Name: methionine functionalized biocompatible block copolymers for targeted plasmid dna delivery
Uploaded: 2019-08-06T12:30:00
Description: Watch this Scientific Journal Video about Methionine Functionalized Biocompatible Block Copolymers for Targeted Plasmid DNA Delivery at JoVE.com

这项研究得到了国家重点研究发展计划(2016YFC0905900号)、国家自然科学基金(第81801827号、81872365号)、江苏省基础研究计划(自然科学基金,No.BK20181086)和江苏省肿瘤医院科研基金(No.ZK201605)。

1. BNHEMA聚合物(PBNHEMA)的合成
<ol><li>将1.87克N、N-之二(2-羟乙酰)甲酰胺(BNHEMA)溶解在聚合瓶中1mL的蒸馏水中。 注:聚合瓶是一个圆底烧瓶,带有橡胶塞和磁搅拌器。</li>
	<li>在 5 mL 烧杯中溶解 0.03 g 的 4-氰化二苯甲酸二硫苯甲酸 (CTP) 和 0.02 g 的 4,4' - 亚祖酸 (4-青酸 ) (ACVA) 中 0.5 mL 的 1,4-二恶烷。然后,将 CTP 和 ACVA 溶液从步骤 1.1 添加到聚合瓶中。</li>
	<li>通过三个冷冻泵-解冻循环,用氮气?...

<ol>
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本研究介绍了一系列BNHEMA-b-APMA块状聚合物阳离子基因载体。这些块状聚合物是通过可逆的添加-碎片链转移(RAFT)方法合成的。引入亲水段BNHEMA以提高溶解度。对美氨酸和瓜尼丁组进行了改造,以提高靶能力和转染效率5.MBG共聚物中的APMA链含量增加,核化减少了mBG/pDNA聚体颗粒尺寸。颗粒大小和表面电位使复合物易于穿过细胞膜,适用于转染。实验的关键在于严格控制BNHEMA单体和CTP的摩...

近年来,基因疗法已出现以核酸的治疗性输送为治疗各种疾病的药物。包括质粒DNA(pDNA)和小干扰RNA(siRNA)在内的基因药物的开发依赖于药物输送系统(DDS)2的稳定性和效率。在所有DDS中,阳离子聚合物载体具有稳定性好、免疫原性低、易制制剂和改性等优点,使阳离子聚合物载体具有广阔的应用前景。为了在生物医学中的实际应用,研究人员必须找到一种高效、低毒性、具有良好的靶向能力的阳离子聚合物载体。在所有聚合物载体中,块共聚物是使用最广泛的药物输送系统之一。块共聚物被深入研究,因为它们的自组装特性和在药物输送中形成云母、微球和纳米粒子的能力5。块共聚物可以通过活聚合或点击化学方法合成。
1956年,Szwarc等人提出了活聚合的课题,将其定义为无链断裂反应的6,7。从那时起,已经开发出多种技术,用这种方法合成聚合物;因此,活聚合被认为是聚合物科学的一个里程碑。活聚合可分为活阴离子聚合、活阳离子聚合和可逆失活基聚合(RDRP)9。活阴离子/阳离子聚合具有有限的应用范围,由于其严格的反应条件10。受控/活基聚合(CRP)反应条件温和,处置方便,产量好,是近年来的主要研究重点。在CRP中,活性传播链可逆钝化为休眠链,以降低自由基的浓度,避免传播链基的双分子反应。只有当非活性休眠传播链可逆地动画化为链基时,添加聚合才能继续。可逆添加-裂变链转移(RAFT)聚合作为最有前途的活基聚合形式之一,是一种适用于分子量和结构可控、分子量窄的块状聚合物的屈服方法。分布,并携带功能组12。成功进行RAFT聚合的关键是链转移剂(通常是二硫酯)的作用,后者具有非常高的链传递常数。
本文设计了一种RAFT聚合法,制备BNHEMA-b-APMA块状聚合物,以4,4'-亚索比(4-青黄酸)(ACVA)作为起始剂,4-氰化二苯甲酸二硫苯甲酸(CTP)作为链转移剂。RAFT聚合被两次用于将BNHEMA引入阳离子聚合物载体。随后,用甲胺磷和甲胺酰胺试剂1-酰胺盐酸基苯甲酸酯对APMA链中的胺组进行了修饰。利用关尼酰胺试剂和甲酰胺聚合物骨架结构的正电荷,提高了所得块状聚合物载体的细胞吸收效率。

<table>
<tbody>
<tr>
<td>1-hydroxybenzotriazole</td>
<td>Macklin Biochemical Co., Ltd,China</td>
<td>H810970</td>
<td>&ge;97.0%</td>
</tr>
<tr>
<td>1,4-dioxane</td>
<td>Sinopharm chemical reagent Co., Ltd, China</td>
<td>10008918</td>
<td>AR</td>
</tr>
<tr>
<td>1-amidinopyrazole Hydrochloride</td>
<td>Aladdin Co., Ltd., China</td>
<td>A107935</td>
<td>98%</td>
</tr>
<tr>
<td>1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride</td>
<td>Aladdin Co., Ltd., China</td>
<td>E106172</td>
<td>AR</td>
</tr>
<tr>
<td>4,4&#x2019;-azobis(4-cyanovaleric acid)</td>
<td>Aladdin Co., Ltd., China</td>
<td>A106307</td>
<td>Analytical reagent (AR)</td>
</tr>
<tr>
<td>4-cyano-4-(phenylcarbonothioylthio)pentanoic Acid</td>
<td>Aladdin Co., Ltd., China</td>
<td>C132316</td>
<td>&#x003E;97%(HPLC)</td>
</tr>
<tr>
<td>Acetate</td>
<td>Sinopharm chemical reagent Co., Ltd, China</td>
<td>81014818</td>
<td>AR</td>
</tr>
<tr>
<td>Acetone</td>
<td>Sinopharm chemical reagent Co., Ltd, China</td>
<td>10000418</td>
<td>AR</td>
</tr>
<tr>
<td>Agarose</td>
<td>Aladdin Co., Ltd., China</td>
<td>A118881</td>
<td>High resolution</td>
</tr>
<tr>
<td>Ascorbic acid</td>
<td>Aladdin Co., Ltd., China</td>
<td>A103533</td>
<td>AR</td>
</tr>
<tr>
<td>DMSO</td>
<td>Aladdin Co., Ltd., China</td>
<td>D103272</td>
<td>AR</td>
</tr>
<tr>
<td>Ethylene glycol</td>
<td>Aladdin Co., Ltd., China</td>
<td>E103319</td>
<td>AR</td>
</tr>
<tr>
<td>N-(3-aminopropyl)methacrylamide hydrochloride</td>
<td>Aladdin Co., Ltd., China</td>
<td>N129096</td>
<td>&ge;98.0%(HPLC)</td>
</tr>
<tr>
<td>N,N-bis(2-hydroxyethyl)methacrylamide</td>
<td>ZaiQi Bio-Tech Co.,Ltd, China</td>
<td>CF259748</td>
<td>&ge;98.0%(HPLC)</td>
</tr>
<tr>
<td>Ninhydrin</td>
<td>Aladdin Co., Ltd., China</td>
<td>N105629</td>
<td>AR</td>
</tr>
<tr>
<td>PBS buffer</td>
<td>Aladdin Co., Ltd., China</td>
<td>P196986</td>
<td>pH 7.4</td>
</tr>
<tr>
<td>Plasmid DNA</td>
<td>BIOGOT Co., Ltd, China</td>
<td>pDNA-EGFP</td>
<td>pDNA-EGFP</td>
</tr>
<tr>
<td>Plasmid DNA</td>
<td>BIOGOT Co., Ltd, China</td>
<td>Pdna</td>
<td>pDNA</td>
</tr>
<tr>
<td>Sodium carbonate decahydrate</td>
<td>Aladdin Co., Ltd., China</td>
<td>S112589</td>
<td>AR</td>
</tr>
<tr>
<td>Trimethylamine</td>
<td>Aladdin Co., Ltd., China</td>
<td>T103285</td>
<td>AR</td>
</tr>
</tbody>
</table>

methionine functionalized biocompatible block copolymers for targeted plasmid dna delivery

可逆添加-碎片链转移(RAFT)聚合融合了基聚合和活聚合的优点。本作品介绍了通过RAFT聚合制备蛋氨酸功能化生物相容性块共聚物。首先,N,N-二乙二醇(2-羟基苯甲酸酯)甲酰胺-b-N-(3-氨基丙烯酰胺)甲酰胺(BNHEMA-b-APMA,BA)通过RAFT聚合合成,使用4,4'-亚索比(4-青黄酸)(ACVA)作为启动剂和4-氰化二苯甲酸二甲苯甲酸(CTP)作为链转移剂。随后,N,N-bis(2-羟基)甲酰胺-b-N-(3-关尼诺丙基)甲酰胺(美聚氨酸嫁接BNHEMA-b-GPMA,mBG)通过用甲胺和瓜尼丁修饰APMA中的胺组制备组。合成了三种块状聚合物,mBG1、mBG2和mBG3进行比较。使用宁西林反应来量化APMA含量;mBG1、mBG2 和 mBG3 分别占 APMA 的 21%、37% 和 52%。凝胶渗透色谱(GPC)结果表明,BA共聚物的分子量为16,200(BA1)、20,900(BA2)和27,200(BA3)克/摩尔。研究了获得块共聚物基因载体的质粒DNA(pDNA)复合能力。当pDNA分别与mBG1、mBG2、mBG3完全复合时,电荷比(N/P)为8、16和4。当mBG/pDNA多聚体N/P比高于1时,mBG的Zeta电位为正。在 16 和 32 之间的 N/P 比率下,mBG/pDNA 聚丛的平均颗粒大小在 100-200 nm 之间。总体而言,这项工作说明了块共聚载体合成的简单和方便的方案。

根据表1所示的聚合目标程度喂食BNHEMA;mBG的合成过程如图1所示。 首先,利用四环烷酸二硫二甲苯二甲酸作为链转移剂,在水二恶烷系统中采用可逆添加-碎片链转移(RAFT)方法制备BNHEMA同质聚酯。其次,PBNHEMA作为链转移剂,制备BNHEMA-b-APMA块聚合物。APMA单体根据表1所示的聚合目标程度进行喂食。进行了凝胶渗透色谱(GPC),以检测不同进给比的BA分子量(<s...

Watch this Scientific Journal Video about Methionine Functionalized Biocompatible Block Copolymers for Targeted Plasmid DNA Delivery at JoVE.com

Methionine Functionalized Biocompatible Block Copolymers for Targeted Plasmid DNA Delivery

本作品通过可逆添加-碎片链转移(RAFT)方法介绍了蛋氨酸功能化生物相容性块共聚物(mBG)的制备。研究了获得mBG的质粒DNA复合能力及其转染效率。RAFT方法对聚合含有特殊功能组的单体非常有益。

用于靶向质粒DNA输送的美聚氨酸功能化生物相容性块共聚物

Reversible addition-fragmentation chain transfer (RAFT) polymerization integrates the advantages of radical polymerization and living polymerization. This ...

Cationic聚合物药物载体具有稳定性好、免疫原性低、制备和改性简单等优点。在这里，我们提供了一个快速和简单的方法，其合成。可逆添加-碎片链转移聚合法是一种适用于具有受控分子量和结构及携带功能群的组块聚合物的方法。这些药物携带者可以同时携带不同的药物，以实现癌症、炎症和其他疾病的协作治疗。IFT聚合是一种经典方法，该协议给出了它在基因治疗中应用的例子。这种聚合物合成成功的关键是精确控制反应温度。使用油浴比水浴更可取。要开始此过程，请获得带橡胶塞和磁力搅拌器的圆底烧瓶作为聚合瓶。将1.87克双羟基 HEMA 溶解在聚合瓶中一毫升蒸馏水中。在五毫升烧杯中，将 0.03 克 CTP 和 0.02 克 ACVA 溶解在 0.5 毫升 1、4-二氧烷中。将此混合物加入聚合瓶。然后，使用冷凝水疏水阀将溶液冻结在聚合瓶中。将瓶子固定到铁支撑上，并使用用针头跳闸的导管吸尘并注入反应混合物中的氮气。然后，密封聚合瓶，并在室温下解冻溶液30分钟。重复此冻结泵解冻循环三次。在此之后，将瓶子放入70摄氏度的油浴中，让溶液在氮气下24小时反应。第二天，在零摄氏度下冷却聚合瓶，打开橡胶塞，以终止聚合反应。接下来，在负20摄氏度的冰箱中预冷丙酮两小时，以50比1的比例与聚合瓶中的反应溶液混合。将混合物在8，200倍g下离心10分钟，以去除丙酮并收集沉淀物。为了净化合成的多双羟基 HEMA，将收集的沉淀物溶解在两毫升的纯水中。然后，以 1 比 50 的比例与 100 毫升预冷丙酮混合。将溶液在8，200倍g下离心10分钟，收集沉淀物。重复溶解、混合和离心沉淀物的净化过程三次。首先，在5毫升蒸馏水中溶解0.96克APMA和0.93克纯化聚双羟基水马。将 0.01 克 ACVA 溶解在 0.5 毫升 1，4 二恶烷中，并将其添加到 APMA 和聚双羟基 HEMA 溶液中。将混合物转移到聚合瓶中，用干氮气通风一小时。然后，将聚合瓶放入70摄氏度的油浴中，让它在氮气下24小时反应。第二天，在零摄氏度下冷却聚合瓶，打开橡胶塞，终止聚合工艺溶液。首先，将MCF-7细胞以每井2万个细胞的密度将MCF-7细胞播种到六井板的井中。在37摄氏度的加湿培养箱中培养细胞，用5%的二氧化碳培养细胞12小时。在此之后，用含有阳离子聚合物和pDNA多丛的新鲜培养基代替不同氮磷比的培养基。培养细胞6小时，然后用两毫升新鲜RPMI 1640培养基取代培养基。继续培养48小时。然后，收集细胞，并使用流动细胞计检测绿色荧光。本研究通过可逆添加-碎片链转移法，对获得mBG的质粒DNA复合能力及其转染效率进行了调查，mBG/pDNA聚丙烯的平均粒径和泽塔电位分别是124纳米和15.7毫伏，N-P比为16。电泳迟钝显示，N-P比为零的pDNA可以在加糖凝胶中不受约束地移动，并观察为凝胶成像器中的条纹。当pDNA与mBG复合时，pDNA的运动会迟钝，随后，频带的亮度会降低。这表明当N到P高于4时，mBG可以完全使pDNA变得复杂。然后使用标准 MTT 测定测量 mBG/pDNA 聚丛的细胞毒性。这些结果表明，mBG/pDNA 聚丛的细胞毒性比 PEI/pDNA 多面体具有 4、8、16 和 32 的 N-P- P- P 比。同样可以看到，mBG/pDNA聚丙烯的细胞毒性随着N-P比的增加而增加。这种增加的细胞毒性是带正充电的GPMA成分的结果。根据细胞毒性结果选择pDNA转染实验中使用的N-P比。通过测量GB荧光强度，比较了mBG1、mBG2和mBG3的转染能力，结果表明mBG3是最佳基因载体。重要的是要排出从淤泥圆底烧瓶中排出的空气，并保持反应温度。获得的聚合物药物载体可应用于化疗药物和基因药物的联运，以协同治疗耐药癌症。进一步探讨基因药物与化疗药物结合的分子机制，治疗耐药肿瘤。丙酮的急性毒性低毒性。应避免使用钥匙、吸入或接触眼睛或皮肤。避免在加热过程中出现烫伤的风险。

Research

JoVE Journal

Chemistry

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

微波辅助分子内Diels-Alder反应的功能化萘/变色染料的合成脱氢

Functionalized naphthalenes have applications in a variety of research fields ranging from the synthesis of natural or biologically active molecules to ...

科研

化学

Synthesis and Characterization of Functionalized Metal-organic Frameworks

功能化的合成与表征金属 - 有机骨架

Metal-organic frameworks have attracted extraordinary amounts of research attention, as they are attractive candidates for numerous industrial and ...

Preparation and Characterization of SDF-1&#945;-Chitosan-Dextran Sulfate Nanoparticles

Preparation and Characterization of SDF-1ÃƒÅ½Ã‚Â±-Chitosan-Dextran Sulfate Nanoparticles

SDF-1α - 壳聚糖硫酸葡聚糖纳米粒子的制备与表征

Chitosan (CS) and dextran sulfate (DS) are charged polysaccharides (glycans), which form polyelectrolyte complex-based nanoparticles when mixed under ...

Functionalization of Single-walled Carbon Nanotubes with Thermo-reversible Block Copolymers and Characterization by Small-angle Neutron Scattering

单壁碳纳米管与热可逆嵌段共聚物及表征功能化小角度中子散射

We demonstrate a protocol for single-walled carbon nanotube functionalization using thermo-sensitive PEO-PPO-PEO triblock copolymers in an aqueous ...

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

从螺旋聚碳化二亚胺共聚物及其三唑衍生物获得自组装形貌

A facile method for the preparation of polycarbodiimide-based secondary structures (e.g., nano-rings, &#34;craters,&#34; fibers, looped fibers, fibrous ...

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

半导体回转金属硫框架结晶的硫醇构建块的合成

We present a method for preparing thioester molecules as the masked form of the thiol linkers and their utilization for accessing a semiconducting and ...

Preparation of Poly(pentafluorophenyl acrylate) Functionalized SiO2 Beads for Protein Purification

Preparation of Polypentafluorophenyl acrylate Functionalized SiO2 Beads for Protein Purification

We demonstrate a simple method to prepare poly(pentafluorophenyl acrylate) (poly(PFPA)) grafted silica beads for antibody immobilization and subsequent ...

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

通过结晶驱动生物降解块共聚物的自组装合成单分散圆柱状纳米粒子

The production of monodisperse cylindrical micelles is a significant challenge in polymer chemistry. Most cylindrical constructs formed from diblock ...

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

功能化单有机硼化合物共轭法高效合成全碳第四纪中心

The conjugate addition of organometallic reagents to &#945;,&#946;-unsaturated carbonyls represents an important method to generate C&#8211;C bonds in the ...