N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
Synonym(s):N-(1-Phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-amine
- CAS NO.:662163-81-7
- Empirical Formula: C20H22N4
- Molecular Weight: 318.42
- MDL number: MFCD04077630
- Update Date: 2023-09-04 16:42:00
What is N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine?
Description
Importazole is a cell-permeable inhibitor of importin-β, which transports cargo molecules bearing a nuclear localization signal into the nucleus. 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. Importazole does not interfere with transportin-mediated nuclear import or chromosomal maintenance 1 (CRM1)-mediated nuclear export. Importazole inhibits nuclear import of topoisomerase IIβ binding protein 1 (TopBP1) in Xenopus egg extracts and of NF-κB in multiple myeloma cells. It also induces defects in spindle and microtubule formation in vitro.
The Uses of N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
Importazole is an importin-β inhibitor.
The Uses of N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
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
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
Properties of N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
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. |
Safety information for N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
Computed Descriptors for N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine
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