Chemical and photolytical transformation of biomedically significant compounds in the presence of deuterated solvents

Abstract The effect of the nature of solvent on the properties of biomedically important compounds is of particular importance. The conversion of certain biomedical compounds with deuterated solvents is an area of research that has not been accorded adequate recognition in the literature. We explored this area in the interest of shedding some light on the possible effects of solvent on the nature of the solute. The transformation of specific medically important compounds such as bilirubin, thymine, uracil, dehydrocholesterol (7-DHC) and vitamin D 3 was observed in the presence of deuterated solvents such as heavy water and deuterated chloroform. The products of the relevant reactions were confirmed spectrophotometrically. An additional feature to our investigation involved the photolysis of the aforementioned compounds by solar irradiation. The pure samples were dissolved in solutions of the deuterated solvents, corresponding to concentrations of typically 10 −2 mM, and exposed to sunlight for about 15–30 min. The deuterated solvents caused chemical transformation in all chemical compounds tested, and produced intense characteristic absorbance maxima between 200 and 700 nm. Sunlight exposure was also effective in either augmenting the effects of deuterated solvent as in bilirubin and 7-DHC or reducing it as with thymine or having no effect as with uracil or completely changing it as in vitamin D 3 . It has been shown that the use of deuterated solvents produces unique chemical and photochemical conversions of bilirubin, 7-DHC, thymine, uracil and vitamin D 3 . This was attributed to the fact that deuterated compounds display a somewhat different chemistry to their ordinary counterparts and that possibly thermodynamic considerations could be responsible for the novel transformations.