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Chemical Structure| 480-44-4 Chemical Structure| 480-44-4
Chemical Structure| 480-44-4

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Acacetin shows inhibiton of the proliferation and induction apoptosis for cancer cells. It is a flavonoid purified from the bark of acacia farnesiana with anti-peroxidant, antiarthritic, and anti-inflammatory activities,

Synonyms: 5,7-Dihydroxy-4'-methoxyflavone; LY064233; Acacetin. NSC 76061.

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Citations

Product Citations

Yun, Sun ; Lee, Yu-Jin ; Choi, Jiyeon ; Kim, Nam Doo ; Han, Dong Cho ; Kwon, Byoung-Mog

Abstract: Signal transducer and activator of transcription 3 (STAT3) plays a critical role in the formation and growth of human cancer. Therefore, STAT3 is a therapeutic target for cancer drug discovery. Acacetin, a flavone present in various plants, inhibits constitutive and inducible STAT3 activation in STAT3-activated DU145 prostate cancer cells. Acacetin inhibits STAT3 activity by directly binding to STAT3, which we confirmed by a pull-down assay with a biotinylated compound and two level-free methods, namely, a drug affinity responsive target stability (DARTS) experiment and a cellular thermal shift assay (CETSA). Acacetin inhibits STAT3 phosphorylation at the tyrosine 705 residue and nuclear translocation in DU145 cells, which leads to the downregulation of STAT3 target genes. Acacetin then induces apoptosis in a time-dependent manner. Interestingly, acacetin induces the production of reactive oxygen species (ROS) that are not involved in the acacetin-induced inhibition of STAT3 activation because the suppressed p-STAT3 level is not rescued by treatment with GSH or NAC, which are general ROS inhibitors. We also found that acacetin inhibits tumor growth in xenografted nude mice. These results suggest that acacetin, as a STAT3 inhibitor, could be a possible drug candidate for targeting STAT3 for the treatment of cancer in humans.

Keywords: STAT3 inhibitor ; acacetin ; antitumor ; label-free methods ; natural product

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Product Details of Acacetin

CAS No. :480-44-4
Formula : C16H12O5
M.W : 284.26
SMILES Code : O=C1C=C(C2=CC=C(OC)C=C2)OC3=C1C(O)=CC(O)=C3
Synonyms :
5,7-Dihydroxy-4'-methoxyflavone; LY064233; Acacetin. NSC 76061.
English Name :5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
MDL No. :MFCD00016936
InChI Key :DANYIYRPLHHOCZ-UHFFFAOYSA-N
Pubchem ID :5280442

Safety of Acacetin

Application In Synthesis of Acacetin

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 480-44-4 ]

[ 480-44-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 520-27-4 ]
  • [ 480-44-4 ]
  • 2
  • [ 480-44-4 ]
  • [ 6601-66-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate 2: pyridine; aqueous KOH-solution; potassium peroxo disulfate / anschliessendes Erwaermen mit Natriumsulfit und wss. Salzsaeure 3: potassium carbonate; acetone
  • 3
  • [ 3386-32-1 ]
  • [ 480-44-4 ]
  • [ 2648822-78-8 ]
YieldReaction ConditionsOperation in experiment
80.28% With sodium carbonate In benzene at 20 - 130℃; for 8h; 1 Example 1 Dissolve 23g acacetin in 100mL anhydrous benzene solution, add 69.1g octadecyl p-toluenesulfonate at room temperature, stir to dissolve, heat up to 130, add sodium carbonate, react for 8h, detect by thin layer chromatography After the reaction is complete, cool to room temperature, filter, extract the filtrate with ethyl acetate, wash the organic phase with 5% hydrochloric acid solution, saturated brine, and water successively, dry and concentrate to obtain a concentrated solution. Add 6 times the weight of silica gel to the concentrated solution. Mix the sample, dry the mixed sample silica gel at 3040, elution chromatography on a silica gel column, the eluent is a mixture of petroleum ether and ethyl acetate, the volume ratio of the two is 6:1, collect the column chromatography solution, 45 The extract is concentrated to dryness, and the extract is further purified by high performance liquid chromatography. The conditions of high performance liquid chromatography are as follows: the chromatographic column is an octadecylsilane bonded silica gel column, and its model is Agilent XDB-C18, 250 *4.6um, 5um, the mobile phase is a methanol solution with a volume ratio of methanol to water of 80:25, the mobile phase flow rate is 2.0mL/min, the injection volume is 15uL, the UV detection wavelength is 285nm, and the column temperature is room temperature. According to the UV detection results, Collect the eluent for 25 to 26 minutes, and concentrate the eluent under reduced pressure to obtain the acacetin derivative. The yield was 80.28%.
 

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