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

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2017
2856.pdf (5.906Mb)
Authors
Aleksić, Ivana
Petković, Miloš
Jovanović, Miloš
Milivojević, Dušan
Vasiljević, Branka
Nikodinović-Runić, Jasmina
Senerović, Lidija
Article (Published version)
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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 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 derivative
Source:
Frontiers in Microbiology, 2017, 8
Publisher:
  • 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
[ Google Scholar ]
53
35
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2858
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - 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 . .

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