Bactericidal Effect of Fluorine-Containing Derivatives of Ascorbic Acid

Abstract

The in vitro bactericidal effect of eight fluorine-containing derivatives of ascorbic acid (AsA) was investigated. 2,6-Bis-O-perfluorooctanoyl-AsA (No.8), 2,3-bis-O-(1,1,2,3,3,3-hexafluoropropyl)-AsA (No.10) and 2,6-bis-O-(7,H-dodecafluoroheptanoyl)-AsA (No.12) exhibited 10〜50 times greater bactericidal effect than AsA. In addition. Nos. 8, 10 and 12 exhibited bactericidal effect against AsA-insensitive bacteria. The reaction mechanism of bactericidal effects of Nos. 8, 10 and 12 was investigated. Bubbling oxygen through the reaction mixture enhanced the effect, while bubbling nitrogen inhibited it. Addition of H_2O_2 and transition metals to the reaction mixture enhanced the effect, while addition of reducing agents, chelating agents and radical scavengers inhibited it. The findings indicate that reactive oxygen species are responsible for the reaction mechanism. The increase in the bactericidal effect is attributed to the introduction at C(2) and C(3) or C(2) and C(6) of substituents containing highly electronegative fluorine.