Event Title

Further Examination of Formed Adducts from the Reactions of Decanal and Trans-2-Decenal with Each Nucleoside of DNA

Presenter Information

Neil Ranals, Minnesota State University - MankatoFollow

Location

CSU Ballroom

Start Date

21-4-2014 10:00 AM

End Date

21-4-2014 11:30 AM

Student's Major

Chemistry and Geology

Student's College

Science, Engineering and Technology

Mentor's Name

Danae Quirk-Dorr

Mentor's Email Address

danae.quirk-dorr@mnsu.edu

Mentor's Department

Chemistry and Geology

Mentor's College

Science, Engineering and Technology

Second Mentor's Name

Mary Hadley

Second Mentor's Email Address

mary.hadley@mnsu.edu

Second Mentor's Department

Chemistry and Geology

Second Mentor's College

Science, Engineering and Technology

Description

Organic substances containing decanal and trans-2-decenal have been touted to potentially possess anti-cancer properties. Since it has also been reported that chemical reactions involving biological and synthetic factors often form adducts with DNA, the anti-cancer properties of decanal and trans-2-decenal may be due to formed adducts with DNA. These formed adducts could terminate cancer-causing replication in cells. The purpose of this research was to further examine the adducts that formed from the interactions of two aldehydes, decanal and trans¬2-decenal, with guanosine and explore potential reactions between these aldehydes and the nucleosides 2’-deoxyadenosine, 2’-deoxycytidine, and thymidine. Past research showed that L-arginine promotes the reactivity of aldehydes toward DNA, so it was utilized in these reactions. These reactions of the aldehydes with the each nucleoside, at 70˚C for 48 hours, were analyzed via 1H NMR and HPLC. In addition to the reactions described above, Macro-scale reactions of each aldehyde with guanosine were conducted to obtain a greater quantity of adduct for purification and structural determination. The reactions were monitored by TLC and silica gel column chromatography was used in the purification of the formed adducts. 1H NMR, HPLC, and UV spectroscopy were utilized in the partial characterization of the formed adducts. Determining the structure of the adducts formed in these reactions may give insight into the reported anti-cancer properties of these compounds.