CYC116 | CAS#693228-63-6 | MedKoo Biosciences

MedKoo Cat#: 200844 | Name: CYC116

Description:

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

CYC116 is an orally bioavailable small molecule multi-kinase inhibitor with antineoplastic activity. Aurora kinase/VEGFR 2 inhibitor CYC116 inhibits Aurora kinases A and B and vascular endothelial growth factor receptor 2 (VEGFR2), resulting in disruption of the cell cycle, rapid cell death, and the inhibition of angiogenesis. Aurora kinases are serine/threonine protein kinases that are only expressed in actively dividing cells and are critical in division or mitosis. VEGFR2 is a receptor tyrosine kinase that appears to account for most of the mitogenic and chemotactic effects of vascular endothelial growth factor (VEGF) on adult endothelial cells.

Chemical Structure

CYC116

CAS#693228-63-6 (free base)

Theoretical Analysis

MedKoo Cat#: 200844

Name: CYC116

CAS#: 693228-63-6 (free base)

Chemical Formula: C18H20N6OS

Exact Mass: 368.1419

Molecular Weight: 368.46

Elemental Analysis: C, 58.68; H, 5.47; N, 22.81; O, 4.34; S, 8.70

Price and Availability

Size	Price	Availability
50mg	USD 350.00	2 Weeks
100mg	USD 550.00	2 Weeks
200mg	USD 950.00	2 Weeks
500mg	USD 1,850.00	2 Weeks

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Related CAS #

1059105-22-4 (tautomer) 693228-63-6 (free base) CYC116 HCl

Synonym

CYC116; CYC 116; CYC-116;

IUPAC/Chemical Name

4-methyl-5-(2-(4-morpholinophenylamino)pyrimidin-4-yl)thiazol-2-amine

InChi Key

GPSZYOIFQZPWEJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H20N6OS/c1-12-16(26-17(19)21-12)15-6-7-20-18(23-15)22-13-2-4-14(5-3-13)24-8-10-25-11-9-24/h2-7H,8-11H2,1H3,(H2,19,21)(H,20,22,23)

SMILES Code

NC1=NC(C)=C(C2=NC(NC3=CC=C(N4CCOCC4)C=C3)=NC=C2)S1

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, not in water

Shelf Life

>5 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

CYC-116 is a potent aurora A and aurora B inhibitor with Kis of 8 and 9 nM, respectively.

In vitro activity:

The degranulation in BMMCs caused by antigen was inhibited by CYC116 in a dose-dependent manner (IC50, ∼1.42 µM) (Fig. 2A). Reference: Biomol Ther (Seoul). 2019 May 1;27(3):311-317. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6513188/

In vivo activity:

Through cell-based screening of kinase-directed compound collection, this study discovered that a subset of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amines (including CYC116) were potent cytotoxic agents against cancer cell lines, suppressed mitotic histone H3 phosphorylation, and caused aberrant mitotic phenotypes. It was subsequently established that these compounds were in fact potent inhibitors of aurora A and B kinases. The anticancer effects of lead compound 4-methyl-5-(2-(4-morpholinophenylamino)pyrimidin-4-yl)thiazol-2-amine (18; K(i) values of 8.0 and 9.2 nM for aurora A and B, respectively) were shown to emanate from cell death following mitotic failure and increased polyploidy as a consequence of cellular inhibition of aurora A and B kinases. Reference: J Med Chem. 2010 Jun 10;53(11):4367-78. https://pubmed.ncbi.nlm.nih.gov/20462263/

	Solvent	mg/mL	mM
Solubility
	DMSO	16.3	44.32
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.68
	DMF	1.3	3.39

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 368.46 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. Park YH, Kim HW, Kim HS, Nam ST, Lee D, Lee MB, Min KY, Koo J, Kim SJ, Kim YM, Kim HS, Choi WS. An Anti-Cancer Drug Candidate CYC116 Suppresses Type I Hypersensitive Immune Responses through the Inhibition of Fyn Kinase in Mast Cells. Biomol Ther (Seoul). 2019 May 1;27(3):311-317. doi: 10.4062/biomolther.2018.148. PMID: 30332888; PMCID: PMC6513188. 2. Wang S, Midgley CA, Scaërou F, Grabarek JB, Griffiths G, Jackson W, Kontopidis G, McClue SJ, McInnes C, Meades C, Mezna M, Plater A, Stuart I, Thomas MP, Wood G, Clarke RG, Blake DG, Zheleva DI, Lane DP, Jackson RC, Glover DM, Fischer PM. Discovery of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amine aurora kinase inhibitors. J Med Chem. 2010 Jun 10;53(11):4367-78. doi: 10.1021/jm901913s. PMID: 20462263.

In vitro protocol:

In vivo protocol:

1. Wang, Shudong; Midgley, Carol A.; Scaerou, Frederic; Grabarek, Joanna B.; Griffiths, Gary; Jackson, Wayne; Kontopidis, George; McClue, Steven J.; McInnes, Campbell; Meades, Christopher; Mezna, Mokdad; Plater, Andy; Stuart, Iain; Thomas, Mark P.; Wood, Gavin; Clarke, Rosemary G.; Blake, David G.; Zheleva, Daniella I.; Lane, David P.; Jackson, Robert C.; Glover, David M.; Fischer, Peter M. Discovery of N-Phenyl-4-(thiazol-5-yl)pyrimidin-2-amine Aurora Kinase Inhibitors. Journal of Medicinal Chemistry (2010), 53(11), 4367-4378. CODEN: JMCMAR ISSN:0022-2623. CAN 152:582870 AN 2010:596947 2. MacCallum, David; Green, Simon. Combination of CNDAC with a 2-substituted-4-heteroaryl-pyrimidine amine and use thereof in the treatment of a proliferative disorder. PCT Int. Appl. (2007), 48pp. CODEN: PIXXD2 WO 2007132228 A1 20071122 CAN 147:534652 AN 2007:1333052 3. Maccallum, David; Green, Simon. Combination of a 2-substituted-4-heteroaryl-pyrimidine amine with a cytotoxic drug and use thereof in the treatment of a proliferative disorder. PCT Int. Appl. (2007), 81pp. CODEN: PIXXD2 WO 2007132220 A1 20071122 CAN 147:548092 AN 2007:1332845 4. MacCallum, David; Green, Simon. Combined anticancer pyrimidine-thiazole aurora kinase inhibitors. PCT Int. Appl. (2007), 58pp. CODEN: PIXXD2 WO 2007132221 A1 20071122 CAN 147:548079 AN 2007:1331264 5. Benigni, Ariela; Zoja, Carla; Remuzzi, Giuseppe; Giannella-Borradori, Athos. Method of treatment and compositions for a disease associated with antinuclear antibodies. PCT Int. Appl. (2006), 87 pp. CODEN: PIXXD2 WO 2006021803 A2 20060302 CAN 144:267267 AN 2006:193566 6. Kontopidis, George; McInnes, Campbell; Pandalaneni, Sravan R.; McNae, Iain; Gibson, Darren; Mezna, Mokdad; Thomas, Mark; Wood, Gavin; Wang, Shudong; Walkinshaw, Malcolm D.; Fischer, Peter M. Differential Binding of Inhibitors to Active and Inactive CDK2 Provides Insights for Drug Design. Chemistry & Biology (Cambridge, MA, United States) (2006), 13(2), 201-211. CODEN: CBOLE2 ISSN:1074-5521. CAN 144:343077 AN 2006:183501 7. Wang, Shudong; Meades, Christopher; Wood, Gavin; O'Boyle, Janice; McInnes, Campbell; Fischer, Peter. Preparation of pyrimidine derivs. as inhibitors of cyclin-dependent kinases. PCT Int. Appl. (2004), 127 pp. CODEN: PIXXD2 WO 2004043953 A1 20040527 CAN 141:7130 AN 2004:430798 8. McInnes, Campbell; Wang, Shudong; Anderson, Sian; O'Boyle, Janice; Jackson, Wayne; Kontopidis, George; Meades, Christopher; Mezna, Mokdad; Thomas, Mark; Wood, Gavin; Lane, David P.; Fischer, Peter M. Structural Determinants of CDK4 Inhibition and Design of Selective ATP Competitive Inhibitors. Chemistry & Biology (2004), 11(4), 525-534. CODEN: CBOLE2 ISSN:1074-5521. CAN 142:51189 AN 2004:324510