Oxidative stress is defined as a disturbance in the balance between the production of reactive oxygen species (free radicals) and antioxidant defenses. Reactive oxygen species are harmful to the body because they have the potential to cause damage lipids, proteins, RNA, and DNA. Thus, the inability of the body to metabolize these species could be the cause of numerous diseases such as, atherosclerosis, diabetic, cancer, rheumatoid arthritis, cardio vascular diseases, and chronic inflammation. In the study of the C3'-thymidinyl radical, several damage lesions have been identified. Among these are 3'-oxothymidine and its associated elimination products. 3'-oxothymidine was postulated to form as a result of the generation of the C3'-radical under anaerobic conditions; however, we have also observed its formation in the presence of oxygen as well. One of the resulting elimination product is 2-Methylene-3(2H) furanone, a characteristic biomarker of oxidative DNA damage occurring at the C-3' and C-2' of DNA. The high reactivity of the lesion has made its isolation, identification and quantification difficult. Taking advantage of known synthetic routes we report the synthesis and quantification of thiol analogs of 2-methylene 3(2H) furanone to facilitate its isolation. LC-MS analysis was then conducted to establish a standard concentration curve that will enable us to routinely quantify 2-methylene-3 (2H) furanone release from DNA damage.

Method for the analysis and quantification of 3-methylene furanone: A biomarker of oxidative damage to DNA

254th National Meeting (2017)

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