Page last updated: 2024-11-12

dimethoxycurcumin

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Description

dimethoxycurcumin: has antineoplsatic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9952605
CHEMBL ID261295
SCHEMBL ID2622436
MeSH IDM0511409

Synonyms (29)

Synonym
1,7-bis-(3,4-dimethoxy-phenyl)-hepta-1,6-diene-3,5-dione
(1e,6e)-1,7-bis(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
di-o-methylcurcumin
CHEMBL261295
tetramethoxycurcumin
bdbm50067038
(1e,4z,6e)-1,7-bis-(3,4-dimethoxy-phenyl)-5-hydroxy-hepta-1,4,6-trien-3-one
bdbm50285604
160096-59-3
dimethoxycurcumin
veratryl curcuminoid
dimethoxy curcumin
1,6-heptadiene-3,5-dione, 1,7-bis(3,4-dimethoxyphenyl)-, (1e,6e)-
SCHEMBL2622436
1,7-bis(3,4-dimethoxyphenyl)-1,6-heptadiene-3,5-dione
HMJSBVCDPKODEX-NXZHAISVSA-N
HMS3650D11
J-009673
dimethoxycurcumin(dimc)
AKOS032953608
BCP17149
sr-01000946328
SR-01000946328-1
Q27276138
EX-A4222
DTXSID101316356
CS-0020657
1,7-bis-(3,4-dimethoxyphenyl)hepta-1,6-diene-3,5-dione
HY-100977

Research Excerpts

Overview

Dimethoxycurcumin (DMC) is a synthetic analog of curcumin with superior inter-related pro-oxidant and anti-cancer activity, and metabolic stability. It is found in Curcuma longa Linn., which is known to possess significant activity against various cancer cell lines.

ExcerptReferenceRelevance
"Dimethoxycurcumin (DMC) is a more soluble and stable curcumin analog."( Modulation of the activity of histone lysine methyltransferases and demethylases by curcumin analog in leukaemia cells.
Abd Elmageed, ZY; Fandy, TE; Malkaram, SA; Sawesi, S, 2022
)
1.44
"Dimethoxycurcumin (DMC) is an analog of curcumin with superior efficacy in various disease models. "( Preparation, characterization, in vivo pharmacokinetics, and biodistribution of polymeric micellar dimethoxycurcumin for tumor targeting.
Gong, F; Hao, S; Jiang, Y; Liu, H; Liu, K; Mu, H; Xu, H, 2015
)
2.08
"Dimethoxycurcumin (DiMC) is a synthetic analog of curcumin with superior inter-related pro-oxidant and anti-cancer activity, and metabolic stability. "( Biological and pharmacological evaluation of dimethoxycurcumin: A metabolically stable curcumin analogue with a promising therapeutic potential.
Barati, N; Pirro, M; Sahebkar, A; Teymouri, M, 2018
)
2.18
"Dimethoxycurcumin (DMC) is a lipophilic analog of curcumin found in Curcuma longa Linn., which is known to possess significant activity against various cancer cell lines. "( Incorporation of dimethoxycurcumin into charged liposomes and the formation kinetics of fractal aggregates of uncharged vectors.
Demetzos, C; Hadjidemetriou, M; Pippa, N; Pispas, S, 2013
)
2.17

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic study in rats revealed that in vivo drug exposure of DMC was significantly increased and prolonged by intravenously administering DMC-loaded micelles when compared with the same dose of free DMC dissolved in dimethyl sulfoxide."( Preparation, characterization, in vivo pharmacokinetics, and biodistribution of polymeric micellar dimethoxycurcumin for tumor targeting.
Gong, F; Hao, S; Jiang, Y; Liu, H; Liu, K; Mu, H; Xu, H, 2015
)
0.63

Bioavailability

ExcerptReferenceRelevance
" Further, DiMC could find application as an alternative to curcumin, which is currently used in several clinical studies, due to its superior bioavailability and comparable efficacy."( Dimethoxycurcumin, a metabolically stable analogue of curcumin, exhibits anti-inflammatory activities in murine and human lymphocytes.
Checker, R; Kohli, V; Patwardhan, RS; Priyadarsini, KI; Sandur, SK; Sharma, D, 2011
)
1.81
"Although curcumin suppresses the growth of a variety of cancer cells, its poor absorption and low systemic bioavailability have limited its translation into clinics as an anticancer agent."( Stronger proteasomal inhibition and higher CHOP induction are responsible for more effective induction of paraptosis by dimethoxycurcumin than curcumin.
Choi, KS; Kang, YJ; Kim, EY; Kim, HS; Kim, IA; Kim, IY; Kim, MA; Kim, SA; Lee, BY; Lee, JA; Lee, K; Lee, YS; Park, JH; Yoon, AR; Yoon, MJ; Yun, CO, 2014
)
0.61
"Curcumin is an ideal chemopreventive and antitumor agent characterized by poor bioavailability and low stability."( Curcumin and dimethoxycurcumin induced epigenetic changes in leukemia cells.
Abdallah, I; Buttolph, T; Carlson, S; Fandy, TE; Glass, KC; Hassan, HE, 2015
)
0.79
" Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism."( Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
Deck, LM; Hunsaker, LA; Royer, RE; Vander Jagt, DL; Vander Jagt, TA; Whalen, LJ, 2018
)
0.48
"In spite of their extensive medicinal properties, cur and curcuminoids have poor solubility and bioavailability due to their hydrophobicity."( Curcumin-C3 Complexed with α-, β-cyclodextrin Exhibits Antibacterial and Antioxidant Properties Suitable for Cancer Treatments.
Huang, FY; Kumar, R; Reddy, DNK; Wang, SP, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Dose-response effects of an ethanol crude extract were investigated in the writhing and formalin tests in mice and rats, respectively."( Identification of some bioactive metabolites and inhibitory receptors in the antinociceptive activity of Tagetes lucida Cav.
Díaz-Reval, MI; González-Trujano, ME; Gutiérrez-Valentino, C; Hernández-Arámburo, MY; Pellicer, F, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Nuclear factor erythroid 2-related factor 2Homo sapiens (human)EC50 (µMol)16.60000.06002.61679.9000AID1348956
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
response to ischemiaNuclear factor erythroid 2-related factor 2Homo sapiens (human)
regulation of transcription by RNA polymerase IINuclear factor erythroid 2-related factor 2Homo sapiens (human)
inflammatory responseNuclear factor erythroid 2-related factor 2Homo sapiens (human)
response to oxidative stressNuclear factor erythroid 2-related factor 2Homo sapiens (human)
proteasomal ubiquitin-independent protein catabolic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of gene expressionNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of cardiac muscle cell apoptotic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of neuron projection developmentNuclear factor erythroid 2-related factor 2Homo sapiens (human)
protein ubiquitinationNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of blood coagulationNuclear factor erythroid 2-related factor 2Homo sapiens (human)
endoplasmic reticulum unfolded protein responseNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to oxidative stressNuclear factor erythroid 2-related factor 2Homo sapiens (human)
PERK-mediated unfolded protein responseNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to glucose starvationNuclear factor erythroid 2-related factor 2Homo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of blood vessel endothelial cell migrationNuclear factor erythroid 2-related factor 2Homo sapiens (human)
regulation of innate immune responseNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cell redox homeostasisNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of angiogenesisNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of DNA-templated transcriptionNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of transcription by RNA polymerase IINuclear factor erythroid 2-related factor 2Homo sapiens (human)
regulation of embryonic developmentNuclear factor erythroid 2-related factor 2Homo sapiens (human)
aflatoxin catabolic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of glucose importNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to hydrogen peroxideNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to copper ionNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to tumor necrosis factorNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to hypoxiaNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to xenobiotic stimulusNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to fluid shear stressNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to laminar fluid shear stressNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of ferroptosisNuclear factor erythroid 2-related factor 2Homo sapiens (human)
integrated stress response signalingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of cellular response to hypoxiaNuclear factor erythroid 2-related factor 2Homo sapiens (human)
regulation of cellular response to oxidative stressNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of hematopoietic stem cell differentiationNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of oxidative stress-induced intrinsic apoptotic signaling pathwayNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of glutathione biosynthetic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of ERAD pathwayNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cellular response to angiotensinNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of vascular associated smooth muscle cell migrationNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of ubiquitin-dependent protein catabolic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
regulation of removal of superoxide radicalsNuclear factor erythroid 2-related factor 2Homo sapiens (human)
negative regulation of endothelial cell apoptotic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
positive regulation of reactive oxygen species metabolic processNuclear factor erythroid 2-related factor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificNuclear factor erythroid 2-related factor 2Homo sapiens (human)
transcription coregulator bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificNuclear factor erythroid 2-related factor 2Homo sapiens (human)
DNA bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
DNA-binding transcription factor activityNuclear factor erythroid 2-related factor 2Homo sapiens (human)
protein bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
protein domain specific bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
ubiquitin protein ligase bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
sequence-specific DNA bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
molecular condensate scaffold activityNuclear factor erythroid 2-related factor 2Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingNuclear factor erythroid 2-related factor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
mediator complexNuclear factor erythroid 2-related factor 2Homo sapiens (human)
non-membrane-bounded organelleNuclear factor erythroid 2-related factor 2Homo sapiens (human)
nucleusNuclear factor erythroid 2-related factor 2Homo sapiens (human)
nucleoplasmNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cytoplasmNuclear factor erythroid 2-related factor 2Homo sapiens (human)
Golgi apparatusNuclear factor erythroid 2-related factor 2Homo sapiens (human)
centrosomeNuclear factor erythroid 2-related factor 2Homo sapiens (human)
cytosolNuclear factor erythroid 2-related factor 2Homo sapiens (human)
plasma membraneNuclear factor erythroid 2-related factor 2Homo sapiens (human)
RNA polymerase II transcription regulator complexNuclear factor erythroid 2-related factor 2Homo sapiens (human)
chromatinNuclear factor erythroid 2-related factor 2Homo sapiens (human)
protein-DNA complexNuclear factor erythroid 2-related factor 2Homo sapiens (human)
nucleusNuclear factor erythroid 2-related factor 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1348957Activation of Nrf2 (unknown origin) expressed in human HepG2 cells at 15 uM after 5 hrs by ARE-driven luciferase reporter gene assay relative to control2018European journal of medicinal chemistry, Jan-01, Volume: 143Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID323180Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCK22008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
Synthesis and exploration of novel curcumin analogues as anti-malarial agents.
AID1348956Activation of Nrf2 (unknown origin) expressed in human HepG2 cells after 5 hrs by ARE-driven luciferase reporter gene assay2018European journal of medicinal chemistry, Jan-01, Volume: 143Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID466926Selectivity index, ratio of EC50 for HEK cells to EC50 for Leishmania major Friedlin promastigotes2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID466920Antileishmanial activity against Leishmania major Friedlin promastigotes after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID466919Antitrypanosomal activity against multidrug-resistant Trypanosoma brucei brucei B48 after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID466922Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID466918Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei deltaTbat1-KO after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID475505Binding affinity to amyloid beta (1 to 42) oligomers by change in fluorescence at 100 uM after 10 mins2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID410461Antiproliferative activity against human MCF7 cells after 72 hrs by MTS-PMS assay2009Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1
Synthesis and evaluation of electron-rich curcumin analogues.
AID475504Binding affinity to amyloid beta (1 to 42) fibrils by change in fluorescence at 100 uM after 10 mins2009Bioorganic & medicinal chemistry letters, Sep-01, Volume: 19, Issue:17
A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta.
AID323181Antimalarial activity against chloroquine-resistant Plasmodium falciparum MP142008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
Synthesis and exploration of novel curcumin analogues as anti-malarial agents.
AID466921Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 amastigotes after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID1348958Effect on firefly luciferase activity expressed in human HepG2 cells at low concentration after 5 hrs by luminescence assay2018European journal of medicinal chemistry, Jan-01, Volume: 143Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin.
AID466917Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by alamar blue assay2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species.
AID410462Antiproliferative activity against human SKBR3 cells after 72 hrs by MTS-PMS assay2009Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1
Synthesis and evaluation of electron-rich curcumin analogues.
AID515080Antimycobacterial activity against Mycobacterium tuberculosis H37Ra after 24 hrs by microtiter alamar blue assay2010European journal of medicinal chemistry, Oct, Volume: 45, Issue:10
Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (16.22)29.6817
2010's27 (72.97)24.3611
2020's4 (10.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.92

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.92 (24.57)
Research Supply Index3.64 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other35 (94.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]