BISDEMETHOXYCURCUMIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H16O4
Molecular Weight	308.3279
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2

InChI

InChIKey=PREBVFJICNPEKM-YDWXAUTNSA-N

InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28075008
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23873854 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26777574

Bisdemethoxycurcumin (BDMC) is a minor constituent (approximately 3%) of curcuminoids that has been shown to be more stable than the other two main curcuminoids, that is, curcumin and desmethoxycurcumin. Bisdemethoxycurcumin inhibits the proliferation and survival of several types of tumor cells including colon cancer cells, breast cancer cells, leukemia cells, and glioma cells. In addition, Bisdemethoxycurcumin suppresses cancer invasion and has the highest anti-metastatic potency in HT1080 human fibrosarcoma cells among the three curcuminoids. Bisdemethoxycurcumin has been reported to possess anti-oxidant and anti-inflammatory activities. However, the underlying molecular mechanisms responsible for the inhibitory action of Bisdemethoxycurcumin on tumor invasion and migration have remained largely unknown. More interestingly, the anti-cancer effects of Bisdemethoxycurcumin are comparable to and sometimes more potent than those of curcumin in different conditions.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Wnt signaling pathway 13 Target ID: GO:0016055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28075008	Inhibitor 8297
Detoxification of Reactive Oxygen Species 1 Target ID: WP2824 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28075008	Inhibitor 8297
p53 signaling 1 Target ID: WP2902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28075008	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28075008	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.	1997 Sep 12	9301668
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.	2005 Jun 15	15885658
Comparison of suppressive effects of demethoxycurcumin and bisdemethoxycurcumin on expressions of inflammatory mediators in vitro and in vivo.	2008 Apr	18449507
Immune defects in Alzheimer's disease: new medications development.	2008 Dec 3	19090986
Comparison of inhibitory potency of three different curcuminoid pigments on nitric oxide and tumor necrosis factor production of rat primary microglia induced by lipopolysaccharide.	2008 Dec 5	18838107
Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS.	2008 Sep	18481332
Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines.	2008 Sep	18034345
Comparative antiulcer effect of bisdemethoxycurcumin and curcumin in a gastric ulcer model system.	2009 Apr	19188055
Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease.	2009 Feb	18930076
Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA.	2009 Feb	18495463

Patents

Sample Use Guides

In Vivo Use Guide

Mice were treated with Bisdemethoxycurcumin as a dose of either 1 or 5 g/kg diet for 15 weeks.

Route of Administration: Oral

In Vitro Use Guide

NCI-H460 cells at a density of 5Ч105 cells/ml were maintained on 12-well plates with RPMI-1640 medium for 24 h and then incubated with or without 35 μM of Bisdemethoxycurcumin for 24 h. At the end of incubation, cells were collected from each treatment and total RNA was extracted by using the Qiagen RNeasy Mini Kit (Qiagen, Inc, Valencia, CA, USA)

Name

Type

Language

BISDEMETHOXYCURCUMIN

Common Name

English

BISDESMETHOXYCURCUMIN

Common Name

English

BISDESMETHOXYCURCUMIN (CONSTITUENT OF TURMERIC) [DSC]

Common Name

English

BIS-DEMETHOXYCURCUMIN [INCI]

Common Name

English

1,6-HEPTADIENE-3,5-DIONE, 1,7-BIS(4-HYDROXYPHENYL)-, (1E,6E)-

Systematic Name

English

BIS-DEMETHOXYCURCUMIN

Official Name

English

INS NO.100(III)

Common Name

English

1,7-BIS-(4-HYDROXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE

Systematic Name

English

DIDEMETHOXYCURCUMIN

Common Name

English

BISDESMETHOXYCURCUMIN [USP-RS]

Common Name

English

CURCUMIN III

Common Name

English

E-100(III)

Common Name

English

INS-100(III)

Common Name

English

Classification Tree Code System Code

DSLD

3710 (Number of products:81)