Bisdemethoxycucurmin
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Bisdemethoxycucurmin (Curcumin III) is a curcuminoid compound and an inhibitor of P-glycoprotein and ferroptosis. Bisdemethoxycucurmin exhibits multiple activities such as anti-oxidation, anti-inflammation and anti-tumor. Bisdemethoxycucurmin can be used for the research of tumors and inflammatory diseases.
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研究用途以外に使用した場合、当社は一切の責任を負いかねます。
- 純度: 98.77%
- CAS 番号: 24939-16-0
- 分子式: C19H16O4
- 分子量:308.33
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保管条件:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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生物活性
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Cell Line
|
Type | Value | Description | References |
|---|---|---|---|---|
| A-431 | IC50 |
>100 μM
Compound: BDC
|
Cytotoxicity against human A431 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
Cytotoxicity against human A431 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
|
[PMID: 29605808] |
| A549 | IC50 |
38.1 μM
Compound: Bisdemethoxycurcumin
|
Cytotoxicity against human A549 cells after 72 hrs by crystal violet staining based microplate reader analysis
Cytotoxicity against human A549 cells after 72 hrs by crystal violet staining based microplate reader analysis
|
[PMID: 23153397] |
| Caco-2 | IC50 |
>100 μM
Compound: 1b
|
Cytotoxicity against human Caco2 cells assessed as decrease in cell viability after 48 hrs by MTT assay
Cytotoxicity against human Caco2 cells assessed as decrease in cell viability after 48 hrs by MTT assay
|
[PMID: 27843113] |
| Caco-2 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of differentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
Growth inhibition of differentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
|
[PMID: 27521589] |
| Caco-2 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of differentiated human Caco2 cells measured after 72 hrs by SRB assay
Growth inhibition of differentiated human Caco2 cells measured after 72 hrs by SRB assay
|
[PMID: 27521589] |
| Caco-2 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of undifferentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
Growth inhibition of undifferentiated human Caco2 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
|
[PMID: 27521589] |
| Caco-2 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of undifferentiated human Caco2 cells measured after 72 hrs by SRB assay
Growth inhibition of undifferentiated human Caco2 cells measured after 72 hrs by SRB assay
|
[PMID: 27521589] |
| CHO-K1 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of CHOK1 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
Growth inhibition of CHOK1 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
|
[PMID: 27521589] |
| CHO-K1 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of CHOK1 cells measured after 72 hrs by SRB assay
Growth inhibition of CHOK1 cells measured after 72 hrs by SRB assay
|
[PMID: 27521589] |
| CHO-K1 | IC50 |
91.4 μM
Compound: 1b
|
Cytotoxicity against CHOK1 cells assessed as decrease in cell viability after 48 hrs by MTT assay
Cytotoxicity against CHOK1 cells assessed as decrease in cell viability after 48 hrs by MTT assay
|
[PMID: 27843113] |
| DLD-1 | IC50 |
>40 μM
Compound: BDC
|
Cytotoxicity against human DLD1 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
Cytotoxicity against human DLD1 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
|
[PMID: 29605808] |
| DU-145 | IC50 |
30.1 μM
Compound: bisdemethoxycurcumin
|
Cytotoxicity against human DU145
Cytotoxicity against human DU145
|
[PMID: 16038556] |
| EA.hy 926 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of human EAhy926 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
Growth inhibition of human EAhy926 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
|
[PMID: 27521589] |
| EA.hy 926 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of human EAhy926 cells measured after 72 hrs by SRB assay
Growth inhibition of human EAhy926 cells measured after 72 hrs by SRB assay
|
[PMID: 27521589] |
| EA.hy 926 | IC50 |
54.3 μM
Compound: 1b
|
Cytotoxicity against human EAhy926 cells assessed as decrease in cell viability after 48 hrs by MTT assay
Cytotoxicity against human EAhy926 cells assessed as decrease in cell viability after 48 hrs by MTT assay
|
[PMID: 27843113] |
| EOL1 | IC50 |
22.3 μM
Compound: 4
|
Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay
Cytotoxicity against human EOL-1 cells after 48 hrs by MTT assay
|
[PMID: 24689857] |
| HEK293 | EC50 |
200 μM
Compound: 3
|
Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay
Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay
|
[PMID: 20004045] |
| HepG2 | IC50 |
>100 μM
Compound: 1b
|
Cytotoxicity against human HepG2 cells assessed as decrease in cell viability after 48 hrs by MTT assay
Cytotoxicity against human HepG2 cells assessed as decrease in cell viability after 48 hrs by MTT assay
|
[PMID: 27843113] |
| HepG2 | IC50 |
>50 μM
Compound: bisdemethoxycurcumin
|
Cytotoxicity against human HepG2
Cytotoxicity against human HepG2
|
[PMID: 16038556] |
| HepG2 | IC50 |
62.9 μM
Compound: Bisdemethoxycurcumin
|
Cytotoxicity against human HepG2 cells after 72 hrs by crystal violet staining based microplate reader analysis
Cytotoxicity against human HepG2 cells after 72 hrs by crystal violet staining based microplate reader analysis
|
[PMID: 23153397] |
| HepG2 | IC50 |
75.5 μM
Compound: 1c
|
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 48 hrs by MTT assay
|
[PMID: 26894841] |
| HL-60 | IC50 |
25.12 μM
Compound: bisdemethoxycurcumin
|
Cytotoxicity against human HL60
Cytotoxicity against human HL60
|
[PMID: 16038556] |
| HT-1080 | IC50 |
7 μM
Compound: BDMC
|
Decrease in UPA expression in human HT1080 cells
Decrease in UPA expression in human HT1080 cells
|
[PMID: 31336310] |
| HT-29 | IC50 |
>100 μM
Compound: 1b
|
Cytotoxicity against human HT-29 cells assessed as decrease in cell viability after 48 hrs by MTT assay
Cytotoxicity against human HT-29 cells assessed as decrease in cell viability after 48 hrs by MTT assay
|
[PMID: 27843113] |
| HT-29 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of human HT-29 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
Growth inhibition of human HT-29 cells assessed as mitochondrial activity measured after 72 hrs by MTT assay
|
[PMID: 27521589] |
| HT-29 | IC50 |
>25 μM
Compound: 1b; BDMC
|
Growth inhibition of human HT-29 cells measured after 72 hrs by SRB assay
Growth inhibition of human HT-29 cells measured after 72 hrs by SRB assay
|
[PMID: 27521589] |
| KB | CC50 |
8.5 μM
Compound: 11c
|
Compound concentration required to reduce the exponential growth of KB cells by 50%
Compound concentration required to reduce the exponential growth of KB cells by 50%
|
[PMID: 9767632] |
| KB | IC50 |
21.44 μM
Compound: 3
|
Cytotoxicity against human KB cells assessed as growth inhibition by resazurin microplate assay
Cytotoxicity against human KB cells assessed as growth inhibition by resazurin microplate assay
|
[PMID: 24857542] |
| LNCaP | IC50 |
19.7 μM
Compound: 2
|
Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay
Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay
|
[PMID: 19249204] |
| MCF7 | IC50 |
24.3 μM
Compound: 2
|
Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay
Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay
|
[PMID: 19249204] |
| MCF7 | IC50 |
33.78 μM
Compound: bisdemethoxycurcumin
|
Cytotoxicity against human MCF7
Cytotoxicity against human MCF7
|
[PMID: 16038556] |
| MCF7 | IC50 |
48.9 μM
Compound: BDC
|
Cytotoxicity against human MCF7 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
Cytotoxicity against human MCF7 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
|
[PMID: 29605808] |
| MDA-MB-231 | IC50 |
11 mM
Compound: BDMC
|
Increase in MMP3 level in human MDA-MB-231 cells after 24 hrs by ELISA
Increase in MMP3 level in human MDA-MB-231 cells after 24 hrs by ELISA
|
[PMID: 31336310] |
| MDA-MB-231 | IC50 |
21.9 μM
Compound: 2
|
Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay
Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT assay
|
[PMID: 19249204] |
| MDA-MB-231 | IC50 |
24 μM
Compound: bisdemethoxycurcumin
|
Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated 4 hrs before TGF-beta challenge measured after 24 hrs by radioimmunoassay
Inhibition of TGF-beta-induced PTHrP secretion in human MDA-MB-231 cells treated 4 hrs before TGF-beta challenge measured after 24 hrs by radioimmunoassay
|
[PMID: 23145932] |
| MDA-MB-231 | IC50 |
38.5 μM
Compound: Bisdemethoxycurcumin
|
Cytotoxicity against human MDA-MB-231 cells after 72 hrs by crystal violet staining based microplate reader analysis
Cytotoxicity against human MDA-MB-231 cells after 72 hrs by crystal violet staining based microplate reader analysis
|
[PMID: 23153397] |
| MT4 | CC50 |
13 μM
Compound: 11c
|
Compound concentration required to reduce the exponential growth of MT-4 cells by 50%
Compound concentration required to reduce the exponential growth of MT-4 cells by 50%
|
[PMID: 9767632] |
| NCI-H460 | IC50 |
88.1 μM
Compound: bisdemethoxycurcumin
|
Cytotoxicity against human NCI-H460
Cytotoxicity against human NCI-H460
|
[PMID: 16038556] |
| PC-12 | ED50 |
2 μg/mL
Compound: 5, bisdemethoxycurcumin
|
Protection against beta-amyloid (25 to 35) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay
Protection against beta-amyloid (25 to 35) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay
|
[PMID: 12350137] |
| PC-12 | ED50 |
3.5 μg/mL
Compound: 5, bisdemethoxycurcumin
|
Protection against beta-amyloid (1 to 42) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay
Protection against beta-amyloid (1 to 42) insult in rat PC12 cells assessed as viable cells after 24 hrs by MTT assay
|
[PMID: 12350137] |
| PC-3 | IC50 |
27.3 μM
Compound: 2
|
Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay
Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay
|
[PMID: 19249204] |
| WRL68 | IC50 |
45.4 μM
Compound: BDC
|
Cytotoxicity against human WRL68 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
Cytotoxicity against human WRL68 cells preincubated for 4 hrs followed by incubation in compound free media for 24 hrs by MTT assay
|
[PMID: 29605808] |
Bisdemethoxycucurmin (24 h) inhibits lipid peroxidation in primary rat nucleus pulposus cells treated with TNF-α[1].
Bisdemethoxycucurmin (1-10 μg/mL; 4 h) is cytotoxic and inhibits DNA synthesis in human chronic myeloid leukemia cells[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
-
Animal Model:Swiss bald (hairless) female mice treated DMBA (HY-W011845)[2]
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Dosage:72.5 μg
-
Administration:Topical application; 7 times: applied 3 days before and twice weekly for 3 weeks after DMBA (HY-W011845) treatment
-
Result:Significantly reduced the incidence of skin papillomas from 100% in the DMBA-only group to 75%.
Decreased the mean number of papillomas per mouse from 6.5 to 2.8.
化学情報
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CAS 番号 24939-16-0
-
性状 Solid
-
分子量 308.33
-
分子式 C19H16O4
-
Color Light yellow to orange
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SMILES
O=C(CC(/C=C/C1=CC=C(O)C=C1)=O)/C=C/C2=CC=C(O)C=C2
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別名
Curcumin III; Didemethoxycurcumin
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Structure Classification
-
Initial Source
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輸送条件
Room temperature in continental US; may vary elsewhere.
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保管条件
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
溶剤 & 溶解度
DMSO : 66.67 mg/mL (216.23 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
濃度 (開始) × 体積 (開始) = 濃度 (終了) × 体積 (終了)
純度とドキュメンテーション
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データシート (269 KB)
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SDS (393 KB)
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- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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取扱説明書 (2659 KB)
参考文献
[1]. Zhang P, et al. Cynarin alleviates intervertebral disc degeneration via protecting nucleus pulposus cells from ferroptosis. Biomed Pharmacother. 2023 Sep;165:115252. [Content Brief]
[3]. Chearwae W, et al. Biochemical mechanism of modulation of human P-glycoprotein (ABCB1) by curcumin I, II, and III purified from Turmeric powder. Biochem Pharmacol. 2004 Nov 15;68(10):2043-52. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.2433 mL | 16.2164 mL | 32.4328 mL | 81.0820 mL |
| 5 mM | 0.6487 mL | 3.2433 mL | 6.4866 mL | 16.2164 mL | |
| 10 mM | 0.3243 mL | 1.6216 mL | 3.2433 mL | 8.1082 mL | |
| 15 mM | 0.2162 mL | 1.0811 mL | 2.1622 mL | 5.4055 mL | |
| 20 mM | 0.1622 mL | 0.8108 mL | 1.6216 mL | 4.0541 mL | |
| 25 mM | 0.1297 mL | 0.6487 mL | 1.2973 mL | 3.2433 mL | |
| 30 mM | 0.1081 mL | 0.5405 mL | 1.0811 mL | 2.7027 mL | |
| 40 mM | 0.0811 mL | 0.4054 mL | 0.8108 mL | 2.0270 mL | |
| 50 mM | 0.0649 mL | 0.3243 mL | 0.6487 mL | 1.6216 mL | |
| 60 mM | 0.0541 mL | 0.2703 mL | 0.5405 mL | 1.3514 mL | |
| 80 mM | 0.0405 mL | 0.2027 mL | 0.4054 mL | 1.0135 mL | |
| 100 mM | 0.0324 mL | 0.1622 mL | 0.3243 mL | 0.8108 mL |