Synthesis of Poly(acyclic orthoester)s: Acid‐Sensitive Biomaterials for Enhancing Immune Responses of Protein Vaccine

Xing Yumeng; Xu Zunkai; Liu Tao; Shi Linqi; Kohane Daniel; Guo Shutao

摘要

Abstract > While poly(acyclic orthoester)s (PAOEs) have many appealing features for drug delivery, their application is significantly hindered by a lack of facile synthetic methods. Reported here is a simple method for synthesizing acyclic diketene acetal monomers from diols and vinyl ether, and their polymerization with a diol to first synthesize PAOEs. The PAOEs rapidly hydrolyze at lysosomal pH. With the help of a cationic lipid, ovalbumin, a model vaccine antigen was efficiently loaded into PAOEs nanoparticles using a double emulsion method. These nanoparticles efficiently delivered ovalbumin into the cytosol of dendritic cells and demonstrated enhanced antigen presentation over poly(lactic‐ co ‐glycolic acid) (PLGA) nanoparticles. PAOEs are promising vehicles for intracellular delivery of biopharmaceuticals and could increase the utility of poly(orthoesters) in biomedical research. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > 虽然聚（无环Orthoester）（Paoes）具有许多吸引药物递送的吸引力，但它们的应用是由于缺乏容易的合成方法而显着阻碍。这里报道的是一种简单的方法，用于将来自二醇和乙烯基醚的无环二酮缩醛单体合成，以及它们与二醇的聚合以首先合成可选。可在溶酶体pH下快速水解。借助阳离子脂质，卵磷蛋白，使用双乳法有效地将模型疫苗抗原有效地装载到Paina纳米颗粒中。这些纳米颗粒有效地递送到树突细胞的细胞溶溶胶中，并证明了聚（乳酸）的增强抗原呈递 co </ i> - 乙醇酸）（PLGA）纳米颗粒。 Paoes是用于细胞内递送生物制药的有前途的车辆，并且可以增加聚（矫形器）在生物医学研究中的效用。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第18期</span><b style="margin: 0 2px;">|</b><span>共5页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xing Yumeng&option=202" target="_blank" rel="nofollow">Xing Yumeng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xu Zunkai&option=202" target="_blank" rel="nofollow">Xu Zunkai;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Tao&option=202" target="_blank" rel="nofollow">Liu Tao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Shi Linqi&option=202" target="_blank" rel="nofollow">Shi Linqi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kohane Daniel&option=202" target="_blank" rel="nofollow">Kohane Daniel;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Guo Shutao&option=202" target="_blank" rel="nofollow">Guo Shutao;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Key Laboratory of Functional Polymer Materials of Ministry of EducationNankai UniversityTianjin 300071 China;</p> <p>Key Laboratory of Functional Polymer Materials of Ministry of EducationNankai UniversityTianjin 300071 China;</p> <p>Key Laboratory of Functional Polymer Materials of Ministry of EducationNankai UniversityTianjin 300071 China;</p> <p>Key Laboratory of Functional Polymer Materials of Ministry of EducationNankai UniversityTianjin 300071 China;</p> <p>Laboratory for Biomaterials and Drug DeliveryHarvard Medical School300 Longwood Avenue Boston MA 02115 USA;</p> <p>Key Laboratory of Functional Polymer Materials of Ministry of EducationNankai UniversityTianjin 300071 China;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=biomaterials&option=203" rel="nofollow">biomaterials;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=drug delivery&option=203" rel="nofollow">drug delivery;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=esters&option=203" rel="nofollow">esters;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nanoparticles&option=203" rel="nofollow">nanoparticles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polymers&option=203" rel="nofollow">polymers;</a> </p> <div class="translation"> 机译：生物材料;药物递送;酯;纳米颗粒;聚合物; 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=谭天伟&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,谭天伟</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=翁靖一&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,翁靖一</a> <span> <a href="/journal-cn-56821/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 现代化工 </a> </span> <span> . 2008</span><span>,第S2期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-27142_thesis/020221766331.html">聚丁二酸丁二酯/聚丁二酸丙二酯共聚物的合成与结晶性能研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐永祥&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 徐永祥</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐军&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,徐军</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=孙元碧&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,孙元碧</a> <span> <a href="/conference-cn-27142/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2004全国高分子材料科学与工程研讨会 </a> <span> <span> . 2004</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312429176.html">含磷杂环膦(磷)酸酯的合成与性质研究：1.含磷杂环a-取代烃基膦酸酯的合成及除草活性研究;2.含磷杂环双膦(磷)酸酯的合成及阻燃性能研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=左娜&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 左娜</a> <span> . 2007</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061202324577.html">环胍催化剂法合成聚己二酸丁二醇酯‑共‑对苯二甲酸丁二醇酯的工艺方法</a> <b>[P]</b> . <span> 中国专利： CN104031253B </span> <span> . 2017.02.01</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120102706775.html">环胍催化剂法合成聚己二酸丁二醇酯-共-对苯二甲酸丁二醇酯的工艺方法</a> <b>[P]</b> . <span> 中国专利： CN104031253A </span> <span> . 2014-09-10</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130450889719.html">Altered g protein or rsv polypeptide, use of it, nucleic acid molecule encoding an altered g protein or rsv polypeptide, nucleic acid construction, recombinant host cell, processes of producing an altered g protein or rsv polypeptide immunogenic composition , to induce an immune response in a vertebrate, to inhibit the induction of disease increase after vaccination and subsequent infection of a vertebrate with rsv and to immunize a vertebrate against rsv, vaccine composition, vaccine, and, composition immunogenic</a> <b>[P]</b> . <span> 外国专利：  BR9812240A </span> <span> . 2000-07-18</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：改变的g蛋白或rsv多肽的用途，其用途，编码改变的g蛋白或rsv多肽的核酸分子，核酸构建，重组宿主细胞，产生改变的g蛋白或rsv多肽免疫原性组合物的过程以诱导免疫应答脊椎动物，以抑制在接种和随后感染rsv脊椎动物后诱导疾病增加，并针对rsv，疫苗组合物，疫苗和具有免疫原性的组合物免疫脊椎动物 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130420364154.html">Vaccinal vehicle to induce cellular immune response that includes the encapsulation in lipid vesicles Proteins obtained from the Anemone Stichodactyla helianthus together with an Antigen; composItion comprising the vaccinal vaccinal Vehicle; use of the composition for strengthening of the immune response.</a> <b>[P]</b> . <span> 外国专利：  CL2012003674A1 </span> <span> . 2013-07-12</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：诱导细胞免疫反应的疫苗载体，包括将脂质体封装在脂小泡中，该蛋白质是从葵花海葵Stichodactyla helianthus中获得的，以及一种抗原;包括疫苗疫苗载体的组合物;该组合物用于增强免疫应答的用途。 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130450888314.html">Hmw protein of the isolated chlamydia species, isolated nucleic acid molecule, recombinant expression vector, transformed host cell, isolated recombinant protein or fragment or analog thereof, immunogenic composition, antigenic composition, processes to produce an immune response in an animal, anti- serum, antibodies, diagnostic reagent, to detect anti-chlamydia antibodies in a test sample, to detect the presence of chlamydia in a test sample, to prevent, treat or ameliorate a chlamydia-related disorder in a host in need of this treatment , and to determine the presence of nucleic acid encoding an hmw protein or a fragment or analog thereof in a sample, diagnostic kits to detect antibodies to chlamydia, and to determine the presence of nucleic acid encoding an hmw protein or fragment or analog thereof in a sample, vaccine composition, and pharmaceutical composition The</a> <b>[P]</b> . <span> 外国专利：  BR9813841A </span> <span> . 2000-10-03</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：分离的衣原体物种的Hmw蛋白，分离的核酸分子，重组表达载体，转化的宿主细胞，分离的重组蛋白或其片段或类似物，免疫原性组合物，抗原性组合物，在动物中产生免疫应答的过程，抗血清，抗体，诊断试剂，用于检测测试样品中的衣原体抗体，检测测试样品中的衣原体，预防，治疗或缓解需要此治疗的宿主中的衣原体相关疾病，并确定样品中是否存在编码hmw蛋白或其片段或类似物的核酸，诊断试剂盒以检测针对衣原体的抗体以及确定样品，疫苗组合物中是否存在编码hmw蛋白或其片段或类似物的核酸和药物成分 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028161377','4',7,2,1,'',this,24)" class="delivery" prompt="010401" 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