Rhamnolipids functionalized with basic amino acids: Synthesis, aggregation behavior, antibacterial activity and biodegradation studies

Silva, Anderson Ramos da; Manresa, Ángeles; Pinazo, Aurora; Garcı́a, M. Teresa; Pérez, Lourdes

doi:10.1016/j.colsurfb.2019.05.037

Cited by 27 publications

(17 citation statements)

References 54 publications

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“…These values indicate that these amino acid conjugates have more powerful surface activities than SL-COOH, which reduce the ST to 47.3 mN/m, while the CMC is 120 mg/L . Although arginine is a hydrophilic amino acid, protection of the carboxy terminus with a methyl group and the protonated guanido moiety at pH 7.4 enhanced the surface activities of the arginine conjugates. The arginine derivatives at a pH value of 7.4 leaded to a higher surface activity than the anionic SL-COOH at a pH value of 7.4 but lower than that of protonated SL-COOH at a pH value of 3.5 .…”

Section: Resultsmentioning

confidence: 92%

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Efficient Preparation of Sophorolipids and Functionalization with Amino Acids to Furnish Potent Preservatives

Tang

Jin

Cui

et al. 2021

J. Agric. Food Chem.

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The development of new preservatives is an ongoing investigation in the food industry, especially those which are safe and environmentally friendly. In this study, biosurfactant sophorolipids (SLs) functionalized with amino acids were developed as efficient preservative agents. SLs were first isolated from fermentation broth by Candida bombicola ATCC 22214, hydrolyzed, and purified by extraction. The typical recovery is around 70%, while the extracted material consists of over 90% deacetylated acidic SLs (SL-COOH). Four types of SL derivatives were then synthesized via dicyclohexylcarbodiimide amidation reactions from prepared SL-COOH. Among the derivatives produced, the arginine SL conjugates (SL-D-Arg) displayed the highest activity against Grampositive bacteria and fungi and even inhibited the cell growth of Gram-negative bacteria and mildew. Furthermore, the arginine conjugates performed the broadest antimicrobial activity among the derivatives evaluated. The sterilization dosage of the arginine conjugates against the food-spoilage pathogen Bacillus spp. was 63−125 mg/L, in contrast to 250 mg/L for the enterotoxin producer Staphylococcus aureus and 500 mg/L for fungi. More importantly, SL-D-Arg displayed excellent biocompatibility, with a therapeutic index of over 7.94. SL-D-Arg has excellent potential as an alternative to traditional chemical preservatives.

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Section: Resultsmentioning

confidence: 92%

“…Functionalization with arginine significantly improved the adhesion of the SLs to the negatively charged bacterial cell surface. , The arginine SL conjugates were extremely effective against both B. subtilis and B.…”

Section: Resultsmentioning

confidence: 92%

Efficient Preparation of Sophorolipids and Functionalization with Amino Acids to Furnish Potent Preservatives

Tang

Jin

Cui

et al. 2021

J. Agric. Food Chem.

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“…[ 62 , 63 ]. The DNA affinity of LAM and the 8.2LM formulation was similar to that of monocatenary surfactants with long alkyl chains [ 64 , 65 ]. In this context, it has been reported that arginine-based lipids also exhibit DNA-binding properties through the hydrogen bonds of the guanidinium group [ 66 ].…”

Section: Resultsmentioning

confidence: 99%

Biocompatible Catanionic Vesicles from Arginine-Based Surfactants: A New Strategy to Tune the Antimicrobial Activity and Cytotoxicity of Vesicular Systems

et al. 2020

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Their stability and low cost make catanionic vesicles suitable for application as drug delivery systems. In this work we prepared catanionic vesicles using biocompatible surfactants: two cationic arginine-based surfactants (the monocatenary Nα-lauroyl-arginine methyl ester—LAM and the gemini Nα,Nϖ-bis(Nα-lauroylarginine) α, ϖ-propylendiamide—C3(CA)2) and three anionic amphiphiles (the single chain sodium dodecanoate, sodium myristate, and the double chain 8-SH). The critical aggregation concentration, colloidal stability, size, and charge density of these systems were comprehensively studied for the first time. These catanionic vesicles, which form spontaneously after mixing two aqueous solutions of oppositely charged surfactants, exhibited a monodisperse population of medium-size aggregates and good stability. The antimicrobial and hemolytic activity of the vesicles can be modulated by changing the cationic/anionic surfactant ratio. Vesicles with a positive charge efficiently killed Gram-negative and Gram-positive bacteria as well as yeasts; the antibacterial activity declined with the decrease of the cationic charge density. The catanionic systems also effectively eradicated MRSA (Methicillin-resistant Staphylococcus Aureus) and Pseudomonas aeruginosa biofilms. Interestingly, the incorporation of cholesterol in the catanionic mixtures improved the stability of these colloidal systems and considerably reduced their cytotoxicity without affecting their antimicrobial activity. Additionally, these catanionic vesicles showed good DNA affinity. Their antimicrobial efficiency and low hemolytic activity render these catanionic vesicles very promising candidates for biomedical applications.

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“…This affects cell surface charge and alters hydrophobicity in a manner similar to the action of synthetic cationic surfactants. They can also make bacteria more susceptible to antimicrobial agents, as they can prevent the formation of biofilms [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Biosurfactants: Properties and Applications in Drug Delivery, Biotechnology and Ecotoxicology

et al. 2021

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Surfactants are amphiphilic compounds having hydrophilic and hydrophobic moieties in their structure. They can be of synthetic or of microbial origin, obtained respectively from chemical synthesis or from microorganisms’ activity. A new generation of ecofriendly surfactant molecules or biobased surfactants is increasingly growing, attributed to their versatility of applications. Surfactants can be used as drug delivery systems for a range of molecules given their capacity to create micelles which can promote the encapsulation of bioactives of pharmaceutical interest; besides, these assemblies can also show antimicrobial properties. The advantages of biosurfactants include their high biodegradability profile, low risk of toxicity, production from renewable sources, functionality under extreme pH and temperature conditions, and long-term physicochemical stability. The application potential of these types of polymers is related to their properties enabling them to be processed by emulsification, separation, solubilization, surface (interfacial) tension, and adsorption for the production of a range of drug delivery systems. Biosurfactants have been employed as a drug delivery system to improve the bioavailability of a good number of drugs that exhibit low aqueous solubility. The great potential of these molecules is related to their auto assembly and emulsification capacity. Biosurfactants produced from bacteria are of particular interest due to their antibacterial, antifungal, and antiviral properties with therapeutic and biomedical potential. In this review, we discuss recent advances and perspectives of biosurfactants with antimicrobial properties and how they can be used as structures to develop semisolid hydrogels for drug delivery, in environmental bioremediation, in biotechnology for the reduction of production costs and also their ecotoxicological impact as pesticide alternative.

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Rhamnolipids functionalized with basic amino acids: Synthesis, aggregation behavior, antibacterial activity and biodegradation studies

Cited by 27 publications

References 54 publications

Efficient Preparation of Sophorolipids and Functionalization with Amino Acids to Furnish Potent Preservatives

Efficient Preparation of Sophorolipids and Functionalization with Amino Acids to Furnish Potent Preservatives

Biocompatible Catanionic Vesicles from Arginine-Based Surfactants: A New Strategy to Tune the Antimicrobial Activity and Cytotoxicity of Vesicular Systems

Biosurfactants: Properties and Applications in Drug Delivery, Biotechnology and Ecotoxicology

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