Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives

2017
Authors
Aleksić, Ivana
Petković, Miloš

Jovanović, Miloš

Milivojević, Dušan
Vasiljević, Branka

Nikodinović-Runić, Jasmina

Senerović, Lidija

Article (Published version)
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A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibi...ting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties.
Keywords:
rhamnolipids / di-rhamnolipids / biofilms / cell adhesion / amide derivativeSource:
Frontiers in Microbiology, 2017, 8Publisher:
- Frontiers Media Sa, Lausanne
Funding / projects:
- European Society of Clinical Microbiology and Infectious Diseases (ESCMID)
DOI: 10.3389/fmicb.2017.02454
ISSN: 1664-302X
PubMed: 29276509
WoS: 000417465000001
Scopus: 2-s2.0-85037666494
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PharmacyTY - JOUR AU - Aleksić, Ivana AU - Petković, Miloš AU - Jovanović, Miloš AU - Milivojević, Dušan AU - Vasiljević, Branka AU - Nikodinović-Runić, Jasmina AU - Senerović, Lidija PY - 2017 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2858 AB - A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibiting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties. PB - Frontiers Media Sa, Lausanne T2 - Frontiers in Microbiology T1 - Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives VL - 8 DO - 10.3389/fmicb.2017.02454 ER -
@article{ author = "Aleksić, Ivana and Petković, Miloš and Jovanović, Miloš and Milivojević, Dušan and Vasiljević, Branka and Nikodinović-Runić, Jasmina and Senerović, Lidija", year = "2017", abstract = "A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibiting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties.", publisher = "Frontiers Media Sa, Lausanne", journal = "Frontiers in Microbiology", title = "Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives", volume = "8", doi = "10.3389/fmicb.2017.02454" }
Aleksić, I., Petković, M., Jovanović, M., Milivojević, D., Vasiljević, B., Nikodinović-Runić, J.,& Senerović, L.. (2017). Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives. in Frontiers in Microbiology Frontiers Media Sa, Lausanne., 8. https://doi.org/10.3389/fmicb.2017.02454
Aleksić I, Petković M, Jovanović M, Milivojević D, Vasiljević B, Nikodinović-Runić J, Senerović L. Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives. in Frontiers in Microbiology. 2017;8. doi:10.3389/fmicb.2017.02454 .
Aleksić, Ivana, Petković, Miloš, Jovanović, Miloš, Milivojević, Dušan, Vasiljević, Branka, Nikodinović-Runić, Jasmina, Senerović, Lidija, "Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives" in Frontiers in Microbiology, 8 (2017), https://doi.org/10.3389/fmicb.2017.02454 . .