Name: PROTAC CRABP-II Degrader-1
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

≥95%

Solubility

10 mM in DMSO

Appearance

Solid Powder

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Shipping

Room temperature in continental US; may vary elsewhere

IUPACName

(2E,4E,6E,8E)-9-[(3E)-3-[2-[2-[2-[(2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoyl]oxyethoxy]ethylamino]-2-oxoethoxy]imino-2,6,6-trimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Synonyms

Retinoic acid, 4-[[[(11S,14S,15R)-15-amino-14-hydroxy-11-(2-methylpropyl)-2,10,13-trioxo-16-phenyl-6,9-dioxa-3,12-diazahexadec-1-yl]oxy]imino]-, (4E)-; (2E,4E,6E,8E)-9-((E)-3-((((11S,14S,15R)-15-Amino-14-hydroxy-11-isobutyl-2,10,13-trioxo-16-phenyl-6,9-dioxa-3,12-diazahexadecyl)oxy)imino)-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid; (4E)-4-[[[(11S,14S,15R)-15-Amino-14-hydroxy-11-(2-methylpropyl)-2,10,13-trioxo-16-phenyl-6,9-dioxa-3,12-diazahexadec-1-yl]oxy]imino]retinoic acid

Density

1.15±0.1 g/cm3

InChI Key

XEMRMMAFXLINDA-XVCXXHFGSA-N

InChI

InChI=1S/C42H60N4O9/c1-28(2)24-36(45-40(51)39(50)34(43)26-32-14-9-8-10-15-32)41(52)54-23-22-53-21-20-44-37(47)27-55-46-35-18-19-42(6,7)33(31(35)5)17-16-29(3)12-11-13-30(4)25-38(48)49/h8-17,25,28,34,36,39,50H,18-24,26-27,43H2,1-7H3,(H,44,47)(H,45,51)(H,48,49)/b13-11+,17-16+,29-12+,30-25+,46-35+/t34-,36+,39+/m1/s1

SMILES

CC1=C(C(CCC1=NOCC(=O)NCCOCCOC(=O)C(CC(C)C)NC(=O)C(C(CC2=CC=CC=C2)N)O)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C

Mechanism

Target: Targets cellular retinoic acid-binding protein II (CRABP-II) for experimental targeted protein degradation studies.

Binding Site: Binds the CRABP-II retinoid-binding cavity and recruited E3 ligase ligand site to support productive ternary complex formation.

Mechanism of Action: PROTAC CRABP-II Degrader-1 is designed for use in PROTAC or targeted protein degradation experiments directed toward cellular retinoic acid-binding protein II (CRABP-II). The bifunctional molecule links a target-recognition element to cereblon, promoting proximity between the protein of interest and ubiquitination machinery. Productive ternary-complex formation can drive polyubiquitination and proteasome-dependent target depletion, allowing researchers to compare pharmacological inhibition with protein removal. It is suitable for evaluating degradation potency, kinetics, pathway selectivity, and downstream signaling consequences in engineered or disease-relevant cellular models.

Applications

• PROTAC-Mediated Targeted Degradation: PROTAC CRABP-II Degrader-1 facilitates the targeted degradation of Cellular Retinoic Acid Binding Protein-II (CRABP-II), enabling researchers to study the protein's role in retinoic acid signaling pathways. This approach aids in dissecting CRABP-II's involvement in cellular differentiation and proliferation.

• Protein Function Analysis: By utilizing PROTAC CRABP-II Degrader-1, scientists can achieve selective degradation of CRABP-II, allowing for precise analysis of its functional contributions in various cellular contexts. This method is invaluable for elucidating protein interactions and downstream effects in biochemical pathways.

• Mechanistic Pathway Exploration: Employing PROTAC CRABP-II Degrader-1 offers a strategic advantage in exploring the mechanistic pathways regulated by CRABP-II. This targeted degradation tool provides insights into how CRABP-II influences gene expression and metabolic processes, aiding in the development of novel therapeutic strategies.

• Drug Discovery Research: The application of PROTAC CRABP-II Degrader-1 in drug discovery research allows for the identification of potential therapeutic targets by observing the effects of CRABP-II modulation. This approach enhances the understanding of disease mechanisms and supports the development of targeted therapies.

1. Protein knockdown using methyl bestatin-ligand hybrid molecules: design and synthesis of inducers of ubiquitination-mediated degradation of cellular retinoic acid-binding proteins.

Itoh, Y., Ishikawa, M., Naito, M. and Hashimoto, Y., 2010. Journal of the American Chemical Society, 132(16), pp.5820-5826.

Induction of selective degradation of target proteins by small molecules (protein knockdown) would be useful for biological research and treatment of various diseases. To achieve protein knockdown, we utilized the ubiquitin ligase activity of cellular inhibitor of apoptosis protein 1 (cIAP1), which is activated by methyl bestatin (MeBS, 2). We speculated that formation of an artificial (nonphysiological) complex of cIAP1 and a target protein would be induced by a hybrid molecule consisting of MeBS (2) linked to a ligand of the target protein, and this would lead to cIAP1-mediated ubiquitination and subsequent proteasomal degradation of the target protein. To verify this hypothesis, we focused on cellular retinoic acid-binding proteins (CRABP-I and -II) and designed hybrid molecules (compounds 4) consisting of MeBS (2) coupled via spacers of various lengths to all-trans retinoic acid (ATRA, 3), a ligand of CRABPs. Compounds 4 induced selective loss of CRABP-I and -II proteins in cells. We confirmed that 4b induced formation of a complex of cIAP1 and CRABP-II in vitro and induced proteasomal degradation of CRABP-II in cells. When neuroblastoma IMR-32 cells were treated with 4b, the level of CRABP-II was reduced and cell migration was inhibited, suggesting potential value of CRABP-II-targeting therapy for controlling tumor metastasis. Our results indicate that 4b possesses sufficient activity, permeability, and stability in cells to be employed in cellular assays. Hybrid molecules such as 4 should be useful not only as chemical tools for studying the biological/physiological functions of CRABPs but also as candidate therapeutic agents targeting CRABPs.

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It is commonly abbreviated as: C₁V₁ = C₂V₂