The relationship between structural parameters and antibacterial biofilm activity for alkyl rhamnoside as a novel amphiphilic material

doi:10.5246/jcps.2018.12.082

Abstract

Abstract:

In the present study, we aimed to explore the structure-activity relationship for the new amphiphilic material rhamnoside with antibacterial biofilm activity, and provide the basis for selecting rhamnoside with the optimum antibacterial biofilm activity. A series of alkyl rhamnosides with different carbon chain lengths were obtained by a simple and effective synthesis method. The structure was characterized by ¹H NMR spectrum, and their critical micelle concentration (CMC) was measured by fluorescence probe method. The hydrophilic and lipophilic balance (HLB) value was obtained by calculation. The minimal inhibitory concentration (MIC) of Staphylococcus aureus was determined by the broth double dilution method. The effect of biofilm inhibition and biofilm disruption was assayed by crystal violet method. The results showed that with the increase of carbon chain length, the CMC and HLB of alkyl rhamnosides displayed a linear downward trend, indicating that the lipophilicity and surface activityof the alkyl rhamnoside were increased. At the same time, the antibacterial activity in vitro produced the maximum, ie, 12-hydroxydecanoyl rhamnoside had the strongest antibacterial activity in vitro. Similarly, this material also exhibited the strongest antibacterial biofilm activity in vitro. The results of this study demonstrated that the most potent active material was obtained through the structure-activity relationship and it could be applied antibacterial biofilms in clinical practice.

Key words: Biofilm, Alkyl rhamnoside, Amphiphilic material, Structure-activity relationship

CLC Number:

R943

Supporting:

Guanghua Peng, Wenxi Zhang, Maoyuan Song, Mengya Yin, Jiaxing Wang, Jiajia Li, Yajie Liu, Yuanyuan Zhang, Xinru Li, Guiling Li. The relationship between structural parameters and antibacterial biofilm activity for alkyl rhamnoside as a novel amphiphilic material[J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(12): 817-823.

References

[1] Davey, M.E.; Caiazza, N.C.; O'Toole, G.A. Rhamnolipid surfactant production affects biofilm architecture in Pseudomonas aeruginosa PAO1. J. Bacteriol. 2003, 185, 1027-1036.

[2] Davey, M.E.; O’toole, G.A. Microbial biofilms: from ecology to molecular genetics. Microbiol. Mol. Biol. Rev. 2000, 64, 847-867.

[3] Costerton, J.W.; Stewart, P.S.; Greenberg, E.P. Bacterial biofilms: a common cause of persistent infections. Science. 1999, 284, 1318-1322.

[4] Teixeira, P.C.; Leite, G.M.; Domingues, R.J.; Silva, J.; Gibbs, P.A.; Ferreira, J.P. Antimicrobial effects of a microemulsion and a nanoemulsion on enteric and other pathogens and biofilms. Int. J. Food Microbiol. 2007, 118, 15-19.

[5] Otto, M. Staphylococcal biofilms. Curr. Top. Microbiol. Immunol. 2008, 322, 207-228.

[6] Brindle, E.R.; Miller, D.A.; Stewart, P.S. Hydrodynamic deformation and removal of Staphylococcus epidermidis biofilms treated with urea, chlorhexidine, iron chloride, or DispersinB. Biotechnol. Bioeng. 2011, 108, 2968-2977.

[7] Høiby, N.; Bjarnsholt, T.; Givskov, M.; Molin, S.; Ciofu, O. Antibiotic resistance of bacterial biofilms. Int. J. Antimicrob. Agents. 2010, 35, 322-332.

[8] Boles, B.R.; Thoendel, M.; Singh, P.K. Rhamnolipids mediate detachment of Pseudomonas aeruginosa from biofilms. Mol. Microbiol. 2005, 57, 1210-1223.

[9] Zeraik, A.E.; 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.

[10] Boyle, K.E.; Heilmann, S.; van Ditmarsch, D.; Xavier, J.B. Exploiting social evolution in biofilms. Curr. Opin. Microbiol. 2013, 16, 207-212.

[11] Jensen, P.Ø.; Bjarnsholt, T.; Phipps, R.; Rasmussen, T.B.; Calum, H.; Christoffersen, L.; Moser, C.; Williams, P.; Pressler, T.; Givskov, M.; Høiby, N. Rapid necrotic killing of polymorphonuclear leukocytes is caused by quorum-sensing-controlled production of rhamnolipid by Pseudomonas aeruginosa. Microbiology (Reading, Engl.) 2007, 153, 1329-1338.

[12] 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.

[13] Sowada, R.; McGowan, J. Calculation of HLB values. Tenside Surfact. Det. 1992, 29, 109-113.

[14] Li, X.R.; Yang, Z.L.; Yang, K.W.; Zhou, Y.X.; Chen, X.W.; Zhang, Y.H.; Wang, F.; Liu, Y.; Ren, L.J. Self-assembled polymeric micellar nanoparticles as nanocarriers for poorly soluble anticancer drug ethaselen. Nanoscale Res. Lett. 2009, 4, 1502-1511.

[15] Dalili, D.; Amini, M.; Faramarzi, M.A.; Fazeli, M.R.; Khoshayand, M.R.; Samadi, N. 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.