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923907

Sigma-Aldrich

6F,C5-Pomalidomide-piperazine-piperidine-4-carbothioamide hydrochloride

Synonyme(s) :

2-(2,6-Dioxopiperidin-3-yl)-5-fluoro-6-(4-(piperidine-4-carbonothioyl)piperazin-1-yl)isoindoline-1,3-dione hydrochloride, Crosslinker–E3 ligase ligand conjugate, Protein degrader building block

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About This Item

Formule empirique (notation de Hill):
C23H26FN5O4S · xHCl
Poids moléculaire :
487.55 (free base basis)
Code UNSPSC :
12352101
Nomenclature NACRES :
NA.21

ligand

6F,C5-Pomalidomide

Niveau de qualité

100

Pertinence de la réaction

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

Groupe fonctionnel

amine

Température de stockage

2-8°C

Chaîne SMILES 

O=C1C(N2C(C(C=C(F)C(N3CCN(C(C4CCNCC4)=S)CC3)=C5)=C5C2=O)=O)CCC(N1)=O.Cl

Application

Protein degrader building block 6F,C5-Pomalidomide-piperazine-piperidine-4-carbothioamide hydrochloride enables the synthesis of molecules for targeted protein degradation and PROTAC® (proteolysis-targeting chimeras) research. This conjugate contains a Cereblon (CRBN) recruiting ligand, a rigid linker, and a pendant amine for reactivity with a carboxylic acid on the target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and degrader, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a terminal amine, parallel synthesis can be used to more quickly generate degrader libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Protein Degrader Building Blocks

Autres remarques

Targeted Protein Degradation by Small Molecules

Small-Molecule PROTACS: New Approaches to Protein Degradation

Targeted Protein Degradation: from Chemical Biology to Drug Discovery

Impact of linker length on the activity of PROTACs

Informations légales

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

911771

Lenalidomide-Photoswitch1-NH2 hydrochloride, ≥95%

911763

C5 Lenalidomide-PEG1-piperazine hydrochloride, ≥95%

915572

Pomalidomide-dipiperazine-NH2 hydrochloride, ≥95%

916536

Pomalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride

917729

C5 Lenalidomide-piperazine-pyridine-alkyne-NH2 hydrochloride, ≥95%

919357

(S,R,S)-AHPC-PEG1-piperazine hydrochloride, ≥95%

918350

C5 Lenalidomide-alkyne-piperidine hydrochloride, ≥95%

918687

(S,R,S)-AHPC-alkyne-piperidine hydrochloride

919896

C5 Lenalidomide-dipiperazine-NH2 hydrochloride

920606

(S,R,S)-AHPC-piperazine-pyridine-alkyne-NH2 hydrochloride

920746

Pomalidomide-benzyl-piperazine hydrochloride

920762

(S,R,S)-AHPC-benzyl-piperazine hydrochloride

920754

C5 Lenalidomide-benzyl-piperazine hydrochloride

920789

Pomalidomide-pyridine-PEG1-piperazine hydrochloride

920797

C5 Lenalidomide-pyridine-PEG1-piperazine hydrochloride, ≥95%

920800

C5 Lenalidomide-methylamino-PEG1-NH2 hydrochloride, ≥95%

920843

(S,R,S)-VL285 Phenol-PEG1-piperazine hydrochloride

920827

(S,R,S)-AHPC-methylamino-PEG1-NH2 hydrochloride

921300

C5 Lenalidomide-pyrimidine-piperazine-PEG1-NH2 hydrochloride, ≥95%

921319

Pomalidomide-methylamino-PEG1-NH2 hydrochloride

921432

(S,R,S)-AHPC-pyridine-PEG1-piperazine hydrochloride

922153

(S,R,S)-VL285 Phenol-C3-piperazine hydrochloride

922161

(S,R,S)-VL285 Phenol-methylamino-PEG1-NH2 hydrochloride

921939

(S,R,S)-AHPC-pyrimidine-piperazine-PEG1-NH2 hydrochloride

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H360D

Classification des risques

Repr. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

Daniel P Bondeson et al.
Annual review of pharmacology and toxicology, 57, 107-123 (2016-10-13)
Protein homeostasis networks are highly regulated systems responsible for maintaining the health and productivity of cells. Whereas therapeutics have been developed to disrupt protein homeostasis, more recently identified techniques have been used to repurpose homeostatic networks to effect degradation of
Kedra Cyrus et al.
Molecular bioSystems, 7(2), 359-364 (2010-10-06)
Conventional genetic approaches have provided a powerful tool in the study of proteins. However, these techniques often preclude selective manipulation of temporal and spatial protein functions, which is crucial for the investigation of dynamic cellular processes. To overcome these limitations
Momar Toure et al.
Angewandte Chemie (International ed. in English), 55(6), 1966-1973 (2016-01-13)
The current inhibitor-based approach to therapeutics has inherent limitations owing to its occupancy-based model: 1) there is a need to maintain high systemic exposure to ensure sufficient in vivo inhibition, 2) high in vivo concentrations bring potential for off-target side effects, and 3) there is
Philipp M Cromm et al.
Cell chemical biology, 24(9), 1181-1190 (2017-06-27)
Traditional pharmaceutical drug discovery is almost exclusively focused on directly controlling protein activity to cure diseases. Modulators of protein activity, especially inhibitors, are developed and applied at high concentration to achieve maximal effects. Thereby, reduced bioavailability and off-target effects can

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