| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H18O5 |
| Molecular Weight | 338.3539 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O
InChI
InChIKey=HJTVQHVGMGKONQ-LUZURFALSA-N
InChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
| Molecular Formula | C20H18O5 |
| Molecular Weight | 338.3539 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
Demethoxycurcumin is a derivative or curcumin and represents one of the major active components of curcumin products isolated from Curcumae sp. In preclinical models, Demethoxycurcumin inhibits LPS-induced nitric oxide (NO) production, and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. Demethoxycurcumin also inhibits NF-kB dependent iNOS, TNFα and IL-1β expression in LPS-treated rat microglial cells. Demethoxycurcumin suppresses the expression of MMPs and ICAM-1 in MDA-MB-231 human breast cancer cells by inhibition of NF-kB. Demethoxycurcumin is currently in Phase I clinical trials.
Originator
Approval Year
Sourcing
PubMed
Patents
Sample Use Guides
500 mg (95% curcumin, 5% desmethoxycurcumin) twice per day for 2 weeks.
Route of Administration:
Oral
Cytotoxicity of compound 7 (Demethoxycurcumin) were evaluated against a panel of 8 cancer cell lines; lung (A549), prostate (DU-145), skin (SK-MEL-5), pancreatic (BxPC-3), liver (Hep G2), colon (HT-29), breast (MCF-7) and (MDA-MB-231). Cell lines were cultured in DMEM media supplemented with 2 mM L-glutamine, 10% fetal bovine serum, 50 mkg/ml gentamycin and 2.5 mkg/ml amphotericin B, maintained in a 37 C humid atmosphere of 5% CO2 cell incubator. Samples and drug standards (cisplatin and vinblastine sulfate) were dissolved in DMSO and immediately diluted with DMEM media to yield a final DMSO concentration of less than 0.5% v/v. Cells were plated into 96-well microplates at 5,000–10,000 cells per well and maintained in the cell incubator for 24 h. Then, 100 mkL of samples were introduced in triplicates to a final concentration of 15–150 mkM. Drug standards were also introduced to a final concentration of 0.03–2000 mkM (cisplatin) and 0.002–100 mkM (vinblastine sulfate). Cells were further incubated for 48 h and then, cell viability was determined according to the manufacturer protocol of a commercial MTS assay kit