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Merck
CN

911771

Sigma-Aldrich

Lenalidomide-Photoswitch1-NH2 hydrochloride

≥95%

别名:

(E)-N-(4-Aminobutyl)-2-(4-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)diazenyl)-2,6-dimethoxyphenoxy)acetamide hydrochloride, PHOTAC template, Photoswitchable protein degrader building block for PROTAC® research

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About This Item

经验公式(希尔记法):
C27H32N6O7 · xHCl
分子量:
552.58 (free base basis)
MDL编号:
UNSPSC代码:
12352101

ligand

lenalidomide

质量水平

方案

≥95%

表单

powder or crystals

反应适用性

reactivity: carboxyl reactive
reagent type: ligand-linker conjugate

存货情况

available only in USA

官能团

amine

储存温度

2-8°C

SMILES字符串

NCCCCNC(COC1=C(OC)C=C(/N=N/C2=CC=CC3=C2CN(C4C(NC(CC4)=O)=O)C3=O)C=C1OC)=O.Cl

InChI

1S/C27H32N6O7.ClH/c1-38-21-12-16(13-22(39-2)25(21)40-15-24(35)29-11-4-3-10-28)31-32-19-7-5-6-17-18(19)14-33(27(17)37)20-8-9-23(34)30-26(20)36;/h5-7,12-13,20H,3-4,8-11,14-15,28H2,1-2H3,(H,29,35)(H,30,34,36);1H/b32-31+;

InChI key

BEBAPHRSEIHKIQ-MRRLHAJBSA-N

应用

Learn more: Technology Spotlight: Degrader Building Blocks for Targeted Protein DegradationPortal: Building PROTAC® Degraders for Targeted Protein DegradationProtein degrader building block Lenalidomide-Photoswitch1-NH2 hydrochloride enables the synthesis of PHOtochemically TArgeting Chimeras (PHOTACs), or photoswitchable proteolysis-targeting chimeras (PROTACs) that can be reversibly activated with different wavelengths of light. Developed in the Trauner and Pagano labs, PHOTACs are inactive in the dark but are activated to the cis isomer via irradiation at 390 nm and reversibly deactivated at wavelengths >450 nm. As described in Reynders, et al, this conjugate was used to prepare PHOTAC-I-3 and contains a Cereblon (CRBN)-recruiting ligand, an azobenzene photoswitchable crosslinker, and pendant amine for reactivity with an acid on the target warhead. Light-mediated control of the resulting PHOTAC affords advanced temporal and spatial control of targeted protein degradation.

Suggested wavelengths for photoswitching:
  • Switch to cis isomer: 390 nm (380-400 nm)
  • Switch to trans isomer (thermally more stable isomer): >450 nm
    Low-intensity light needed for photoactivation is not cytotoxic.
Browse our full offering of degrader building blocks that streamlines the synthesis of degrader libraries.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Learn more:

法律信息

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

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Zhi-Wei Wang et al.
Trends in cell biology, 30(10), 749-751 (2020-08-29)
PROteolysis-TArgeting Chimeras (PROTACs) have been developed for targeting specific protein destruction. Two recent studies in Science Advances by Liu et al. and Reynders et al. reported a novel technology, PHOtochemically TArgeting Chimeras (PHOTACs) or opto-PROTAC, which is light-induced control of
Martin Reynders et al.
Science advances, 6(8), eaay5064-eaay5064 (2020-03-05)
PROTACs (PROteolysis TArgeting Chimeras) are bifunctional molecules that target proteins for ubiquitylation by an E3 ligase complex and subsequent degradation by the proteasome. They have emerged as powerful tools to control the levels of specific cellular proteins. We now introduce

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