Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates
Özdemir, Zulal, Šaman, David, Bertula, Kia, Lahtinen, Manu, Bednárová, Lucie, Pazderková, Markéta, Rárová, Lucie, Nonappa, Wimmer, Zdeněk. (2021). Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates. Langmuir, 37(8), 2693-2706. https://doi.org/10.1021/acs.langmuir.0c03335
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LangmuirAuthors
Nonappa |
Date
2021Discipline
Epäorgaaninen ja analyyttinen kemiaEpäorgaaninen kemiaInorganic and Analytical ChemistryInorganic ChemistryCopyright
© 2021 American Chemical Society
Natural and abundant plant triterpenoids are attractive starting materials for the synthesis of conformationally rigid and chiral building blocks for functional soft materials. Here, we report the rational design of three oleanolic acid–triazole–spermine conjugates, containing either one or two spermine units in the target molecules, using the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The resulting amphiphile-like molecules 2 and 3, bearing just one spermine unit in the respective molecules, self-assemble into highly entangled fibrous networks leading to gelation at a concentration as low as 0.5% in alcoholic solvents. Using step-strain rheological measurements, we show rapid self-recovery (up to 96% of the initial storage modulus) and sol ⇔ gel transition under several cycles. Interestingly, rheological flow curves reveal the thixotropic behavior of the gels. To the best of our knowledge, this kind of behavior was not shown in the literature before, neither for a triterpenoid nor for its derivatives. Conjugate 4, having a bolaamphiphile-like structure, was found to be a nongelator. Our results indicate that the position and number of spermine units alter the gelation properties, gel strength, and their self-assembly behavior. Preliminary cytotoxicity studies of the target compounds 2–4 in four human cancer cell lines suggest that the position and number of spermine units affect the biological activity. Our results also encourage exploring other triterpenoids and their derivatives as sustainable, renewable, and biologically active building blocks for multifunctional soft organic nanomaterials.
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The authors are thankful for the funding of this research from the MPO through grants FV10599 (Z.Ö.) and FV30300 (Z.W.). We acknowledge the provision of facilities and technical support by the Aalto University Nanomicroscopy Center (Aalto-NMC). We thank Dr. S. Hietala for useful discussions on rheology. Part of this work was also carried out under the framework of the Centre of Excellence in Molecular Engineering of Biosynthetic Hybrid Materials (HYBER 2014-2019) and the Photonics Research and Innovation (PRIEN) flagship program. Z.Ö . thanks the Erasmus+ program of the EU for funding her study visit to Aalto University, Finland. L.R. thanks the Czech Science Foundation for grant no. 19-01383S. ...License
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