Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans |
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| Affiliation: | 1. University of Belgrade, Faculty of Pharmacy, Department of Organic Chemistry, Vojvode Stepe 450, Belgrade, Serbia;2. University of Belgrade, Institute of Molecular Genetics and Genetic Engineering, Vojvode Stepe 444 a, Belgrade, Serbia;3. UCD School of Biomolecular and Biomedical Science, University College Dublin, Belfield, Dublin 4, Ireland;4. University of Belgrade, Institute of General and Physical Chemistry, Studentski trg 12/V, Belgrade, Serbia;5. University of Belgrade, School of Medicine, Institute of Forensic Medicine, Deligradska 31 a, Belgrade, Serbia;1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 201203, PR China;2. School of Life Science, Shanghai University, 99 Shangda Road, Shanghai 200444, PR China;1. Department of Food Science and Biotechnology, Dongguk University-Seoul, Ilsandong-gu, Goyang-si, Gyenggi-do 410820, Republic of Korea;2. Department of Chemistry, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad 500 085, India;3. Shroff S.R. Rotary Institute of Chemical Technology, Valia 393 135, India;1. Chemistry Department, Syracuse University, Syracuse, NY 13244-4100, United States;2. Department of Nutritional Sciences, University of Connecticut, Storrs, CT 06269-4017, United States;1. Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università di Messina, v.le F. Stagno D’Alcontres 31, 98166 Messina, Italy;2. Istituto per i Polimeri, Compositi e Biomateriali, Consiglio Nazionale delle Ricerche, via P. Gaifami 18, 95126 Catania, Italy;3. Dipartimento di Scienze del Farmaco, Università di Catania, viale A. Doria 6, 95125 Catania, Italy;1. Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People’s Republic of China;2. Guangdong Province Engineering Technology Research Institute of T. C. M., Guangdong Provincial Key Laboratory of Research and Development in Traditional Chinese Medicine, Guangzhou 510095, People’s Republic of China;3. School of Biotechnology and Health Sciences, Wuyi University, 99 Yingbin Road, Jiangmen 529020, People’s Republic of China;4. Guangzhou University of Chinese Medicine, Guangdong Second Traditional Chinese Medicine Hospital, Guangzhou 510095, People’s Republic of China;5. Molecular Laboratory, School of Biomedical Science, University of Western Australia, Perth, Western Australia, Australia |
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| Abstract: | Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties.Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 µg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces. |
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| Keywords: | Adhesion Biofilm Lipopeptides Rhamnolipids |
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