3,6-Diamino-10-methylacridan:  Uncharged Precursor of Acriflavine and Its Unique Antimicrobial Activity

Topical application of NADH for the treatment of rosacea and contact dermatitis

“…For many years NADH has not been considered for therapeutic use because this compound is rather unstable, especially in acid solutions 5–7 and undergoes general acid catalysed hydration reactions. Mechanistic aspects concerning the oxidation of NADH to NAD + (the oxidized form of the coenzyme) have been studied in our laboratories 8–12 . It has been found that in one‐electron oxidation conditions (oxidation with molecular oxygen) primarily generated NADH radical cations can undergo further oxidation to finally form NAD + .…”

Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors

“…À and H 2 O 2 (Scheme S1, ESIw). 13,14 The presence of a proximal hydroxyl group appeared to diminish carbonyl p-character (IR spectroscopy, Fig. S6, ESIw); and enhanced electronegativity on the carbonyl oxygen (computational analysis, Fig.…”

Direct Characterization of Radical Species Generated on One-Electron Oxidation of 3,6-Diamino-10-methylacridan

“…A recent report from our laboratory has revealed that 3,6-diamino-10-methylacridan ( 1H ) can be prepared in chemically pure form and oxidized spontaneously by molecular oxygen in water to acriflavine ( 1 + ) . As the oxidation of 1H to 1 + was found to be quantitative, therefore 1H can be regarded as an uncharged precursor of 1 + .…”

“…The above requirement for precursor 1 + seems to be fulfilled by 1H . Indeed, the antimicrobial properties of 1H were found to be superior to those of 1 + , which seems to be associated with preferential diffusion of 1H through the plasma membranes as well as with synergic antimicrobial effects of 1 + and reactive forms of oxygen …”

“…Indeed, the antimicrobial properties of 1H were found to be superior to those of 1 + , which seems to be associated with preferential diffusion of 1H through the plasma membranes as well as with synergic antimicrobial effects of 1 + and reactive forms of oxygen. 4 In view of the above discussion it seems important to establish the mechanism of 1H oxidation and to characterize any reactive intermediates involved in this process. This paper describes our efforts aimed at direct characterization of the radical cation (1H •+ ) and the radical (1 • ).…”