Sebastian Sharol, Rohila Yajat, Yadav Eqvinshi, Bhardwaj Priya, Sudheer Babu Yangala, Maruthi Mulaka, Ansari Azaj, Gupta Manoj K
Department of Chemistry, School of Basic Sciences, Central University of Haryana, Mahendergarh 123031, Haryana, India.
Department of Biochemistry, School of Interdisciplinary and Applied Sciences, Central University of Haryana, Mahendergarh 123031, Haryana,India.
Biomacromolecules. 2024 Feb 12;25(2):975-989. doi: 10.1021/acs.biomac.3c01074. Epub 2024 Jan 8.
Low-molecular-mass gelators, due to their excellent biocompatibility, low toxicological profile, innate biodegradability and ease of fabrication have garnered significant interest as they self-assemble through non-covalent interactions. In this study, we have designed and synthesized a series of six α-amidoamides by varying the hydrophobic alkyl chain length (C-C), which were well characterized using different spectral techniques. These α-amidoamides formed self-assembled aggregates in a DMSO/water solvent system affording organo/hydrogels at 0.66% w/v, which is the minimum gelation concentration (MGC) making them as remarkable supergelators. The various functionalities present in these gelators such as amides and alkyl chain length pave the way toward excellent gelation mechanism through hydrogen bonding and van der Waals interaction as evidenced from FTIR spectroscopy. Notably, as the chain length increased, organo/hydrogels became more thermally stable. Rheological results showed that the stability and strength of these gelators were considerably impacted by variations in chain length. The SEM morphology revealed dense sheet architectures of the organo/hydrogel samples. Organo/hydrogels have a significant impact on the advancement of innovative drug delivery systems that respond to various stimuli, ushering in a new era in pharmaceutical technology. Inspired by this, we encapsulated curcumin, a chemopreventive medication, into the gel core and further released gel-to-sol transition induced by pH variation at 37 °C, without any alteration in structure-activity relationship. The drug release behavior was observed by UV-vis spectroscopy. Moreover, cell viability and cell invasion experiments demonstrate that the gel formulations exhibit high biocompatibility and low cytotoxicity. Among the tested formulations, exhibited remarkable efficacy in controlling A549 cell migration, suggesting significant potential for applications in the pharmaceutical industry.
低分子量凝胶剂由于其优异的生物相容性、低毒理学特性、固有的生物降解性和易于制备，在通过非共价相互作用进行自组装时引起了极大的关注。在本研究中，我们通过改变疏水烷基链长度（C-C）设计并合成了一系列六种α-酰胺基酰胺，并使用不同的光谱技术对其进行了充分表征。这些α-酰胺基酰胺在二甲基亚砜/水溶剂体系中形成自组装聚集体，在0.66% w/v时形成有机/水凝胶，这是最低凝胶化浓度（MGC），使其成为卓越的超级凝胶剂。这些凝胶剂中存在的各种官能团，如酰胺和烷基链长度，通过氢键和范德华相互作用为优异的凝胶化机制铺平了道路，傅里叶变换红外光谱证实了这一点。值得注意的是，随着链长度的增加，有机/水凝胶变得更热稳定。流变学结果表明，这些凝胶剂的稳定性和强度受到链长度变化的显著影响。扫描电子显微镜形态显示了有机/水凝胶样品的致密片状结构。有机/水凝胶对响应各种刺激的创新药物递送系统的发展具有重大影响，开创了制药技术的新纪元。受此启发，我们将一种化学预防药物姜黄素封装到凝胶核心中，并在37℃下通过pH变化诱导凝胶到溶胶的转变进一步释放，而结构-活性关系没有任何改变。通过紫外-可见光谱观察药物释放行为。此外，细胞活力和细胞侵袭实验表明，凝胶制剂表现出高生物相容性和低细胞毒性。在测试的制剂中，在控制A549细胞迁移方面表现出显著疗效，表明在制药行业具有巨大的应用潜力。
