Reversine
CS-870 · REVERSINE · Reversine, >96% · Reversine, >=98% · REVERSINE USP/EP/BP · Picropodophyllin (PPP) · Reversine, 10 mM in DMSO · 2-(4-MORPHOLINOANILINO)-6-CYCLOHEXYLAMINOPURINE
식별자 및 물리적 특성
| CAS No. | 656820-32-5 |
|---|---|
| 분자식 | C21H27N7O |
| 평균 분자량 | 393.5 g/mol |
| 단동위원소 질량 | 393.22770851 g/mol |
| SMILES | c1nc2nc(Nc3ccc(N4CCOCC4)cc3)nc(NC3CCCCC3)c2[nH]1 |
| InChIKey | ZFLJHSQHILSNCM-UHFFFAOYSA-N |
| PubChem CID | 210332 |
| ChEMBL | CHEMBL188343 |
| ChEBI | CHEBI:70723 |
| EC No. | 636-256-0 |
| DTXSID | DTXSID8041113 |
화학 및 물리적 성질
| XLogP | 3.9 |
|---|---|
| 극성 표면적 | 91 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 7 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 29 |
| 형식 전하 | 0 |
| 복잡도 | 503 |
| 녹는점 | 305℃ (decomposition) |
| 끓는 점 | 736.4±70.0 °C(Predicted) |
| 밀도 | 1.343±0.06 g/cm3(Predicted) |
| 저장 조건 | 2-8°C |
| 용해도 | DMSO: 7 mg/mL, 가용성 |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 10.51±0.10(Predicted) |
| 색상 | 회백색 |
| 안정성 | 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다. |
| InChI | 1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27) |
| InChIKey | ZFLJHSQHILSNCM-UHFFFAOYSA-N |
| SMILES | C1CCC(CC1)Nc2nc(Nc3ccc(cc3)N4CCOCC4)nc5nc[nH]c25 |
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 수질 위해 등급(WGK) | 3 |
| 위험 문구(R) | 22 |
| 위험 표시 | Xn |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Reversine is a 2,6-disubstituted purine derivative that was originally found to induce dedifferentiation of C2C12 culture myoblast cells into stem cell progenitors when used at a concentration of 5 μM for four days. Depending on cell type, reversine promotes either differentiation or dedifferentiation. For example, in NT2 neuronal and HL-60 human promyelocytic leukemia cells, it induces differentiation. It inhibits the Aurora A, B, and C kinases with IC50 values of 98-876 nM and acts as an antagonist at the adenosine A3 receptor with a Ki value of 0.66 μM. Reversine is also used for studies of chromosome segregation. It inhibits the mitotic spindle checkpoint enzyme MPS1 with IC50 values of 6 and 2.8 nM for its kinase domain and full-length version, respectively). Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling.
용도
Reversine acts as a potent human A3 adenosine receptor antagonist and pan-aurora A/B/C kinase inhibitor. Used for stem cell differentiation.