TAE226
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MedKoo CAT#: 406127

CAS#: 761437-28-9

Description: TAE226 is a novel and potent ATP competitive inhibitor of FAK and IGF-IR with potential anticancer activity. TAE226 can block FAK and IGF-IR signaling pathways. TAE226 inhibited the phosphorylation of FAK as well as the downstream effectors AKT, extracellular signal-related kinase, and S6 ribosomal protein in multiple glioma cell lines. TAE226 induced a concentration-dependent decrease in cellular proliferation with an associated G(2) cell cycle arrest in every cell line and an increase in apoptosis in a cell-line-specific manner. TAE226 also decreased glioma cell adhesion, migration, and invasion through an artificial extracellular matrix.


Chemical Structure

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TAE226
CAS# 761437-28-9

Theoretical Analysis

MedKoo Cat#: 406127
Name: TAE226
CAS#: 761437-28-9
Chemical Formula: C23H25ClN6O3
Exact Mass: 468.16767
Molecular Weight: 468.936
Elemental Analysis: C, 58.91; H, 5.37; Cl, 7.56; N, 17.92; O, 10.24

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 650.0 Ready to ship
200.0mg USD 850.0 Ready to ship
500.0mg USD 1450.0 Ready to ship
1.0g USD 2350.0 Ready to ship
2.0g USD 3850.0 2 Weeks
5.0g USD 5650.0 2 Weeks
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Synonym: NVPTAE226, NVP TAE226, NVP-TAE226, TAE226, TAE226, TAE 226

IUPAC/Chemical Name: 2-((5-chloro-2-((2-methoxy-4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide

InChi Key: UYJNQQDJUOUFQJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H25ClN6O3/c1-25-22(31)16-5-3-4-6-18(16)27-21-17(24)14-26-23(29-21)28-19-8-7-15(13-20(19)32-2)30-9-11-33-12-10-30/h3-8,13-14H,9-12H2,1-2H3,(H,25,31)(H2,26,27,28,29)

SMILES Code: O=C(NC)C1=CC=CC=C1NC2=NC(NC3=CC=C(N4CCOCC4)C=C3OC)=NC=C2Cl

Appearance: White to light yellow 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

Biological target: NVP-TAE 226 (TAE226) is a dual FAK and IGF-1R inhibitor with IC50s of 5.5 nM and 140 nM, respectively.
In vitro activity: Then, the effect of TAE226 on phosphorylation of FAK, Akt and ERK1/2 was evaluated using 4T1 cells in vitro. Phosphorylation of FAK at Y397, Akt at S473 and ERK was observed in 4T1 cells (Fig. 2a). TAE226 inhibited phosphorylation of FAK at Y397, resulting in suppression of phosphorylation of Akt at S473 and ERK1/2 in 4T1 cells 1 h after treatment (Fig. 2a). Reference: BMC Res Notes. 2019 Jun 18;12(1):347. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6582604/
In vivo activity: Anti-tumor activity of TAE226 was evaluated in the MIA PaCa-2 subcutaneous and orthotopic xenograft models. Oral administration of TAE226 efficiently inhibited MIA PaCa-2 tumor growth at all doses tested. After 14 days treatment, T/C values were 50% at 10 mg/kg and 13% at 30 mg/kg, qd for 7×/week (Fig. 1c, Table S2). At a dose of 100 mg/kg, qd for 5×/week, tumor regression (17%) was observed (Fig. 1c). TAE226 also inhibited MIA PaCa-2 orthotopic tumor growth in pancreas dose-dependently (Fig. 1d). Reference: BMC Res Notes. 2019 Jun 18;12(1):347. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6582604/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 51.33 109.46
DMF 30.0 63.97
DMF:PBS (pH 7.2) (1:1) 0.5 1.07

Preparing Stock Solutions

The following data is based on the product molecular weight 468.936 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. Fukami S, Tomioka D, Murakami Y, Honda T, Hatakeyama S. Pharmacological profiling of a dual FAK/IGF-1R kinase inhibitor TAE226 in cellular and in vivo tumor models. BMC Res Notes. 2019 Jun 18;12(1):347. doi: 10.1186/s13104-019-4389-7. PMID: 31215459; PMCID: PMC6582604. 2. Moritake H, Saito Y, Sawa D, Sameshima N, Yamada A, Kinoshita M, Kamimura S, Konomoto T, Nunoi H. TAE226, a dual inhibitor of focal adhesion kinase and insulin-like growth factor-I receptor, is effective for Ewing sarcoma. Cancer Med. 2019 Dec;8(18):7809-7821. doi: 10.1002/cam4.2647. Epub 2019 Nov 6. PMID: 31692287; PMCID: PMC6912025.
In vitro protocol: 1. Fukami S, Tomioka D, Murakami Y, Honda T, Hatakeyama S. Pharmacological profiling of a dual FAK/IGF-1R kinase inhibitor TAE226 in cellular and in vivo tumor models. BMC Res Notes. 2019 Jun 18;12(1):347. doi: 10.1186/s13104-019-4389-7. PMID: 31215459; PMCID: PMC6582604. 2. Moritake H, Saito Y, Sawa D, Sameshima N, Yamada A, Kinoshita M, Kamimura S, Konomoto T, Nunoi H. TAE226, a dual inhibitor of focal adhesion kinase and insulin-like growth factor-I receptor, is effective for Ewing sarcoma. Cancer Med. 2019 Dec;8(18):7809-7821. doi: 10.1002/cam4.2647. Epub 2019 Nov 6. PMID: 31692287; PMCID: PMC6912025.
In vivo protocol: 1. Fukami S, Tomioka D, Murakami Y, Honda T, Hatakeyama S. Pharmacological profiling of a dual FAK/IGF-1R kinase inhibitor TAE226 in cellular and in vivo tumor models. BMC Res Notes. 2019 Jun 18;12(1):347. doi: 10.1186/s13104-019-4389-7. PMID: 31215459; PMCID: PMC6582604. 2. Moritake H, Saito Y, Sawa D, Sameshima N, Yamada A, Kinoshita M, Kamimura S, Konomoto T, Nunoi H. TAE226, a dual inhibitor of focal adhesion kinase and insulin-like growth factor-I receptor, is effective for Ewing sarcoma. Cancer Med. 2019 Dec;8(18):7809-7821. doi: 10.1002/cam4.2647. Epub 2019 Nov 6. PMID: 31692287; PMCID: PMC6912025.

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1: Kurio N, Shimo T, Fukazawa T, Okui T, Hassan NM, Honami T, Horikiri Y, Hatakeyama S, Takaoka M, Naomoto Y, Sasaki A. Anti-tumor effect of a novel FAK inhibitor TAE226 against human oral squamous cell carcinoma. Oral Oncol. 2012 Nov;48(11):1159-70. doi: 10.1016/j.oraloncology.2012.05.019. Epub 2012 Jul 4. PubMed PMID: 22766511.

2: Hao HF, Takaoka M, Bao XH, Wang ZG, Tomono Y, Sakurama K, Ohara T, Fukazawa T, Yamatsuji T, Fujiwara T, Naomoto Y. Oral administration of FAK inhibitor TAE226 inhibits the progression of peritoneal dissemination of colorectal cancer. Biochem Biophys Res Commun. 2012 Jul 13;423(4):744-9. doi: 10.1016/j.bbrc.2012.06.030. Epub 2012 Jun 13. PubMed PMID: 22705303.

3: Kurio N, Shimo T, Fukazawa T, Takaoka M, Okui T, Hassan NM, Honami T, Hatakeyama S, Ikeda M, Naomoto Y, Sasaki A. Anti-tumor effect in human breast cancer by TAE226, a dual inhibitor for FAK and IGF-IR in vitro and in vivo. Exp Cell Res. 2011 May 1;317(8):1134-46. doi: 10.1016/j.yexcr.2011.02.008. Epub 2011 Feb 19. PubMed PMID: 21338601.

4: Schultze A, Decker S, Otten J, Horst AK, Vohwinkel G, Schuch G, Bokemeyer C, Loges S, Fiedler W. TAE226-mediated inhibition of focal adhesion kinase interferes with tumor angiogenesis and vasculogenesis. Invest New Drugs. 2010 Dec;28(6):825-33. doi: 10.1007/s10637-009-9326-5. Epub 2009 Sep 26. PubMed PMID: 19784551.

5: Hehlgans S, Lange I, Eke I, Cordes N. 3D cell cultures of human head and neck squamous cell carcinoma cells are radiosensitized by the focal adhesion kinase inhibitor TAE226. Radiother Oncol. 2009 Sep;92(3):371-8. doi: 10.1016/j.radonc.2009.08.001. Epub 2009 Sep 2. PubMed PMID: 19729215.

6: Lietha D, Eck MJ. Crystal structures of the FAK kinase in complex with TAE226 and related bis-anilino pyrimidine inhibitors reveal a helical DFG conformation. PLoS One. 2008;3(11):e3800. doi: 10.1371/journal.pone.0003800. Epub 2008 Nov 24. PubMed PMID: 19030106; PubMed Central PMCID: PMC2582962.

7: Wang ZG, Fukazawa T, Nishikawa T, Watanabe N, Sakurama K, Motoki T, Takaoka M, Hatakeyama S, Omori O, Ohara T, Tanabe S, Fujiwara Y, Shirakawa Y, Yamatsuji T, Tanaka N, Naomoto Y. TAE226, a dual inhibitor for FAK and IGF-IR, has inhibitory effects on mTOR signaling in esophageal cancer cells. Oncol Rep. 2008 Dec;20(6):1473-7. PubMed PMID: 19020730.

8: Beierle EA, Trujillo A, Nagaram A, Golubovskaya VM, Cance WG, Kurenova EV. TAE226 inhibits human neuroblastoma cell survival. Cancer Invest. 2008 Mar;26(2):145-51. doi: 10.1080/07357900701577475. PubMed PMID: 18259944.

9: Halder J, Lin YG, Merritt WM, Spannuth WA, Nick AM, Honda T, Kamat AA, Han LY, Kim TJ, Lu C, Tari AM, Bornmann W, Fernandez A, Lopez-Berestein G, Sood AK. Therapeutic efficacy of a novel focal adhesion kinase inhibitor TAE226 in ovarian carcinoma. Cancer Res. 2007 Nov 15;67(22):10976-83. PubMed PMID: 18006843.

10: Golubovskaya VM, Virnig C, Cance WG. TAE226-induced apoptosis in breast cancer cells with overexpressed Src or EGFR. Mol Carcinog. 2008 Mar;47(3):222-34. PubMed PMID: 17849451.

11: Shi Q, Hjelmeland AB, Keir ST, Song L, Wickman S, Jackson D, Ohmori O, Bigner DD, Friedman HS, Rich JN. A novel low-molecular weight inhibitor of focal adhesion kinase, TAE226, inhibits glioma growth. Mol Carcinog. 2007 Jun;46(6):488-96. PubMed PMID: 17219439.

TAE226

10.0mg / USD 150.0