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901558

Sigma-Aldrich

Lenalidomide

≥95%

Sinonimo/i:

1-Oxo-4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole, 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione, 3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione, E3 Ligase ligand, Ligand for PROTAC® research

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About This Item

Formula empirica (notazione di Hill):
C13H13N3O3
Numero CAS:
191732-72-6
Peso molecolare:
259.26
Numero MDL:
MFCD07772307
Codice UNSPSC:
12352101
NACRES:
NA.22

ligand

lenalidomide

Saggio

≥95%

Stato

powder

Impiego in reazioni chimiche

reagent type: ligand

Punto di fusione

265-268  °C

Temperatura di conservazione

2-8°C

Stringa SMILE

O=C1N(C2CCC(NC2=O)=O)CC3=C1C=CC=C3N

InChI

1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18)
GOTYRUGSSMKFNF-UHFFFAOYSA-N

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Applicazioni

Lenalidomide is a ligand demonstrated to bind the Cereblon (CRBN) protein. Lenalidomide, along with other thalidomide derivatives, are useful for constructing small molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. Explore protein degrader building blocks, E3 ligase ligand-linker conjugates that simplify the synthesis and library generation of PROTACs.

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Altre note

Technology Spotlight: Degrader Building Blocks for Targeted Protein Degradation

Portal: Building PROTAC® Degraders for Targeted Protein Degradation

Structure of the human Cereblon–DDB1–lenalidomide complex reveals basis for responsiveness to thalidomide analogs

Lenalidomide causes selective degradation of IKZF1 and IKZF3 in multiple myeloma cells

The myeloma drug lenalidomide promotes the cereblon-dependent destruction of Ikaros proteins

Note legali

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

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Pomalidomide-PEG5-NH2 hydrochloride

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(S,R,S)-AHPC-PEG6-NH2 hydrochloride, ≥95%

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(S,R,S)-AHPC-PEG5-Alkyne

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(S,R,S)-AHPC-PEG4-Alkyne

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Pittogrammi

Health hazard
GHS08

Avvertenze

Danger

Indicazioni di pericolo

H360D,H373

Classi di pericolo

Repr. 1B - STOT RE 2

Organi bersaglio

Blood

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Scegli una delle versioni più recenti:

Certificati d'analisi (COA)

Lot/Batch Number
MKCN2073
MKCL7838
MKCK5360
MKCH7688
MKCG0047

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Pomalidomide-PEG3-CO2H ≥95%

Sigma-Aldrich

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Sigma-Aldrich

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(S,S,S)-AHPC hydrochloride

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Sigma-Aldrich

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(+)-Thalidomide

Pomalidomide-PEG3-Alkyne ≥95%

Sigma-Aldrich

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Pomalidomide-PEG3-Alkyne

(−)-Thalidomide >98%, solid

Sigma-Aldrich

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(−)-Thalidomide

Pomalidomide-PEG1-NH2 hydrochloride ≥95%

Sigma-Aldrich

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Pomalidomide-PEG1-NH2 hydrochloride

Pomalidomide-PEG5-CO2H ≥95%

Sigma-Aldrich

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Pomalidomide-PEG5-CO2H

Inchul You et al.
Cell chemical biology, 27(1), 66-73 (2019-12-21)
The PI3K/AKT signaling cascade is one of the most commonly dysregulated pathways in cancer, with over half of tumors exhibiting aberrant AKT activation. Although potent small-molecule AKT inhibitors have entered clinical trials, robust and durable therapeutic responses have not been
Philip P Chamberlain et al.
Nature structural & molecular biology, 21(9), 803-809 (2014-08-12)
The Cul4-Rbx1-DDB1-Cereblon E3 ubiquitin ligase complex is the target of thalidomide, lenalidomide and pomalidomide, therapeutically important drugs for multiple myeloma and other B-cell malignancies. These drugs directly bind Cereblon (CRBN) and promote the recruitment of substrates Ikaros (IKZF1) and Aiolos
Richard J Visconti et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 36(10), 1914-1930 (2021-06-27)
Human myeloma bone disease (MBD) occurs when malignant plasma cells migrate to the bone marrow and commence inimical interactions with stromal cells, disrupting the skeletal remodeling process. The myeloma cells simultaneously suppress osteoblastic bone formation while promoting excessive osteoclastic resorption.
Jan Krönke et al.
Science (New York, N.Y.), 343(6168), 301-305 (2013-12-03)
Lenalidomide is a drug with clinical efficacy in multiple myeloma and other B cell neoplasms, but its mechanism of action is unknown. Using quantitative proteomics, we found that lenalidomide causes selective ubiquitination and degradation of two lymphoid transcription factors, IKZF1
Gang Lu et al.
Science (New York, N.Y.), 343(6168), 305-309 (2013-12-03)
Thalidomide-like drugs such as lenalidomide are clinically important treatments for multiple myeloma and show promise for other B cell malignancies. The biochemical mechanisms underlying their antitumor activity are unknown. Thalidomide was recently shown to bind to, and inhibit, the cereblon

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