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Selective O-Alkylation of 2,2′-Bis(hydroxymethyl)propionic Acid to Synthesize Biodegradable Polymers for Drug Delivery Applications
ACS Applied Polymer Materials ( IF 4.4 ) Pub Date : 2020-07-02 , DOI: 10.1021/acsapm.0c00509
Santimukul Santra 1 , Zachary Shaw 1 , Raghunath Narayanam 1 , Vedant Jain 1 , Tuhina Banerjee 1
Affiliation  

A facile synthetic approach to the selective mono- and di-O-alkylation of a β,β-disubstituted hydroxy compound has been demonstrated and applied to the field of polymer chemistry and drug delivery. 2,2′-Bis(hydroxymethyl) propionic acid (bis-MPA) is a β,β-disubstituted hydroxy compound with one carboxylic acid group (AB2 system); therefore, it is a very important starting material in the synthesis of functional aliphatic macromolecules. The etherification (O-alkylation) of bis-MPA was successful with different alkyl functionalities using this facile approach, where 1,4-diazabicyclo [2.2.2] octane was used as a catalyst. This method successfully prevented the reported internal cyclization of bis-MPA, allowing for selective functionalization. Mono- and di-O-alkylated bis-MPA were synthesized selectively in high yields by controlling the equivalent ratio of the reactants and reaction time. Nonuniform bifunctional O-alkylated bis-MPA with different alkyl halides were prepared using the same reaction conditions and have been used for the synthesis of functional polyester polymers. Postsurface functionalization by the means of bromination was demonstrated on the allyl-functionalized linear polyester. All the compounds were characterized by 1H and 13C Nuclear Magnetic Resonance, Fourier transform infrared, thermogravimetric analysis, differential scanning calorimetry, size exclusion chromatography, and electrospray and matrix-assisted laser desorption/ionization–time of flight mass spectroscopic techniques. The synthesized functional polyester polymer was able to formulate stable polymeric nanoparticles using the solvent diffusion method and encapsulate therapeutic drug doxorubicin with higher encapsulation efficiency (EEDoxo = 71%). This facile synthetic approach of O-alkylation provides direction for the synthesis of bis-MPA-based functional linear and dendritic macromolecules for drug delivery and other biomedical applications.

中文翻译:

2,2'-双(羟甲基)丙酸的选择性O-烷基化反应以合成可生物降解的聚合物,用于药物递送应用

已经证明了一种用于β,β-二取代羟基化合物的选择性单-和二-O-烷基化的简便合成方法,并将其应用于聚合物化学和药物递送领域。2,2'-双(羟甲基)丙酸(bis-MPA)是具有一个羧基的β,β-二取代羟基化合物(AB 2系统); 因此,它是功能性脂肪族大分子合成中非常重要的起始原料。使用这种简便的方法,使用1,4-二氮杂双环[2.2.2]辛烷作为催化剂,可在具有不同烷基官能度的情况下成功完成bis-MPA的醚化(O-烷基化)。该方法成功地阻止了报道的bis-MPA内部环化,从而实现了选择性功能化。通过控制反应物的当量比和反应时间,高产率选择性地合成了单-和二-O-烷基化的双-MPA。使用相同的反应条件制备具有不同烷基卤化物的不均匀的双官能O-烷基化双-MPA,并已用于合成功能聚酯聚合物。在烯丙基官能化的线性聚酯上证明了通过溴化的表面后官能化。所有化合物的特征是1 H和13 C核磁共振,傅立叶变换红外,热重分析,差示扫描量热法,尺寸排阻色谱法以及电喷雾和基质辅助激光解吸/电离-飞行时间质谱技术。合成的功能聚酯聚合物能够使用溶剂扩散法配制稳定的聚合物纳米颗粒,并以更高的包封效率(EE Doxo = 71%)包封治疗药物阿霉素。这种简便的O-烷基化合成方法为合成基于bis-MPA的功能性线性和树枝状大分子提供了方向,以用于药物输送和其他生物医学应用。
更新日期:2020-08-14
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