6F,C5-Pomalidomide-4-piperidine-C₁-piperazine hydrochloride

Name: 6F,C5-Pomalidomide-4-piperidine-C<SUB>1</SUB>-piperazine hydrochloride
Brand: ALDRICH
Price: 437 USD

Synonym(s):

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

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50 MG

$437.00

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₂₈FN₅O₄ · xHCl

Molecular Weight:

457.50 (free base basis)

MDL number:

MFCD34602213

UNSPSC Code:

12352200

NACRES:

NA.21

Key Documents

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InChI key

NSESLQMRUIXJGI-UHFFFAOYSA-N

SMILES string

O=C1C(N2C(C(C=C(F)C(N(CC3)CCC3CN4CCNCC4)=C5)=C5C2=O)=O)CCC(N1)=O.Cl

ligand

6F,C5-Pomalidomide

reaction suitability

reactivity: carboxyl reactive, reagent type: ligand-linker conjugate

functional group

amine

storage temp.

2-8°C

Quality Level

100

Related Categories

Chemical Biology

Protein Degrader Building Blocks

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1 of 4

This Item	923885	923931	923877
Sigma-Aldrich 923958 6F,C5-Pomalidomide-4-piperidine-C₁-piperazine hydrochloride	Sigma-Aldrich 923885 Pomalidomide-piperazine-piperidine-4-carboxamide hydrochloride	Sigma-Aldrich 923931 Pomalidomide-4-piperidine-C₁-piperazine hydrochloride	Sigma-Aldrich 923877 Pomalidomide-piperazine-C₁-4-piperidine hydrochloride
reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate	reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate	reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate	reaction suitability reactivity: carboxyl reactive, reagent type: ligand-linker conjugate
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
ligand 6F,C5-Pomalidomide	ligand pomalidomide	ligand pomalidomide	ligand pomalidomide
functional group amine	functional group amine	functional group amine	functional group amine

Application

Protein degrader building block 6F,C5-Pomalidomide-4-piperidine-C₁-piperazine 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

Other Notes

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

Legal Information

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

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pictograms

GHS08

signalword

Danger

hcodes

H360D

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 1B

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000140624

0000134264

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Targeted Protein Degradation by Small Molecules.

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

Impact of linker length on the activity of PROTACs.

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

Small-Molecule PROTACS: New Approaches to Protein Degradation.

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

Targeted Protein Degradation: from Chemical Biology to Drug Discovery.

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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6F,C5-Pomalidomide-4-piperidine-C1-piperazine hydrochloride