Microwaved schiff base dialdehyde cellulose-chitosan hydrogels for sustained drug release with DFT calculations

IF 4.3 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

BMC Chemistry Pub Date : 2025-05-02 DOI:10.1186/s13065-025-01469-3

Hebat-Allah S. Tohamy

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Abstract

Dialdehyde cellulose (DAC) prepared from sugarcane bagasse (SC) by an eco-friendly, fast and low-cost microwave method was used for loading and sustained release of 4-aminoacetophenone (4-AAP). DAC was reacted with chitosan (Ch) and 4-AAP via a Schiff base reaction. FTIR analysis confirmed successful Schiff base formation between DAC and Ch, evidenced by the disappearance of the DAC aldehyde peak at 1716 cm⁻¹ and the appearance of the imine peak at 1631 cm⁻¹, as well as strong hydrogen bonding with incorporated 4-AAP, indicated by a shift in the O–H stretch from 3336 cm⁻¹ to 3330 cm⁻¹.Swelling studies showed increased water absorption with higher 4-AAP content, with 4-AAP@DAC/Ch2 demonstrating pseudo-second-order kinetics and non-Fickian diffusion. The DFT calculations revealed that the 4-AAP@DAC/Ch hydrogel exhibited enhanced stability and reactivity. A significantly reduced HOMO–LUMO energy gap, coupled with negative Pi values, indicated strong interactions between DAC, chitosan, and 4-AAP. The high adsorption energy further supported the observed slow drug release, validating the experimental findings.

Graphical Abstract

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微波希夫碱双醛纤维素-壳聚糖水凝胶缓释用DFT计算

以蔗渣（SC）为原料，采用环保、快速、低成本的微波法制备双醛纤维素（DAC），用于4-氨基苯乙酮（4-AAP）的负载和缓释。DAC与壳聚糖（Ch）和4-AAP通过希夫碱反应反应。FTIR分析证实了DAC和Ch之间成功的席夫碱形成，在1716厘米毒发展时，DAC醛峰消失，而在1631厘米毒发展时，亚胺峰出现，并且与4-AAP形成了强氢键，O-H从3336厘米毒发展到3330厘米毒发展。溶胀研究表明，随着4-AAP含量的增加，吸水率增加，4-AAP@DAC/Ch2表现出伪二级动力学和非菲克扩散。DFT计算表明，4-AAP@DAC/Ch水凝胶表现出增强的稳定性和反应性。显著减小的HOMO-LUMO能隙，加上负Pi值，表明DAC、壳聚糖和4-AAP之间存在强烈的相互作用。高吸附能进一步支持了所观察到的药物缓慢释放，验证了实验结果。图形抽象

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来源期刊

BMC Chemistry Chemistry-General Chemistry

CiteScore

5.30

自引率

2.20%

发文量

审稿时长

27 weeks

期刊介绍： BMC Chemistry, formerly known as Chemistry Central Journal, is now part of the BMC series journals family. Chemistry Central Journal has served the chemistry community as a trusted open access resource for more than 10 years – and we are delighted to announce the next step on its journey. In January 2019 the journal has been renamed BMC Chemistry and now strengthens the BMC series footprint in the physical sciences by publishing quality articles and by pushing the boundaries of open chemistry.