ICRS-PAT 2021

Poly(acrylic anhydrides) bearing salicylic/benzoic acid: Synthesis, characterization and controlled release studies

Arun Yuvaraj Pulikanti Guruprasad Reddy Noam Y. Steinman Abraham J. Domb
School of Pharmacy- Faculty of Medicine, The Hebrew University of Jerusalem, Israel

Abstract

Benzoic acid and salicylic acid derivatives have received significant interest in the biomedical field, agriculture and food industry because of their outstanding antimicrobial, antifungal and anti-inflammatory properties.[1-3] Especially, salicylic acid is a promising candidate in medicine due to potential treatment of cardiovascular diseases and cancers.[1,4] Thus, developing a novel system for the rapid release of benzoic acid and salicylic acid is paramount for the treatment of various microbial and inflammatory diseases in the controlled manner. In this context, various homo and copolymers of poly(acrylic anhydrides) bearing benzoate/salicylate have been designed and synthesized based on the condensation polymerization of salicylic/benzoic acid with poly(acrylic acid) or Eudragit L100 in the presence of acetic anhydride at 160 oC. All of these homo and copolymers of poly(acrylic anhydrides) have been thoroughly characterized using various analytical and spectroscopic techniques including IR, NMR, GPC, TGA-DSC, and elemental analysis. The absence of hydroxyl and carboxyl stretching frequencies and proton resonance signals for salicylic/benzoic acid in the IR and NMR spectroscopy confirms their conversion from individual monomer units into polymer. The release of salicylic/benzoic acid from its corresponding poly(acrylic anhydride) back bone is thoroughly investigated in water by measuring absorption in UV-visible spectroscopy at 298 nm and 225 nm respectively.The results concluded that the homopolymer of poly(acrylic benzoate) showed high release profile for benzoic acid (100% in 42 days) than compared to the poly(acrylic salicylate), whereas salicylic acid shown about 10% release profile in 42 days and poly(salicylic acid) (did not show any release profile for salicylic acid). A detailed release studies of salicylic/benzoic acid from seven different homo/copolymers of poly(acrylic anhydrides) is under progress in our laboratory.

References

[1] Q. Dasgupta, K. Chatterjee, and G. Madras, Mol. Pharmaceutics. 2015, 12, 3479−3489.

[2] F. Yeasmin, H. W. Choi, Int. J. Mol. Sci. 2020, 21, 9049.

[3] A. D. Olmo, J. Calzada, M. Nunez, Crit. Rev. Food. Sci. Nutr. 2017, 57 (14), 3084–3103.

[4] R. A. Gupta, R. N. DuBois, Nat. Rev. Cancer. 2001, 1, 11−21.









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