2,2-Oxybis(ethylamine)
(Synonyms: 2,2'-氧双(乙胺)) 目录号 : GC60014
22-Oxybis(ethylamine) 是一种 PROTAC linker，属于 PEG 类。可用于合成 PROTAC 分子。
Cas No.:2752-17-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
22-Oxybis(ethylamine) is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs[1].
PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins[1].
[1]. An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562
| Cas No. | 2752-17-2 | SDF | |
| 别名 | 2,2'-氧双(乙胺) | ||
| Canonical SMILES | NCCOCCN | ||
| 分子式 | C4H12N2O | 分子量 | 104.15 |
| 溶解度 | 储存条件 | 4°C, protect from light | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 9.6015 mL | 48.0077 mL | 96.0154 mL |
| 5 mM | 1.9203 mL | 9.6015 mL | 19.2031 mL |
| 10 mM | 0.9602 mL | 4.8008 mL | 9.6015 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Equilibrating dynamic [2]rotaxanes
J Org Chem 2007 Aug 31;72(18):6708-13.PMID:17685572DOI:10.1021/jo0708590.
Upon mixing and dehydration, 2,6-diformylpyridine and 2,2'-oxybis(ethylamine) form a dynamic combinatorial library of at least nine members. Through hydrogen bonding and other intermolecular interactions, templating dumbbell molecules select one macrocyclic member of the library, at the expense of all the others, to create [2]rotaxanes. These rotaxanes, however, retain the dynamic character of the library, since a diformylpyridine analogue can exchange with the macrocyclic component in solution. In addition, crystallization of the mixture surprisingly furnishes only the [24]crown-8-like macrocycle on its own--evidence of a kinetic selection process occurring between phase transitions.
Lower denticity leading to higher stability: structural and solution studies of Ln(III)-OBETA complexes
Inorg Chem 2014 Dec 1;53(23):12499-511.PMID:25387307DOI:10.1021/ic5020225.
The heptadentate ligand OBETA (2,2'-oxybis(ethylamine)-N,N,N',N'-tetraacetic acid) was reported to form complexes with Ln(3+) ions more stable than those formed by the octadentate and more popular congener EGTA (ethylene glycol O,O'-bis(ethylamine)-N,N,N',N'-tetraacetic acid). The structural features leading to this puzzling coordination paradox were investigated by X-ray diffraction, solution state NMR, molecular modeling, and relaxometric studies. The stability constant of Gd(OBETA) (log KGdL = 19.37, 0.1 M KCl) is 2 orders of magnitude higher than that of the higher denticity analogue Gd(EGTA) (log KGdL = 17.66, 0.1 M KCl). The half-lives (t1/2) for the dissociation reactions of Gd(OBETA) and Gd(EGTA) ([Cu(2+)]tot = 0.2 mM, [Cit(3-)]tot = 0.5 mM, [PO4(3-)]tot = 1.0 mM, and [CO3(2-)]tot = 25 mM at pH = 7.4 and 25 °C in 0.1 M KCl solution) are 6.8 and 0.63 h, respectively, reflecting the much higher inertness of Gd(OBETA) near physiological conditions. NMR studies and DFT calculations using the B3LYP functional and a large-core ECP indicate that the [Gd(OBETA)(H2O)2](-) complex most likely exists in solution as the Δ(λλ)(δδδδ)A/Λ(δδ)(λλλλ)A enantiomeric pair, with an activation free energy for the enantiomerization process of ∼40 kJ·mol(-1). The metal ion is nine-coordinate by seven donor atoms of the ligand and two inner-sphere water molecules. The X-ray crystal structure of [C(NH2)3]3[Lu(OBETA)(CO3)]·2H2O is in agreement with the predictions of DFT calculations, the two coordinated water molecules being replaced by a bidentate carbonate anion. The (1)H NMRD and (17)O NMR study revealed that the two inner-sphere water molecules in Gd(OBETA) are endowed with a relatively fast water exchange rate (kex(298) = 13 × 10(6) s(-1)). The higher thermodynamic stability and inertness of Ln(OBETA) complexes, peaking in the center of the 4f series, combined with the presence of two coordinated water molecules suggests that Gd(OBETA) is a promising paramagnetic probe for MRI applications.
Targeting Cysteine Located Outside the Active Site: An Effective Strategy for Covalent ALKi Design
J Med Chem 2021 Feb 11;64(3):1558-1569.PMID:33471528DOI:10.1021/acs.jmedchem.0c01707.
Potent inhibitors of ALK are highly desired because of the occurrence of drug resistance. We herein firstly report the development of a rationally designed inhibitor, Con B-1, which can covalently bind to Cys1259, a cysteine located outside the ALK active site by linking a warhead with Ceritinib through a 2,2'-Oxybis(ethylamine) linker. The in vitro and in vivo assays showed ConB-1 is a potent selective ALKi with low toxicity to normal cells. In addition, the molecule showed significant improvement of anticancer activities and potential antidrug resistant activity compared with Ceritinib, demonstrating the covalent inhibitor of ALK can be a promising drug candidate for the treatment of NSCLC. This work may provide a novel perspective on the design of covalent inhibitors.
Lower ligand denticity leading to improved thermodynamic and kinetic stability of the Gd3+ complex: the strange case of OBETA
Chemistry 2012 Jun 18;18(25):7680-5.PMID:22615142DOI:10.1002/chem.201200265.
OBETA, OBETA, you bet: Thermodynamic and kinetic measurements show an apparent paradox. The stability of complexes of lanthanide trivalent ions is higher with the heptadentate ligand OBETA (ethylene glycol-bis(2-aminoethyl ether)-N,N,N',N'-tetraacetic acid) than with its octadentate homologue EGTA (2,2'-oxybis(ethylamine)-N,N,N',N'-tetraacetic acid). The unusual properties of Gd(OBETA)(-) (see structure), combined with the presence of two fast exchanging coordinated water molecules, candidates this complex as an MRI contrast agent.
Synthesis of an Amphiphilic Bis-Aqua Gd(OBETA) Complex for the Preparation of High-Relaxivity Supramolecular Magnetic Resonance Imaging Probes
Chempluschem 2016 Feb;81(2):235-241.PMID:31968768DOI:10.1002/cplu.201500366.
Prompted by the favourable relaxometric, thermodynamic and kinetic properties of the bis-hydrated Gd(OBETA) (OBETA=2,2'-oxybis(ethylamine)-N,N,N',N'-tetraacetic acid) complex, a novel derivative tailored with an n-hexadecyl chain was synthesised. The amphiphilic gadolinium complex was designed and prepared with the aim of obtaining high relaxivity supramolecular aggregates by self-assembly in micelles and liposomes. Thus, lipidic nanoparticles were prepared and characterised by dynamic light scattering and 1 H NMR relaxometry. Relaxivity values of up to 48.3 mm-1 s-1 (20 MHz and 298 K) were registered in liposomal aggregates. The binding to human serum albumin (HSA), evaluated both in terms of affinity and relaxometric properties of the supramolecular adduct, yielded exceptionally high relaxivity values (71.4 mm-1 s-1 at 30 MHz and 298 K).