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Cyclic Dipeptide-Based Ambidextrous Supergelators: Minimalistic Rational Design, Structure-Gelation Studies, and In Situ Hydrogelation
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
2017 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 18, no 11, p. 3581-3590Article in journal (Refereed) Published
Abstract [en]

Ambidextrous supergelators are developed through structure-gelation screening of rationally designed cyclic dipeptides (CDPs). The organo- and hydrogels of CDPs were thoroughly characterized by their minimal gelation concentration (MGC) for organic and aqueous solvents, thermal stability (T-g), and viscoelastic properties. Intermo-lecular hydrogen bonding, the major driving force for gelation was evaluated using temperature-dependent nuclear magnetic resonance (NMR) spectroscopy. The contribution of attractive van der Waals interaction of tBoc group in driving CDP gelation was ascertained using beta-cyclodextrin (beta-CD)-adamantane carboxylic acid (AC)-based host guest gelation and H-1 NMR. studies. The self-assembled fibrous network of CDPs in organic and aqueous solvents responsible for the molecular gelation was elucidated using field emission scanning electron microscopy (FESEM) analysis. Among the CDPs studied CDP-2 found to be supergelator with MGC of 0.3 wt % and form in situ hydrogels under simulated physiological conditions. The in situ gelation property was evaluated by the incorporation of curcumin, as a model study to demonstrate the drug delivery application. Furthermore, supergelator CDP-2 was found to exhibit in cellulo cytocompatibility. Moreover, density functional theory (DFT) calculations were carried out to propose the microscopic structure for the self-assembly of CDP compounds and intermolecular N-H center dot center dot center dot O hydrogen bonding interactions appear to stabilize the fibrous network. The hydrophobic interactions among the tert-butyloxycarbonyl (tBoc) groups and pi-pi stacking interactions between phenyl rings contribute to the further stabilization of self-assembled 2D fibrous networks of CDPs. Overall, the present study highlights the in situ gelation property of CDP-based supergelators and their potential for biomedical and regenerative medicine applications.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2017. Vol. 18, no 11, p. 3581-3590
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:kth:diva-219338DOI: 10.1021/acs.biomac.7b00924ISI: 000415391900015PubMedID: 28856890OAI: oai:DiVA.org:kth-219338DiVA, id: diva2:1162396
Note

QC 20171204

Available from: 2017-12-04 Created: 2017-12-04 Last updated: 2017-12-04Bibliographically approved

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