Poly(Acryloyl-l-Serine): A Reactive Polypeptide to Introduce Zwitterion and Amphiphilicity for Stimuli-Responsiveness and Gelability,Macromolecules

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Poly(Acryloyl-l-Serine): A Reactive Polypeptide to Introduce Zwitterion and Amphiphilicity for Stimuli-Responsiveness and Gelability
Macromolecules ( IF 5.1 ) Pub Date : 2024-02-16 , DOI: 10.1021/acs.macromol.3c02313
Priyanka Dinda ₁ , Joy Das ₁ , Mahammad Anas ₁ , Tarun K. Mandal ₁

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The rising development in the field of synthetic-functionalized polypeptides aids in the generation of advanced biomaterials comprising versatile functionalities, enabling them to be potential candidates for their progressive applications in different areas. Thus, in this work, the ring-opening polymerization (ROP) of a designed acryloyl-l-serine N-carboxyanhydride (SerA NCA) monomer is conducted to produce side-chain acryloyl-functionalized poly(acryloyl-l-serine) [P(AcSer)] for its facile and selective functionalization to introduce zwitterionic and amphiphilic groups for stimuli-responsiveness as well as gelability via Michael addition and radical polymerization. The postfunctionalization of P(AcSer) with l-cysteine (Cys) leads to the formation of the zwitterionic polypeptide, P(AcSer)-g-Cys, which has an isoelectric point (pI) of 2.7. Near the pI, the aqueous P(AcSer)-g-Cys solution exhibits pH-responsiveness (pH ranges of 2.2–4.1), transforming the transparent solution to a cloudy suspension containing insoluble hierarchical nanoaggregates of various dendritic morphologies. Notably, this cloudy suspension undergoes a upper critical solution temperature (UCST)-type phase transition with tunable cloud points, transforming it into a clear solution upon heating. The addition of triethylene glycol monomethyl ether thiol (MTEG-SH) to P(AcSer) produces amphiphilic P(AcSer)-g-MTEG, which forms vesicular nanoassemblies in water and is capable of encapsulating hydrophobic Nile red (NR) dye present in water. Apart from that, grafting of MTEG moiety introduces lower critical solution temperature (LCST) property to P(AcSer)-g-MTEG in water. Thiol-based cross-linkers and ionic-liquid-based cationic cross-linker are employed for the gelation of acryl-functionalized P(AcSer). The obtained polypeptide gel materials exhibit excellent swelling behaviors in organic/aqueous media. Additionally, the cationic polypeptide gel shows profound dye adsorption capacity under exposure to the aqueous solution of eosin B and sulfasalazine.

中文翻译：

聚（丙烯酰-L-丝氨酸）：一种引入两性离子和两亲性的反应性多肽，以实现刺激响应性和凝胶性

合成功能化多肽领域的不断发展有助于产生具有多种功能的先进生物材料，使它们成为在不同领域逐步应用的潜在候选者。因此，在这项工作中，对设计的丙烯酰-L-丝氨酸N-羧酸酐（SerA NCA）单体进行开环聚合（ROP），以产生侧链丙烯酰基功能化的聚（丙烯酰-L-丝氨酸）[P (AcSer)]因其易于和选择性的官能化来引入两性离子和两亲基团，以通过迈克尔加成和自由基聚合来实现刺激响应性以及胶凝性。P(AcSer) 与l -半胱氨酸 (Cys)的后官能化导致形成两性离子多肽 P(AcSer)-g -Cys，其等电点 ( pI ) 为 2.7。在等电点附近，P(AcSer)-g - Cys水溶液表现出 pH 响应性（pH 范围为 2.2-4.1），将透明溶液转变为含有各种树枝状形态的不溶性分层纳米聚集体的混浊悬浮液。值得注意的是，这种浑浊的悬浮液经历了具有可调浊点的上临界溶解温度（UCST）型相变，在加热时将其转变为澄清溶液。将三甘醇单甲醚硫醇 (MTEG-SH) 添加到 P(AcSer) 中会产生两亲性 P(AcSer)- g -MTEG，它在水中形成囊状纳米组装体，并且能够封装水中存在的疏水性尼罗红 (NR) 染料。除此之外，MTEG部分的接枝为P(AcSer)-g-MTEG在水中引入了较低的临界溶解温度(LCST)特性。硫醇基交联剂和离子液体基阳离子交联剂用于丙烯酸官能化 P(AcSer) 的凝胶化。所得多肽凝胶材料在有机/水介质中表现出优异的溶胀行为。此外，阳离子多肽凝胶在暴露于曙红B和柳氮磺吡啶的水溶液下显示出深厚的染料吸附能力。

更新日期：2024-02-16

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