Name: PROTAC CRABP-II Degrader-2
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-[2-[(2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoyl]oxyethoxy]ethoxy]ethylamino]-2-oxoethoxy]imino-2,6,6-trimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Synonyms

(2E,4E,6E,8E)-9-((E)-3-((((14S,17S,18R)-18-amino-17-hydroxy-14-isobutyl-2,13,16-trioxo-19-phenyl-6,9,12-trioxa-3,15-diazanonadecyl)oxy)imino)-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid; SNIPER 2; Retinoic acid, 4-[[[(14S,17S,18R)-18-amino-17-hydroxy-14-(2-methylpropyl)-2,13,16-trioxo-19-phenyl-6,9,12-trioxa-3,15-diazanonadec-1-yl]oxy]imino]-, (4E)-; (4E)-4-[[[(14S,17S,18R)-18-Amino-17-hydroxy-14-(2-methylpropyl)-2,13,16-trioxo-19-phenyl-6,9,12-trioxa-3,15-diazanonadec-1-yl]oxy]imino]retinoic acid; ATRA-MeBS PROTAC

Density

1.15±0.1 g/cm3

InChI Key

LJDTZKKSXVIAPQ-FATAJGLMSA-N

InChI

InChI=1S/C44H64N4O10/c1-30(2)26-38(47-42(53)41(52)36(45)28-34-14-9-8-10-15-34)43(54)57-25-24-56-23-22-55-21-20-46-39(49)29-58-48-37-18-19-44(6,7)35(33(37)5)17-16-31(3)12-11-13-32(4)27-40(50)51/h8-17,27,30,36,38,41,52H,18-26,28-29,45H2,1-7H3,(H,46,49)(H,47,53)(H,50,51)/b13-11+,17-16+,31-12+,32-27+,48-37+/t36-,38+,41+/m1/s1

SMILES

CC1=C(C(CCC1=NOCC(=O)NCCOCCOCCOC(=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-2 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-2 is designed to facilitate the targeted degradation of cellular retinoic acid-binding protein II (CRABP-II). This tool enables researchers to study the functional consequences of CRABP-II depletion, providing insights into its role in retinoic acid signaling pathways and potential implications in cancer research.

• CRABP-II Function Elucidation: By employing PROTAC CRABP-II Degrader-2, scientists can achieve selective degradation of CRABP-II, allowing for the exploration of its involvement in cellular processes. This approach aids in dissecting the protein's contributions to cellular differentiation and proliferation, enhancing the understanding of its biological importance.

• Retinoic Acid Pathway Analysis: Utilizing PROTAC CRABP-II Degrader-2 offers a strategic method to investigate the effects of CRABP-II degradation on the retinoic acid pathway. This application supports the study of downstream effects and potential compensatory mechanisms, advancing knowledge in developmental biology and disease models.

• Protein Degradation Mechanism Studies: PROTAC CRABP-II Degrader-2 serves as an exemplary model for studying the mechanisms of targeted protein degradation. Researchers can leverage this product to examine the efficiency and specificity of PROTAC-induced ubiquitination and proteasomal degradation processes, contributing to the development of novel degradation strategies.

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