Alkyl rhamnosides, a series of amphiphilic materials exerting broad-spectrum anti-biofilm activity against pathogenic bacteria via multiple mechanisms

References

• Davey ME, Caiazza NC, O'Toole GA. Rhamnolipid surfactant production affects biofilm architecture in Pseudomonas aeruginosa PAO1. J Bacteriol. 2003;185:1027–1036.
   PubMed Web of Science ®Google Scholar
• Davey ME, O'Toole GA. Microbial biofilms: from ecology to molecular genetics. Microbiol Mol Biol Rev. 2000;64:847–867.
   PubMed Web of Science ®Google Scholar
• Costerton JW, Stewart PS, Greenberg EP. Bacterial biofilms: a common cause of persistent infections. Science. 1999;284:1318.
   PubMed Web of Science ®Google Scholar
• Teixeira PC, Leite GM, Domingues RJ, et al. Antimicrobial effects of a microemulsion and a nanoemulsion on enteric and other pathogens and biofilms. Int J Food Microbiol.. 2007;118:15–19.
   PubMed Web of Science ®Google Scholar
• Otto M. Staphylococcal biofilms. Curr Top Microbiol Immunol. 2008;322:207–228.
   PubMed Web of Science ®Google Scholar
• Brindle ER, Miller DA, Stewart PS. Hydrodynamic deformation and removal of Staphylococcus epidermidis biofilms treated with urea, chlorhexidine, iron chloride, or DispersinB. Biotechnol Bioeng. 2011;108:2968–2977.
   PubMed Web of Science ®Google Scholar
• Zeraik AE, Nitschke M. Biosurfactants as agents to reduce adhesion of pathogenic bacteria to polystyrene surfaces: effect of temperature and hydrophobicity. Curr Microbiol. 2010;61:554–559.
   PubMed Web of Science ®Google Scholar
• Boyle KE, Heilmann S, van Ditmarsch D, et al. Exploiting social evolution in biofilms. Curr Opin Microbiol. 2013;16:207–212.
   PubMed Web of Science ®Google Scholar
• Jensen PO, Bjarnsholt T, Phipps R, et al. Rapid necrotic killing of polymorphonuclear leukocytes is caused by quorum-sensing-controlled production of rhamnolipid by Pseudomonas aeruginosa. Microbiology. 2007;153:1329–1338.
   PubMed Web of Science ®Google Scholar
• Yu Y, Chen M. A protocol for the synthesis of C8-16alkyl 2,3-isopropylidene-α-l-rhamnosides. J Carbohydr Chem. 2014;33:489–497.
   Web of Science ®Google Scholar
• Yan S, Ding N, Zhang W, et al. An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers. Carbohydr Res. 2012;354:6–20.
   PubMed Web of Science ®Google Scholar
• Liu ZD, Liang PL, Chen XB, et al. Synthesis and characterization of sugar-based quaternary ammonium salt surfactants. Fine Chem. 2007;24:870–880.
   Google Scholar
• Sowada R, McGowan J. Calculation of HLB values. Tenside Surf Detergents. 1992;29:109–113.
   Google Scholar
• Luna JM, Rufino RD, Sarubbo LA, et al. Evaluation antimicrobial and antiadhesive properties of the biosurfactant Lunasan produced by Candida sphaerica UCP 0995. Curr Microbiol. 2011;84:1–1534.
   Google Scholar
• Zou Y, Lee Y, Huh J, et al. Synergistic effect of xylitol and ursolic acid combination on oral biofilms. Restor Dent Endod. 2014;39:288–295.
   PubMedGoogle Scholar
• Dalili D, Amini M, Faramarzi MA, et al. Isolation and structural characterization of Coryxin, a novel cyclic lipopeptide from Corynebacterium xerosis NS5 having emulsifying and anti-biofilm activity. Colloids Surf B Biointerfaces. 2015;135:425–432.
   PubMed Web of Science ®Google Scholar
• Meng Y, Hou X, Lei J, et al. Multi-functional liposomes enhancing target and antibacterial immunity for antimicrobial and anti-biofilm against methicillin-resistant Staphylococcus aureus. Pharm Res. 2016;33:763–775.
   PubMed Web of Science ®Google Scholar
• Dusane DH, Nancharaiah YV, Zinjarde SS, et al. Rhamnolipid mediated disruption of marine Bacillus pumilus biofilms. Colloids Surf B Biointerfaces. 2010;81:242–248.
   PubMed Web of Science ®Google Scholar
• Brycki B, Kozirog A, Kowalczyk I, et al. Synthesis, structure, surface and antimicrobial properties of new oligomeric quaternary ammonium salts with aromatic spacers. Molecules. 2017;22:1810.
   Web of Science ®Google Scholar
• Schreier S, Malheiros SV, de Paula E. Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim Biophys Acta. 2000;1508:210–234.
   PubMed Web of Science ®Google Scholar
• Lister JL, Horswill AR. Staphylococcus aureus biofilms: recent developments in biofilm dispersal. Front Cell Infect Microbiol. 2014;4:178.
   PubMed Web of Science ®Google Scholar
• Kaplan JB. Biofilm dispersal: mechanisms, clinical implications, and potential therapeutic uses. J Dent Res. 2010;89:205–218.
   PubMed Web of Science ®Google Scholar
• Ma Q, Yang Z, Pu M, et al. Engineering a novel c-di-GMP-binding protein for biofilm dispersal. Environ Microbiol. 2011;13:631–642.
   PubMed Web of Science ®Google Scholar
• Gakhar L, Bartlett JA, Penterman J, Jr. et al. PLUNC is a novel airway surfactant protein with anti-biofilm activity. PLoS One. 2010;5:e9098.
   PubMed Web of Science ®Google Scholar
• Resch A, Leicht S, Saric M, et al. Comparative proteome analysis of Staphylococcus aureus biofilm and planktonic cells and correlation with transcriptome profiling. Proteomics. 2006;6:1867–1877.
   PubMed Web of Science ®Google Scholar
• Rebecca Y, Peng C, Shi W, et al. Genetic screen reveals the role of purine metabolism in Staphylococcus aureus persistence to rifampicin. Antibiotics. 2015;4:627–642.
   Google Scholar
• Brady RA, Leid JG, Camper AK, et al. Identification of Staphylococcus aureus proteins recognized by the antibody-mediated immune response to a biofilm infection. Infect Immun. 2006;74:3415–3426.
   PubMed Web of Science ®Google Scholar
• Li L, Cheung A, Bayer AS, et al. The global regulon sarA regulates beta-lactam antibiotic resistance in methicillin-resistant Staphylococcus aureus (MRSA) in vitro and in endovascular infections. J Infect Dis. 2016;214:1421–1429.
   PubMed Web of Science ®Google Scholar
• Khemiri A, Jouenne T, Cosette P. Proteomics dedicated to biofilmology: What have we learned from a decade of research? Med Microbiol Immunol. 2016;205:1–19.
   PubMed Web of Science ®Google Scholar
• Arciola CR, Campoccia D, Speziale P, et al. Biofilm formation in Staphylococcus implant infections. A review of molecular mechanisms and implications for biofilm-resistant materials. Biomaterials. 2012;33:5967–5982.
   PubMed Web of Science ®Google Scholar
• Brooks JL, Jefferson KK. Staphylococcal biofilms: quest for the magic bullet. Adv Appl Microbiol. 2012;81:63–87.
   PubMed Web of Science ®Google Scholar
• Kolar SL, Nagarajan V, Oszmiana A, et al. NsaRS is a cell-envelope-stress-sensing two-component system of Staphylococcus aureus. Microbiology. 2011;157:2206–2219.
   PubMed Web of Science ®Google Scholar
• Waters NR, Samuels DJ, Behera RK, et al. A spectrum of CodY activities drives metabolic reorganization and virulence gene expression in Staphylococcus aureus. Mol Microbiol. 2016;101:495–514.
   PubMed Web of Science ®Google Scholar
• Metselaar KI, den Besten HM, Boekhorst J, et al. Diversity of acid stress resistant variants of Listeria monocytogenes and the potential role of ribosomal protein S21 encoded by rpsU. Front Microbiol. 2015;6:422.
   PubMed Web of Science ®Google Scholar
• Korem M, Gov Y, Rosenberg M. Global gene expression in Staphylococcus aureus following exposure to alcohol. Microb Pathog. 2010;48:74–84.
   PubMed Web of Science ®Google Scholar
• Mirani ZA, Jamil N. Role of extra-cellular fatty acids in vancomycin induced biofilm formation by vancomycin resistant Staphylococcus aureus. Pak J Pharm Sci. 2013;26:383–389.
   PubMed Web of Science ®Google Scholar
• Prax M, Bertram R. Metabolic aspects of bacterial persisters. Front Cell Infect Microbiol. 2014;4:148–148.
   PubMed Web of Science ®Google Scholar
• Petrova OE, Schurr JR, Schurr MJ, et al. Microcolony formation by the opportunistic pathogen Pseudomonas aeruginosa requires pyruvate and pyruvate fermentation. Mol Microbiol. 2012;86:819–835.
   PubMed Web of Science ®Google Scholar
• Park AJ, Murphy K, Krieger JR, et al. A temporal examination of the planktonic and biofilm proteome of whole cell Pseudomonas aeruginosa PAO1 using quantitative mass spectrometry. Mol Cell Proteomics. 2014;13:1095–1105.
   PubMed Web of Science ®Google Scholar
• Imperi F, Leoni L, Visca P. Antivirulence activity of azithromycin in Pseudomonas aeruginosa. Front Microbiol. 2014;5:178.
   PubMed Web of Science ®Google Scholar
• Irie Y, MS, Edwards AN, Wozniak DJ, et al. Pseudomonas aeruginosa biofilm matrix polysaccharide Psl is regulated transcriptionally by RpoS and post-transcriptionally by RsmA. Mol Microbiol. 2010;78:172.
   Web of Science ®Google Scholar
• Deschamps JD, Ogunsola AF, Jameson JB, et al. Biochemical/cellular characterization and inhibitor discovery of Pseudomonas aeruginosa 15-lipoxygenase. Biochemistry. 2016;55:3329–3340.
   PubMed Web of Science ®Google Scholar
• Kannan A, Karumanchi SL, Ramalingam S, et al. Quantitative study on the effect of calcium and magnesium palmitate on the formation of Pseudomonas aeruginosa biofilm. J Microbiol Immunol Infect. 2016;49:988–991.
   PubMedGoogle Scholar
• Sakuragi Y, Kolter R. Quorum-sensing regulation of the biofilm matrix genes (pel) of Pseudomonas aeruginosa. J Bacteriol. 2007;189:5383–5386.
   PubMed Web of Science ®Google Scholar
• Seyer D, Cosette P, Siroy A, et al. Proteomic comparison of outer membrane protein patterns of sessile and planktonic Pseudomonas aeruginosa cells. Biofilms. 2005;2:27–36.
   Google Scholar
• Saville RM, Rakshe S, Haagensen JAJ, et al. Energy-dependent stability of Shewanella oneidensis MR-1 biofilms. J Bacteriol. 2011;193:3257–3264.
   PubMed Web of Science ®Google Scholar
• Guo QYW, Xia B, Jin Y, et al. Identification of a small molecule that simultaneously suppresses virulence and antibiotic resistance of Pseudomonas aeruginosa. Sci Rep. 2016;6:1305–1307.
   Web of Science ®Google Scholar
• Shin S, Ahmed I, Hwang J, et al. A microfluidic approach to investigating a synergistic effect of tobramycin and sodium dodecyl sulfate on Pseudomonas aeruginosa biofilms. Anal Sci. 2016;32:67–73.
   PubMed Web of Science ®Google Scholar