Biomarkers of cigarette smoking and DNA methylating agents: Raman, SERS and DFT study of 3-methyladenine and 7-methyladenine
Journal
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Journal Volume
176
Pages
1-7
Date Issued
Apr-17
Author(s)
Abstract
3-Methyladenine and 7-methyladenine are biomarkers of DNA damage from exposure to methylating agents. For example, the concentration of 3-methyladenine increases significantly in the urine of cigarette smokers. Surface-enhanced Raman spectroscopy (SERS) has shown much potential for detection of biomolecules, including DNA. Much work has been dedicated to the canonical nucleobases, with comparatively fewer investigations of modified DNA and modified DNA nucleobases. Herein, Raman spectroscopy and SERS are used to examine the adsorption orientations of 3-methyladenine and 7-methyladenine on Ag nanoparticles. Density functional theory (DFT) calculations at the B3LYP level are used to support the conclusions via simulated spectra of the nucleobases and of Ag+/nucleobase complexes. The results herein show that 7-methyladenine adsorbs upright via its N3 and N9 atoms side, similarly to adenine. 3-Methyladenine adsorbs in a very tilted or flat orientation on the Ag nanoparticles. These findings will be useful for future SERS or other nanoparticle-based bioanalytical assays for detection of these methyladenines or other modified nucleobases. ? 2016
Subjects
3-Methyladenine; 7-Methyladenine; Adenine analog; Cancer biomarker; DNA methylation; SERS
SDGs
Other Subjects
Alkylation; Biomarkers; Biomolecules; Density functional theory; DNA; Metal nanoparticles; Nanoparticles; Raman spectroscopy; Tobacco; 3-Methyladenine; 7-Methyladenine; Adenine analog; Cancer biomarkers; DNA Methylation; SERS; Silver; 3-methyladenine; 7-methyladenine; adenine; biological marker; gold; metal nanoparticle; adsorption; analogs and derivatives; chemistry; cigarette smoking; DNA methylation; genetics; metabolism; molecular model; quantum theory; Raman spectrometry; static electricity; thermodynamics; ultraviolet spectrophotometry; Adenine; Adsorption; Biomarkers; Cigarette Smoking; DNA Methylation; Gold; Metal Nanoparticles; Models, Molecular; Quantum Theory; Spectrophotometry, Ultraviolet; Spectrum Analysis, Raman; Static Electricity; Thermodynamics
Type
journal article