3-(6-methacrylamidohexanoyl)thiazolidine-2-thione | 831242-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(6-methacrylamidohexanoyl)thiazolidine-2-thione
• 英文别名: 2-methyl-N-[6-oxo-6-(2-thioxothiazolidin-3-yl)hexyl]acrylamide；2-Methyl-N-[6-oxo-6-(2-sulfanylidene-1,3-thiazolidin-3-yl)hexyl]prop-2-enamide；2-methyl-N-[6-oxo-6-(2-sulfanylidene-1,3-thiazolidin-3-yl)hexyl]prop-2-enamide
• CAS: 831242-02-5
• 化学式: C₁₃H₂₀N₂O₂S₂
• 分子量: 300.446
• InChiKey: SMBGENSJFFLHAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-天冬氨酸-4-苄酯 、 3-(6-methacrylamidohexanoyl)thiazolidine-2-thione 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Poly[N-(2-hydroxypropyl)methacrylamide] Conjugates of Inhibitors of the ABC Transporter That Overcome Multidrug Resistance in Doxorubicin-Resistant P388 Cells in Vitro

  摘要：

  The effects of novel polymeric therapeutics based on water-soluble N-(2-hydroxypropyl)methacrylamide copolymers (P(HPMA)) bearing the anticancer drug doxorubicin (Dox), an inhibitor of ABC transporters, or both, on the viability and the proliferation of the murine monocytic leukemia cell line P388 (parental cell line) and its doxorubicin-resistant subline P388/MDR were studied in vitro. The inhibitor derivatives 5-methyl-4-oxohexanoyl reversin 121 (MeOHe-R121) and 5-methyl-4-oxohexanoyl ritonavir ester (MeOHe-RIT), showing the highest inhibitory activities, were conjugated to the P(HPMA) via the biodegradable pH-sensitive hydrazone bond, and the ability of these conjugates to block the ATP driven P-glycoprotein (P-gp) efflux pump was tested. The P(HPMA) conjugate P-Ahx-NH-N═MeOHe-R121 showed a dose-dependent increase in the ability to sensitize the P388/MDR cells to Dox from 1.5 to 24 μM, and achieved an approximately 50-fold increase in sensitization at 24 μM. The P(HPMA) conjugate P-Ahx-NH-N═MeOHe-RIT showed moderate activity at 6 μM (∼10 times higher sensitization) and increased sensitization by 50-fold at 12 μM. The cytostatic activity of the P(HPMA) conjugate P-Ahx-NH-N═MeOHe-R121(Dox) containing Dox and the P-gp inhibitor MeOHe-R121, both bound via hydrazone bonds to the P(HPMA) carrier, was almost 30 times higher than that of the conjugate P-Ahx-NH-N═Dox toward the P388/MDR cells in vitro. A similar result was observed for P-Ahx-NH-N═MeOHe-RIT(Dox), which exhibited almost 10 times higher cytostatic activity than P-Ahx-NH-N═Dox.

  DOI：

  10.1021/bm500649q
• 作为产物：
  描述：

  2-巯基噻唑啉 、 6-[(2-甲基 -1-氧代烯丙基)氨基]己酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-(6-methacrylamidohexanoyl)thiazolidine-2-thione
  参考文献：
  名称：

  Impact of Polymer-TLR-7/8 Agonist (Adjuvant) Morphology on the Potency and Mechanism of CD8 T Cell Induction

  摘要：

  小分子Toll样受体-7和-8激动剂（TLR-7/8a）可以作为疫苗佐剂用于诱导CD8 T细胞免疫，但需要特定的配方以防止全身毒性，并将佐剂活性集中在淋巴组织中。在此，我们将TLR-7/8a共价结合到不同组成、链结构和流体动力学行为的聚合物上（约300 nm亚微米粒子、约10 nm胶束和约4 nm的柔性随机卷曲），并评估这些聚合物-TLR-7/8a结合物的参数如何影响其在体内的佐剂活性。将TLR-7/8a连接到任何聚合物组成上，系统性细胞因子（毒性）几乎减少了10倍。此外，淋巴结细胞因子产生和针对蛋白抗原诱导的CD8 T细胞的强度随着聚合物-TLR-7/8a的流体动力学半径增加而增加，亚微米粒子诱导的响应强度最高。值得注意的是，聚合物-TLR-7/8a诱导的CD8 T细胞反应依赖于CCR2+单核细胞和IL-12，而小分子TLR-7/8a的反应（意外地在疫苗接种部位引流的淋巴结中持续存在，半衰期为15小时）对单核细胞和IL-12的依赖性较小，但需要I型干扰素。这项研究展示了合成佐剂的模块化特性如何通过不同的免疫机制进行化学编程，以改变体内的免疫反应。

  DOI：

  10.1021/acs.biomac.8b01473

文献信息

• [EN] POLYMER ADJUVANT<br/>[FR] ADJUVANT POLYMÈRE
  申请人：ISIS INNOVATION

  公开号：WO2016055812A1

  公开（公告）日：2016-04-14

  The invention relates to an adjuvant comprising Pattern Recognition Receptor (PRR) agonist molecules linked to polymer chains that are capable of undergoing particle formation in aqueous conditions, or in aqueous conditions in response to external stimuli; and methods of treatment or prevention of disease using such an adjuvant.

  该发明涉及一种辅助剂，其包括与聚合物链相连的模式识别受体（PRR）激动子分子，这些聚合物链能够在水性条件下形成颗粒，或者在水性条件下响应外部刺激形成颗粒；以及使用这种辅助剂进行疾病治疗或预防的方法。
• POLYMER ADJUVANT
  申请人：Oxford University Innovation Limited

  公开号：EP3215189A1

  公开（公告）日：2017-09-13
• MULTIFUNCTIONAL COPOLYMERS FOR NUCLEIC ACID DELIVERY
  申请人：Manoharan Muthiah

  公开号：US20130236968A1

  公开（公告）日：2013-09-12

  The present invention relates to multifunctional polymers represented by the following formula: The invention further provides methods for their preparation and methods for site-specific delivery of nucleic acids by combining them with targeting ligands, endosomolytic ligands and/or PK modulator ligands.
• [EN] MULTIFUNCTIONAL COPOLYMERS FOR NUCLEIC ACID DELIVERY<br/>[FR] COPOLYMÈRES MULTIFONCTIONNELS POUR L'ADMINISTRATION D'ACIDES NUCLÉIQUES
  申请人：ALNYLAM PHARMACEUTICALS INC

  公开号：WO2011163121A1

  公开（公告）日：2011-12-29

  The present invention relates to multifunctional polymers represented by the following formula: The invention further provides methods for their preparation and methods for site- specific delivery of nucleic acids by combining them with targeting ligands, endosomolytic ligands and/or PK modulator ligands.
• [EN] COMPOSITIONS FOR TOPICAL APPLICATIONS<br/>[FR] COMPOSITIONS DESTINÉES À DES APPLICATIONS TOPIQUES
  申请人：VECTUM PHARMA S L

  公开号：WO2012049453A2

  公开（公告）日：2012-04-19

  Disclosed is an amphiphilic copolymer that can be used in film-forming compositions for dermal applications. The amphiphilic copolymer is characterized by having a defined structure with a hydrophilic polymer backbone and pendant hydrophobic groups. When applied to the skin, the copolymer rearranges in contact with the lipid-rich domains of the outermost layer of the skin, resulting in stable film formation. The amphiphilic copolymer contains active ingredients covalently attached, such as sunscreens, humectants,, cosmeceuticals or dermatologically active drugs or colourings, resulting in skin immobilization of the active ingredient.