| Identification | Back Directory | [Name]
N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine | [CAS]
662163-81-7 | [Synonyms]
CS-2426
ImportazoL
Importazole
N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
4-Quinazolinamine, N-(1-phenylethyl)-2-(1-pyrrolidinyl)- | [Molecular Formula]
C20H22N4 | [MDL Number]
MFCD04077630 | [MOL File]
662163-81-7.mol | [Molecular Weight]
318.42 |
| Chemical Properties | Back Directory | [Boiling point ]
516.8±42.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >5mg/mL | [form ]
powder | [pka]
7.27±0.59(Predicted) | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Importazole is a cell-permeable inhibitor of importin-β, which transports cargo molecules bearing a nuclear localization signal into the nucleus.1 Importazole prevents nuclear import of GFP-tagged nuclear factor of activated T cells (NFAT-GFP) in HEK293 cells (IC50 = 15 μM), which is reversible upon importazole washout.1 Importazole does not interfere with transportin-mediated nuclear import or chromosomal maintenance 1 (CRM1)-mediated nuclear export.1 Importazole inhibits nuclear import of topoisomerase IIβ binding protein 1 (TopBP1) in Xenopus egg extracts and of NF-κB in multiple myeloma cells.2,3 It also induces defects in spindle and microtubule formation in vitro.4 | [Uses]
Importazole has been used:
- to inhibit importin-β and to elucidate the mechanism of enhanced nuclear localization of heat shock protein 70 (HSP70) by vaccinia-related kinase 3 (VRK3)
- to treat COS?7 cells transfected with the expressing vectors of WT HNF4α , S78A, and S78D to study its effect
- as a KPNB inhibitor to determine whether CREB-regulated co-activator 1 (CRTC1) would be escorted into the nucleus by the classical nuclear localizing sequence (NLS)- dependent machinery
- as a functional inhibitor of Importin β in embryo treatment
- as an?importin?inhibitor to treat the transfected H1299 cells to block nuclear translocation of phosphorylated p53-RS
| [Uses]
Importazole is an importin-β inhibitor. | [Definition]
ChEBI: N-(1-phenylethyl)-2-(1-pyrrolidinyl)-4-quinazolinamine is a member of quinazolines. | [Biochem/physiol Actions]
Importazole is an inhibitor of importin-β transport receptors. During interphase, the transport receptor importin-β carries cargoes into the nucleus, where RanGTP releases them. Importazole somehow disrupts the importin/RAN interaction. Importazole is selective among other transporters. Compounds are imported into, but not out of, cells. | [References]
1) Soderholm et al. (2011), Importazole, a small molecule inhibitor of the transport receptor importin-β; ACS Chem. Biol., 6 700
2) Bird et al. (2013), RanGTP and CLASP1 cooperate to position the mitotic spindle; Mol. Biol. Cell, 24 2506
3) Bai et al. (2014), Importin β-dependent nuclear import of TopBP1 in ATR-Chk1 checkpoint in Xenopus egg extracts; Cell Signal., 26 857
4) Yan et al. (2015), Importin β1 mediates nuclear factor-κB signal transduction into the nuclei of myeloma cells and affects their proliferation and apoptosis; Cell Signal., 27 851
5) Zhu et al. (2018), KPNB1 inhibition disrupts proteostasis and triggers unfolded protein response-mediated apoptosis in glioblastoma cells; Oncogene 37 2936 |
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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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