Pyridine catalyzed acylation of electrospun chitosan membranes by C6-C12 acyl chlorides: Effect of reaction time and chain length
Pyridine catalyzed acylation of electrospun chitosan membranes by C6-C12 acyl chlorides: Effect of reaction time and chain length
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DOI：
10.1016/j.carpta.2024.100443
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发表时间：
2024-02-02
影响因子：
5.5
通讯作者：
Jennings，Jessica Amber
中科院分区：
文献类型：
--
作者：
Yeasmin，Rabeta;Abuhussein，Ezzuddin;Jennings，Jessica Amber
通过静电纺丝制造的壳聚糖纳米纤维膜由于其增加的表面积而对药物输送应用具有吸引力。纺丝纤维含有三氟乙酸盐（TFA），这种盐在生理溶液中会引起纳米纤维结构的膨胀和丧失，并且具有细胞毒性。本文报道了一种静电纺丝后处理方法，使用脂肪酰基氯化物和吡啶对具有不同酰基链长度（C6, C8， C10和C12）的膜进行o -酰基化。与酰氯在碱性环境下分别进行2、3、4、5小时的o酰化反应。采用FTIR、NMR、接触角、XPS和SEM等多种理化表征技术对酰基链长和反应时间的影响进行了评价。酰基化纳米纤维表现出疏水性，并允许在不损害纳米纤维结构的情况下去除细胞毒性TFA盐。纤维直径随着取代酰基链长度的增加而增加。当反应时间较长时，酰基链的取代度没有明显变化，表明反应在2小时内完成。这可能允许更快地修饰膜，以潜在地应用于疏水药物的输送。
Chitosan nanofiber membranes manufactured via electrospinning are attractive for drug delivery applications due to their increased surface area. The as-spun fibers contain trifluoroacetate (TFA)-salts that cause swelling and loss of nanofiber structure in physiological solutions and are cytotoxic. Here, a post-electrospinning treatment has been reported using fatty acyl chlorides and pyridine to O-acylate the membranes with different acyl chain-length (C6, C8, C10, and C12). The O-acylation reactions were carried out with acyl chlorides in a basic environment for 2 hr, 3 hr, 4 hr and, 5 hr. The effects of the acyl chain length and the reaction time were assessed using various physio-chemical characterization techniques including FTIR, NMR, Contact Angle, XPS, and SEM. The acylated nanofibers displayed hydrophobic properties and allowed the removal of the cytotoxic TFA salts without compromising the nanofibrous structure. The fiber diameter increased with the increasing length of the substituted acyl chain. The degree of substitution of the acyl chains did not change significantly when reacted for a longer period indicating the completion of the reaction within 2 hr. This could allow the faster modification of the membranes for potential application in the delivery of hydrophobic drugs.