| Field | Specification |
|---|---|
| Target | |
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| Applications | |
| Molecular weight | |
| Molecular formula | C15H10O4 |
| SMILES | |
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Compound Overview
Alizarin 2-methyl ether is a DNA topoisomerase inhibitor that blocks the relaxation of supercoiled DNA via DNA topoisomerase I and II. It promotes adipocyte differentiation by increasing lipid accumulation and possesses antidiabetic and insulin-sensitizing properties, and it can be used in research related to human colon cancer, P-388 lymphocytic leukemia, and diabetes[1][2][3]. It has a molecular formula of C15H10O4 and a molecular weight of 254.24 g/mol.
Physical & Chemical Properties
| CAS Number | 6003-11-8 |
|---|---|
| Molecular Formula | C15H10O4 |
| Molecular Weight | 254.24 g/mol |
| SMILES | O=C1C2=C(C(C3=C(C(OC)=CC=C13)O)=O)C=CC=C2 |
| Target | Topoisomerase I, Topoisomerase II |
| Signaling Pathway | Cell Cycle/DNA Damage |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
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 your institution's chemical hygiene plan.
In Vitro
In calf thymus DNA topoisomerase I assays, Alizarin 2-methyl ether (20-100 μM; 30 min) gives 75% inhibition at 100 μM and 17% inhibition at 20 μM[1]. At 20-100 μM for 30 min, Alizarin 2-methyl ether inhibits human DNA topoisomerase II by 49% at 100 μM, with no inhibition at 20 μM[1]. Alizarin 2-methyl ether shows no significant cytotoxicity toward human breast carcinoma MCF-7 cells (IC50 greater than 100 μM)[1]. Alizarin 2-methyl ether is likewise not significantly cytotoxic to human liver carcinoma HepG2 cells (IC50 greater than 100 μM)[1]. Against human colon carcinoma HT-29 cells, Alizarin 2-methyl ether is cytotoxic, with an IC50 of 51.6 μM[1]. In 3T3-L1 mouse preadipocytes, Alizarin 2-methyl ether (100 μM; 8 days) promotes adipocyte differentiation and raises relative fat accumulation to 131% of that in insulin-treated control cells[3].
Cell Differentiation Assay[3]
| Cell Line | 3T3-L1 mouse preadipocytes |
|---|---|
| Concentration | 100 μM |
| Incubation Time | 8 days |
| Result | Enhanced adipocyte differentiation, resulting in a relative fat accumulation level of 131% compared to insulin-treated control cells. Reached statistically significant effect relative to the insulin-treated control. |
In Vivo
In P-388 lymphocytic leukemia in BDF1 mice, Alizarin 2-methyl ether (10 mg/kg/day) shows marginal antileukemic activity, with a T/C value of 126%[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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