10-Undecanhydroxamic acid, a hydroxamate derivative of the undecanoic acid, has strong antimicrobial activity through a mechanism that limits iron availability

Abstract

Undecanoic acid (UDA) is a fatty acid with significant antimycotic activity. In this work we have synthesized 10-undecanhydroxamic acid, a hydroxamate derivative of the UDA, and tested its antimicrobial activity on different microorganisms. Our results demonstrate that this compound has higher efficacy than UDA against a variety of fungi and bacteria. Analysis of the intracellular concentration of protein involved in iron transport in Salmonella enterica serovar Typhimurium suggests that its antimicrobial effect actually relies on the ability to chelate iron ions, providing an efficient mechanism to interfere with microbial growth.

In vitro susceptibility to antimycotic drug undecanoic acid, a medium-chain fatty acid, is nutrient-dependent in the dermatophyte Trichophyton rubrum

“…Undecanoic acid (UDA), a medium-chain fatty acid, is the most fungitoxic in the C 7:0 -C 18:0 series, which has been used in the treatment of dermatophytoses in humans (Ammendola et al 2009;Garg and Muller 1993). Trichophyton rubrum is a cosmopolitan and anthropophilic fungus able to invade keratinized tissue, causing infection in human skin and nails.…”

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

“…The presence of two singlet peaks for NH and NH 2 at δ 3.88 ppm and δ 7.49 ppm, respectively, revealed the formation of undec-10-ene hydrazide 3. The appearance of singlet signal ranging from δ 7.49 to 10.72 ppm in the synthesized compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) confirmed the presence of NH of hydrazide derivatives. The appearance of singlet signal of CH proton in compounds 5 at δ 7.92 ppm revealed the formation of N=CH bond in the synthesized derivative.…”

“…The synthesis of the intermediate (2,3) and target compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) was performed according to reactions outlined in Schemes 1 and 2. A methanolic solution of undecylenic acid 1 was refluxed in the presence of sulfuric acid to yield the methyl ester undecylenic acid (2).…”

“…Undecylenic acid also has antiviral properties effective in skin infections caused by herpes simplex [4]. Reported data suggested that undec-10-enoic acid and their derivatives can make a complex with iron ions, which afford an effective mechanism to stop the bacterial growth [5]. Further, the previous studies performed by us revealed the significance of different acid derivatives, including undec-10-enoic hydrazide-hydrazone derivatives as antibacterial and antifungal agents [6][7][8][9][10][11].…”

Feasibility of unsaturated fatty acid feedstocks as green alternatives in bio‐oil refinery

“…Undecylenic monoethanolamide, which is used in the treatment of fungal infections such as dermatophytosis and scalp disease caused by athlete's foot and has antifungal, antibacterial and antiviral properties, is used in antifungal cream. 10‐Undecahydroxamic acid is more effective than undecylenic acid against various fungi and bacteria . In a study on Salmonella enterica servar typhimurium , a mechanism was reported to be effective because it interferes with the growth of salmonella by forming iron and coordination compounds .…”