Amphiphilic kanamycin, synthesized by the introduction of hydrophobic group in kanamycin, is in great interest to the researcher due to their novel antifungal activity. The compounds synthesized by the modification of 4” or/and 6” hydroxyl group of kanamycin have wide spectrum antifungal activity against both plant pathogens and human pathogens. Despite excellent antifungal activity of these membrane-permeabilizing compounds, the requirement of multiple synthetic steps causes the cost of the compounds much higher than the commercial antifungal compounds in the market. To overcome this issue, we have newly synthesized amphiphilic compounds by the one-step modification 6’ amine group of the kanamycin. The new lead compounds have prominent antifungal activity as previously reported amphiphilic kanamycin with mild antibacterial activity. The cost of production of these new compounds are comparable to the marketed antifungal compounds and only consist of natural moieties; kanamycin and fatty acid. The fluorescent analogs synthesized using a similar synthetic procedure was used to study the fungal selective activity of amphiphilic kanamycin. The fluorescent imaging of the fungal, bacterial and human cells treated with the fluorescent analogs showed that the compounds can permeabilize the fungal cells at a faster rate and lower concentration relative to bacterial and human cells. The newly reported synthetic strategy opens the door for possible use of the amphiphilic kanamycin in the treatment of the fungal infection and the fungal selective properties of the fluorogenic amphiphilic kanamycin have potential to be used in the diagnosis of the fungal infections.

Amphiphilic kanamycin for treatment and diagnosis of the fungal infection

2019 Fall National Meeting

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