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| Targets |
Aryl hydrocarbon receptor (AhR); cancer cell proliferation targets. GW 610 is an antitumor benzothiazole that shows growth-inhibitory activity against several cancer cell lines. It interacts with the aryl hydrocarbon receptor (AhR), displacing [³H]tetrachlorodibenzo-p-dioxin with an IC₅₀ of 25.0 nM and a Ki of 6.8 nM. The compound's antiproliferative effects on MCF-7 and MDA-MB-468 cells are potentiated by the AhR antagonist alpha-naphthoflavone, suggesting that its mechanism of action may involve AhR-mediated pathways.
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| ln Vitro |
MCF-7, MDA 468, KM 12, and HCC 2998 cells are inhibited from proliferating by GW 610, with GI50s of <0.1 nM, <0.1 nM, 290 nM, and 0.25 nM, respectively[1]. In MDA-MB-468, MCF-7, KM12, and HCC2998 cells, GW 610 (0.1–1 μM) stimulates CYP1A1 mRNA and protein, but only in breast cancer cells does it induce CYP2S1 and CYP2W1[3].
GW 610 demonstrates potent antiproliferative activity against a range of human cancer cell lines. In MCF-7 and MDA-MB-468 human breast cancer cells, growth inhibition (GI₅₀) values of less than 0.1 nM are observed. Against other cell lines, GI₅₀ values include 290.0 nM for KM12 cells, 0.25 nM for HCC2998 cells, and varying values for HCT116 and HT29 cells up to 5400.0 nM. The compound exhibits cytotoxic effects on MCF10A, A549, COLO205, and MCF7 cells with IC₅₀ values between 13,940.0 nM and 25,220.0 nM, induces apoptosis in COLO205 cells, and causes cell cycle arrest. |
| ln Vivo |
In vivo studies of GW 610 are limited, as the compound is primarily used as an in vitro research tool. As an antitumor benzothiazole with potent activity against lung, colon, and breast cancer cell lines, it has potential for evaluation in animal models of these cancers. However, specific in vivo efficacy data are not available in publicly accessible sources. The compound is intended for research use only and is not for human or veterinary use.
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| Enzyme Assay |
Non-cell-based assays for GW 610 include aryl hydrocarbon receptor (AhR) binding assays. The compound displaces [³H]tetrachlorodibenzo-p-dioxin from AhR with an IC₅₀ of 25.0 nM and a Ki of 6.8 nM. Standard analytical methods including HPLC, NMR, and mass spectrometry are used for compound characterization and purity assessment. The compound has a purity of ≥98% and appears as a crystalline solid.
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| Cell Assay |
Western Blot Analysis[3]
Cell Types: MDA- MB-468, MCF-7, KM12, and HCC2998 cells Tested Tested Concentrations: 0.1, 1 μM Incubation Duration: 48 hrs (hours) Experimental Results: Induced CYP1A1 mRNA and protein in all cell lines including KM12 and HCC2998 CRC cells. Induced CYP2S1 and CYP2W1 mRNA and protein expression in MDA-MB-468 and MCF-7 breast cancer cells. Cell-based assays for GW 610 use various cancer cell lines to assess its antiproliferative activity. Cells are cultured in appropriate medium and treated with GW 610 at various concentrations. Cell viability and growth inhibition (GI₅₀) are measured using standard assays such as SRB or MTT. The compound shows potent activity in MCF-7 and MDA-MB-468 breast cancer cells (GI₅₀ < 0.1 nM). Apoptosis induction is assessed in COLO205 cells, and cell cycle analysis is performed by flow cytometry. The AhR antagonist alpha-naphthoflavone can be used to study the role of AhR in the compound's activity. |
| Animal Protocol |
In vivo studies of GW 610 are limited. Based on its potent anticancer activity against lung, colon, and breast cancer cell lines, potential animal models include tumor xenograft models of these cancers. Standard protocols for xenograft studies involve subcutaneous implantation of cancer cells in immunodeficient mice, followed by administration of the compound and measurement of tumor volume over time. However, specific published in vivo data for GW 610 are not available.
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| ADME/Pharmacokinetics |
GW 610 has a molecular formula of C₁₅H₁₂FNO₂S and a molecular weight of 289.33 g/mol. The IUPAC name is 2-(3,4-dimethoxyphenyl)-5-fluorobenzo[d]thiazole. The compound is soluble in DMSO (3 mg/mL, ~10.36 mM) but insoluble in water and ethanol. It appears as a crystalline solid with a green color. Storage: powder at -20°C for 3 years; in solvent at -80°C for 1 year. Purity is ≥98%.
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| Toxicity/Toxicokinetics |
Specific toxicity data for GW 610 are limited. The compound exhibits potent antiproliferative activity against cancer cell lines (GI₅₀ < 0.1 nM in MCF-7 and MDA-MB-468 cells), indicating significant biological activity at very low concentrations. It also shows cytotoxic effects on various cell lines with IC₅₀ values in the micromolar range. Standard laboratory safety practices should be followed when handling this compound, including the use of personal protective equipment. It is intended for research use only and is not for human or veterinary use.
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| References |
[1]. Mortimer CG, et, al. Antitumor benzothiazoles. 26.(1) 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell
[2]. Aiello S, et, al. Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). J Med Chem. 2008 Aug 28;51(16):5135-9. [3]. Tan BS, et, al. CYP2S1 and CYP2W1 mediate 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (GW-610, NSC 721648) sensitivity in breast and colorectal cancer cells. Mol Cancer Ther. 2011 Oct;10(10):1982-92. |
| Additional Infomation |
GW 610 (NSC 721648) is a fluorinated 2-arylbenzothiazole antitumor agent that shows potent and selective anticancer activity against lung, colon, and breast cancer cell lines. The compound demonstrates exceptionally potent antiproliferative activity, with GI₅₀ values of less than 0.1 nM in MCF-7 and MDA-MB-468 breast cancer cells. It interacts with the aryl hydrocarbon receptor (AhR), displacing [³H]tetrachlorodibenzo-p-dioxin with an IC₅₀ of 25.0 nM and a Ki of 6.8 nM. The compound induces apoptosis and causes cell cycle arrest in cancer cells. It is for research use only.
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| Molecular Formula |
C15H12FNO2S
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|---|---|
| Molecular Weight |
289.32
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| Exact Mass |
289.057
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| CAS # |
872726-44-8
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| PubChem CID |
6712941
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| Appearance |
Light yellow to brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
422.8±55.0 °C at 760 mmHg
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| Flash Point |
209.5±31.5 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.619
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| LogP |
4.7
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
20
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| Complexity |
333
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| Defined Atom Stereocenter Count |
0
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| SMILES |
FC1C=C2C(SC(C3C=C(OC)C(OC)=CC=3)=N2)=CC=1
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| InChi Key |
ZRLSVQBGBBYEAZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H12FNO2S/c1-18-12-5-3-9(7-13(12)19-2)15-17-11-8-10(16)4-6-14(11)20-15/h3-8H,1-2H3
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| Chemical Name |
2-(3,4-dimethoxyphenyl)-5-fluoro-1,3-benzothiazole
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 25 mg/mL (86.41 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4564 mL | 17.2819 mL | 34.5638 mL | |
| 5 mM | 0.6913 mL | 3.4564 mL | 6.9128 mL | |
| 10 mM | 0.3456 mL | 1.7282 mL | 3.4564 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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