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AB287107

A-485

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(1 Publication)

MW 536.5 Da, Purity >98%. A potent and selective p300/CREB-binding protein (CBP) HAT domain inhibitor (IC50 values are 2.6 and 9.8 nM for the CBP-bromodomain HAT-C/H3 (BHC) and p300-BHC domains, respectively). A-485 displays > 1000-fold selectivity over closely related HATs. It decreases acetylated histone H3 lysine 27 (H3K27Ac), but not H3K9Ac, levels in PC3 cells in a concentration-dependent manner. A-485 reduces proliferation of non-small cell lung cancer (NSCLC), small cell lung cancer, triple-negative breast cancer, mantel cell lymphoma, multiple myeloma, non-Hodgkin's, and acute myeloid leukemia cell lines.

View Alternative Names

CBP_HUMAN, CREB-binding protein, Cyclic AMP responsive enhancer binding protein, E1A binding protein p300, E1A-associated protein p300, EP300: E1A binding protein p300, EP300_HUMAN, Histone acetyltransferase p300, KAT3A, KAT3B, RSTS, RSTS2, RTS, Rubinstein Taybi syndrome, p300 HAT

Key facts

CAS number

1889279-16-6

Purity

>98%

Form

Solid

form

Molecular weight

536.5 Da

Molecular formula

C<sub>2</sub><sub>5</sub>H<sub>2</sub><sub>4</sub>F<sub>4</sub>N<sub>4</sub>O<sub>5</sub>

PubChem

118958122

Nature

Synthetic

Solubility

>40 mg/ml in DMSO

>40 mg/ml in Ethanol

Biochemical name

N-(4-Fluorobenzyl)-2-((R)-5-(3-methylureido)-2',4'-dioxo-2,3-dihydrospiro[indene-1,5'-oxazolidin]-3'-yl)-N-((S)-1,1,1-trifluoropropan-2-yl)acetamide

Biological description

A potent and selective p300/CREB-binding protein (CBP) HAT domain inhibitor (IC50 values are 2.6 and 9.8 nM for the CBP-bromodomain HAT-C/H3 (BHC) and p300-BHC domains, respectively). A-485 displays > 1000-fold selectivity over closely related HATs. It decreases acetylated histone H3 lysine 27 (H3K27Ac), but not H3K9Ac, levels in PC3 cells in a concentration-dependent manner. A-485 reduces proliferation of non-small cell lung cancer (NSCLC), small cell lung cancer, triple-negative breast cancer, mantel cell lymphoma, multiple myeloma, non-Hodgkin's, and acute myeloid leukemia cell lines.

Canonical smiles

CC(C(F)(F)F)N(CC1=CC=C(C=C1)F)C(=O)CN2C(=O)C3(CCC4=C3C=CC(=C4)NC(=O)NC)OC2=O

Isomeric smiles

C[C@@H](C(F)(F)F)N(CC1=CC=C(C=C1)F)C(=O)CN2C(=O)[C@]3(CCC4=C3C=CC(=C4)NC(=O)NC)OC2=O

InChi

InChI=1S/C25H24F4N4O5/c1-14(25(27,28)29)32(12-15-3-5-17(26)6-4-15)20(34)13-33-21(35)24(38-23(33)37)10-9-16-11-18(7-8-19(16)24)31-22(36)30-2/h3-8,11,14H,9-10,12-13H2,1-2H3,(H2,30,31,36)/t14-,24+/m0/s1

InChiKey

VRVJKILQRBSEAG-LFPIHBKWSA-N

IUPAC Name

N-[(4-fluorophenyl)methyl]-2-[(3R)-6-(methylcarbamoylamino)-2',4'-dioxospiro[1,2-dihydroindene-3,5'-1,3-oxazolidine]-3'-yl]-N-[(2S)-1,1,1-trifluoropropan-2-yl]acetamide

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Product details

This product is manufactured by BioVision, an Abcam company and was previously called B2601 A-485. B2601-1 is the same size as the 1 mg size of ab287107.
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Properties and storage information

Shipped at conditions
Blue Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
It is important to note that this product is reported to be light sensitive|Store in the dark
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The CREBBP and p300 also known as KAT3B are essential transcriptional coactivators. Mechanically they function as acetyltransferases adding acetyl groups to histones which leads to the relaxation of chromatin structure and the activation of gene transcription. This process is critical for transcription regulation in eukaryotic cells. CREBBP has a molecular weight of approximately 265 kDa and is expressed in various tissues throughout the body including the heart lung and brain. Both of them possess bromodomain functions important for recognizing acetyl-lysine residues.
Biological function summary

CREBBP and p300 operate by interacting with a wide array of transcription factors and serve as scaffold proteins. They facilitate the assembly of large multiprotein complexes necessary for efficient initiation elongation or termination of transcription. Through acetylation these proteins modulate the activity of over 400 target proteins influencing diverse cellular processes like cell growth differentiation and repair. As part of the transcriptional activation complex CREBBP and p300 also acetylate non-histone proteins affecting their stability and function.

Pathways

CREBBP and p300 play pivotal roles in pathways such as the Notch signaling and the cAMP response element-binding protein (CREB) pathway. In the CREB pathway they interact with CREB to enhance the transcription of genes essential for neuronal activity and plasticity. In the Notch signaling pathway they contribute to cell fate decisions in developmental processes. These proteins collaborate with other histone acetyltransferases to maintain the dynamic regulation of gene expression.

Defects or mutations in CREBBP and p300 associate with Rubinstein-Taybi syndrome (RSTS) and certain cancers such as gastric cancer. In RSTS haploinsufficiency of the protein results in a range of developmental abnormalities due to impaired transcriptional regulation. In cancers abnormal acetyltransferase activity alters cell cycle regulation and apoptosis contributing to tumorigenesis. Their interaction with tumor suppressors and oncogenes highlights their integral role in maintaining cellular homeostasis and disease prevention.
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Product protocols

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Publications (1)

Recent publications for all applications. Explore the full list and refine your search

Clinical cancer research : an official journal of the American Association for Cancer Research 10:1430-8 PubMed14977846

2004

An angiogenesis inhibitor E7820 shows broad-spectrum tumor growth inhibition in a xenograft model: possible value of integrin alpha2 on platelets as a biological marker.

Applications

Unspecified application

Species

Unspecified reactive species

Taro Semba,Yasuhiro Funahashi,Naoto Ono,Yuji Yamamoto,Naoko Hata Sugi,Makoto Asada,Kentaro Yoshimatsu,Toshiaki Wakabayashi
View all publications
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