N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine Chemical Properties

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

WGK Germany 

3

N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-aMine Usage And Synthesis

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.

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] JONATHAN F. SODERHOLM. Importazole, a Small Molecule Inhibitor of the Transport Receptor Importin-β[J]. ACS Chemical Biology, 2011, 6 7: 700-708. DOI:10.1021/cb2000296
[2] STEPHEN L BIRD  Karsten W  Rebecca Heald. RanGTP and CLASP1 cooperate to position the mitotic spindle.[J]. Molecular Biology of the Cell, 2013, 24 16: 2506-2514. DOI:10.1091/mbc.e13-03-0150
[3] LIPING BAI  Shan Y  W Matthew Michael. Importin β-dependent nuclear import of TopBP1 in ATR–Chk1 checkpoint in Xenopus egg extracts[J]. Cellular signalling, 2014, 26 5: Pages 857-867. DOI:10.1016/j.cellsig.2014.01.006
[4] WENQING YAN . Importin β1 mediates nuclear factor-κB signal transduction into the nuclei of myeloma cells and affects their proliferation and apoptosis[J]. Cellular signalling, 2015, 27 4: Pages 851-859. DOI:10.1016/j.cellsig.2015.01.013
[5] ZHI-CHUAN ZHU. KPNB1 inhibition disrupts proteostasis and triggers unfolded protein response-mediated apoptosis in glioblastoma cells[J]. Oncogene, 2018, 37 22: 2936-2952. DOI:10.1038/s41388-018-0180-9

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