eCF506
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MedKoo CAT#: 407331

CAS#: 1914078-41-3

Description: eCF506 is the first, potent and selective SRC inhibitor that inhibits SRC at subnanomolar concentration (IC50 < 0.5 nM) with a 1000-fold selectivity over ABL. eCF506 exhibits excellent water solubility, an optimal DMPK profile and oral bioavailability, halts SRC-associated neuromast migration in zebrafish embryos without inducing life-threatening heart defects, and inhibits SRC phosphorylation in tumor xenografts in mice. eCF506 targets a molecule called Src tyrosine kinase that is required for breast cancer cells to grow and spread. eCF506 may be highly effective at blocking growth of breast cancer cells.

Chemical Structure

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eCF506
CAS# 1914078-41-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407331
Name: eCF506
CAS#: 1914078-41-3
Chemical Formula: C26H38N8O3
Exact Mass: 510.31
Molecular Weight: 510.643
Elemental Analysis: C, 61.16; H, 7.50; N, 21.94; O, 9.40

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3650 Ready to ship
2g USD 6250 Ready to ship
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Synonym: eCF506; eCF-506; eCF 506.

IUPAC/Chemical Name: tert-butyl (4-(4-amino-1-(2-(4-(dimethylamino)piperidin-1-yl)ethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenyl)carbamate

InChi Key: GMPQGWXPDRNCBL-UHFFFAOYSA-N

InChi Code: InChI=1S/C26H38N8O3/c1-26(2,3)37-25(35)30-19-8-7-17(15-20(19)36-6)22-21-23(27)28-16-29-24(21)34(31-22)14-13-33-11-9-18(10-12-33)32(4)5/h7-8,15-16,18H,9-14H2,1-6H3,(H,30,35)(H2,27,28,29)

SMILES Code: COC1=CC(C2=NN(CCN3CCC(N(C)C)CC3)C4=NC=NC(N)=C42)=CC=C1NC(OC(C)(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: >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

More Info:

Biological target: eCF506 is a highly potent and orally bioavailable inhibitor of the non-receptor tyrosine kinase Src with an IC50 of less than 0.5 nM.
In vitro activity: eCF506 induces a very potent antiproliferative effect in both MCF7 and MDA-MB-231 cells. eCF506 inhibits phosphorylation of SRC and FAK at low nanomolar levels, with complete inhibition observed at 100 nM. eCF506 significantly reduces cell motility at 10 nM as early as 6 h into the study, with equivalent efficacy to dasatinib. eCF506 exclusively inhibits SFK, with subnanomolar IC50 values against SRC and YES (IC50=0.5, 2.1 nM). It is important to highlight that eCF506 displays a vast difference in activity (>950-fold difference) between ABL and its primary target SRC. Reference: J Med Chem. 2016 May 26;59(10):4697-710. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/27115835/
In vivo activity: To determine the effects of eCF506 (11a) on cell migration in vivo, Tg(brn3c:mGFP) transgenic zebrafish53 that express green fluorescent protein (GFP) in the mechanosensory hair cells of the lateral line (which form part of the neuromasts) was treated with 11a for 2 d and measured the distance of the last neuromast to the tip of the tail (marked by the end of the notochord and the presence of black melanocytes, Figure7a, in red). 11a significantly reduced neuromast migration (>100 μm in average) with minimal effect on the development of the embryos (Figure7a–c). In contrast, dasatinib treatment at >10 μM resulted in severe cardiotoxicity and death of most embryos. At concentrations that were compatible with embryo survival (1–10 μM), dasatinib did not inhibit the migration of neuromasts, whereas it did still induce a patent cardiotoxic phenotype (note heart enlargement in Figure7c). Further safety studies (see Figure S8) showed that dual ABL/SRC inhibitor PP20 also induces severe cardiotoxicity in zebrafish even after short treatment. These results, which correlate with the essential role of ABL in heart development and healing, suggests that the selectivity of 11a over ABL might be advantageous for therapy when ABL inhibition is not required. Reference: J Med Chem. 2016 May 26;59(10):4697-710. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/27115835/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 15.0 29.38
Ethanol 15.0 29.38

Preparing Stock Solutions

The following data is based on the product molecular weight 510.64 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:
In vitro protocol: 1. Fraser C, Dawson JC, Dowling R, Houston DR, Weiss JT, Munro AF, Muir M, Harrington L, Webster SP, Frame MC, Brunton VG, Patton EE, Carragher NO, Unciti-Broceta A. Rapid Discovery and Structure-Activity Relationships of Pyrazolopyrimidines That Potently Suppress Breast Cancer Cell Growth via SRC Kinase Inhibition with Exceptional Selectivity over ABL Kinase. J Med Chem. 2016 May 26;59(10):4697-710. doi: 10.1021/acs.jmedchem.6b00065. Epub 2016 May 4. PMID: 27115835; PMCID: PMC4885109.
In vivo protocol: 1. Fraser C, Dawson JC, Dowling R, Houston DR, Weiss JT, Munro AF, Muir M, Harrington L, Webster SP, Frame MC, Brunton VG, Patton EE, Carragher NO, Unciti-Broceta A. Rapid Discovery and Structure-Activity Relationships of Pyrazolopyrimidines That Potently Suppress Breast Cancer Cell Growth via SRC Kinase Inhibition with Exceptional Selectivity over ABL Kinase. J Med Chem. 2016 May 26;59(10):4697-710. doi: 10.1021/acs.jmedchem.6b00065. Epub 2016 May 4. PMID: 27115835; PMCID: PMC4885109. 2. Sergeys J, Van Hove I, Hu TT, Temps C, Carragher NO, Unciti-Broceta A, Feyen JHM, Moons L, Porcu M. The retinal tyrosine kinome of diabetic Akimba mice highlights potential for specific Src family kinase inhibition in retinal vascular disease. Exp Eye Res. 2020 Aug;197:108108. doi: 10.1016/j.exer.2020.108108. Epub 2020 Jun 23. PMID: 32590005.

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1: Fraser C, Dawson JC, Dowling R, Houston DR, Weiss JT, Munro AF, Muir M, Harrington L, Webster SP, Frame MC, Brunton VG, Patton EE, Carragher NO, Unciti-Broceta A. Rapid Discovery and Structure-Activity Relationships of Pyrazolopyrimidines That Potently Suppress Breast Cancer Cell Growth via SRC Kinase Inhibition with Exceptional Selectivity over ABL Kinase. J Med Chem. 2016 May 26;59(10):4697-710. doi: 10.1021/acs.jmedchem.6b00065. Epub 2016 May 4. PubMed PMID: 27115835; PubMed Central PMCID: PMC4885109.