6-oxo-6-(2-thioxothiazolidin-3-yl)hexanoic acid | 1188510-53-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-oxo-6-(2-thioxothiazolidin-3-yl)hexanoic acid
• 英文别名: 6-Oxo-6-(2-sulfanylidene-1,3-thiazolidin-3-yl)hexanoic acid
• CAS: 1188510-53-3
• 化学式: C₉H₁₃NO₃S₂
• 分子量: 247.339
• InChiKey: SIRKBJKTPFXNKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,1-三(羟甲基)乙烷 、 6-oxo-6-(2-thioxothiazolidin-3-yl)hexanoic acid 在 2-(dimethylamino)pyridinium p-toluenesulfonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 以67.2%的产率得到3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 6-oxo-6(2-thioxothiazolidin-3-yl)hexanoate
  参考文献：
  名称：

  Synthesis, Characterization, and Bioactivity of Mid-Functional PolyHPMA−Lysozyme Bioconjugates

  摘要：

  A thiazolidine-2-thione mid-functionalized chain transfer agent (CTA) was synthesized and used as a reversible addition fragmentation chain transfer (RAFT) polymerization agent to prepare poly(N-(2-hydroxypropyl)methacrylamide) (polyHPMA) with mid-chain thiazolidine-2-thione functionality. The synthesized polymers were fully analyzed by H-1 NMR and GPC, confirming well-defined structures (predesigned molecular weights, narrow polydispersities, and high functionalization efficiencies). A subsequent hydrolysis/analysis of the polymers was performed to verify their mid-functional structures. These mid-functionalized polymers were then incubated with a model protein (lysozyme) to generate branched polymer protein bioconjugates. The bioactivity of the branched polymer protein conjugate was tested and compared to similar molecular weight linear polyHPMA-protein bioconjugate; the branched polymer protein conjugate remained much more protein activity, indicating the mid-chain-functional polyHPMA was more selective in its conjugation reaction on the lysozyme surface when compared with conjugation reactions involving terminal-functional polyHPMA. This straightforward methodology, described herein, for the synthesis of branched polymer protein bioconjugates strikes a balance between protein protection by the attachment of polymer chains and the subsequent bioactivity retention of the bioconjugate.

  DOI：

  10.1021/ma100142w

文献信息

• Protein Release from Biodegradable PolyHPMA-Lysozyme Conjugates Resulting in Bioactivity Enhancement
  作者：Lei Tao、Gaojian Chen、Lixiang Zhao、Jiangtao Xu、Edwin Huang、Aiping Liu、Christopher P. Marquis、Thomas P. Davis

  DOI：10.1002/asia.201000729

  日期：2011.6.6

  polymer chain ends fixed by biodegradable disulfide bonds. The functional polyHPMA chains were subsequently conjugated to protein (lysozyme) by exploiting reactions between the thiazolidine‐2‐thione functionality and amine residues on the protein surface to form covalent amide linkages. The in vitro bioactivities of the lysozyme–polyHPMA conjugates were assessed by using Micrococcus lysodeikticus cells

  合成了一种新型的可生物降解的噻唑烷-2-硫酮功能链转移剂，并将其用作可逆的附加断裂链转移剂，以制备具有预定分子量和窄多分散性的明确定义的半遥远的聚-N-（2-羟丙基）甲基丙烯酰胺（polyHPMAs）。 。蛋白质反应性基团噻唑烷-2-硫酮位于通过可生物降解的二硫键固定的聚合物链末端。随后，利用噻唑烷-2-硫酮官能团与蛋白质表面的胺残基之间的反应，将功能性的聚HPMA链与蛋白质（溶菌酶）偶联，形成共价酰胺键。用溶菌微球菌评估了溶菌酶-polyHPMA偶联物的体外生物活性。细胞作为底物。缀合过程后，溶菌酶的生物活性显着降低。但是，从生物结合物中裂解聚合物链（在还原条件下）会产生游离蛋白并显着恢复生物活性。通过对小鼠皮下注射进行体内测试，并清楚地证明与天然蛋白相比，蛋白质-聚合物结合物的蛋白水解降解降低，表明通过结合策略可有效保护蛋白质。这种生物可逆的偶联方法可以在蛋白质保护和有效的生物活性维持之间取得平衡。