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MedKoo Cat#: 563535 | Name: ETP-45658
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Description:

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

ETP-45658 is a PI3-kinase inhibitor, also ihibiting DNA-PK and mTOR.

Chemical Structure

ETP-45658
ETP-45658
CAS#1198357-79-7

Theoretical Analysis

MedKoo Cat#: 563535

Name: ETP-45658

CAS#: 1198357-79-7

Chemical Formula: C16H17N5O2

Exact Mass: 311.1382

Molecular Weight: 311.34

Elemental Analysis: C, 61.72; H, 5.50; N, 22.49; O, 10.28

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 600.00 2 Weeks
100mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
ETP-45658; ETP 45658; ETP45658;
IUPAC/Chemical Name
3-[1-Methyl-4-(4-morpholinyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenol
InChi Key
BJVRNXSHJLDZJR-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H17N5O2/c1-20-15-13(10-17-20)16(21-5-7-23-8-6-21)19-14(18-15)11-3-2-4-12(22)9-11/h2-4,9-10,22H,5-8H2,1H3
SMILES Code
OC1=CC=CC(C2=NC(N3CCOCC3)=C4C(N(C)N=C4)=N2)=C1
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
Shelf Life
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Potent PI 3-kinase inhibitor; also inhibits DNA-PK and mTOR.
In vitro activity:
ETP-45658 treatment triggered a potent cell cycle arrest phenotype characterised by significant G1 and G2 peaks with little to no S-phase or sub-G1 cell population (Figure 1C). MDA-MB231 cells were grown in a two-dimensional matrigel transwell chamber and following treatment with ETP-45658 (or PI-103), cell invasion was evaluated (Figure S1E in Additional file 1). ETP45658 (and PI-103) inhibited the capacity of MDA-MB231 cells to migrate through the matrigel without significantly affecting cell viability, confirming an anti-proliferation rather than an apoptotic response following PI3K inhibition. Reference: Breast Cancer Res. 2014; 16: 482. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4303209/
In vivo activity:
As shown in Fig. 4C, the level of phosphorylated Akt on serine 473 was noticeably lower in the mammary ducts of transgenic mice injected with ETP-45658 as compared with the vehicle-treated mice. The phosphorylation of Akt was decreased to 50% of the control level (p = 0.001). The phosphorylation status of p70S6K on theonine 389 and eIF4G on serine 1108 were also examined. In all cases, a clear reduction of the levels of phosphorylation was observed (Fig. 4C). Treatment with ETP-45658 induced a significant reduction in the phosphorylation in the markers tested (Fig. 4C). These results confirm that ETP-45658 inhibits PI3K signaling in vivo. Reference: J Biol Chem. 2009 Oct 9; 284(41): 28392–28400. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2788888/
Solvent mg/mL mM
Solubility
DMSO 31.1 99.99
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 311.34 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. Hill R, Kalathur RK, Callejas S, Colaço L, Brandão R, Serelde B, Cebriá A, Blanco-Aparicio C, Pastor J, Futschik M, Dopazo A, Link W. A novel phosphatidylinositol 3-kinase (PI3K) inhibitor directs a potent FOXO-dependent, p53-independent cell cycle arrest phenotype characterized by the differential induction of a subset of FOXO-regulated genes. Breast Cancer Res. 2014 Dec 9;16(6):482. doi: 10.1186/s13058-014-0482-y. PMID: 25488803; PMCID: PMC4303209. 2. Link W, Oyarzabal J, Serelde BG, Albarran MI, Rabal O, Cebriá A, Alfonso P, Fominaya J, Renner O, Peregrina S, Soilán D, Ceballos PA, Hernández AI, Lorenzo M, Pevarello P, Granda TG, Kurz G, Carnero A, Bischoff JR. Chemical interrogation of FOXO3a nuclear translocation identifies potent and selective inhibitors of phosphoinositide 3-kinases. J Biol Chem. 2009 Oct 9;284(41):28392-28400. doi: 10.1074/jbc.M109.038984. Epub 2009 Aug 18. PMID: 19690175; PMCID: PMC2788888.
In vitro protocol:
1. Hill R, Kalathur RK, Callejas S, Colaço L, Brandão R, Serelde B, Cebriá A, Blanco-Aparicio C, Pastor J, Futschik M, Dopazo A, Link W. A novel phosphatidylinositol 3-kinase (PI3K) inhibitor directs a potent FOXO-dependent, p53-independent cell cycle arrest phenotype characterized by the differential induction of a subset of FOXO-regulated genes. Breast Cancer Res. 2014 Dec 9;16(6):482. doi: 10.1186/s13058-014-0482-y. PMID: 25488803; PMCID: PMC4303209. 2. Link W, Oyarzabal J, Serelde BG, Albarran MI, Rabal O, Cebriá A, Alfonso P, Fominaya J, Renner O, Peregrina S, Soilán D, Ceballos PA, Hernández AI, Lorenzo M, Pevarello P, Granda TG, Kurz G, Carnero A, Bischoff JR. Chemical interrogation of FOXO3a nuclear translocation identifies potent and selective inhibitors of phosphoinositide 3-kinases. J Biol Chem. 2009 Oct 9;284(41):28392-28400. doi: 10.1074/jbc.M109.038984. Epub 2009 Aug 18. PMID: 19690175; PMCID: PMC2788888.
In vivo protocol:
1. Link W, Oyarzabal J, Serelde BG, Albarran MI, Rabal O, Cebriá A, Alfonso P, Fominaya J, Renner O, Peregrina S, Soilán D, Ceballos PA, Hernández AI, Lorenzo M, Pevarello P, Granda TG, Kurz G, Carnero A, Bischoff JR. Chemical interrogation of FOXO3a nuclear translocation identifies potent and selective inhibitors of phosphoinositide 3-kinases. J Biol Chem. 2009 Oct 9;284(41):28392-28400. doi: 10.1074/jbc.M109.038984. Epub 2009 Aug 18. PMID: 19690175; PMCID: PMC2788888.
1: Hill R, Kalathur RK, Callejas S, Colaço L, Brandão R, Serelde B, Cebriá A, Blanco-Aparicio C, Pastor J, Futschik M, Dopazo A, Link W. A novel phosphatidylinositol 3-kinase (PI3K) inhibitor directs a potent FOXO-dependent, p53-independent cell cycle arrest phenotype characterized by the differential induction of a subset of FOXO-regulated genes. Breast Cancer Res. 2014 Dec 9;16(6):482. doi: 10.1186/s13058-014-0482-y. PubMed PMID: 25488803; PubMed Central PMCID: PMC4303209. 2: Link W, Oyarzabal J, Serelde BG, Albarran MI, Rabal O, Cebriá A, Alfonso P, Fominaya J, Renner O, Peregrina S, Soilán D, Ceballos PA, Hernández AI, Lorenzo M, Pevarello P, Granda TG, Kurz G, Carnero A, Bischoff JR. Chemical interrogation of FOXO3a nuclear translocation identifies potent and selective inhibitors of phosphoinositide 3-kinases. J Biol Chem. 2009 Oct 9;284(41):28392-400. doi: 10.1074/jbc.M109.038984. Epub 2009 Aug 18. PubMed PMID: 19690175; PubMed Central PMCID: PMC2788888.