N-ヘテロ芳香族の電子的性状(第17報) : リボフラビンとスルファニルアミド, p-アミノ安息香酸および関連化合体との電荷移動型相互作用

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Reddish coloration took place upon mixing riboflavin and sulfanilamide in high concentrations, and the nature of interactions between riboflavin and compounds related to sulfanilamide including p-aminobenzoic acid was investigated. New absorption bands were observed in the vicinity of 370 and 500mμ in the difference spectra of mixed systems of riboflavin and sulfanilamide related compounds. Analysis of the data of these two difference bands through |the Benesi-Hildebrand equiation revealed that 1 : 1 complexes were formed. Furthermore, it was also revealed from the values of K, ΔH, and ΔS, as well as solvent effects that sulfanilamide and p-aminobenzoic acid behave quite similarly in interacting with riboflavin. A reciprocally correspondent relationship was found to exist between the two difference bands ; whereas the band at about 500 mμ was more distinct in aqueous medium, the one at about 370 mμ was more distinct in non-aqueous media. It was presumed that charge-transfer interaction which is dominant in non-aqueous media (occurrence of the band around 370 mμ) proceeds to the extent of formation of riboflavin semiquinone (occurrence of the band around 500 mμ). It was found from the effects of pH on absorbances at the longer wavelength maxima that undissociated species of both riboflavin and sulfanilamide compounds are more favorable for the complex formation reactions. These results for complex formation in aqueous medium has been confirmed also through the examination of changes in solubility of riboflavin which took place in the presence of sulfanilamides compunds. Possible correlations of sulfanilamides-riboflavin complexing to the metabolic disturbance of vitamin B_2 which is incidental to administration of sulfonamide drugs have also been referred to.
社団法人日本薬学会の論文
1968-01-25

N-ヘテロ芳香族の電子的性状(第17報) : リボフラビンとスルファニルアミド, p-アミノ安息香酸および関連化合体との電荷移動型相互作用

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