2-D08
- Product Name
- 2-D08
- CAS No.
- 144707-18-6
- Chemical Name
- 2-D08
- Synonyms
- 2-D08;2-D08 >=98% (HPLC);2-D08, 10 mM in DMSO;2',3',4'-Trihydroxyflavone;2-(2,3,4-Trihydroxyphenyl)-4H-chromen-4-one;2-(2,3,4-Trihydroxyphenyl)-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 2-(2,3,4-trihydroxyphenyl)-;2-D08/2-(2,3,4-Trihydroxyphenyl)-4H-1-benzopyran-4-one;Ubiquitin ligase,Axl,2-D08,Tyro3,E3 ligating enzyme,Ubiquitin activating enzyme,Inhibitor,E1 activating enzyme,inhibit,2-D-08,2 D08,E1/E2/E3 Enzyme,2D08,E2 conjugating enzyme,Mer,Ubiquitin conjugating enzyme,TAM Receptor
- CBNumber
- CB33067528
- Molecular Formula
- C15H10O5
- Formula Weight
- 270.24
- MOL File
- 144707-18-6.mol
2-D08 Property
- Boiling point:
- 517.9±50.0 °C(Predicted)
- Density
- 1.548±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- ≥74.6 mg/mL in DMSO; ≥1.76 mg/mL in EtOH with gentle warming and ultrasonic; insoluble in H2O
- form
- powder
- pka
- 7.45±0.40(Predicted)
- color
- white to beige
Safety
- WGK Germany
- 3
- HS Code
- 2932990090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML1052
- Product name
- 2-D08
- Purity
- ≥98% (HPLC)
- Packaging
- 5MG
- Price
- $121
- Updated
- 2025/07/31
- Product number
- SML1052
- Product name
- 2-D08
- Purity
- ≥98% (HPLC)
- Packaging
- 25MG
- Price
- $489
- Updated
- 2025/07/31
- Product number
- 20459
- Product name
- 2-D08
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 20459
- Product name
- 2-D08
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $100
- Updated
- 2024/03/01
- Product number
- 20459
- Product name
- 2-D08
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $139
- Updated
- 2024/03/01
2-D08 Chemical Properties,Usage,Production
Uses
2-D08 has been used as a small ubiquitin-like modifier (SUMO)ylation inhibitor.
Biological Activity
2-d08 (2’,3’,4’-trihydroxyflavone) is a sumoylation inhibitor.protein sumoylation is a dynamic posttranslational modification involved in various biological processes, such as cellular homeostasis and development. sumoylation has been reported to play a key role in cancer, though so far there are few small molecule probes available.
Biochem/physiol Actions
2-D08 is a potent and cell-permeable inhibitor of sumoylation that block the transfer of SUMO (small ubiquitin-like modifier) from the E2 enzyme (Ubc9) thioester conjugate to the substrate.
Synthesis
7143-46-6
144707-18-6
General procedure for the synthesis of 2',3',4'-trihydroxyflavones using the compound (CAS: 7143-46-6) as starting material: flavone 13 (100 mg, 0.32 mmol, 1.0 equiv) was dissolved in 12 mL of dichloromethane. Boron tribromide (BBr3, 1.067 mL, 6.4 mmol, 20 eq.) was slowly added to the solution at room temperature and the reaction mixture was stirred for 48 hours. Upon completion of the reaction, the mixture was slowly poured into ice water and the precipitate formed was collected by filtration. The crude product was purified by fast column chromatography to afford 2',3',4'-trihydroxyflavone as a yellow amorphous solid (40 mg, 46% yield). The structure of the product was confirmed by the following characterization data: 1H NMR (400 MHz, DMSO-d6) δ: 10.02 (brs, 1H), 9.55 (brs, 1H), 8.89 (brs, 1H), 8.01 (dd, 1H, J = 1.5, 7.6 Hz), 7.78 (dt, 1H, J = 2.0, 7.6 Hz), 7.69 (d, 1H, J = 8.5 Hz), 7.45 (t, 1H, J = 7.5 Hz), 7.34 (d, 1H, J = 8.9 Hz), 7.11 (s, 1H), 6.54 (d, 1H, J = 9.0 Hz).13C NMR (125 MHz, DMSO-d6) δ: 117.5, 161.8, 156.1, 149.7 , 147.5, 134.2, 133.5, 123.4, 125.0, 123.6, 119.3, 118.6, 110.3, 109.5, 108.1. high-resolution mass spectrometry (HRMS) calculated value ([M + H]+) 271.0601, measured value 271.0597.
in vitro
2-d08 was identified as a cell permeable, mechanistically unique inhibitor of protein sumoylation. this compound was found to be able to block sumoylation of topoisomerase i in two different cancer cell lines when co-dosed with camptothecin. in addition, futher analyses indicated that 2-d08 inhibited sumoylation via preventing transfer of small ubiquitin-like modifier (sumo) from the ubc9-sumo thioester to the substrate without affecting sumo-activating enzyme e1 (sae-1/2) or e2 ubc9-sumo thioester formation, a mechanism of action that was unprecedented before [1]. moreover, it was found that 2-d08 at 100 μm could effectively inhibit 10 μm camptothecin induced topoisomerase i sumoylation in breast cancer without affecting overall cellular protein ubiquitinations [2].
IC 50
Axl
References
[1] kim ys, keyser sg, schneekloth js jr. synthesis of 2',3',4'-trihydroxyflavone (2-d08), an inhibitor of protein sumoylation. bioorg med chem lett. 2014 feb 15;24(4):1094-7.
[2] kim ys, nagy k, keyser s, schneekloth js jr. an electrophoretic mobility shift assay identifies a mechanistically unique inhibitor of protein sumoylation. chem biol. 2013 apr 18;20(4):604-13.
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View Lastest Price from 2-D08 manufacturers
- Product
- 2-D08 144707-18-6
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98%HPLC
- Supply Ability
- 10t
- Release date
- 2019-12-24