Role of molecular interactions between biosurfactant surfactin and alkylbenzenesulfonate

References

• Md, F . Biosurfactant: Production and Application. J. Pet. Environ. Biotechnol. 2012, 3 , 2.
   Google Scholar
• Lang, S . Biological Amphiphiles (Microbial Biosurfactants). Curr. Opin. Colloid Interface Sci. 2002, 7 , 12–20. DOI: 10.1016/S1359-0294(02)00007-9.
   Web of Science ®Google Scholar
• Hirata, Y. ; Ryu, M. ; Oda, Y. ; Igarashi, K. ; Nagatsuka, A. ; Furuta, T. ; Sugiura, M . Novel Characteristics of Sophorolipids, Yeast Glycolipid Biosurfactants, as Biodegradable Low-Foaming Surfactants. J. Biosci. Bioeng. 2009, 108 , 142–146. DOI: 10.1016/j.jbiosc.2009.03.012.
   PubMed Web of Science ®Google Scholar
• Edwards, K. R. ; Lepo, J. E. ; Lewis, M. A . Toxicity Comparison of Biosurfactants and Synthetic Surfactants Used in Oil Spill Remediation to Two Estuarine Species. Mar. Pollut. Bull. 2003, 46 , 1309–1316. DOI: 10.1016/S0025-326X(03)00238-8.
   PubMed Web of Science ®Google Scholar
• Rufino, R. D. ; de Luna, J. M. ; de Campos Takaki, G. M. ; Sarubbo, L. A . Characterization and Properties of the Biosurfactant Produced by Candida lipolytica UCP 0988. Electron. J. Biotechnol. 2014, 17 , 34–38. DOI: 10.1016/j.ejbt.2013.12.006.
   Web of Science ®Google Scholar
• Saborimanesh, N. ; Mulligan, C. N . Effect of Sophorolipid Biosurfactant on Oil Biodegradation by the Natural Oil-Degrading Bacteria on the Weathered Biodiesel, Diesel and Light Crude Oil. J. Biorem. Biodegrad. 2015, 06 , 314–321.
   Google Scholar
• Dasari, S. ; Venkata Subbaiah, K. ; Wudayagiri, R. ; Valluru, L . Biosurfactant-Mediated Biodegradation of Polycyclic Aromatic Hydrocarbons—Naphthalene. Biorem. J. 2014, 18 , 258–265. DOI: 10.1080/10889868.2014.933169.
   Web of Science ®Google Scholar
• Wang, H. ; Gang, H. ; Ye, R. ; Mu, B . Interaction between Biosurfactant Surfactin and Cationic Surfactant Cetyl Trimethyl Ammonium Bromide in Mixed Micelle. Colloid Polym. Sci. 2014, 292 , 3169–3176. DOI: 10.1007/s00396-014-3366-x.
   Web of Science ®Google Scholar
• Ishigami, Y. ; Osman, M. ; Nakahara, H. ; Sano, Y. ; Ishiguro, R. ; Matsumoto, M . Significance of r-Sheet Formation for Micellization and Surface Adsorption of Surfactin. Colloids Surf. B. 1995, 4 , 341–348. DOI: 10.1016/0927-7765(94)01183-6.
   Web of Science ®Google Scholar
• Liu, Q. ; Lin, J. ; Wang, W. ; Huang, H. ; Li, S . Production of Surfactin Isoforms by Bacillus subtilis BS-37 and Its Applicability to Enhanced Oil Recovery under Laboratory Conditions. Biochem. Eng. J. 2015, 93 , 31–37. DOI: 10.1016/j.bej.2014.08.023.
   Web of Science ®Google Scholar
• Vaz, D. A. ; Gudina, E. J. ; Alameda, E. J. ; Teixeira, J. A. ; Rodrigues, L. R . Performance of a Biosurfactant Produced by a Bacillus subtilis Strain Isolated from Crude Oil Samples as Compared to Commercial Chemical Surfactants. Colloids Surf. B. Biointerfaces 2012, 89 , 167–174. DOI: 10.1016/j.colsurfb.2011.09.009.
   PubMed Web of Science ®Google Scholar
• Nguyen, T. T. ; Youssef, N. H. ; McInerney, M. J. ; Sabatini, D. A . Rhamnolipid Biosurfactant Mixtures for Environmental Remediation. Water Res. 2008, 42 , 1735–1743. DOI: 10.1016/j.watres.2007.10.038.
   PubMed Web of Science ®Google Scholar
• Youssef, N. H. ; Nguyen, T. ; Sabatini, D. A. ; McInerney, M. J . Basis for Formulating Biosurfactant Mixtures to Achieve Ultra Low Interfacial Tension Values against Hydrocarbons. J. Ind. Microbiol. Biotechnol. 2007, 34 , 497–507. DOI: 10.1007/s10295-007-0221-9.
   PubMed Web of Science ®Google Scholar
• Chen, M. ; Dong, C. ; Penfold, J. ; Thomas, R. K. ; Smyth, T. J. P. ; Perfumo, A. ; Marchant, R. ; Banat, I. M. ; Stevenson, P. ; Parry, A. ; et al. Influence of Calcium Ions on Rhamnolipid and Rhamnolipid/Anionic Surfactant Adsorption and Self-Assembly. Langmuir 2013, 29 , 3912–3923. DOI: 10.1021/la400432v.
   PubMed Web of Science ®Google Scholar
• Jin, L. ; Garamus, V. M. ; Liu, F. ; Xiao, J. ; Eckerlebe, H. ; Willumeit-Römer, R. ; Mu, B. ; Zou, A . Interaction of a Biosurfactant, Surfactin with a Cationic Gemini Surfactant in Aqueous Solution. J. Colloid Interface Sci. 2016, 481 , 201–209. DOI: 10.1016/j.jcis.2016.07.044.
   PubMed Web of Science ®Google Scholar
• Bais, D. ; Trevisan, A. ; Lapasin, R. ; Partal, P. ; Gallegos, C . Rheological Characterization of Polysaccharide-Surfactant Matrices for Cosmetic O/W Emulsions. J. Colloid Interface Sci. 2005, 290 , 546–556. DOI: 10.1016/j.jcis.2005.04.044.
   PubMed Web of Science ®Google Scholar
• Dang, T. Q. C. ; Chen, Z. ; Nguyen, T. B. N. ; Bae, W . The Potential of Enhanced Oil Recovery by Micellar/Polymer Flooding in Heterogeneous Reservoirs. Energy Sources Part A. 2014, 36 , 1540–1554. DOI: 10.1080/15567036.2010.549912.
   Google Scholar
• Park, S. ; Lee, E. S. ; Wan, R. W. S . Adsorption Behaviors of Surfactants for Chemical Flooding in Enhanced Oil Recovery. J. Ind. Eng. Chem. 2014, 21 , 1239–1245. DOI: 10.1016/j.jiec.2014.05.040.
   Web of Science ®Google Scholar
• Spernath, A. ; Yaghmur, A. ; Aserin, A. ; Hoffman, R. E. ; Garti, N . Food-Grade Microemulsions Based on Nonionic Emulsifiers: media to Enhance Lycopene Solubilization. J. Agric. Food Chem. 2002, 50 , 6917–6922. DOI: 10.1021/jf025762n.
   PubMed Web of Science ®Google Scholar
• Kong, L. ; Gang, H. ; Wang, Z. ; Li, T. ; Jafta, C. J. ; Fei, D. ; Ye, R. ; Mu, B . Micellization in Binary Biosurfactant/Synthetic Surfactant Systems: Effects of Temperature and Hydrophobic Group Structure of Alkyl Benzenesulfonate. Colloids Surf. A. 2018, 551 , 174–184. DOI: 10.1016/j.colsurfa.2018.04.048.
   Google Scholar
• Haddad, N. I. A. ; Liu, X. ; Yang, S. ; Mu, B . Surfactin Isomers from Bacillus subtilis HSO121: Separation and Characterization. Protein Pept. Lett. 2008, 15 , 265–269. DOI: 10.2174/092986608783744225.
   PubMed Web of Science ®Google Scholar
• Zhao, Y. ; Yang, S. Z. ; Mu, B. Z . Quantitative Analyses of the Isoforms of Surfactin Produced by Bacillus subtilis HSO 121 Using GC-MS. Anal. Sci. 2012, 28 , 789–793. DOI: 10.2116/analsci.28.789.
   PubMed Web of Science ®Google Scholar
• Rosen, M. J. ; Kunjappu, J. T . Surfactants and Interfacial Phenomena . Hoboken, NJ: John Wiley & Sons, Inc., Publication; 2012.
   Google Scholar
• Maget-Dana, R. ; Ptak, M . Interfacial Properties of Surfactin. J. Colloid Interface Sci. 1992, 153 , 285–291. DOI: 10.1016/0021-9797(92)90319-H.
   Web of Science ®Google Scholar
• Liu, F. ; Xiao, J. ; Garamus, V. M. ; Almasy, L. ; Willumeit, R. ; Mu, B. ; Zou, A . Interaction of the Biosurfactant, Surfactin with Betaines in Aqueous Solution. Langmuir 2013, 29 , 10648–10657. DOI: 10.1021/la400683u.
   PubMed Web of Science ®Google Scholar
• Shen, H. H. ; Lin, T. W. ; Thomas, R. K. ; Taylor, D. J. ; Penfold, J . Surfactin Structures at Interfaces and in Solution: The Effect of pH and Cations. J. Phys. Chem. B . 2011, 115 , 4427–4435. DOI: 10.1021/jp109360h.
   PubMed Web of Science ®Google Scholar
• Gallet, X. ; Deleu, M. ; Razafindralambo, H. ; Jacques, P. ; Thonart, P. ; Paquot, M. ; Brasseur, R . Computer Simulation of Surfactin Conformation at a Hydrophobic/Hydrophilic Interface. Langmuir 1999, 15 , 2409–2413. DOI: 10.1021/la980954r.
   Web of Science ®Google Scholar
• Gang, H.-Z. ; Liu, J.-F. ; Mu, B.-Z . Molecular Dynamics Study of Surfactin Monolayer at the Air/Water Interface. J. Phys. Chem. B . 2011, 115 , 12770–12777. DOI: 10.1021/jp206350j.
   PubMed Web of Science ®Google Scholar
• Goussous, S. A. ; Casford, M. T. L. ; Murphy, A. C. ; Salmond, G. P. C. ; Leeper, F. J. ; Davies, P. B . Structure of the Fundamental Lipopeptide Surfactin at the Air/Water Interface Investigated by Sum Frequency Generation Spectroscopy. J. Phys. Chem. B. 2017, 121 , 5072–5077. DOI: 10.1021/acs.jpcb.7b03476.
   PubMed Web of Science ®Google Scholar
• Shen, H. H. ; Thomas, R. K. ; Chen, C. Y. ; Darton, R. C. ; Baker, S. C. ; Penfold, J . Aggregation of the Naturally Occurring Lipopeptide, Surfactin, at Interfaces and in Solution: An Unusual Type of Surfactant? Langmuir 2009, 25 , 4211–4218. DOI: 10.1021/la802913x.
   PubMed Web of Science ®Google Scholar
• Gang, H. ; Liu, J. ; Mu, B . Interfacial Behavior of Surfactin at the Decane/Water Interface: A Molecular Dynamics Simulation. J. Phys. Chem. B . 2010, 114 , 14947–14954. DOI: 10.1021/jp1057379.
   PubMed Web of Science ®Google Scholar
• Murphy, D. S. ; Zhu, Z. H. ; Yuan, X. Y. ; Rosen, M. J . Relationship of Structure to Properties of Surfactants. 15 Isomeric Sulfated Polyoxyethylenated Guerbet Alcohols. J. Am. Oil Chem. Soc. 1990, 67 , 197–204. DOI: 10.1007/BF02540642.
   Web of Science ®Google Scholar
• Watry, M. ; Richmond, G . Comparison of the Adsorption of Linear Alkanesulfonate and Linear Alkylbenzenesulfonate Surfactants at Liquid Interfaces. J. Am. Chem. Soc. 2000, 122 , 875–883. DOI: 10.1021/ja9917666.
   Web of Science ®Google Scholar
• Hait, S. ; Majhi, P. ; Blume, A. ; Moulik, S . A Critical Assessment of Micellization of Sodium Dodecyl Benzene Sulfonate (SDBS) and Its Interaction with Poly (Vinyl Pyrrolidone) and Hydrophobically Modified Polymers, JR 400 and LM 200. J. Phys. Chem. B. 2003, 107 , 3650–3658. DOI: 10.1021/jp027379r.
   Web of Science ®Google Scholar
• Rosen, M. J. ; Hua, X. Y . Surface Concentrations and Molecular Interactions in Binary Mixtures of Surfactants. J. Colloid Interface Sci. 1982, 86 , 164–172. DOI: 10.1016/0021-9797(82)90052-2.
   Web of Science ®Google Scholar
• Singh, K. ; Marangoni, D. G . Synergistic Interactions in the Mixed Micelles of Cationic Gemini with Zwitterionic Surfactants: The pH and Spacer Effect. J. Colloid. Interface Sci. 2007, 315 , 620–626. DOI: 10.1016/j.jcis.2007.06.062.
   PubMed Web of Science ®Google Scholar
• Onaizi, S. A. ; Nasser, M. S. ; Twaiq, F. A . Micellization and Interfacial Behavior of a Synthetic Surfactant–Biosurfactant Mixture. Colloids Surf. A. 2012, 415 , 388–393. DOI: 10.1016/j.colsurfa.2012.09.014.
   Google Scholar
• Deleu, M. ; Bouffioux, O. ; Razafindralambo, H. ; Paquot, M. ; Hbid, C. ; Thonart, P. ; Jacques, P. ; Brasseur, R . Interaction of Surfactin with Membranes: A Computational Approach. Langmuir 2003, 19 , 3377–3385. DOI: 10.1021/la026543z.
   Web of Science ®Google Scholar
• Gershman, J. W . Physico-Chemical Properties of Solutions of Para Long Chain Alkylbenzenesulfonates. J. Phys. Chem. 1957, 61 , 581–584. DOI: 10.1021/j150551a015.
   Web of Science ®Google Scholar
• Chavda, S. ; Bahadur, P. ; Aswal, V. K . Interaction between Nonionic and Gemini (Cationic) Surfactants: effect of Spacer Chain Length. J. Surfact. Deterg. 2011, 14 , 353–362. DOI: 10.1007/s11743-011-1263-6.
   Web of Science ®Google Scholar
• Rubingh, D. N.; Mittal K. L. Solution Chemistry of Surfactants. Vol. 1. Plenum Press: New York, NY, 1979; pp. 337–354.
   Google Scholar
• Cheng, D. C. ; Gulari, E . Micellization and Intermicellar Interactions in Aqueous Sodium Dodecyl Benzene Sulfonate Solutions. J. Colloid Interface Sci. 1982, 90 , 410–423. DOI: 10.1016/0021-9797(82)90308-3.
   Web of Science ®Google Scholar
• Caponetti, E. ; Triolo, R. ; Ho, P. C. ; Johnson, J. ; Magid, L. ; Butler, P. ; Payne, K . A Small Angle Neutron Scattering (SANS) Study of Micellar Structure and Growth of a Straight-Chain Benzene Sulfonate: comparison with an Isomeric Branched Chain Surfactant. J. Colloid Interface Sci. 1987, 116 , 200–210. DOI: 10.1016/0021-9797(87)90111-1.
   Web of Science ®Google Scholar
• Parekh, P. ; Varade, D. ; Parikh, J. ; Bahadur, P . Anionic–Cationic Mixed Surfactant Systems: micellar Interaction of Sodium Dodecyl Trioxyethylene Sulfate with Cationic Gemini Surfactants. Colloids Surf. A. 2011, 385 , 111–120. DOI: 10.1016/j.colsurfa.2011.05.057.
   Web of Science ®Google Scholar
• Paria, S . The Mixing Behavior of n-Alkylpyridinium Bromide–NP-9 Mixed Surfactant Systems. Colloids Surf. A. 2006, 281 , 113–118. DOI: 10.1016/j.colsurfa.2006.02.023.
   Google Scholar
• De Lisi, R. ; Inglese, A. ; Milioto, S. ; Pellerito, A . Excess Free Energy, Enthalpy and Entropy of Surfactant-Surfactant Mixed Micelle Formation. Fluid Phase Equilib. 1996, 126 , 273–287. DOI: 10.1016/S0378-3812(96)03100-7.
   Web of Science ®Google Scholar