Synthesis, characterization, and micellar behavior of amphiphilic chitosan bearing sulfate and anisaldehyde imine groups
DOI:
https://doi.org/10.21831/jps.v30i1.89435Keywords:
amphiphilic polymers, chitosan derivatives, delivery systems, schiff baseAbstract
Amphiphilic chitosan derivatives bearing sulfate and anisaldehyde imine (anisimine) groups were successfully synthesized and characterized for potential applications as functional biomaterials. The synthesis involved two key steps: (1) sulfation of chitosan using chlorosulfonic acid to introduce O-sulfate groups, and (2) Schiff base formation via reaction with p-anisaldehyde to generate N-anisimine functionalities. Structural modifications were confirmed by Fourier-transform infrared (FTIR) spectroscopy, which showed characteristic absorption bands at ~1250 cm⁻¹ and ~820 cm⁻¹ corresponding to O=S=O stretching of sulfate, and a C=N stretch at ~1640 cm⁻¹ indicating imine formation. Proton nuclear magnetic resonance (1H-NMR) spectra further verified the successful attachment of aromatic protons from p-anisaldehyde and the disappearance of primary amine peaks, confirming imination. The amphiphilic behavior and micelle-forming ability of the N-anisimine-O-sulfated (NAOS) chitosan were evaluated using pyrene as a hydrophobic fluorescent probe for determining the critical micelle concentration (CMC), which was found to be 0.012 mg/mL. The observed low CMC value indicates strong self-assembly capability in aqueous media. These results suggest that NAOS chitosan possesses promising structural and surface-active properties suitable for advanced applications in drug delivery and cosmetic formulations.
References
Aguiar, J., Carpena, P., Molina-Bolı́var, J. A., & Carnero Ruiz, C. (2003). On the determination of the critical micelle concentration by the pyrene 1:3 ratio method. Journal of Colloid and Interface Science, 258(1), 116–122. https://doi.org/10.1016/S0021-9797(02)00082-6
Diab, M. A., El-Sonbati, A. Z., Al-Halawany, M. M., & Bader, D. M. D. (2012). Thermal Stability and Degradation of Chitosan Modified by Cinnamic Acid. Open Journal of Polymer Chemistry, 02(01), 14–20. https://doi.org/10.4236/ojpchem.2012.21003
Dimassi, S., Tabary, N., Chai, F., Blanchemain, N., & Martel, B. (2018). Sulfonated and sulfated chitosan derivatives for biomedical applications: A review. Carbohydrate Polymers, 202, 382–396. https://doi.org/10.1016/j.carbpol.2018.09.011
Gao, Y., Wang, L., Zhang, X., Zhou, Z., Shen, X., Hu, H., Sun, R., & Tang, J. (2023). Advances in Self-Assembled Peptides as Drug Carriers. Pharmaceutics, 15(2), 482. https://doi.org/10.3390/pharmaceutics15020482
Jaidee, A., Rachtanapun, P., & Luangkamin, S. (2012). <sup>1</sup>H-NMR Analysis of Degree of Substitution in N,O-Carboxymethyl Chitosans from Various Chitosan Sources and Types. Advanced Materials Research, 506, 158–161. https://doi.org/10.4028/www.scientific.net/AMR.506.158
Lazaridou, M., Moroni, S., Klonos, P., Kyritsis, A., Bikiaris, D. N., & Lamprou, D. A. (2025). 3D-printed hydrogels based on amphiphilic chitosan derivative loaded with levofloxacin for wound healing applications. International Journal of Polymeric Materials and Polymeric Biomaterials, 74(2), 67–84. https://doi.org/10.1080/00914037.2024.2314610
Pol, T., Chonkaew, W., Hocharoen, L., Niamnont, N., Butkhot, N., Roshorm, Y. M., Kiatkamjornwong, S., Hoven, V. P., & Pratumyot, K. (2022). Amphiphilic Chitosan Bearing Double Palmitoyl Chains and Quaternary Ammonium Moieties as a Nanocarrier for Plasmid DNA. ACS Omega, 7(12), 10056–10068. https://doi.org/10.1021/acsomega.1c06101
Sharma, D., & Singh, J. (2017). Synthesis and Characterization of Fatty Acid Grafted Chitosan Polymer and Their Nanomicelles for Nonviral Gene Delivery Applications HHS Public Access. Bioconjug Chem, 28(11), 2772–2783. https://doi.org/10.1021/acs.bioconj-chem.7b00505
Suendo, V., Ahmad, L. O., & Valiyaveetiil, S. (2010). Deasetilasi Kitin secara Bertahap dan Pengaruhnya terhadap Derajat Deasetilasi serta Massa molekul Kitosan. Jurnal Kimia Indonesia, 5(1), 17–21.
Zvezdova, D. (2010). Synthesis and characterization of chitosan from marine sources in Black Sea. Scientific Works of The Rousse University By Bulgaria, 49, 65–69.
Published
How to Cite
Issue
Section
Citation Check
License
Copyright (c) 2026 DRPM UNY
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Who Can Submit?
Any individual may submit an original manuscript for consideration for publication in Jurnal Penelitian Saintek as long as they hold the copyright to the work or are authorized by the copyright owner(s) to submit it. Authors retain initial ownership of the copyrights to their works prior to publication, except in cases where, as a condition of employment, they have agreed to transfer copyright to their employer.
User Rights
Jurnal Penelitian Saintek is an Open Access journal. Users are granted the right to read, download, copy, distribute, print, search, or link to the full texts of articles, provided they comply with the conditions of the Creative Commons Attribution-ShareAlike License 4.0 (CC BY-SA 4.0).
https://creativecommons.org/licenses/by-sa/4.0/
Author Rights
Authors retains copyrights.
Jurnal Penelitian Saintek by http://journal.uny.ac.id/index.php/saintek is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
