SU6656 | CAS#330161-87-0 | SRC inhibitor

MedKoo Cat#: 406731 | Name: SU6656

Description:

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

SU6656 is a potent and selective dual inhibitor of Src family kinases and Aurora kinase. SU6656 modulates CTGF (connective tissue growth factor) expression in an ERK-dependent manner. SU6656 induces caspase-independent cell death in FRO anaplastic thyroid carcinoma cells and therapeutic synergy in human synovial sarcoma growth, invasion and angiogenesis in vivo.

Chemical Structure

SU6656

CAS#330161-87-0

Theoretical Analysis

MedKoo Cat#: 406731

Name: SU6656

CAS#: 330161-87-0

Chemical Formula: C19H21N3O3S

Exact Mass: 371.1304

Molecular Weight: 371.45

Elemental Analysis: C, 61.44; H, 5.70; N, 11.31; O, 12.92; S, 8.63

Price and Availability

Size	Price	Availability
50mg	USD 250.00	2 Weeks
100mg	USD 450.00	2 Weeks
200mg	USD 750.00	2 Weeks
500mg	USD 1,650.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks

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Synonym

SU6656; SU 6656; SU-6656.

IUPAC/Chemical Name

(Z)-N,N-dimethyl-2-oxo-3-((4,5,6,7-tetrahydro-1H-indol-2-yl)methylene)indoline-5-sulfonamide

InChi Key

LOGJQOUIVKBFGH-YBEGLDIGSA-N

InChi Code

InChI=1S/C19H21N3O3S/c1-22(2)26(24,25)14-7-8-18-15(11-14)16(19(23)21-18)10-13-9-12-5-3-4-6-17(12)20-13/h7-11,20H,3-6H2,1-2H3,(H,21,23)/b16-10-

SMILES Code

O=S(C1=CC2=C(NC(/C2=C\C(N3)=CC4=C3CCCC4)=O)C=C1)(N(C)C)=O

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:

SU6656 is a Src family kinases inhibitor with IC50s of 280, 20, 130, 170 nM for Src, Yes, Lyn, and Fyn, respectively. SU6656 inhibits FAK phosphorylation at Y576/577, Y925, Y861 sites and inhibits p-AKT.

In vitro activity:

This study demonstrates the potential benefit of SFK inhibition in head and neck squamous cell carcinoma (HNSCC), but also the challenges due to non-specificities of the different drugs. Proliferation on three HNSCC cell lines was blocked by SU6656, PP2 and dasatinib. With respect to cell kill, dasatinib was most effective, while SU6656 showed moderate and PP2 minor effects. Cellular signaling was affected differently, with only SU6656 showing clear SFK specific effects on signaling. Reference: Head Neck. 2023 Jan;45(1):147-155. https://pubmed.ncbi.nlm.nih.gov/36285353/

In vivo activity:

SU6656 uncouples bone formation from resorption by inhibiting osteoclast development, function and survival, and by enhancing BMP-mediated osteoblast differentiation. SU6656-treated mice exhibited increased bone mineral density, cortical thickness, cancellous bone volume and trabecular thickness. SU6656 inhibited bone resorption in mice as shown by reduced osteoclast number, and diminished expressions of Oscar, Trap5b and CtsK. SU6656 did not affect Rankl or Opg expressions. Reference: Bone. 2018 Aug;113:95-104. https://pubmed.ncbi.nlm.nih.gov/29751129/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	53.84

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 371.45 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. Vu AT, Akingunsade L, Hoffer K, Petersen C, Betz CS, Rothkamm K, Rieckmann T, Bussmann L, Kriegs M. Src family kinase targeting in head and neck tumor cells using SU6656, PP2 and dasatinib. Head Neck. 2023 Jan;45(1):147-155. doi: 10.1002/hed.27216. Epub 2022 Oct 25. PMID: 36285353. 2. Cicha I, Zitzmann R, Goppelt-Struebe M. Dual inhibition of Src family kinases and Aurora kinases by SU6656 modulates CTGF (connective tissue growth factor) expression in an ERK-dependent manner. Int J Biochem Cell Biol. 2014 Jan;46:39-48. doi: 10.1016/j.biocel.2013.11.014. Epub 2013 Nov 22. PMID: 24275091. 3. Thouverey C, Ferrari S, Caverzasio J. Selective inhibition of Src family kinases by SU6656 increases bone mass by uncoupling bone formation from resorption in mice. Bone. 2018 Aug;113:95-104. doi: 10.1016/j.bone.2018.05.006. Epub 2018 May 8. PMID: 29751129. 4. Arai R, Tsuda M, Watanabe T, Ose T, Obuse C, Maenaka K, Minami A, Ohba Y. Simultaneous inhibition of Src and Aurora kinases by SU6656 induces therapeutic synergy in human synovial sarcoma growth, invasion and angiogenesis in vivo. Eur J Cancer. 2012 Oct;48(15):2417-30. doi: 10.1016/j.ejca.2011.12.028. Epub 2012 Jan 13. PMID: 22244830.

In vitro protocol:

In vivo protocol:

1. Thouverey C, Ferrari S, Caverzasio J. Selective inhibition of Src family kinases by SU6656 increases bone mass by uncoupling bone formation from resorption in mice. Bone. 2018 Aug;113:95-104. doi: 10.1016/j.bone.2018.05.006. Epub 2018 May 8. PMID: 29751129. 2. Arai R, Tsuda M, Watanabe T, Ose T, Obuse C, Maenaka K, Minami A, Ohba Y. Simultaneous inhibition of Src and Aurora kinases by SU6656 induces therapeutic synergy in human synovial sarcoma growth, invasion and angiogenesis in vivo. Eur J Cancer. 2012 Oct;48(15):2417-30. doi: 10.1016/j.ejca.2011.12.028. Epub 2012 Jan 13. PMID: 22244830.

1: Blake RA, Broome MA, Liu X, Wu J, Gishizky M, Sun L, Courtneidge SA. SU6656, a selective src family kinase inhibitor, used to probe growth factor signaling. Mol Cell Biol. 2000 Dec;20(23):9018-27. doi: 10.1128/MCB.20.23.9018-9027.2000. PMID: 11074000; PMCID: PMC86555. 2: Bowman T, Broome MA, Sinibaldi D, Wharton W, Pledger WJ, Sedivy JM, Irby R, Yeatman T, Courtneidge SA, Jove R. Stat3-mediated Myc expression is required for Src transformation and PDGF-induced mitogenesis. Proc Natl Acad Sci U S A. 2001 Jun 19;98(13):7319-24. doi: 10.1073/pnas.131568898. Epub 2001 Jun 12. PMID: 11404481; PMCID: PMC34666. 3: Simon AR, Takahashi S, Severgnini M, Fanburg BL, Cochran BH. Role of the JAK- STAT pathway in PDGF-stimulated proliferation of human airway smooth muscle cells. Am J Physiol Lung Cell Mol Physiol. 2002 Jun;282(6):L1296-304. doi: 10.1152/ajplung.00315.2001. PMID: 12003786. 4: Sorkina T, Huang F, Beguinot L, Sorkin A. Effect of tyrosine kinase inhibitors on clathrin-coated pit recruitment and internalization of epidermal growth factor receptor. J Biol Chem. 2002 Jul 26;277(30):27433-41. doi: 10.1074/jbc.M201595200. Epub 2002 May 20. PMID: 12021271. 5: Lu H, Shah P, Ennis D, Shinder G, Sap J, Le-Tien H, Fantus IG. The differentiation of skeletal muscle cells involves a protein-tyrosine phosphatase-alpha-mediated C-Src signaling pathway. J Biol Chem. 2002 Nov 29;277(48):46687-95. doi: 10.1074/jbc.M209643200. Epub 2002 Sep 25. PMID: 12351660. 6: Tatton L, Morley GM, Chopra R, Khwaja A. The Src-selective kinase inhibitor PP1 also inhibits Kit and Bcr-Abl tyrosine kinases. J Biol Chem. 2003 Feb 14;278(7):4847-53. doi: 10.1074/jbc.M209321200. Epub 2002 Dec 9. PMID: 12475982. 7: Voytyuk O, Lennartsson J, Mogi A, Caruana G, Courtneidge S, Ashman LK, Rönnstrand L. Src family kinases are involved in the differential signaling from two splice forms of c-Kit. J Biol Chem. 2003 Mar 14;278(11):9159-66. doi: 10.1074/jbc.M211726200. Epub 2003 Jan 2. PMID: 12511554. 8: Hashimoto R, Fujimaki K, Jeong MR, Christ L, Chuang DM. Lithium-induced inhibition of Src tyrosine kinase in rat cerebral cortical neurons: a role in neuroprotection against N-methyl-D-aspartate receptor-mediated excitotoxicity. FEBS Lett. 2003 Mar 13;538(1-3):145-8. doi: 10.1016/s0014-5793(03)00167-4. PMID: 12633868. 9: Song C, Zhang Y, Parsons CG, Liu YF. Expression of polyglutamine-expanded huntingtin induces tyrosine phosphorylation of N-methyl-D-aspartate receptors. J Biol Chem. 2003 Aug 29;278(35):33364-9. doi: 10.1074/jbc.M304240200. Epub 2003 Jun 16. PMID: 12810713. 10: Servitja JM, Marinissen MJ, Sodhi A, Bustelo XR, Gutkind JS. Rac1 function is required for Src-induced transformation. Evidence of a role for Tiam1 and Vav2 in Rac activation by Src. J Biol Chem. 2003 Sep 5;278(36):34339-46. doi: 10.1074/jbc.M302960200. Epub 2003 Jun 16. PMID: 12810717. 11: Song L, Turkson J, Karras JG, Jove R, Haura EB. Activation of Stat3 by receptor tyrosine kinases and cytokines regulates survival in human non-small cell carcinoma cells. Oncogene. 2003 Jul 3;22(27):4150-65. doi: 10.1038/sj.onc.1206479. PMID: 12833138. 12: Tapia JA, García-Marin LJ, Jensen RT. Cholecystokinin-stimulated protein kinase C-delta kinase activation, tyrosine phosphorylation, and translocation are mediated by Src tyrosine kinases in pancreatic acinar cells. J Biol Chem. 2003 Sep 12;278(37):35220-30. doi: 10.1074/jbc.M303119200. Epub 2003 Jul 3. PMID: 12842900. 13: Sanguinetti AR, Cao H, Corley Mastick C. Fyn is required for oxidative- and hyperosmotic-stress-induced tyrosine phosphorylation of caveolin-1. Biochem J. 2003 Nov 15;376(Pt 1):159-68. doi: 10.1042/BJ20030336. PMID: 12921535; PMCID: PMC1223754. 14: Demir AY, Groothuis PG, Nap AW, Punyadeera C, de Goeij AF, Evers JL, Dunselman GA. Menstrual effluent induces epithelial-mesenchymal transitions in mesothelial cells. Hum Reprod. 2004 Jan;19(1):21-9. doi: 10.1093/humrep/deh042. PMID: 14688152. 15: Paveliev M, Airaksinen MS, Saarma M. GDNF family ligands activate multiple events during axonal growth in mature sensory neurons. Mol Cell Neurosci. 2004 Mar;25(3):453-9. doi: 10.1016/j.mcn.2003.11.010. PMID: 15033173. 16: Reinehr R, Becker S, Höngen A, Haüssinger D. The Src family kinase Yes triggers hyperosmotic activation of the epidermal growth factor receptor and CD95. J Biol Chem. 2004 Jun 4;279(23):23977-87. doi: 10.1074/jbc.M401519200. Epub 2004 Mar 23. Erratum in: J Biol Chem. 2004 Jul 23;279(30):31990. PMID: 15039424. 17: Talmor-Cohen A, Tomashov-Matar R, Eliyahu E, Shapiro R, Shalgi R. Are Src family kinases involved in cell cycle resumption in rat eggs? Reproduction. 2004 Apr;127(4):455-63. doi: 10.1530/rep.1.00104. PMID: 15047936. 18: Lusková P, Dráber P. Modulation of the Fcepsilon receptor I signaling by tyrosine kinase inhibitors: search for therapeutic targets of inflammatory and allergy diseases. Curr Pharm Des. 2004;10(15):1727-37. doi: 10.2174/1381612043384538. PMID: 15180535. 19: Talmor-Cohen A, Tomashov-Matar R, Tsai WB, Kinsey WH, Shalgi R. Fyn kinase- tubulin interaction during meiosis of rat eggs. Reproduction. 2004 Oct;128(4):387-93. doi: 10.1530/rep.1.00266. PMID: 15454633. 20: Reinehr R, Becker S, Wettstein M, Häussinger D. Involvement of the Src family kinase yes in bile salt-induced apoptosis. Gastroenterology. 2004 Nov;127(5):1540-57. doi: 10.1053/j.gastro.2004.08.056. PMID: 15521021.