The dipole moment is a of these three molecules is an interesting study because in each case, the dipole moment is primarily influenced by the presence of electronegative atoms. Our experiment helps us understand the effects of substituents at C5 dipole moment of uracil.
#CHEMISTRY GAUSSIAN SOFTWARE DIPOLE MOMENT SERIES#
The numerical values of the dipole moments also help us in evaluating the quantum mechanical calculations of electronic charge distribution, particularly in a series of homologous compounds, as in our experiment. Interpretation of dipole moments by electronic charge distribution contributes to the understanding the molecular electronic structure and helps us gain deeper insight. The dipole moment is considered to be an elementary physiochemical property of a molecule.
Unlike Fluorouracil, these bases are regularly used by a healthy cell to construct new nucleotides (for multiplication, repair, etc.) Thymine is one of the four nucleobases of DNA. As can be seen from the figure below, the molecules only differ in what substituent each has on C-5.įig 2: Molecular structures of Uracil, 5-Fluorouracil, and Thymine.
Another structural analog of Uracil is Thymine. 10ĥ-Fluorouracil is a derivative of Uracil. However, it should be used in moderate/regulated amounts since the side effects of unregulated exposure can be severe.
#CHEMISTRY GAUSSIAN SOFTWARE DIPOLE MOMENT SKIN#
Both of these factors cause DNA damage, therefore ultimately inhibiting cell replication.ĥ FU is also seldom found in skin creams used for other conditions.
With inhibition of Thymidylate synthase, an imbalance of nucleotides results and increased levels of dUTP arise. dTMP is one of the three nucleotides (dTMP, dTTP, and dTDP) that eventually produce a thymine molecule. 9 “The mechanism of cytotoxicity of 5-FU has been ascribed to the misincorporation of fluoronucleotides into RNA and DNA and to the inhibition of the nucleotide synthetic enzyme thymidylate synthase.” 9 Thymidylate synthase is an enzyme that catalyzes the conversion of deoxyuridine monophosphate (dUMP) to deoxythymidine monophosphate (dTMP). 9Cancer cells often use more uracil than normal cells, which indicates that uracil metabolism is a potential target for antimetabolite chemotherapy. The fluoro pyrimidine drug, 5-fluorouracil (5-FU) does both. Antimetabolite drugs function by impeding vital biosynthetic processes or by being assimilated into macromolecules, and inhibiting their normal functioning. 10 5- Fluorouracil belongs to the family of drugs called theantimetabolites. The purpose of this experiment is to calculate the dipole moment of the anticancer drug, 5- Fluorouracil, and compare the numerical value with that of two other pyrimidines, Thymine and Uracil.įig 1: Molecular structure of 5- Fluoro uracil (drawn by ChemBioDraw).ĥ- Fluorouracil is apyrimidine analog (nucleoside analogs that mimic the molecular structure of pyrimidines) of uracil molecule that functions as an anti-cancer drug it is used in the treatment of several types of cancer, including that of rectum, colon, head and neck cancer.
The experiment gave insight to typical dipole moment values of uracil derivatives, and how the dipole moment of aromatic molecules can be influenced in the presence of –F, or -CH 3 substituent. The dipole moments of other pyrimidine analogs, namely Thymine and Uracil, were also calculated and compared with literature values. In this experiment, the dipole moment of 5- Fluorouracil molecule was determined using the Gaussian software, and compared with literature values. Theoretical studies on 5- fluorouracil to calculate its dipole moment, and how the values compare with other pyrimidine analog (namely uracil and thymine) and that of literature.
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