Importazole HCl | CAS#662163-81-7

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

MedKoo CAT#: 329642

CAS#: Importazole HCl

Description: 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 HCl

CAS# Importazole HCl

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329642
Name: Importazole HCl
CAS#: Importazole HCl
Chemical Formula: C20H23ClN4
Exact Mass: 0.00
Molecular Weight: 354.882
Elemental Analysis: C, 67.69; H, 6.53; Cl, 9.99; N, 15.79

Price and Availability

Size	Price	Availability
200mg	USD 750	2 weeks
500mg	USD 1650	2 weeks
1g	USD 2950	2 weeks
2g	USD 5250	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 662163-81-7 (free base) Importazole HCl

Synonym: Importazole, Importazole hydrochloride, Importazole HCl.

IUPAC/Chemical Name: N-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-amine hydrochloride

InChi Key: CVZZTLGULJBEHN-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H22N4.ClH/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);1H

SMILES Code: CC(NC1=C2C=CC=CC2=NC(N3CCCC3)=N1)C4=CC=CC=C4.[H]Cl

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

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Product Data:

Product Data

Instruction:

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Biological target:	Importazole is a small molecule inhibitor of the 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). Reference: ACS Chem Biol. 2011 Jul 15;6(7):700-8. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/21469738/
In vivo activity:	TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 354.88 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.

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:	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 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:	TBD

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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.

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