We report the formation of aqueous gels at low concentrations (less than 1 wt%) of an amphiphilic drug, a derivative of a chromane-2-carboxylic acid, at pH values 6.2-6.4. Formation of gels in the vicinity of the apparent pK(a) of the drug suggests that on the molecular level, the gels are composed
Water Gelation of an Amino Acid-Based Amphiphile
✍ Scribed by Debapratim Das; Antara Dasgupta; Sangita Roy; Rajendra Narayan Mitra; Sisir Debnath; Prasanta Kumar Das
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 191 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
The water immobilization by a simple amino acid‐containing cationic surfactant was investigated. A variety of techniques, such as ^1^H NMR spectroscopy, circular dichroism (CD), steady‐state fluorescence spectroscopy, and field‐emission scanning electron microscopy (FESEM) were applied to determine the formation and architecture of the hydrogel. The new gelator with a minimum gelation concentration (MGC) of 0.3 % w/v shows prolonged stability and a low melting temperature (39 °C). ^1^H NMR experiments revealed that intermolecular hydrogen bonding between the amide groups and π–π stacking of the indole rings are the two regulating parameters for gelation. Furthermore, fluorescence studies with 8‐anilino‐1‐naphthalenesulfonic acid (ANS) as the probe indicate the participation of hydrophobicity during gelation. The luminescence study using both ANS and pyrene, along with FESEM results, indicate a critical concentration, well below the MGC, at which fibres begin to form. These cross‐link further to give thicker fibers, leading to the formation of a hydrogel (0.3 % w/v). This new hydrogelator expresses high supramolecular chirality, as evidenced by the CD spectra. In addition, the gelator molecule was found to be nontoxic up to a concentration of 4 mM (0.2 % w/v). The high supramolecular chirality, prolonged stability, low melting point, and biocompatibility of the molecule make it a focus of chemical and biological interest.
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