| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C30H36Br2N4O2 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
EB-3D selectively inhibits choline kinase α (ChoKα), with an IC50 of 1 μM against ChoKα1. It affects ChoKα expression, AMPK activation, apoptosis, endoplasmic reticulum stress, and lipid metabolism, and it shows strong antiproliferative effects across a panel of T-leukemia cell lines, consistent with anti-cancer activity[1][2][3]. It is supplied as a white to off-white solid (C30H36Br2N4O2, MW 644.44) at 99.64% purity.
Physical & Chemical Properties
| CAS Number | 1839150-63-8 |
|---|---|
| Molecular Formula | C30H36Br2N4O2 |
| Molecular Weight | 644.44 g/mol |
| Purity | 99.64% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | CN(C1=CC=[N+](CC2=CC=C(OCCOC3=CC=C(C[N+]4=CC=C(N(C)C)C=C4)C=C3)C=C2)C=C1)C.[Br-].[Br-] |
| Signaling Pathway | PI3K/Akt/mTOR; Epigenetics; Apoptosis |
| Solubility | In Vitro: DMSO: 50 mg/mL (77.59 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) H2O: ≥ 9.09 mg/mL (14.11 mM) * "≥" means soluble, but saturation unknown. |
| Storage | 4°C, sealed storage, away from moisture. In solvent: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target
IC50: 1 μM; Kd: 0.7 μM[3]
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 50 mg/mL (77.59 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
| H2O | ≥ 9.09 mg/mL (14.11 mM) | — |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); sealed storage, away from moisture; avoid repeated freeze-thaw cycles.
If water is used as the stock solvent, dilute to the working solution and sterilize it through a 0.22 μm filter before use.
Data provided by the manufacturer.
In Vitro
EB-3D (0-100 μM; 72 hours) shows excellent antiproliferative activity across a wide cohort of T-leukemic cell lines, with GI50 values (13) in the nanomolar range[1]. Apoptosis is induced in leukemia cell lines by EB-3D (1.25-5μM; 24 hours)[1]. EB-3D (0.5-1 μM; 24 hours) triggers a G0/G1 arrest that leads to apoptosis[1]. At 0.3 μM for 48 hours, EB-3D produces an initial spike of AMPKα activation after 30 minutes, followed by a later rise in T172 phosphorylation[1]. In HepG2 cells, EB-3D (1-40 μM; 48 hours) inhibits cell growth with a GI50 of 14.55 μM[2]. In leukemia T-cells, EB-3D deregulates the AMPK-mTOR pathway and induces apoptosis[1].
Cell Proliferation Assay[1]
| Cell Line | JURKAT, CCRF-CEM, HSB-2, MOLT-16, DNA-41, LOUCY, PEER, ALL-SIL cells |
|---|---|
| Concentration | 0.001, 0.01, 0.1, 1, 10, 100 μM |
| Incubation Time | 72 hours |
| Result | Inhibited JURKAT, CCRF-CEM, HSB-2, MOLT-16, DNA-41, LOUCY, PEER, and ALL-SIL cells growth with GI50s of 136.2, 478.8, 17.7, 0.9, 60.6, 200, 265, and 132 nM, respectively. |
Apoptosis Analysis[1]
| Cell Line | Jurkat, CCRF-CEM and HSB-2 cells |
|---|---|
| Concentration | 1.25, 2.5, 5 μM |
| Incubation Time | 24 hours |
| Result | Induced apoptosis in leukemia cell lines. |
Cell Cycle Analysis[1]
| Cell Line | Jurkat, CCRF-CEM and HSB-2 cells |
|---|---|
| Concentration | 0.5, 1 μM |
| Incubation Time | 24 hours |
| Result | Induces cell cycle arrest in G0/G1 phase. |
Western Blot Analysis[1]
| Cell Line | Jurkat cells |
|---|---|
| Concentration | 0.3 μM |
| Incubation Time | 48 hours |
| Result | Showed a first spike of activation of AMPKα after 30 minutes of treatment and a later increase in the phosphorylation of T172. The increase in S79 phosphorylation of its main target ACC (acetyl-coenzyme A (CoA) carboxylase), followed the same pattern. This rapid activation of AMPK, in turn induced a consequent reduction in mTOR phosphorylation that is visible already at 30’ and that becomes amplified at longer time probably due to the interruption of feedback loops that are characteristic of mTOR connecting pathways. |
In Vivo
In the syngeneic orthotopic E0771-C57BL/6 mouse model, EB-3D (1 mg/kg; i.p.; every other day) impairs mammary tumor growth[4]. EB-3D (2.5 mg/kg; every other day for 4 weeks) reduces the number of spontaneous lung macro- and micrometastasis[4].
| Animal Model | E0771-C57BL/6 mice[4] |
|---|---|
| Dosage | I.p.; every other day for 4 weeks |
| Administration | 2.5 mg/kg |
| Result | A reduction of the number of spontaneous lung macro- and micrometastasis. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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Choline kinase inhibition promotes ER-phagy. J Lipid Res 2022 Aug;63(8):100213. PMID: 35447137
Regulation of cancer cell ferroptosis by PTRF/Cavin-1. Free Radic Res 2024 May-Jun;58(6-7):417-429. PMID: 39079051
