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.
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.
https://cornerstone.lib.mnsu.edu/urs/2012/poster-session-A/32
