BAY 61-3606
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MedKoo CAT#: 406177

CAS#: 732983-37-8 (free base)

Description: BAY 61-3606 is a potent (Ki = 7.5 nM) and selective inhibitor of Syk kinase. BAY 61-3606 inhibited not only degranulation (IC50 values between 5 and 46 nM) but also lipid mediator and cytokine synthesis in mast cells. BAY 61-3606 was highly efficacious in basophils obtained from healthy human subjects (IC50 = 10 nM) and seems to be at least as potent in basophils obtained from atopic (high serum IgE) subjects (IC50 = 8.1 nM). B cell receptor activation and receptors for Fc portion of IgG signaling in eosinophils and monocytes were also potently suppressed by BAY 61-3606.


Chemical Structure

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BAY 61-3606
CAS# 732983-37-8 (free base)

Theoretical Analysis

MedKoo Cat#: 406177
Name: BAY 61-3606
CAS#: 732983-37-8 (free base)
Chemical Formula: C20H18N6O3
Exact Mass: 390.14404
Molecular Weight: 390.4
Elemental Analysis: C, 61.53; H, 4.65; N, 21.53; O, 12.29

Price and Availability

Size Price Availability Quantity
100.0mg USD 850.0 2 Weeks
200.0mg USD 1450.0 2 Weeks
500.0mg USD 2450.0 2 Weeks
1.0g USD 3650.0 2 Weeks
2.0g USD 5250.0 2 Weeks
5.0g USD 7950.0 2 Weeks
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Synonym: BAY 613606; BAY613606; BAY-613606.

IUPAC/Chemical Name: 2-((7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl)amino)nicotinamide

InChi Key: SPMFEULFGGPQLN-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H18N6O3.2ClH/c1-28-15-6-5-12(10-16(15)29-2)14-11-17-22-8-9-26(17)20(24-14)25-19-13(18(21)27)4-3-7-23-19;;/h3-11H,1-2H3,(H2,21,27)(H,23,24,25);2*1H

SMILES Code: O=C(N)C1=C(NC2=NC(C3=CC=C(OC)C(OC)=C3)=CC4=NC=CN24)N=CC=C1.

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

Product Data:

Biological target: BAY 61-3606 is a Syk inhibitor with an IC50 of 10 nM.
In vitro activity: Spleen tyrosine kinase (Syk) inhibitor Bay 61-3606 was identified as a TRAIL sensitizer. Amplification of TRAIL-induced apoptosis by Bay 61-3606 was accompanied by the strong activation of Bak, caspases, and DNA fragmentation. In mechanism of action, Bay 61-3606 sensitized cells to TRAIL via two mechanisms regulating myeloid cell leukemia sequence-1 (Mcl-1). First, Bay 61-3606 triggered ubiquitin-dependent degradation of Mcl-1 by regulating Mcl-1 phosphorylation. Second, Bay 61-3606 downregulated Mcl-1 expression at the transcription level. In this context, Bay 61-3606 acted as an inhibitor of Cyclin-Dependent Kinase (CDK) 9 rather than Syk. Reference: PLoS One. 2015 Dec 31;10(12):e0146073. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4697837/
In vivo activity: Oral administration of BAY 61-3606 to rats significantly suppressed antigen-induced passive cutaneous anaphylactic reaction, bronchoconstriction, and bronchial edema at 3 mg/kg. Furthermore, BAY 61-3606 attenuated antigen-induced airway inflammation in rats. Reference: J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. https://jpet.aspetjournals.org/content/306/3/1174.long

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 8.75 22.41

Preparing Stock Solutions

The following data is based on the product molecular weight 390.4 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: 1. Kim SY, Park SE, Shim SM, Park S, Kim KK, Jeong SY, Choi EK, Hwang JJ, Jin DH, Chung CD, Kim I. Bay 61-3606 Sensitizes TRAIL-Induced Apoptosis by Downregulating Mcl-1 in Breast Cancer Cells. PLoS One. 2015 Dec 31;10(12):e0146073. doi: 10.1371/journal.pone.0146073. PMID: 26720004; PMCID: PMC4697837. 2. Du J, Wang Y, Chen D, Ji G, Ma Q, Liao S, Zheng Y, Zhang J, Hou Y. BAY61-3606 potentiates the anti-tumor effects of TRAIL against colon cancer through up-regulating DR4 and down-regulating NF-κB. Cancer Lett. 2016 Dec 28;383(2):145-153. doi: 10.1016/j.canlet.2016.10.002. Epub 2016 Oct 6. PMID: 27721019. 3. Yamamoto N, Takeshita K, Shichijo M, Kokubo T, Sato M, Nakashima K, Ishimori M, Nagai H, Li YF, Yura T, Bacon KB. The orally available spleen tyrosine kinase inhibitor 2-[7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]nicotinamide dihydrochloride (BAY 61-3606) blocks antigen-induced airway inflammation in rodents. J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. doi: 10.1124/jpet.103.052316. Epub 2003 May 23. PMID: 12766258.
In vitro protocol: 1. Kim SY, Park SE, Shim SM, Park S, Kim KK, Jeong SY, Choi EK, Hwang JJ, Jin DH, Chung CD, Kim I. Bay 61-3606 Sensitizes TRAIL-Induced Apoptosis by Downregulating Mcl-1 in Breast Cancer Cells. PLoS One. 2015 Dec 31;10(12):e0146073. doi: 10.1371/journal.pone.0146073. PMID: 26720004; PMCID: PMC4697837. 2. Du J, Wang Y, Chen D, Ji G, Ma Q, Liao S, Zheng Y, Zhang J, Hou Y. BAY61-3606 potentiates the anti-tumor effects of TRAIL against colon cancer through up-regulating DR4 and down-regulating NF-κB. Cancer Lett. 2016 Dec 28;383(2):145-153. doi: 10.1016/j.canlet.2016.10.002. Epub 2016 Oct 6. PMID: 27721019.
In vivo protocol: 1. Yamamoto N, Takeshita K, Shichijo M, Kokubo T, Sato M, Nakashima K, Ishimori M, Nagai H, Li YF, Yura T, Bacon KB. The orally available spleen tyrosine kinase inhibitor 2-[7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]nicotinamide dihydrochloride (BAY 61-3606) blocks antigen-induced airway inflammation in rodents. J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. doi: 10.1124/jpet.103.052316. Epub 2003 May 23. PMID: 12766258. 2. Du J, Wang Y, Chen D, Ji G, Ma Q, Liao S, Zheng Y, Zhang J, Hou Y. BAY61-3606 potentiates the anti-tumor effects of TRAIL against colon cancer through up-regulating DR4 and down-regulating NF-κB. Cancer Lett. 2016 Dec 28;383(2):145-153. doi: 10.1016/j.canlet.2016.10.002. Epub 2016 Oct 6. PMID: 27721019.

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1: Mitra R, Bhagavatula ID, Gope R. BAY 61-3606, CDKi, and sodium butyrate treatments alter gene expression in human vestibular schwannomas and cause cell death in vitro. Ecancermedicalscience. 2012;6:285. doi: 10.3332/ecancer.2012.285. Epub 2012 Dec 20. PubMed PMID: 23304241; PubMed Central PMCID: PMC3530378.

2: Scheib JL, Sullivan CS, Carter BD. Jedi-1 and MEGF10 signal engulfment of apoptotic neurons through the tyrosine kinase Syk. J Neurosci. 2012 Sep 19;32(38):13022-31. PubMed PMID: 22993420; PubMed Central PMCID: PMC3464495.

3: Lau KS, Zhang T, Kendall KR, Lauffenburger D, Gray NS, Haigis KM. BAY61-3606 affects the viability of colon cancer cells in a genotype-directed manner. PLoS One. 2012;7(7):e41343. doi: 10.1371/journal.pone.0041343. Epub 2012 Jul 18. PubMed PMID: 22815993; PubMed Central PMCID: PMC3399817.

4: Yang WS, Chang JW, Han NJ, Lee SK, Park SK. Spleen tyrosine kinase mediates high glucose-induced transforming growth factor-β1 up-regulation in proximal tubular epithelial cells. Exp Cell Res. 2012 Sep 10;318(15):1867-76. doi: 10.1016/j.yexcr.2012.05.016. Epub 2012 May 31. PubMed PMID: 22659134.

5: Robak T, Robak E. Tyrosine kinase inhibitors as potential drugs for B-cell lymphoid malignancies and autoimmune disorders. Expert Opin Investig Drugs. 2012 Jul;21(7):921-47. doi: 10.1517/13543784.2012.685650. Epub 2012 May 22. Review. PubMed PMID: 22612424.

6: Arthur JF, Qiao J, Shen Y, Davis AK, Dunne E, Berndt MC, Gardiner EE, Andrews RK. ITAM receptor-mediated generation of reactive oxygen species in human platelets occurs via Syk-dependent and Syk-independent pathways. J Thromb Haemost. 2012 Jun;10(6):1133-41. doi: 10.1111/j.1538-7836.2012.04734.x. PubMed PMID: 22489915.

7: Wang X, Mychajlowycz M, Lau C, Gutierrez C, Scott JA, Chow CW. Spleen tyrosine kinase mediates BEAS-2B cell migration and proliferation and human rhinovirus-induced expression of vascular endothelial growth factor and interleukin-8. J Pharmacol Exp Ther. 2012 Feb;340(2):277-85. doi: 10.1124/jpet.111.186429. Epub 2011 Oct 26. PubMed PMID: 22031919.

8: Gioia R, Leroy C, Drullion C, Lagarde V, Etienne G, Dulucq S, Lippert E, Roche S, Mahon FX, Pasquet JM. Quantitative phosphoproteomics revealed interplay between Syk and Lyn in the resistance to nilotinib in chronic myeloid leukemia cells. Blood. 2011 Aug 25;118(8):2211-21. doi: 10.1182/blood-2010-10-313692. Epub 2011 Jul 5. PubMed PMID: 21730355.

9: Sanderson MP, Gelling SJ, Rippmann JF, Schnapp A. Comparison of the anti-allergic activity of Syk inhibitors with optimized Syk siRNAs in FcepsilonRI-activated RBL-2H3 basophilic cells. Cell Immunol. 2010;262(1):28-34. doi: 10.1016/j.cellimm.2009.12.004. Epub 2009 Dec 14. PubMed PMID: 20053395.

10: Yang WS, Seo JW, Han NJ, Choi J, Lee KU, Ahn H, Lee SK, Park SK. High glucose-induced NF-kappaB activation occurs via tyrosine phosphorylation of IkappaBalpha in human glomerular endothelial cells: involvement of Syk tyrosine kinase. Am J Physiol Renal Physiol. 2008 May;294(5):F1065-75. doi: 10.1152/ajprenal.00381.2007. Epub 2008 Mar 19. PubMed PMID: 18353872.



Additional Information

  Related:
 648903-57-5 (BAY 61-3606 2HCl)
732983-37-8 (BAY 61-3606 free)