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Asymmetrical, symmetrical, divalent, and Y-shaped (bola)amphiphiles : the relationship between the molecular structure and self-assembly in amino derivatives of sophorolipid biosurfactants

(2019) JOURNAL OF PHYSICAL CHEMISTRY B. 123(17). p.3841-3858
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Abstract
Conventional head-chain but also more exotic divalent, Gemini, or bolaform amphiphiles have in common welldefined hydrophilic and hydrophobic blocks with often a predictable self-assembly behavior. However, new categories of amphiphiles, such as microbial biosurfactants, challenge such conventional understanding because of the poorly defined boundaries between the hydrophilic and hydrophobic portions. Microbial glycolipids, such as sophorolipids, rhamnolipids, or cellobioselipids, interesting biodegradable, nontoxic, alternatives to synthetic surfactants, all represent interesting examples of atypical amphiphiles with partially predictable self-assembly properties. However, their limited molecular diversity strongly limits their application potential. For this reason, we used them as ready-made platform to prepare a whole class of new derivatives. In particular, a broad range of amino derivatives of sophorolipid biosurfactant was recently prepared with the goal of producing biobased antimicrobial and transfection agents, of which the efficiency strongly depends on their molecular structure and unpredictable self-assembly behavior. The new compounds contain a set of asymmetrical and symmetrical bolaamphiphiles, the latter with three or four hydrophilic centers, divalent amphiphiles with asymmetric polar headgroups and even Y-shaped amphiphiles, bearing two sophorose groups connected to one nitrogen atom. In this contribution, we employ small-angle X-ray scattering to establish a relationship between their peculiar molecular structures and the self-assembly properties in water. We find that all divalent and Y-shaped compounds form micelles, of which the hydrophilic shell is composed of a bulky sophorose C-x(x = 8,11)-amine moiety, with aggregation numbers between 30 and 100. On the contrary, most symmetrical and asymmetrical bolaamphiphiles display poor self-assembly properties, generally showing aggregation numbers below 20, especially in the presence of either short spacers or large spacers containing hydrophilic centers.
Keywords
GEMINI SURFACTANTS, SUPRAMOLECULAR ASSEMBLIES, INTERFACIAL PROPERTIES, MICROBIAL-PRODUCTION, DYNAMICS SIMULATION, PHASE-BEHAVIOR, WATER, MICELLES, SCATTERING, PH

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Chicago
Baccile, Niki, Elisabeth Delbeke, Martha Brennich, Chloé Seyrig, Jonas Everaert, Sophie Roelants, Wim Soetaert, Inge Van Bogaert, Kevin Van Geem, and Christian Stevens. 2019. “Asymmetrical, Symmetrical, Divalent, and Y-shaped (bola)amphiphiles : the Relationship Between the Molecular Structure and Self-assembly in Amino Derivatives of Sophorolipid Biosurfactants.” Journal of Physical Chemistry B 123 (17): 3841–3858.
APA
Baccile, N., Delbeke, E., Brennich, M., Seyrig, C., Everaert, J., Roelants, S., Soetaert, W., et al. (2019). Asymmetrical, symmetrical, divalent, and Y-shaped (bola)amphiphiles : the relationship between the molecular structure and self-assembly in amino derivatives of sophorolipid biosurfactants. JOURNAL OF PHYSICAL CHEMISTRY B, 123(17), 3841–3858.
Vancouver
1.
Baccile N, Delbeke E, Brennich M, Seyrig C, Everaert J, Roelants S, et al. Asymmetrical, symmetrical, divalent, and Y-shaped (bola)amphiphiles : the relationship between the molecular structure and self-assembly in amino derivatives of sophorolipid biosurfactants. JOURNAL OF PHYSICAL CHEMISTRY B. 2019;123(17):3841–58.
MLA
Baccile, Niki et al. “Asymmetrical, Symmetrical, Divalent, and Y-shaped (bola)amphiphiles : the Relationship Between the Molecular Structure and Self-assembly in Amino Derivatives of Sophorolipid Biosurfactants.” JOURNAL OF PHYSICAL CHEMISTRY B 123.17 (2019): 3841–3858. Print.
@article{8618184,
  abstract     = {Conventional head-chain but also more exotic divalent, Gemini, or bolaform amphiphiles have in common welldefined hydrophilic and hydrophobic blocks with often a predictable self-assembly behavior. However, new categories of amphiphiles, such as microbial biosurfactants, challenge such conventional understanding because of the poorly defined boundaries between the hydrophilic and hydrophobic portions. Microbial glycolipids, such as sophorolipids, rhamnolipids, or cellobioselipids, interesting biodegradable, nontoxic, alternatives to synthetic surfactants, all represent interesting examples of atypical amphiphiles with partially predictable self-assembly properties. However, their limited molecular diversity strongly limits their application potential. For this reason, we used them as ready-made platform to prepare a whole class of new derivatives. In particular, a broad range of amino derivatives of sophorolipid biosurfactant was recently prepared with the goal of producing biobased antimicrobial and transfection agents, of which the efficiency strongly depends on their molecular structure and unpredictable self-assembly behavior. The new compounds contain a set of asymmetrical and symmetrical bolaamphiphiles, the latter with three or four hydrophilic centers, divalent amphiphiles with asymmetric polar headgroups and even Y-shaped amphiphiles, bearing two sophorose groups connected to one nitrogen atom. In this contribution, we employ small-angle X-ray scattering to establish a relationship between their peculiar molecular structures and the self-assembly properties in water. We find that all divalent and Y-shaped compounds form micelles, of which the hydrophilic shell is composed of a bulky sophorose C-x(x = 8,11)-amine moiety, with aggregation numbers between 30 and 100. On the contrary, most symmetrical and asymmetrical bolaamphiphiles display poor self-assembly properties, generally showing aggregation numbers below 20, especially in the presence of either short spacers or large spacers containing hydrophilic centers.},
  author       = {Baccile, Niki and Delbeke, Elisabeth and Brennich, Martha and Seyrig, Chloé and Everaert, Jonas and Roelants, Sophie and Soetaert, Wim and Van Bogaert, Inge and Van Geem, Kevin and Stevens, Christian},
  issn         = {1520-6106},
  journal      = {JOURNAL OF PHYSICAL CHEMISTRY B},
  keywords     = {GEMINI SURFACTANTS,SUPRAMOLECULAR ASSEMBLIES,INTERFACIAL PROPERTIES,MICROBIAL-PRODUCTION,DYNAMICS SIMULATION,PHASE-BEHAVIOR,WATER,MICELLES,SCATTERING,PH},
  language     = {eng},
  number       = {17},
  pages        = {3841--3858},
  title        = {Asymmetrical, symmetrical, divalent, and Y-shaped (bola)amphiphiles : the relationship between the molecular structure and self-assembly in amino derivatives of sophorolipid biosurfactants},
  url          = {http://dx.doi.org/10.1021/acs.jpcb.9b01013},
  volume       = {123},
  year         = {2019},
}

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