2-(4-HYDROXY-3-METHOXYPHENYL)BENZOTHIAZOLE
2-(4-HYDROXY-3-METHOXYPHENYL)BENZOTHIAZOLE Basic information
- Product Name:
- 2-(4-HYDROXY-3-METHOXYPHENYL)BENZOTHIAZOLE
- Synonyms:
-
- 2-(4-HYDROXY-3-METHOXYPHENYL)BENZOTHIAZOLE
- YL-109
- 4-(benzo[d]thiazol-2-yl)-2-Methoxyphenol
- Y109
- Y-109
- Y-109;Y109
- 4-(3H-1,3-benzothiazol-2-ylidene)-2-methoxycyclohexa-2,5-dien-1-one
- 4-(1,3-Benzothiazol-2-yl)-2-methoxyphenol
- CAS:
- 36341-25-0
- MF:
- C14H11NO2S
- MW:
- 257.31
- Product Categories:
-
- Inhibitors
- Mol File:
- 36341-25-0.mol
2-(4-HYDROXY-3-METHOXYPHENYL)BENZOTHIAZOLE Chemical Properties
- storage temp.
- 2-8°C
- solubility
- DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:9): 0.1 mg/ml; Ethanol: 1 mg/ml
- form
- A crystalline solid
- color
- Light yellow to yellow
2-(4-HYDROXY-3-METHOXYPHENYL)BENZOTHIAZOLE Usage And Synthesis
Uses
YL-109 is an antitumor agent that can induce carboxyl terminus of Hsp70-interacting protein (CHIP) expression through aryl hydrocarbon receptor (AhR) signaling. YL-109 has ability to inhibit breast cancer cell growth and invasiveness[1].
Biological Activity
YL-109 is a novel antitumor agent that inhibits the growth and invasion of breast cancer cells in vitro and in vivo.
Synthesis
121-33-5
137-07-5
36341-25-0
General procedure for the synthesis of 2-(4-hydroxy-3-methoxyphenyl)benzothiazole from vanillin and 2-aminobenzenethiol: In a catalytic reaction, a mixture of vanillin (3 mmol), 2-aminobenzenethiol (3 mmol) and CdS nanorods (5 mg) was placed in a 100 mL double-walled quartz flask equipped with a water inlet and outlet to maintain the reaction temperature at room temperature. The reaction was carried out in methanol (20 mL) and the reaction mixture was exposed to visible light for the indicated time under stirring conditions (see Table 3). The progress of the reaction was monitored by thin layer chromatography (TLC) and gas chromatography (GC). Upon completion of the reaction, methanol was removed by rotary evaporation and the residue was dissolved in dichloromethane. The catalyst was separated from the reaction mixture by centrifugation. Subsequently, the dichloromethane was evaporated to dryness and the product was purified by silica gel G60 column chromatography.
in vitro
YL-109 (0.001-10 μM; 96 h or 24 h) inhibits cell proliferation, motility, and invasiveness in breast cancer cells.
YL-109 (1 μM) increases both CHIP mRNA and protein levels in MDA-MB-231 cells.
Cell Proliferation Assay
| Cell Line: | < td class="col2"> MCF-7 and MDA-MB-231 cells|
| Concentration: | 0.001, 0.01, 0.1, 1, 10 μM |
| Incubation Time: | 96 hours |
| Result: | Strongly inhibited cell proliferation of MCF-7 and MDA-MB-231 cells in a dose-dependent manner (IC 50 =85.8 nM and 4.02 μM, respectively). |
in vivo
YL-109 (15 mg/kg; sc for every 2 d) inhibits both tumor growth and cancer metastasis of breast cancer cells in vivo.
< /p>
| Animal Model: | BALB/cAjcl-nu/nu female mice (4-5 weeks) inoculated with MCF-7 or MDA-MB-231 cells |
| Dosage: | 15 mg/kg |
| Administration: < /td> | Sc every 2 days for 63 days |
| Result: | Suppressed tumor growth in mice injected with MCF-7 and MDA-MB-231 cells. |
References
[1] Hiyoshi H, et al. 2-(4-Hydroxy-3-methoxyphenyl)-benzothiazole suppresses tumor progression and metastatic potential of breast cancer cells by inducing ubiquitin ligase CHIP. Sci Rep. 2014 Nov 18;4:7095. DOI:10.1038/srep07095
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