| Identification | Back Directory | [Name]
4-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione | [CAS]
1957236-10-0 | [Synonyms]
Thalidomide-4-PEG3-NH2
Thalidomide-O-PEG2-amine
Thalidomide-O-PEG2-Amine TFA salt
4-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione
4-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
4-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
4-[2-[2-(2-Aminoethoxy)ethoxy]ethoxy]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
1H-Isoindole-1,3(2H)-dione, 4-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-2-(2,6-dioxo-3-piperidinyl)- | [Molecular Formula]
C19H23N3O7 | [MOL File]
1957236-10-0.mol | [Molecular Weight]
405.4 |
| Chemical Properties | Back Directory | [Boiling point ]
648.7±55.0 °C(Predicted) | [density ]
1.375±0.06 g/cm3(Predicted) | [solubility ]
DMF, DCM, methanol | [pka]
10.70±0.40(Predicted) | [Appearance]
white crystalline solid |
| Hazard Information | Back Directory | [Description]
Thalidomide-containing building block with PEG2-linker and amino group, which can be conjugated to other functionalized linkers and target protein ligands.
The amino group is highly reactive and can undergo reactions with carboxylic acids, activated esters (NHS, STP, etc.), carbonyls (such as ketones and aldehydes), and more.
Proteolysis targeting chimeras (PROTACs) are cell-permeable heterobifunctional molecules that can remove specific proteins from the cell. One end of such molecule contains a ligand to bind to the target, and the second end recruits the E3 ligase complex. Close proximity results in substrate polyubiquitination and subsequent protein degradation by cellular proteasome.
There are several types of E3 ligases that are practically suitable for such a purpose. Thalidomide is the ligand capable of recruiting Cereblon (CRBN) E3 ligase. | [Uses]
Thalidomide-PEG3-NH2 is a synthesized E3 ligase ligand-linker conjugate that incorporates the Thalidomide based cereblon ligand and a linker used in PROTAC technology[1]. | [IC 50]
Cereblon | [References]
[1] Sato T, et al. Cereblon-Based Small-Molecule Compounds to Control Neural Stem Cell Proliferation in Regenerative Medicine.?Front Cell Dev Biol. 2021;9:629326. Published 2021 Mar 11. DOI:10.3389/fcell.2021.629326
[2] Nalawansha DA, et al. PROTACs: An Emerging Therapeutic Modality in Precision Medicine. Cell Chem Biol. 2020;27(8):998-997. DOI:10.1016/j.immuni.2020.07.018 |
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