Event Title

Identification of Metabolic Adducts Formed Between the Common Food Contaminant, HMF, and DNA

Location

CSU Ballroom

Start Date

9-4-2012 10:00 AM

End Date

9-4-2012 11:30 AM

Student's Major

Chemistry and Geology

Student's College

Science, Engineering and Technology

Mentor's Name

Danae Quirk Dorr

Mentor's Department

Chemistry and Geology

Mentor's College

Science, Engineering and Technology

Description

5-Sulfoxymethylfurfural (SMF) is a metabolite of the common heat-related food contaminant, 5-hydroxymethylfurfural (HMF). Investigations of HMF in vitro showed no mutagenic activity, but HMF was found to be mildly carcinogenic in female mice. HMF is thought to be converted in vivo by sulfotransferase enzymes into SMF, which is a stronger carcinogen. Until recently, SMF had not been detected as a metabolite of HMF in humans or rodents, but the conversion of HMF to SMF in mice following administration of HMF has now been confirmed and quantified. No literature yet exists that investigates the structure or prevalence of SMF adducts with DNA. In this study, we examined SMF and its reactions with DNA in order to elucidate the structure of any such adducts. After synthesizing SMF, reaction standards were made by allowing SMF to react with nucleosides of DNA under physiological conditions (pH 7.2, 37º C). SMF was then combined with Calf Thymus DNA (CT DNA) under the same conditions. Nuclear Magnetic Resonance (NMR) spectroscopy and High-Performance Liquid Chromatography with UV detection (HPLV-UV) were used to investigate the products of these reactions.

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Apr 9th, 10:00 AM Apr 9th, 11:30 AM

Identification of Metabolic Adducts Formed Between the Common Food Contaminant, HMF, and DNA

CSU Ballroom

5-Sulfoxymethylfurfural (SMF) is a metabolite of the common heat-related food contaminant, 5-hydroxymethylfurfural (HMF). Investigations of HMF in vitro showed no mutagenic activity, but HMF was found to be mildly carcinogenic in female mice. HMF is thought to be converted in vivo by sulfotransferase enzymes into SMF, which is a stronger carcinogen. Until recently, SMF had not been detected as a metabolite of HMF in humans or rodents, but the conversion of HMF to SMF in mice following administration of HMF has now been confirmed and quantified. No literature yet exists that investigates the structure or prevalence of SMF adducts with DNA. In this study, we examined SMF and its reactions with DNA in order to elucidate the structure of any such adducts. After synthesizing SMF, reaction standards were made by allowing SMF to react with nucleosides of DNA under physiological conditions (pH 7.2, 37º C). SMF was then combined with Calf Thymus DNA (CT DNA) under the same conditions. Nuclear Magnetic Resonance (NMR) spectroscopy and High-Performance Liquid Chromatography with UV detection (HPLV-UV) were used to investigate the products of these reactions.

Recommended Citation

Hovey, Cameron. "Identification of Metabolic Adducts Formed Between the Common Food Contaminant, HMF, and DNA." Undergraduate Research Symposium, Mankato, MN, April 9, 2012.
http://cornerstone.lib.mnsu.edu/urs/2012/poster-session-A/32