P 22077
- Product Name
- P 22077
- CAS No.
- 1247819-59-5
- Chemical Name
- P 22077
- Synonyms
- P 22077;CS-1115;P22077 ，S7133;P 22077; P-22077;P 22077 USP/EP/BP;P 22077, 10 mM in DMSO;USP7/USP47 Inhibitor, P 22077;1-(5-(2,4-difluorophenylthio)-4-nitrothiophen-2-yl)ethanone;1-[5-[(2,4-Difluorophenyl)thio]-4-n-itro-2-thienyl]-ethanone;1-[5-(2,4-difluorophenyl)sulfanyl-4-nitro-2-thienyl]ethanone
- CBNumber
- CB02668437
- Molecular Formula
- C12H7F2NO3S2
- Formula Weight
- 315.32
- MOL File
- 1247819-59-5.mol
P 22077 Property
- Melting point:
- 146 - 148°C
- Boiling point:
- 395.4±42.0 °C(Predicted)
- Density
- 1.53±0.1 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- Soluble in DMSO (up to 25 mg/ml)
- form
- solid
- color
- Off-white
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H302Harmful if swallowed
H372Causes damage to organs through prolonged or repeated exposure
H410Very toxic to aquatic life with long lasting effects
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P273Avoid release to the environment.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 662142
- Product name
- DUB Inhibitor VI, P22077
- Purity
- The DUB Inhibitor VI, P22077 controls the biological activity of DUB. This small molecule/inhibitor is primarily used for Protease Inhibitors applications.
- Packaging
- 25 mg
- Price
- $252
- Updated
- 2025/07/31
- Product number
- 4485
- Product name
- P22077
- Purity
- ≥99%(HPLC)
- Packaging
- 10
- Price
- $201
- Updated
- 2021/12/16
- Product number
- 4485
- Product name
- P22077
- Purity
- ≥99%(HPLC)
- Packaging
- 50
- Price
- $817
- Updated
- 2021/12/16
- Product number
- P122470
- Product name
- P22077
- Packaging
- 50mg
- Price
- $360
- Updated
- 2021/12/16
- Product number
- 256138
- Product name
- P 22077
- Packaging
- 10mg
- Price
- $446
- Updated
- 2021/12/16
P 22077 Chemical Properties,Usage,Production
Description
P22077 (1247819-59-5) is a selective (tested against 23 other DUBs) inhibitor of USP7 (IC50?= 8 μM) and the closely related USP47.1,2?It destabilizes claspin, a scaffolding protein involved in regulating Chk1 kinase, a DNA damage response enzyme.2?P22077 inhibits neuroblastoma growth?via?induction of p53-mediated apoptosis.3?N-Myc was destabilized by P22077 inhibition of USP7 in human neuroblastoma cells.4?It was able to stabilize p53 levels in conjunction with an Mdm2 inhibitor (Nutlin-3,?Cat# 10-1350)?in HCT116 colorectal carcinoma cells.5
Uses
P22077 is an analog of the ubiquitin-specific protease (USP7) inhibitor P5091. It inhibits USP7, as well.
Synthesis
42456-75-7
1996-44-7
1247819-59-5
1. 2-Acetyl-5-chlorothiophene (4.00 g, 24.8 mmol) was added in batches to fuming nitric acid (24 mL) cooled in an ice bath. 2. The reaction mixture was stirred at room temperature for 30 minutes and then poured into 200 mL of ice water. 3. The precipitated solid was extracted with ether, and the organic phase was dried, filtered, and concentrated in vacuum to afford the crude product 1-(5-chloro-4-nitrothiophen-2-yl)ethan-1-one (4.50 g, yellow solid), which did not require further purification. 4. 2,4-difluorothiophenol (4.30 g, 29.4 mmol) was added to a solution of sodium methanolate (1.40 g, 26.3 mmol) in methanol (250 mL). 5. The mixture was stirred at room temperature for 20 minutes before the crude product 1-(5-chloro-4-nitrothiophen-2-yl)ethan-1-one (5.50 g) was added. 6. The mixture was stirred overnight and then water (250 mL) was added, the solid formed was collected by filtration and dried under vacuum at 40 °C. The product was reconstituted by acetonitrile over a 2-minute period. 7. The product was recrystallized twice by acetonitrile to give 1-(5-((2,4-difluorophenyl)thio)-4-nitrothiophen-2-yl)ethanone (3.30 g, 39% yield) as a white solid. 8. 1H NMR (300 MHz, DMSO) δ 8.50, 8.00, 7.97, 7.95, 7.9, 7.71, 7.70, 7.68, 7.67, 7.65, 7.64, 7.43, 7.40, 7.37, 2.50.
in vivo
P 22077 (15 mg/kg, i.p. 21 days) shows potent antitumor activities in an xenograft mouse model bearing IMR-32-derived tumors; P 22077 also exhibits antitumor effects after treatment at 10 mg/kg for 14 days in mice bearing SH-SY5Y-derived tumors, and at 20 mg/kg for 12 days in mice bearing NGP-derived tumors[2].
storage
Store at +4°C
References
[1] XUFAN TIAN. Characterization of selective ubiquitin and ubiquitin-like protease inhibitors using a fluorescence-based multiplex assay format.[J]. Assay and drug development technologies, 2011, 9 2: 165-173. DOI:10.1089/adt.2010.0317
[2] MIKAEL ALTUN. Activity-based chemical proteomics accelerates inhibitor development for deubiquitylating enzymes.[J]. Chemistry & biology, 2011: 1401-1412. DOI:10.1016/j.chembiol.2011.08.018
[3] Y-H FAN. USP7 inhibitor P22077 inhibits neuroblastoma growth via inducing p53-mediated apoptosis[J]. Cell Death & Disease, 2013, 4 10: e867-e867. DOI:10.1038/cddis.2013.400
[4] OMID TAVANA. HAUSP deubiquitinates and stabilizes N-Myc in neuroblastoma[J]. Nature Medicine, 2016, 22 10: 1180-1186. DOI:10.1038/nm.4180
[5] OMID TAVANA Wei G Hongbin Sun. Targeting HAUSP in both p53 wildtype and p53-mutant tumors.[J]. Cell Cycle, 2018, 17 7: 823-828. DOI:10.1080/15384101.2018.1456293
P 22077 Preparation Products And Raw materials
Raw materials
Preparation Products
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