A1 Journal article (refereed)
Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid–Spermine Conjugates (2021)

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

JYU authors or editors

Publication details

All authors or editors: Özdemir, Zulal; Šaman, David; Bertula, Kia; Lahtinen, Manu; Bednárová, Lucie; Pazderková, Markéta; Rárová, Lucie; Nonappa; Wimmer, Zdeněk

Journal or series: Langmuir

ISSN: 0743-7463

eISSN: 1520-5827

Publication year: 2021

Publication date: 17/02/2021

Volume: 37

Issue number: 8

Pages range: 2693-2706

Publisher: American Chemical Society (ACS)

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/acs.langmuir.0c03335

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/85110

Publication is parallel published: https://urn.fi/URN:NBN:fi:tuni-202112219449

Abstract

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.

Keywords: organic compounds; triterpenes; supramolecular chemistry; gels; functional materials

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2021

JUFO rating: 2