Supramolecular gels from sugar-linked triazole amphiphiles for drug entrapment and release for topical application

• Published in: RSC advances Vol. 9; no. 34; pp. 19819 - 19827
• Main Authors: Sharma, Komal, Joseph, Jojo P, Sahu, Adarsh, Yadav, Narender, Tyagi, Mohit, Singh, Ashmeet, Pal, Asish, Kartha, K. P. Ravindranathan
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 27.06.2019; The Royal Society of Chemistry
• Subjects: Alkynes; Chemistry; Crosslinking; Cycloaddition; Drugs; Entrapment; Formulations; Gels; Ibuprofen; Low molecular weights; Mechanical properties; Rheological properties; Self-assembly; Supramolecular compounds; Triazoles; X-ray diffraction
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/c9ra02868d

A simple molecular framework obtained by cross-linking a hydrophobic chain with S , S - and R , R -tetritol by the copper-catalysed azide-alkyne cycloaddition reaction is found to serve as an excellent bioisostere for self-assembly. The hexadecyl-linked triazolyl tetritol composite spontaneously self-assembles in n -hepane and methanol to form hierarchical organogels. Microscopic analyses and X-ray diffraction studies demonstrate eventual formation of nanotubes through lamellar assembly of the amphiphiles. A rheological investigation shows solvent-dictated mechanical properties that obey power law behavior similar to other low molecular weight gelators (LMOGs). The gel network was then utilized for the entrapment of drugs e.g. ibuprofen and 5-fluorouracil, with tunable mechanical behaviour under applied stress. The differential release profiles of the drugs over a period of a few hours as a result of the relative spatio-temporal location in the supramolecular network can be utilized for topical formulations. Spontaneous formation of hierarchical supramolecular gels show solvent dictated self-assembly and spatio-temporal positioning of drug molecules in the network accounting for differential release profiles for topical application.