Synthesis of lightly crosslinked zwitterionic polymer‐based bioinspired adhesives for intestinal tissue sealing

Kim Minkyu; Ondrusek Brian A.; Lee Choogon; Douglas Wade G.; Chung Hoyong

摘要

ABSTRACT > In this report, we have developed a new bioinspired medical adhesive capable of providing a leak‐proof barrier for application to intestinal anastomoses. The newly synthesized adhesive is a terpolymer possessing three different repeating units: (1) A zwitterionic polymer, poly(sulfobetaine methacrylate) (polySBMA), for increased hydrophilicity and biocompatibility, (2) a 3,4‐dihydroxy‐L‐phenylalanine (DOPA) segment which contains the catechol group, and (3) poly(ethylene glycol) dimethacrylate (PEGDMA) for light crosslinking, which will be used to strengthen the polymer adhesion properties by providing debonding resistance. The chemical structure of the terpolymer, poly( N ‐methacryloyl‐3,4‐dihydroxyl‐L‐phenylalanine ‐co‐ sulfobetaine methacrylate‐ co ‐poly(ethylene glycol) dimethacrylate) (poly(MDOPA‐ co ‐SBMA‐ co ‐PEGDMA)), synthesized following a convenient and reproducible radical polymerization was clearly confirmed by 1 H NMR. The terpolymer adhesive displayed the optimal adhesion properties when containing 1.5–2.5 mol % of crosslinker, PEGDMA, according to the measured maximum adhesion strength and work of adhesion, characterized by lap shear strength tests utilizing porcine skin. The adhesive did not show cytotoxicity when tested with human embryonic kidney (HEK293A) cells. Ex vivo anastomosis experiments using porcine intestine demonstrated that the new poly(MDOPA‐ co ‐SBMA‐ co ‐PEGDMA) is a promising biomedical adhesive which successfully prevents leakage from the sutured intestinal tissue. ? 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 </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 XMLNS =“http://www.wiley.com/namespaces/wiley”type =“main”> <title类型=“main”>抽象</ title> >在本报告中，我们开发了一个新的Bioinspired医用粘合剂能够为肠吻合术应用提供防漏屏障。新合成的粘合剂是具有三种不同的重复单元的三元共聚物：（1）两性离子聚合物，聚（磺基甲酸甲基丙烯酸酯）（聚合物），用于增加亲水性和生物相容性，（2）A 3,4-二羟基-1-苯丙氨酸（DOPA ）含有儿茶酚基团的细胞和（3）聚（乙二醇）二甲基丙烯酸酯（PEGDMA），用于通过提供脱粘性来加强聚合物粘合性能。三元共聚物的化学结构，聚（ n℃ - 甲基-3,4-二羟基甲基-1-苯丙氨酸 -Co - -</ i>氟甲酸甲基丙烯酸酯 - CO </ i> - 聚氯酸二甲基丙烯酸酯）（聚（MDOPA- <I> CO-S> -SBMA- <I> -PEGDMA），通过< sup> 1 </ sup> h nmr。根据含有1.5-2.5mol％的交联剂，PEGDMA，根据测量的最大粘合强度和粘合性的工作，表征着萜烯聚合物粘合剂，其特征在于利用猪皮的膝盖剪切强度试验。当用人胚胎肾（HEK293A）细胞测试时，粘合剂未显示细胞毒性。前vivo </ i>使用猪肠的吻合术实验证明了新的聚（MDOPA- <I> CO> -SBMA- <I> CO -PEGDMA）是一个有前途的生物医学粘合剂成功地防止缝合肠组织的泄漏。还是2018 Wiley期刊，Inc.J.Colom。 SCI。，A部分：polym。化学。 2018 </ b> </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-35621/'>《Journal of Polymer Science, Part A. Polymer Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第14期</span><b style="margin: 0 2px;">|</b><span>共11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=Kim Minkyu&option=202" target="_blank" rel="nofollow">Kim Minkyu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ondrusek Brian A.&option=202" target="_blank" rel="nofollow">Ondrusek Brian A.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lee Choogon&option=202" target="_blank" rel="nofollow">Lee Choogon;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Douglas Wade G.&option=202" target="_blank" rel="nofollow">Douglas Wade G.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chung Hoyong&option=202" target="_blank" rel="nofollow">Chung Hoyong;</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>Department of Chemical and Biomedical EngineeringFlorida State University 2525 Pottsdamer Street Building A Suite A131Tallahassee Florida 32310;</p> <p>Department of Chemical and Biomedical EngineeringFlorida State University 2525 Pottsdamer Street Building A Suite A131Tallahassee Florida 32310;</p> <p>Department of Biomedical SciencesFlorida State UniversityTallahassee Florida 32306;</p> <p>General Surgery Residency Program at Tallahassee Memorial Healthcare College of Medicine Florida State University 1401 Centerville Road Suite 107Tallahassee Florida 32308;</p> <p>Department of Chemical and Biomedical EngineeringFlorida State University 2525 Pottsdamer Street Building A Suite A131Tallahassee Florida 32310;</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/1184.html" title="有机化学">有机化学;</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=adhesive synthesis&option=203" rel="nofollow">adhesive synthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=anastomosis&option=203" rel="nofollow">anastomosis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=biomedical adhesive&option=203" rel="nofollow">biomedical adhesive;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=bioinspired adhesive&option=203" rel="nofollow">bioinspired adhesive;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=DOPA&option=203" rel="nofollow">DOPA;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=zwitterionic polymer&option=203" rel="nofollow">zwitterionic polymer;</a> </p> <div class="translation"> 机译：粘合剂合成;吻合术;生物医学粘合剂;生物透明粘合剂;多巴;两性离子聚合物; </div> </li> </ul> </div> </div> <div class="literature cardcommon" id="literaturereference" style="display:none"> <div class="similarity "> <h3 class="all_title" id="enpatent111">引文网络</h3> <div class="referencetab clearfix"> <ul id="referencedaohang"> <li dataid="referenceul">参考文献</li> <li dataid="citationul">引证文献</li> <li dataid="commonreferenceul">共引文献</li> <li dataid="commoncitationul">同被引文献</li> <li dataid="tworeferenceul">二级参考文献</li> <li dataid="twocitationul">二级引证文献</li> </ul> </div> <div class="reference_details" id="referenceList"> <ul id="referenceul"></ul> <ul id="citationul"></ul> <ul id="commonreferenceul"></ul> <ul id="commoncitationul"></ul> <ul id="tworeferenceul"></ul> <ul id="twocitationul"></ul> </div> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704020726132.html">Synthesis of lightly crosslinked zwitterionic polymer‐based bioinspired adhesives for intestinal tissue sealing</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kim Minkyu&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Kim Minkyu,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ondrusek Brian A.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Ondrusek Brian A.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lee Choogon&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Lee Choogon,</a> <a href="/journal-foreign-35621/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of Polymer Science, Part A. 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. 2008.10.22</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130499803404.html">Zwitterionic crosslinked polymer-based adhesives</a> <b>[P]</b> . <span> 外国专利：  US10982121B2 </span> <span> . 2021-04-20</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：两性离子交联聚合物基粘合剂 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130401681234.html">ZWITTERIONIC CROSSLINKED POLYMER-BASED ADHESIVES</a> <b>[P]</b> . <span> 外国专利：  US2020332161A1 </span> <span> . 2020-10-22</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：两性交联聚合物基胶粘剂 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130417907808.html">Methods for sealing an 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