Research Information System
Russian Journal of Physical Chemistry B, vol.13, no.1, pp.49-61, 2019 (SCI-Expanded)
In this article N-(4-nitrophenyl)acrylamide has been synthesized and characterized both experimentally and theoretically. The synthesized monomer was characterized experimentally by Fourier Transform Infrared, Nuclear Magnetic Resonance spectroscopic techniques and theoretically by Density Functional Theory and Time-Dependent Density Functional Theory methods at Coulomb Attenuated Method level. To investigate the natural toxicity and reactivity of the title molecule optimized at the Density Functional Theory/Coulomb Attenuated Method- Becke three-parameter Lee-Yang-Parr level, the chemical reactivity descriptors were calculated based on the rotational barriers. Using the Parr formula, the interaction between N-(4-nitrophenyl)acrylamide molecule and nucleic acid bases (adenine, thymine, cytosine, uracil and guanine) phenylalanine and histidine an Aryl Hydrocarbon hydroxylase receptors were investigated. Charge transfer that is important in the formation of chemically bonded adducts causing cancer has been calculated quantitatively. In addition, in vitro cytotoxicity of N-(4-nitrophenyl)acrylamide on HeLa cell lines has been studied. It has been found that the half maximal inhibitory concentration value of N-(4-nitrophenyl)acrylamide is 1 mM in HeLa cells. Our results show that N-(4-nitrophenyl)acrylamide, an acrylamide-based molecule that is accepted as toxic by the World Health Organization, has low toxicity on cancer cells by experimental study and, in theory, it has low toxicity according to calculations of reactivity descriptors, therefore can be used for biomedical research.