Indole, Phenyl, and Phenol Groups: The Role of the Comonomer on Gene Delivery in Guanidinium Containing Methacrylamide Terpolymers,Macromolecular Rapid Communications

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Indole, Phenyl, and Phenol Groups: The Role of the Comonomer on Gene Delivery in Guanidinium Containing Methacrylamide Terpolymers
Macromolecular Rapid Communications ( IF 4.2 ) Pub Date : 2020-12-04 , DOI: 10.1002/marc.202000580
Franz J Hack ₁ , Ceren Cokca ₂ , Sebastian Städter ₂ , Juliana Hülsmann ₁ , Kalina Peneva _{2,

3} , Dagmar Fischer ₁

Affiliation

This report highlights the importance of hydrophobic groups mimicking the side chains of aromatic amino acids, which are tryptophan, phenylalanine, and tyrosine, in guanidinium bearing poly(methacrylamide)s for the design of non‐viral gene delivery agents. Guanidinium containing methacrylamide terpolymers are prepared by aqueous reversible addition–fragmentation chain transfer (aRAFT) polymerization with different hydrophobic monomers, N‐(2‐indolethyl)methacrylamide (IEMA), N‐phenethylmethacrylamide (PhEMA), or N‐(4‐hydroxyphenethyl)methacrylamide (PhOHEMA) by aiming similar contents. The well‐defined polymers are obtained with a molar mass of ≈15 000 g mol⁻¹ and ≈1.1 dispersity. All terpolymers demonstrate almost comparable in vitro cell viability and hemocompatibility profiles independent of the type of side chain. Although they all form positively charged, enzymatically stable polyplexes with plasmid DNA smaller than 200 nm, the incorporation of the IEMA monomer improve these parameters by demonstrating a higher DNA binding affinity and forming nanoassemblies of about 100 nm. These physicochemical characteristics are correlated with increased transfection rates in CHO‐K1 cells dependent on the type of the monomer and the nitrogen to phosphate (N/P) ratio of the polyplexes, as determined by luciferase reporter gene assays.

中文翻译：

吲哚，苯基和酚基团：共聚单体在含胍基甲基丙烯酰胺三元共聚物的基因传递中的作用

本报告强调了在带有胍基的聚（甲基丙烯酰胺）中，模仿芳香族氨基酸（色氨酸，苯丙氨酸和酪氨酸）的芳香族氨基酸侧链的疏水基团对于设计非病毒基因传递剂的重要性。含有甲基丙烯酰胺的三元共聚物胍是通过水性可逆加成-断裂链转移（其制备一个RAFT）聚合具有不同疏水性单体，Ñ（2- indolethyl）甲基丙烯酰胺（IEMA）， - ñ -phenethylmethacrylamide（PHEMA），或ñ - （4-羟基苯）异丁烯酰胺（PhOHEMA）的目标相似。得到的定义明确的聚合物的摩尔质量为≈15000g mol ^-1分散度约为1.1。所有三元共聚物均显示出几乎可比的体外细胞生存力和血液相容性谱，而与侧链的类型无关。尽管它们都与小于200 nm的质粒DNA一起形成带电的酶稳定多聚体，但IEMA单体的掺入却表现出更高的DNA结合亲和力并形成了约100 nm的纳米组件，从而改善了这些参数。这些理化特性与CHO-K1细胞中转染率的提高有关，取决于依赖于单体类型和多聚体的氮磷比（N / P）的荧光素酶报告基因测定，CHO-K1细胞的转染率增加。

更新日期：2020-12-04

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