tertbutylcarbonyl-cysteine-dithiopyridine | 117310-07-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tertbutylcarbonyl-cysteine-dithiopyridine
• 英文别名: Boc-Cys(S-thiopyridyl)-OH；Boc-Cys(S-TP)-OH；N-Boc-S-2-Pyridinylthio-L-cysteine；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(pyridin-2-yldisulfanyl)propanoic acid
• CAS: 117310-07-3
• 化学式: C₁₃H₁₈N₂O₄S₂
• 分子量: 330.429
• InChiKey: XTLMRQHNCDVULJ-VIFPVBQESA-N

物化性质

• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.52
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tertbutylcarbonyl-cysteine-dithiopyridine 在 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 C₁₆H₂₇N₃OS₂
  参考文献：
  名称：

  [EN] DEPALMITOYLATING COMPOSITIONS AND THE USE THEREOF
  [FR] COMPOSITIONS DE DÉPALMITYLATION ET LEUR UTILISATION

  摘要：

  本文披露了脱棕榈酰化化合物、组合物及其使用方法。

  公开号：

  WO2021030703A1
• 作为产物：
  描述：

  S-乙酰胺基甲基-N-叔丁氧羰基-L-半胱氨酸 以 氘代氯仿 、 氯仿 为溶剂， 反应 0.16h， 生成 tertbutylcarbonyl-cysteine-dithiopyridine
  参考文献：
  名称：

  A new protecting group for the sulfhydryl function of cysteine

  摘要：

  DOI：

  10.1021/jo00262a051

文献信息

• Injectable dendrimer hydrogel nanoparticles
  申请人：Rangaramanujam Kannan

  公开号：US09526794B2

  公开（公告）日：2016-12-27

  The invention discloses injectable hydrogels which are in the form of crosslinked nano beads or particle in the size range 5 nm to 10 μm, comprising PAMAM dendrimer with asymmetrical peripheral end groups such that one of the terminal groups is involved in formation of hydrogel and the other in involved in the conjugation of drugs or imaging agents and their methods of preparation. The said gel is formed by reaction of the PAMAM dendrimer with asymmetrical end groups with other polymer wherein the other polymer is selected from the group of linear, branched, hyperbranched or star shaped polymers with functionalized terminal groups. The PAMAM dendrimer with asymmetrical terminal groups consists of a Generation 2 and above PAMAM dendrimer with symmetrical end groups modified using the amino acids or their modified forms. The gel disclosed in the present invention is formed as small crosslinked particles in the size range 25 nm to 10 μm and is suitable for injectable delivery of hydrogel to any of the body orifices, tissues by intramuscular or subcutaneous route and ocular delivery for the purpose of therapeutic treatment and imaging.

  该发明揭示了一种注射用水凝胶，其以交联的纳米珠或粒子的形式呈现，尺寸范围为5纳米至10微米，包括具有非对称外周末端基团的PAMAM树状聚合物，其中一个末端基团参与水凝胶的形成，另一个参与药物或成像剂的结合以及它们的制备方法。所述凝胶是通过PAMAM树状聚合物与非对称末端基团与其他聚合物发生反应形成的，其中其他聚合物选自线性、支化、超支化或星形聚合物，具有官能化末端基团。具有非对称末端基团的PAMAM树状聚合物由对称末端基团的第2代及以上PAMAM树状聚合物通过氨基酸或其改性形式进行改性而成。本发明披露的凝胶以尺寸范围为25纳米至10微米的小交联颗粒形式存在，适用于通过肌肉内或皮下途径将水凝胶注射到任何身体口腔、组织，以及眼部递送，用于治疗治疗和成像。
• Novel amphiphilic PEG-hydroxycamptothecin conjugates as glutathione-responsive prodrug nanocapsules for cancer chemotherapy
  作者：Na Guo、Tiantian Hao、Xiuzhuan Shang、Tianle Zhang、Huan Liu、Qian Zhang、Jing Wang、Du Jiang、Yao Rong、Yuou Teng、Peng Yu

  DOI：10.1007/s11051-017-3897-4

  日期：2017.6

  hydroxycamptothecin (HCPT) conjugates ( 13a–14d ), which contained a polyethylene glycol moiety and disulfide bond, were designed and synthesized in five to six steps, with overall yields of 20–39%. The anticancer activities and toxicities of these new conjugates were evaluated using an in vitro MTT assay in K562, HepG2, and HT-29 cell lines and HUVECs. The conjugates displayed enhanced antitumor activity and reduced

  设计并合成了一系列新颖的羟基喜树碱（HCPT）共轭物（ 13a-14d ），其中包含聚乙二醇部分和二硫键，分五至六步合成，总收率为20-39％。在K562，HepG2和HT-29细胞系和HUVEC中使用体外MTT分析法评估了这些新缀合物的抗癌活性和毒性。与它们的母体分子HCPT相比，结合物显示出增强的抗肿瘤活性和降低的毒性。在这些缀合物中，化合物 13a 对肿瘤细胞的选择性比对HUVEC高100倍。TEM和DLS实验表明 13a 在水溶液中形成直径约200 nm的纳米胶束，并且该结合物可以经历谷胱甘肽反应降解以在肿瘤部位释放HCPT。这些缀合物的效力增强和毒性降低可能是由于纳米颗粒的增强的渗透和保留（EPR）效应引起的。
• Amino Acid-Functionalized Dendrimers with Heterobifunctional Chemoselective Peripheral Groups for Drug Delivery Applications
  作者：Raghavendra S. Navath、Anupa R. Menjoge、Bing Wang、Roberto Romero、Sujatha Kannan、Rangaramanujam M. Kannan

  DOI：10.1021/bm100186b

  日期：2010.6.14

  Dendrimers have emerged as multifunctional carriers for targeted drug delivery, gene delivery and imaging. Improving the functional versatility at the surface for carrying multiple conjugation reactions is becoming vital. Typically, generation four polyamidoamine (G4-PAMAM) dendrimers bear similar to 64 symmetrical end groups, often requiring different spacers to conjugate various functional groups (drugs and targeting moities), increasing the synthetic steps. In the present study, a simple one-step synthesis to convert each symmetrical end group of G4-PAMAM dendrimers into two reactive, distinct orthogonal and chemoselective groups is described. A near-complete end-capping of the dendrimers (87-93%) with amino acids results in heterobifunctional G4-PAMAM dendrimers bearing a very high (>= 110) diverse peripheral end groups (OH+NHBoc, OH+COOMe, SH+NHBoc, and COOH+NHBoc). Postfunctionalization ability of these dendrimers was evaluated. The heterobifunctional groups at the dendrimer periphery could be chemoselectively conjugated to multiple moities such as drugs (indomethacin and dexamethasone) and drugs and imaging agents (dexamethasone and FITC). These conjugations could be achieved in immediate succession without functional group conversions, eliminating the additional elaborate synthetic steps traditionally required to append specific linkers. Furthermore, one of the two functional handles at periphery was used to develop in situ forming hydrogels, whereas the other handle could be used for conjugating the drugs (e.g., dexamethasone). The heterobifunctional dendrimers with either "NH2 or SH (thiopyridyl protected form)" terminations showed in situ hydrogel formation by cross-linking with N-hydroxysuccinimide or thiol-terminated multiarm polyethylene glycol (20 kDa). The choice of amino acids as versatile linkers would enable biocompatible dendrimer scaffolds for use in drug delivery. zeta-potential measurements showed drastic lowering of the charge on G4-PAMAM-NH2 dendrimers by end-capping with amino acids, whereas in the ease of neutral G4-PAMAM-OH dendrimers, the charge did not increase or decrease substantially. The in vitro cytotoxicity and hemolysis assay showed that the heterobifunctional dendrimers were noncytotoxic in the 100 ng/mL to 1 mg/mL concentration range. With this study, we demonstrate the development of biocompatible dendrimers bearing multiple orthogonal surface groups, enabling the attachment of drugs, imaging agents, and gel formation using minimal synthetic steps.