Lipid‐Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities

Abstract

Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and petroselinic acid‐based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram‐negative and Gram‐positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self‐assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long‐chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long‐chained quaternary ammonium sophorolipids.

Rare fatty acids and lipids in plant oilseeds: occurrence and bioactivity

“…Being a structural isomer of oleic acid, petroselinic acid has been effectively employed in the synthesis of innovative sophorolipids, biosurfactant glycolipid compounds which are produced by fermentation of renewable resources with a number of different nonpathogenic yeasts strains, and have been shown to possess several biological activities such as anticancer, antimicrobial, immunoregulatory and antiviral (de Oliveira et al 2015;Delbeke et al 2016Delbeke et al , 2019.…”

“…Thus fermentation of petroselinic acid with Starmerella bombicola allowed the synthesis of a new petroselinic acid based diacetylated sophorolipid lactone with high potential for self-assembly applications (Delbeke et al 2016). Moreover, from microbiologically produced sophorolipids based on petroselinic acid, a series of new quaternary ammonium sophorolipids with antimicrobial and transfection activities have been also synthesized (Delbeke et al 2019).…”

Biosurfactants and anti-inflammatory activity: A potential new approach towards COVID-19

“… Biosurfactant Structure Microorganism Potential Medical Applications Reference Group Class Glycolipids Rhamnolipids Pseudomonas aeruginosa, Pseudomonas chlororaphis, Pseudomonas fluorescens, Pseudomonas luteola, Pseudomonas putida, Pseudomonas stutzeri, Burkholderia glumae, Burkholderia plantarii, Burkholderia kururiensis, Burkholderia pseudomallei Streptococcus mutans, Streptococcus oralis, Streptococcus sanguinis, Neisseria mucosa, Actinomyces naeslundii. Anti-microbial activity, cytotoxic activity [ 54 ], [ 13 ], [ [55] , [56] , [57] , [58] , [59] ] Sophorolipids Torulopsisbombicola , Candida bombicola, Rhodotorulabogoriensis, Candida albicans, Candida glabrata,Rhodotorulababjevae,Wickerhamielladomercqiae antiviral, antimicrobial and anti-inflammatory, antifungal activity [ 27 ], [ 56 ], [ 12 ], [ [60] , [61] , [62] , [63] , [64] , [65] , [66] , [67] ] Mannosylerythriol lipids Pseudozymaantarctica, Ustilagomaydis antimicrobial activity, antioxidant activity, immunological and neurological property [ 68 ], [ 69 ], [ 70 ], [ 36 ] Trehalolipids Rhodococcuserythropolis, Nocardiaerythropolis, Mycobacterium sp., Arthobacter sp.,Corynebacterium sp. antiviral activity against herpes simplex virus and influenza virus [ 70 ] Lipoprotein Surfactins/Viscosin …”

“… Anti-microbial activity, cytotoxic activity [ 54 ], [ 13 ], [ [55] , [56] , [57] , [58] , [59] ] Sophorolipids Torulopsisbombicola , Candida bombicola, Rhodotorulabogoriensis, Candida albicans, Candida glabrata,Rhodotorulababjevae,Wickerhamielladomercqiae antiviral, antimicrobial and anti-inflammatory, antifungal activity [ 27 ], [ 56 ], [ 12 ], [ [60] , [61] , [62] , [63] , [64] , [65] , [66] , [67] ] Mannosylerythriol lipids Pseudozymaantarctica, Ustilagomaydis antimicrobial activity, antioxidant activity, immunological and neurological property [ 68 ], [ 69 ], [ 70 ], [ 36 ] Trehalolipids Rhodococcuserythropolis, Nocardiaerythropolis, Mycobacterium sp., Arthobacter sp.,Corynebacterium sp. antiviral activity against herpes simplex virus and influenza virus [ 70 ] Lipoprotein Surfactins/Viscosin Bacillus subtilis, Bacillus licheniformis, Pseudomonas libanensis, Pseudomonas fluorescens anticoagulant, antimycoplasma, antiviral, antibacterial, anti-inflammatory [ 57 ], [ 59 ] …”

Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids

“…Nonetheless, genetic engineering takes long time and efforts to develop and yields may be small, while chemical derivatization can virtually provide an infinite variety of molecules. 37 In this regard, sophorolipid esters were synthesized in view of improving the emulsifying properties of acidic sophorolipids, 39,49,50 quaternary ammonium sophorolipid derivatives were developed as transfection carriers 21,51 or to improve the antimicrobial effects of sophorolipids. 51 Finally, the combination of the genetic engineering and chemical derivatization is also interesting, as shown by the development of saturated compounds.…”