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929379

Sigma-Aldrich

Opto-thalidomide-O-acetamide-C4-NH2 hydrochloride

Sinônimo(s):

4,5-Dimethoxy-2-nitrobenzyl 3-(4-(2-((4-aminobutyl)amino)-2-oxoethoxy)-1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidine-1-carboxylate hydrochloride

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About This Item

Fórmula empírica (Notação de Hill):
C29H31N5O12 · xHCl
Peso molecular:
641.58 (free base basis)
Número MDL:
MFCD34704574
Código UNSPSC:
12352101
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

ligand

thalidomide

Nível de qualidade

100

Formulário

powder

grupo funcional

amine

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

COC1=CC(COC(N2C(CCC(N3C(C4=CC=CC(OCC(NCCCCN)=O)=C4C3=O)=O)C2=O)=O)=O)=C(C=C1OC)[N+]([O-])=O.Cl

InChI

1S/C29H31N5O12.ClH/c1-43-21-12-16(19(34(41)42)13-22(21)44-2)14-46-29(40)33-24(36)9-8-18(27(33)38)32-26(37)17-6-5-7-20(25(17)28(32)39)45-15-23(35)31-11-4-3-10-30;/h5-7,12-13,18H,3-4,8-11,14-15,30H2,1-2H3,(H,31,35);1H

chave InChI

SEKXAIYNMUPUDC-UHFFFAOYSA-N

Aplicação

Protein degrader building block Opto-thalidomide-O-acetamide-C4-NH2 hydrochloride enables the synthesis of molecules for light-induced 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

Outras notas

Targeted Protein Degradation by Small Molecules

Light-induced control of protein destruction by opto-PROTAC

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

Informações legais

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

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palavra indicadora

Warning

Frases de perigo

H302,H361d

Classificações de perigo

Acute Tox. 4 Oral - Repr. 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
0000197558
0000173902

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Jing Liu et al.
Science advances, 6(8), eaay5154-eaay5154 (2020-03-05)
By hijacking endogenous E3 ligase to degrade protein targets via the ubiquitin-proteasome system, PROTACs (PRoteolysis TArgeting Chimeras) provide a new strategy to inhibit protein targets that were regarded as undruggable before. However, the catalytic nature of PROTAC potentially leads to
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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