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MedKoo Cat#: 530571 | Name: Importazole free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Importazole is a small molecule inhibitor of the transport receptor importin-β. Importazole specifically inhibits the function of importin-β, likely by altering its interaction with RanGTP. Importazole is a valuable tool to evaluate the function of the importin-β/RanGTP pathway at specific stages during the cell cycle.

Chemical Structure

Importazole free base
Importazole free base
CAS#662163-81-7 (free base)

Theoretical Analysis

MedKoo Cat#: 530571

Name: Importazole free base

CAS#: 662163-81-7 (free base)

Chemical Formula: C20H22N4

Exact Mass: 318.1844

Molecular Weight: 318.42

Elemental Analysis: C, 75.44; H, 6.96; N, 17.60

Price and Availability

Size Price Availability Quantity
10mg USD 85.00 Ready to ship
25mg USD 190.00 Ready to ship
50mg USD 350.00 Ready to ship
100mg USD 550.00 Ready to ship
200mg USD 950.00 Ready to ship
500mg USD 1,650.00 Ready to ship
1g USD 2,950.00 Ready to ship
2g USD 3,950.00 Ready to ship
5g USD 6,850.00 2 weeks
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Related CAS #
662163-81-7 (free base) Importazole HCl
Synonym
Importazole
IUPAC/Chemical Name
N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-amine
InChi Key
HKGJEZIGDHFJFL-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H22N4/c1-15(16-9-3-2-4-10-16)21-19-17-11-5-6-12-18(17)22-20(23-19)24-13-7-8-14-24/h2-6,9-12,15H,7-8,13-14H2,1H3,(H,21,22,23)
SMILES Code
CC(NC1=C2C=CC=CC2=NC(N3CCCC3)=N1)C4=CC=CC=C4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Importazole is a small molecule inhibitor of the nuclear transport receptor importin-β.
In vitro activity:
Although importazole blocked the FRET interaction between CFP-RanGTP and YFP-importin-β in vitro, it did not obviously affect the binding of the two proteins in pull-down assays (Figure S1). To begin elucidating the mechanism of importazole action, importazole was tested to see if it could alter the ability of importin-β to protect RanGTP from RanGAP-stimulated hydrolysis in vitro. Binding curves calculated from these data do not indicate that importazole disrupts the RanGTP/importin-β interaction, and if anything, suggest that importazole may slightly stabilize the complex (Figure S3). The inability of importazole to disrupt the RanGTP/importin-β interaction is not entirely surprising considering the multiple large interaction surfaces between the two proteins. One possible explanation for the importazole-induced FRET change is that importazole binding causes a conformational change that disrupts the CFP-RanGTP/YFP-importin-β FRET interaction without preventing binding. To test whether importazole binds to importin-β in vitro, we used a fluorescent thermal shift assay with the dye Sypro® Orange, since small molecule binding is expected to affect the thermal stability of a protein. Importazole reduced the melting temperature of importin-β by 1.72+/− 0.27 °C (Figure 2, panels a and b), but was unaffected by a related compound of comparable hydrophobicity that did not interfere with CFP-RanGTP/YFP-importin-β FRET (compound 3016, Figure S4, panels c and d, and data not shown). In contrast, importazole did not significantly affect the melting curves of related importin-β family members transportin and CRM1, or that of RanGTP, suggesting that importazole binds preferentially to importin-β (Figure 2, panel c, Figure S5). Going forward, a crystal structure of the RanGTP/importin-β complex in the presence of importazole will likely be necessary to fully elucidate its biochemical mechanism of action. Reference: ACS Chem Biol. 2011 Jul 15;6(7):700-8. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/21469738/
In vivo activity:
Solvent mg/mL mM
Solubility
DMSO 33.0 103.64
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 318.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Soderholm JF, Bird SL, Kalab P, Sampathkumar Y, Hasegawa K, Uehara-Bingen M, Weis K, Heald R. Importazole, a small molecule inhibitor of the transport receptor importin-β. ACS Chem Biol. 2011 Jul 15;6(7):700-8. doi: 10.1021/cb2000296. Epub 2011 Apr 21. PMID: 21469738; PMCID: PMC3137676. 2. Yan WQ, Du J, Jiang H, Hou J. [Effect of nuclear receptor inhibitor importazole on the proliferation and apoptosis of multiple myeloma cells]. Zhonghua Xue Ye Xue Za Zhi. 2013 Apr;34(4):323-6. Chinese. doi: 10.3760/cma.j.issn.0253-2727.2013.04.016. PMID: 23668205.
In vivo protocol:
1: Soderholm JF, Bird SL, Kalab P, Sampathkumar Y, Hasegawa K, Uehara-Bingen M, Weis K, Heald R. Importazole, a small molecule inhibitor of the transport receptor importin-β. ACS Chem Biol. 2011 Jul 15;6(7):700-8. doi: 10.1021/cb2000296. Epub 2011 Apr 21. PubMed PMID: 21469738; PubMed Central PMCID: PMC3137676. 2: Mojica SA, Hovis KM, Frieman MB, Tran B, Hsia RC, Ravel J, Jenkins-Houk C, Wilson KL, Bavoil PM. SINC, a type III secreted protein of Chlamydia psittaci, targets the inner nuclear membrane of infected cells and uninfected neighbors. Mol Biol Cell. 2015 May 15;26(10):1918-34. doi: 10.1091/mbc.E14-11-1530. Epub 2015 Mar 18. PubMed PMID: 25788290; PubMed Central PMCID: PMC4436835. 3: Yan W, Li R, He J, Du J, Hou J. Importin β1 mediates nuclear factor-κB signal transduction into the nuclei of myeloma cells and affects their proliferation and apoptosis. Cell Signal. 2015 Apr;27(4):851-9. doi: 10.1016/j.cellsig.2015.01.013. Epub 2015 Jan 30. PubMed PMID: 25643631. 4: Bird SL, Heald R, Weis K. RanGTP and CLASP1 cooperate to position the mitotic spindle. Mol Biol Cell. 2013 Aug;24(16):2506-14. doi: 10.1091/mbc.E13-03-0150. Epub 2013 Jun 19. PubMed PMID: 23783028; PubMed Central PMCID: PMC3744954. 5: Pathak GK, Ornstein H, Aranda-Espinoza H, Karlsson AJ, Shah SB. Increases in Retrograde Injury Signaling Complex-Related Transcripts in Central Axons following Injury. Neural Plast. 2016;2016:3572506. Epub 2016 Oct 25. PubMed PMID: 27847648; PubMed Central PMCID: PMC5099454. 6: Yan WQ, Du J, Jiang H, Hou J. [Effect of nuclear receptor inhibitor importazole on the proliferation and apoptosis of multiple myeloma cells]. Zhonghua Xue Ye Xue Za Zhi. 2013 Apr;34(4):323-6. doi: 10.3760/cma.j.issn.0253-2727.2013.04.016. Chinese. PubMed PMID: 23668205. 7: Bai L, Michael WM, Yan S. Importin β-dependent nuclear import of TopBP1 in ATR-Chk1 checkpoint in Xenopus egg extracts. Cell Signal. 2014 May;26(5):857-67. doi: 10.1016/j.cellsig.2014.01.006. Epub 2014 Jan 15. PubMed PMID: 24440306; PubMed Central PMCID: PMC3951582. 8: Kublun I, Ehm P, Brehm MA, Nalaskowski MM. Efficacious inhibition of Importin α/β-mediated nuclear import of human inositol phosphate multikinase. Biochimie. 2014 Jul;102:117-23. doi: 10.1016/j.biochi.2014.03.001. Epub 2014 Mar 12. PubMed PMID: 24632208. 9: Roggero VR, Zhang J, Parente LE, Doshi Y, Dziedzic RC, McGregor EL, Varjabedian AD, Schad SE, Bondzi C, Allison LA. Nuclear import of the thyroid hormone receptor α1 is mediated by importin 7, importin β1, and adaptor importin α1. Mol Cell Endocrinol. 2016 Jan 5;419:185-97. doi: 10.1016/j.mce.2015.10.016. Epub 2015 Oct 23. PubMed PMID: 26525414; PubMed Central PMCID: PMC4684427. 10: Maly IV, Hofmann WA. Calcium-regulated import of myosin IC into the nucleus. Cytoskeleton (Hoboken). 2016 Jun;73(7):341-50. doi: 10.1002/cm.21310. Epub 2016 Jun 13. PubMed PMID: 27192697. 11: Li X, Zhao Y, Xia Q, Zheng L, Liu L, Zhao B, Shi J. Nuclear translocation of annexin 1 following oxygen-glucose deprivation-reperfusion induces apoptosis by regulating Bid expression via p53 binding. Cell Death Dis. 2016 Sep 1;7(9):e2356. doi: 10.1038/cddis.2016.259. PubMed PMID: 27584794; PubMed Central PMCID: PMC5059862. 12: Bar Oz M, Kumar A, Elayyan J, Reich E, Binyamin M, Kandel L, Liebergall M, Steinmeyer J, Lefebvre V, Dvir-Ginzberg M. Acetylation reduces SOX9 nuclear entry and ACAN gene transactivation in human chondrocytes. Aging Cell. 2016 Jun;15(3):499-508. doi: 10.1111/acel.12456. Epub 2016 Feb 22. PubMed PMID: 26910618; PubMed Central PMCID: PMC4854920. 13: Iio A, Takagi T, Miki K, Naoe T, Nakayama A, Akao Y. DDX6 post-transcriptionally down-regulates miR-143/145 expression through host gene NCR143/145 in cancer cells. Biochim Biophys Acta. 2013 Oct;1829(10):1102-10. doi: 10.1016/j.bbagrm.2013.07.010. Epub 2013 Aug 9. PubMed PMID: 23932921.