SJF620 hydrochloride

Size	Price	Stock	Quantity
--	$--	In stock

Size

Price

Stock

Quantity

$--

In stock

Purity

≥99%

Solubility

Soluble in DMSO

Storage

Store at -20°C

IUPACName

3-[6-[2-[2-[2-[4-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]ethoxy]ethoxy]ethoxy]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione;hydrochloride

Synonyms

3-(5-{2-[2-(2-{4-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}ethoxy)ethoxy]ethoxy}-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-piperidinedione hydrochloride (1:1); 2,6-Piperidinedione, 3-[5-[2-[2-[2-[4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]ethoxy]ethoxy]ethoxy]-1,3-dihydro-1-oxo-2H-isoindol-2-yl]-, hydrochloride (1:1)

InChI Key

RLEKBKXQGCJLQZ-UHFFFAOYSA-N

InChI

InChI=1S/C41H44N8O7.ClH/c42-38-36-37(27-6-8-31(9-7-27)56-30-4-2-1-3-5-30)46-49(39(36)44-26-43-38)29-14-16-47(17-15-29)18-19-53-20-21-54-22-23-55-32-10-11-33-28(24-32)25-48(41(33)52)34-12-13-35(50)45-40(34)51;/h1-11,24,26,29,34H,12-23,25H2,(H2,42,43,44)(H,45,50,51);1H

Canonical SMILES

C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC(=C3)OCCOCCOCCN4CCC(CC4)N5C6=NC=NC(=C6C(=N5)C7=CC=C(C=C7)OC8=CC=CC=C8)N.Cl

1. Design, synthesis and biological evaluation of Proteolysis Targeting Chimeras (PROTACs) as a BTK degraders with improved pharmacokinetic properties.

Jaime-Figueroa, S., Buhimschi, A.D., Toure, M., Hines, J. and Crews, C.M., 2020. Bioorganic & medicinal chemistry letters, 30(3), p.126877.

A new series of Proteolysis Targeting Chimeras (PROTACs) targeting Bruton's Tyrosine Kinase (BTK) was synthesized, with the goal of improving the pharmacokinetic properties of our previously reported PROTAC, MT802. We recently described the ability of MT802 to induce degradation of both wild-type and C481S mutant BTK in immortalized cells and patient-derived B-lymphocytes. However, the pharmacokinetic properties of MT802 were not suitable for further in vivo development. Therefore, we undertook a systematic medicinal chemistry campaign to overcome this issue and made a series of PROTACs with structural modifications to the linker and E3-recruiting ligand; more specifically, the new PROTACs were synthesized with different von Hippel-Lindau (VHL) and cereblon (CRBN) ligands while keeping the BTK ligand and linker length constant. This approach resulted in an equally potent PROTAC, SJF620, with a significantly better pharmacokinetic profile than MT802. This compound may hold promise for further in vivo exploration of BTK degradation.

Good afternoon, dear team, could you please tell me the biological features of this compound? thank you.

PROTAC for BTK degradation: SJF620 hydrochloride is a PROTAC, meaning it acts as a bridge between BTK and the E3 ubiquitin ligase Cereblon. This triggers the ubiquitination and subsequent degradation of BTK by the proteasome. Potent and selective: SJF620 hydrochloride exhibits potent BTK degradation, with a DC50 (concentration needed to degrade 50% of BTK) of 7.9 nM. It also shows good selectivity for BTK over other proteins. Chemical structure: It features two ligands: one for binding to Cereblon and another for binding to BTK. These ligands are connected by a linker.

8/11/2016

Could you tell me its potential application, thanks.

SJF620 hydrochloride holds promise for treating various B-cell malignancies, such as leukemia and lymphoma, where BTK plays a crucial role. Additionally, it may have potential in autoimmune diseases and inflammatory conditions involving BTK signaling.

25/2/2022

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂