Degrasyn
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MedKoo CAT#: 406176

CAS#: 856243-80-6

Description: Degrasyn, also known as WP1130, is a small molecule that specifically and rapidly down-regulates both wild-type and mutant Bcr/Abl protein without affecting bcr/abl gene expression in chronic myelogenous leukemia (CML) cells. WP1130 was more effective in reducing leukemic versus normal hematopoietic colony formation and strongly inhibited colony formation of cells derived from patients with T315I mutant Bcr/Abl-expressing CML in blast crisis. WP1130 suppressed the growth of K562 heterotransplanted tumors as well as both wild-type Bcr/Abl and T315I mutant Bcr/Abl-expressing BaF/3 cells transplanted into nude mice. WP1130 may be useful in treating CML.


Chemical Structure

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Degrasyn
CAS# 856243-80-6

Theoretical Analysis

MedKoo Cat#: 406176
Name: Degrasyn
CAS#: 856243-80-6
Chemical Formula: C19H18BrN3O
Exact Mass: 383.06332
Molecular Weight: 384.27
Elemental Analysis: C, 59.39; H, 4.72; Br, 20.79; N, 10.94; O, 4.16

Price and Availability

Size Price Availability Quantity
25.0mg USD 250.0 2 Weeks
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 2850.0 2 Weeks
2.0g USD 4350.0 2 Weeks
Bulk inquiry

Synonym: WP1130; WP-1130; WP 1130. Degrasyn

IUPAC/Chemical Name: (S,E)-3-(6-bromopyridin-2-yl)-2-cyano-N-(1-phenylbutyl)acrylamide

InChi Key: LIDOPKHSVQTSJY-VMEIHUARSA-N

InChi Code: InChI=1S/C19H18BrN3O/c1-2-7-17(14-8-4-3-5-9-14)23-19(24)15(13-21)12-16-10-6-11-18(20)22-16/h3-6,8-12,17H,2,7H2,1H3,(H,23,24)/b15-12+/t17-/m0/s1

SMILES Code: O=C(N[C@H](C1=CC=CC=C1)CCC)/C(C#N)=C/C2=NC(Br)=CC=C2

Appearance: white 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, not in water

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 384.27 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: Peng Z, Maxwell DS, Sun D, Bhanu Prasad BA, Schuber PT Jr, Pal A, Ying Y, Han D, Gao L, Wang S, Levitzki A, Kapuria V, Talpaz M, Young M, Showalter HD, Donato NJ, Bornmann WG. Degrasyn-like symmetrical compounds: Possible therapeutic agents for multiple myeloma (MM-I). Bioorg Med Chem. 2014 Feb 15;22(4):1450-8. doi: 10.1016/j.bmc.2013.12.048. Epub 2014 Jan 3. PubMed PMID: 24457091.

2: Perry JW, Ahmed M, Chang KO, Donato NJ, Showalter HD, Wobus CE. Antiviral activity of a small molecule deubiquitinase inhibitor occurs via induction of the unfolded protein response. PLoS Pathog. 2012;8(7):e1002783. doi: 10.1371/journal.ppat.1002783. Epub 2012 Jul 5. PubMed PMID: 22792064; PubMed Central PMCID: PMC3390402.

3: Burkholder KM, Perry JW, Wobus CE, Donato NJ, Showalter HD, Kapuria V, O'Riordan MX. A small molecule deubiquitinase inhibitor increases localization of inducible nitric oxide synthase to the macrophage phagosome and enhances bacterial killing. Infect Immun. 2011 Dec;79(12):4850-7. doi: 10.1128/IAI.05456-11. Epub 2011 Sep 12. PubMed PMID: 21911458; PubMed Central PMCID: PMC3232648.

4: Kapuria V, Levitzki A, Bornmann WG, Maxwell D, Priebe W, Sorenson RJ, Showalter HD, Talpaz M, Donato NJ. A novel small molecule deubiquitinase inhibitor blocks Jak2 signaling through Jak2 ubiquitination. Cell Signal. 2011 Dec;23(12):2076-85. doi: 10.1016/j.cellsig.2011.08.002. Epub 2011 Aug 9. PubMed PMID: 21855629.

5: Sun H, Kapuria V, Peterson LF, Fang D, Bornmann WG, Bartholomeusz G, Talpaz M, Donato NJ. Bcr-Abl ubiquitination and Usp9x inhibition block kinase signaling and promote CML cell apoptosis. Blood. 2011 Mar 17;117(11):3151-62. doi: 10.1182/blood-2010-03-276477. Epub 2011 Jan 19. PubMed PMID: 21248063.

6: Kapuria V, Peterson LF, Fang D, Bornmann WG, Talpaz M, Donato NJ. Deubiquitinase inhibition by small-molecule WP1130 triggers aggresome formation and tumor cell apoptosis. Cancer Res. 2010 Nov 15;70(22):9265-76. doi: 10.1158/0008-5472.CAN-10-1530. Epub 2010 Nov 2. PubMed PMID: 21045142.

7: Pham LV, Tamayo AT, Li C, Bornmann W, Priebe W, Ford RJ. Degrasyn potentiates the antitumor effects of bortezomib in mantle cell lymphoma cells in vitro and in vivo: therapeutic implications. Mol Cancer Ther. 2010 Jul;9(7):2026-36. doi: 10.1158/1535-7163.MCT-10-0238. Epub 2010 Jul 6. PubMed PMID: 20606045.

8: Bartholomeusz G, Talpaz M, Bornmann W, Kong LY, Donato NJ. Degrasyn activates proteasomal-dependent degradation of c-Myc. Cancer Res. 2007 Apr 15;67(8):3912-8. PubMed PMID: 17440106.

9: Bartholomeusz GA, Talpaz M, Kapuria V, Kong LY, Wang S, Estrov Z, Priebe W, Wu J, Donato NJ. Activation of a novel Bcr/Abl destruction pathway by WP1130 induces apoptosis of chronic myelogenous leukemia cells. Blood. 2007 Apr 15;109(8):3470-8. Epub 2007 Jan 3. PubMed PMID: 17202319; PubMed Central PMCID: PMC1852235.

Degrasyn

25.0mg / USD 250.0


Additional Information