Alsterpaullone
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MedKoo CAT#: 206619

CAS#: 237430-03-4

Description: Alsterpaullone, also known as 9-Nitropaullone and NSC 705701, is a derivative of kenpaullone and an ATP-competitive inhibitor of several cyclin-dependent kinases (CDKs) as well as glycogen synthase kinase 3β (GSK3β). Alsterpaullone induces apoptosis by activation of caspase-9 due to perturbation in mitochondrial membrane potential. Alsterpaullone mediated toxicity in HeLa Cells through Apoptosis-Inducing Effect.


Chemical Structure

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Alsterpaullone
CAS# 237430-03-4

Theoretical Analysis

MedKoo Cat#: 206619
Name: Alsterpaullone
CAS#: 237430-03-4
Chemical Formula: C16H11N3O3
Exact Mass: 293.08
Molecular Weight: 293.282
Elemental Analysis: C, 65.53; H, 3.78; N, 14.33; O, 16.37

Price and Availability

Size Price Availability Quantity
50.0mg USD 550.0 2 Weeks
100.0mg USD 950.0 2 Weeks
200.0mg USD 1650.0 2 Weeks
500.0mg USD 2450.0 2 Weeks
1.0g USD 3450.0 2 Weeks
2.0g USD 5850.0 2 Weeks
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Synonym: 9-Nitropaullone; NSC 705701; NSC705701; NSC-705701; Alsterpaullone

IUPAC/Chemical Name: 7,12-dihydro-9-nitro-indolo[3,2-d][1]benzazepin-6(5H)-one

InChi Key: OLUKILHGKRVDCT-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H11N3O3/c20-15-8-12-11-7-9(19(21)22)5-6-14(11)18-16(12)10-3-1-2-4-13(10)17-15/h1-7,18H,8H2,(H,17,20)

SMILES Code: O=C1NC2=CC=CC=C2C(NC3=C4C=C([N+]([O-])=O)C=C3)=C4C1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 293.282 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

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1: Faria CC, Agnihotri S, Mack SC, Golbourn BJ, Diaz RJ, Olsen S, Bryant M, Bebenek M, Wang X, Bertrand KC, Kushida M, Head R, Clark I, Dirks P, Smith CA, Taylor MD, Rutka JT. Identification of alsterpaullone as a novel small molecule inhibitor to target group 3 medulloblastoma. Oncotarget. 2015 Aug 28;6(25):21718-29. PubMed PMID: 26061748; PubMed Central PMCID: PMC4673298.

2: Walters BJ, Lin W, Diao S, Brimble M, Iconaru LI, Dearman J, Goktug A, Chen T, Zuo J. High-throughput screening reveals alsterpaullone, 2-cyanoethyl as a potent p27Kip1 transcriptional inhibitor. PLoS One. 2014 Mar 19;9(3):e91173. doi: 10.1371/journal.pone.0091173. eCollection 2014. PubMed PMID: 24646893; PubMed Central PMCID: PMC3960108.

3: Cui C, Wang Y, Wang Y, Zhao M, Peng S. Alsterpaullone, a Cyclin-Dependent Kinase Inhibitor, Mediated Toxicity in HeLa Cells through Apoptosis-Inducing Effect. J Anal Methods Chem. 2013;2013:602091. doi: 10.1155/2013/602091. Epub 2013 Mar 12. PubMed PMID: 23577282; PubMed Central PMCID: PMC3610382.

4: Trevino M, Stefanik DJ, Rodriguez R, Harmon S, Burton PM. Induction of canonical Wnt signaling by alsterpaullone is sufficient for oral tissue fate during regeneration and embryogenesis in Nematostella vectensis. Dev Dyn. 2011 Dec;240(12):2673-9. doi: 10.1002/dvdy.22774. Epub 2011 Nov 2. PubMed PMID: 22052821; PubMed Central PMCID: PMC3672222.

5: Kunick C, Zeng Z, Gussio R, Zaharevitz D, Leost M, Totzke F, Schächtele C, Kubbutat MH, Meijer L, Lemcke T. Structure-aided optimization of kinase inhibitors derived from alsterpaullone. Chembiochem. 2005 Mar;6(3):541-9. PubMed PMID: 15696597.

6: Greenwald RB, Zhao H, Xia J, Wu D, Nervi S, Stinson SF, Majerova E, Bramhall C, Zaharevitz DW. Poly(ethylene glycol) prodrugs of the CDK inhibitor, alsterpaullone (NSC 705701): synthesis and pharmacokinetic studies. Bioconjug Chem. 2004 Sep-Oct;15(5):1076-83. PubMed PMID: 15366962.

7: Soni DV, Jacobberger JW. Inhibition of cdk1 by alsterpaullone and thioflavopiridol correlates with increased transit time from mid G2 through prophase. Cell Cycle. 2004 Mar;3(3):349-57. Epub 2004 Mar 1. PubMed PMID: 14726692.

8: Lahusen T, De Siervi A, Kunick C, Senderowicz AM. Alsterpaullone, a novel cyclin-dependent kinase inhibitor, induces apoptosis by activation of caspase-9 due to perturbation in mitochondrial membrane potential. Mol Carcinog. 2003 Apr;36(4):183-94. PubMed PMID: 12669310.