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SML3041

Sigma-Aldrich

CRBN-6-5-5-VHL

≥98% (HPLC)

Sinónimos:

CRBN-6-5-5-VHL, (2S,4R)-1-((2S)-2-(5-((5-((6-((2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)hexyl)oxy)pentyl)oxy)pentanamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide, CRBN degrader, CRBN directed PROTAC, CRBN-VHL hetero-PROTAC

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About This Item

Fórmula empírica (notación de Hill):
C51H69N7O10S
Número de CAS:
2362575-45-7
Peso molecular:
972.20
MDL number:
MFCD32705129
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C1C2=C(C=CC=C2C(N1C3C(NC(CC3)=O)=O)=O)NCCCCCCOCCCCCOCCCCC(N[C@H](C(N4[C@H](C(NCC5=CC=C(C=C5)C6=C(C)N=CS6)=O)C[C@@H](O)C4)=O)C(C)(C)C)=O

Biochem/physiol Actions

CRBN-6-5-5-VHL is a cell-permeable and highly potent heterodimerizer comprising E3 ligases recruiting ligands, namely, pomalidomide and VH032-amine that efficiently knocks down Cereblon (CRBN). CRBN-6-5-5-VHL readily forms heteroternary complex and selectively induces CRBN ubiquitination and proteasomal degradation over VHL in a time- and dose-dependent fashion (0.001 to 1 μM). Higher concentrations (10 μM) causes the degradation of neo-substrates IKZF1 and IKZF3 with no effect on pVHL30 or pVHL19 levels.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Christian Steinebach et al.
MedChemComm, 10(6), 1037-1041 (2019-07-16)
A modular chemistry toolbox was developed for cereblon-directed PROTACs. A variety of linkers was attached to a CRBN ligand via the 4-amino position of pomalidomide. We used linkers of different constitution to modulate physicochemical properties. We equipped one terminus of
Christian Steinebach et al.
Chemical communications (Cambridge, England), 55(12), 1821-1824 (2019-01-24)
Small-molecule heterobifunctional degraders can effectively control protein levels and are useful research tools. We assembled proteolysis targeting chimeras (PROTACs) from a cereblon (CRBN) and a von-Hippel-Lindau (VHL) ligase ligand and demonstrated a PROTAC-induced heterodimerization of the two E3 ligases leading
Saeko Kuwahara-Ota et al.
British journal of haematology, 191(5), 784-795 (2020-06-20)
An increase in immunosuppressive myeloid-derived suppressor cells (MDSCs) is associated with disease progression and treatment resistance in multiple myeloma (MM). We investigated the mechanisms underlying MDSC induction, and sought to discover a strategy for prevention of MDSC induction in MM.

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