quinones

Milo Bail Student Center Ballroom

Estrogen is considered the strongest risk factor for breast and other human cancers. Oxidative metabolism of estrogen (Figure 1) generates o-quinones (Qs) that can damage DNA. The most genotoxic oquinone is E2-3,4-Q. Cyclic voltammetry (CV) was done on E2-2,3-Q, E2-3,4-Q, and 1-n-butyl- E2-3,4,Q in order to gain insight into their possible role as redox cycling metabolites. The first reduction potential of E2-2,3-Q, E2-3,4-Q, and 1-n-butyl- E2-3,4,Q was measured at -0.275, -0.495, and -0.965 V, respectively versus a silver/silver chloride reference electrode. The second reduction potential of E2-2,3-Q, E2- 3,4-Q, and 1-n-butyl-E2-3,4,Q was measured at -0.930, -0.935, and -1.440 V, respectively. All reduction potentials became more positive (more easily reduced) at lower pH. 1-n-butyl- E2-3,4,Q reduction potential was significantly made more positive when converted to its conjugate acid (-0.965V vs. +0.275 V). These results indicate that E2-2,3-Q is more easily reduced than E2-3,4-Q. While E2-3,4-Q has more a reversible CV profile indicating it a more likely candidate for redox cycling.