Page last updated: 2024-11-11

dehydroxymethylepoxyquinomicin

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Description

dehydroxymethylepoxyquinomicin: an NF-kappaB inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9881652
CHEMBL ID169300
SCHEMBL ID1671089
MeSH IDM0437654

Synonyms (24)

Synonym
dhmeq
(-)-dhm2eq
dehydroxymethylepoxyquinomicin
(-)-dhmeq
dhmeq cpd
(-)-dehydroxymethylepoxyquinomicin
CHEMBL169300
A819559
2-hydroxy-n-[(1s,6r)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
287194-38-1
287194-40-5
2-hydroxy-n-((1s,2s,6s)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl)benzamide
AKOS015924390
SCHEMBL1671089
DTXSID00432307
CS-5488
HY-14645
IUOMATKBBPCLFR-TUAOUCFPSA-N
2-hydroxy-n-[(1s,2s,6s)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
A912546
F85370
MS-23678
EX-A6855
benzamide, 2-hydroxy-n-[(1s,2s,6s)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-

Research Excerpts

Overview

Dehydroxymethylepoxyquinomicin (DHMEQ) is a novel nuclear factor-kappaB (NF-KappaB) inhibitor that inhibits DNA binding of NF- kappaB components including p65. It is being developed as an anti-inflammatory and anticancer agent.

ExcerptReferenceRelevance
"Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappaB (NF-kappaB) inhibitor that inhibits DNA binding of NF-kappaB components including p65. "( Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.
Ishikawa, Y; Nishiyama, S; Obata, R; Saitoh, T; Suzuki, E; Takasugi, A; Umezawa, K, 2009
)
1.8
"Dehydroxymethylepoxyquinomicin (DHMEQ) is a NF‑κB inhibitor and its structure is related to that of epoxyquinomicin C, which is an antibiotic."( Anti‑inflammatory effects of the NF‑κB inhibitor dehydroxymethylepoxyquinomicin on ARPE‑19 cells.
Ando, Y; Hirakata, A; Keino, H; Kudo, A; Okada, AA; Sato, Y; Umezawa, K; Watanabe, T, 2020
)
1.53
"Dehydroxymethylepoxyquinomicin (DHMEQ) is a novel NF-κB inhibitor that potently inhibits DNA-binding activity of NF-κB, resulting in several therapeutic effects in various pathological conditions."( A novel nuclear factor κB inhibitor, dehydroxymethylepoxyquinomicin, ameliorates puromycin aminonucleoside-induced nephrosis in mice.
Adachi, Y; Ikehara, S; Kaneko, K; Kimata, T; Okigaki, M; Shimo, T; Takaya, J; Tsuji, S; Umezawa, K; Yamanouchi, S, 2013
)
1.38
"Dehydroxymethylepoxyquinomicin (DHMEQ) is a low-m.w. "( Pleiotropic potential of dehydroxymethylepoxyquinomicin for NF-κB suppression via reactive oxygen species and unfolded protein response.
Gu, L; Johno, H; Kato, H; Kitamura, M; Nakajima, S; Takahashi, S; Umezawa, K, 2013
)
2.14
"Dehydroxymethylepoxyquinomicin (DHMEQ) is a new NF-kappaB inhibitor and is effective on various tumor cells with constitutively activated NF-kappaB."( Transient inhibition of NF-kappaB by DHMEQ induces cell death of primary effusion lymphoma without HHV-8 reactivation.
Dabaghmanesh, N; Horie, R; Ishida, T; Katano, H; Matsubara, A; Miyake, A; Nakano, K; Umezawa, K; Watanabe, T, 2009
)
1.07
"Dehydroxymethylepoxyquinomicin (DHMEQ, 1a) is a specific and potent inhibitor of NF-κB, and it is now being developed as an anti-inflammatory and anticancer agent. "( Chemoenzymatic synthesis of (2R,3R,4R)-dehydroxymethylepoxyquinomicin (DHMEQ), a new activator of antioxidant transcription factor Nrf2.
Goto, Y; Hakamata, M; Higashi, T; Niitsu, Y; Shoji, M; Sugai, T; Umezawa, K, 2011
)
2.08
"Dehydroxymethylepoxyquinomicin (DHMEQ) is a newly developed compound that inhibits nuclear factor κB activation and is reported to ameliorate animal models of various inflammatory diseases without significant adverse effects. "( Dehydroxymethylepoxyquinomicin (DHMEQ), a novel NF-kappaB inhibitor, inhibits allergic inflammation and airway remodelling in murine models of asthma.
Konno, S; Nishimura, M; Ozaki, M; Shimizu, K; Todo, S; Umezawa, K; Yamashita, K, 2012
)
3.26
"Dehydroxymethylepoxyquinomicin (DHMEQ) is a new NF-kappaB inhibitor that is a 5-dehydroxymethyl derivative of epoxyquinomicin C, having a 4-hydroxy-5,6-epoxycyclohexenone structure similar to panepoxydone."( Blocking NF-kappaB as a potential strategy to treat adult T-cell leukemia/lymphoma.
Horie, R; Umezawa, K; Watanabe, T, 2006
)
1.06

Compound-Compound Interactions

ExcerptReferenceRelevance
" In this study, we evaluated the immunomodulatory effects of DHMEQ when combined with a donor-specific blood transfusion (DST), and assessed whether the treatment induces tolerance in a mouse heart transplantation model."( Immunomodulatory effect of nuclear factor-κB inhibition by dehydroxymethylepoxyquinomicin in combination with donor-specific blood transfusion.
Aoyagi, T; Goto, R; Hirokata, G; Igarashi, R; Kobayashi, N; Oura, T; Ozaki, M; Shibasaki, S; Shibata, T; Todo, S; Ueki, S; Umezawa, K; Uno, M; Wakayama, K; Yamashita, K; Zaitsu, M, 2012
)
0.62
"In fully mismatched H2-to-H2 heart transplants, DST alone prolonged allograft median survival time to 15 days, whereas when DST was combined with DHMEQ treatment, the graft median survival time was prolonged to 39."( Immunomodulatory effect of nuclear factor-κB inhibition by dehydroxymethylepoxyquinomicin in combination with donor-specific blood transfusion.
Aoyagi, T; Goto, R; Hirokata, G; Igarashi, R; Kobayashi, N; Oura, T; Ozaki, M; Shibasaki, S; Shibata, T; Todo, S; Ueki, S; Umezawa, K; Uno, M; Wakayama, K; Yamashita, K; Zaitsu, M, 2012
)
0.62
"Our results demonstrate the distinctive ability of NF-κB inhibition in combination with donor alloantigen to promote transplantation tolerance through multiple cellular mechanisms."( Immunomodulatory effect of nuclear factor-κB inhibition by dehydroxymethylepoxyquinomicin in combination with donor-specific blood transfusion.
Aoyagi, T; Goto, R; Hirokata, G; Igarashi, R; Kobayashi, N; Oura, T; Ozaki, M; Shibasaki, S; Shibata, T; Todo, S; Ueki, S; Umezawa, K; Uno, M; Wakayama, K; Yamashita, K; Zaitsu, M, 2012
)
0.62

Bioavailability

ExcerptReferenceRelevance
" Our data suggest that daily consumption of coffee might induce BCRP expression in the gastrointestinal tract and may affect the bioavailability of BCRP substrates."( Coffee induces breast cancer resistance protein expression in Caco-2 cells.
Isshiki, M; Tamura, H; Umezawa, K, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID363468Binding affinity to bovine serum albumin2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID1718575Cytotoxicity against human KKU-214 cells assessed as growth inhibition incubated for 48 hrs by MTT assay2021Bioorganic & medicinal chemistry, 01-01, Volume: 29A novel synthetic acanthoic acid analogues and their cytotoxic activity in cholangiocarcinoma cells.
AID363449Inhibition of DNA binding activity of NF-kappaB p65 (1-325) C120S mutant by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID127224Compound was tested for antiarthritic effects on type-II collagen induced arthritis in DBA1/J mice; inhibited2000Bioorganic & medicinal chemistry letters, May-01, Volume: 10, Issue:9
Synthesis of NF-kappaB activation inhibitors derived from epoxyquinomicin C.
AID363464Decrease of TNF-alpha-stimulated NF-kappaB p65 C38S mutant level in human HeLa cell nucleus at 10 ug/mL by Western blot analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363466Decrease of TNF-alpha-stimulated endogenous NF-kappaB p65 level in human HeLa cell nucleus at 10 ug/mL by Western blot analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363462Inhibition of TNF-alpha-stimulated DNA binding activity of NF-kappaB p65 C38S mutant expressed in HeLa cells at 10 ug/mL hrs by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID1460213Inhibition of kappaB DNA binding to NFkappaB p65 in LPS-stimulated mouse RAW264.7 nuclear extract at 3 to 10 ug/ml after 15 mins by colorimetric method2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.
AID449285Antioxidant activity assessed as peroxynitrite radical scavenging activity2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.
AID363453Inhibition of DNA binding activity of NF-kappaB p50 C62S mutant2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363450Inhibition of DNA binding activity of NF-kappaB p65 (1-325) C38S mutant by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363463Decrease of TNF-alpha-stimulated wild type NF-kappaB p65 level in human HeLa cell nucleus at 10 ug/mL by Western blot analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID1718574Cytotoxicity against human KKU-213 cells assessed as growth inhibition incubated for 48 hrs by MTT assay2021Bioorganic & medicinal chemistry, 01-01, Volume: 29A novel synthetic acanthoic acid analogues and their cytotoxic activity in cholangiocarcinoma cells.
AID363465Inhibition of DNA binding activity of NF-kappaB p50 C144S mutant by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363456Inhibition of DNA binding activity of wild type NF-kappaB cRel (1-307)2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID1460227Anti-invasive activity against human ES2 cells at 1 to 10 ug/ml after 24 hrs by Diff-Quick staining based matrigel chamber assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.
AID363458Inhibition of DNA binding activity of wild type NF-kappaB cRel (1-307) by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363446Inhibition of DNA binding activity of NF-kappaB p65 (1-325) Rel subunit at 20 uM by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363455Inhibition of DNA binding activity of NF-kappaB p50 C62S mutant by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363457Inhibition of DNA binding activity of NF-kappaB cRel (1-307) C27S mutant2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID630283Stability of the compound under neutral conditions2011Bioorganic & medicinal chemistry letters, Nov-01, Volume: 21, Issue:21
Design and synthesis of biotinylated DHMEQ for direct identification of its target NF-κB components.
AID1460215Inhibition of LPS-induced NFkappaB p65 activation in mouse RAW264.7 cells at 0.3 to 1 ug/ml preincubated for 30 mins followed by LPS addition measured after 2 hrs by kappaB DNA binding based colorimetric method2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.
AID1460224Inhibition of constitutively activated NFkappaB p65 in human ES2 cells at 3 to 10 ug/ml after 2 hrs by kappaB DNA binding based colorimetric method2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.
AID1460217Inhibition of LPS-induced NFkappaB p65-mediated iNOS induction in mouse RAW264.7 cells assessed as reduction in NO production at 0.3 to 10 ug/ml preincubated for 30 mins followed by LPS addition measured after 24 hrs by Griess assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.
AID363467Inhibition of DNA binding activity of full-length recombinant NF-kappaB p65 Rel subunit C38S mutant at 10 uM by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363445Inhibition of DNA binding activity of full-length recombinant NF-kappaB p65 Rel subunit at 10 uM by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363448Inhibition of DNA binding activity of NF-kappaB p65 (1-325) C38S mutant by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363461Inhibition of TNF-alpha-stimulated DNA binding activity of wild type NF-kappaB p65 expressed in HeLa cells at 10 ug/mL by EMSA2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363454Inhibition of DNA binding activity of wild type NF-kappaB p50 by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID95429Compound was assessed for NF-kB activity using human T cell leukemia Jurkat cells; Less toxic2000Bioorganic & medicinal chemistry letters, May-01, Volume: 10, Issue:9
Synthesis of NF-kappaB activation inhibitors derived from epoxyquinomicin C.
AID363459Inhibition of DNA binding activity of NF-kappaB cRel (1-307) C27S mutant by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363452Inhibition of DNA binding activity of wild type NF-kappaB p502008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363460Inhibition of DNA binding activity of NF-kappaB p522008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID449284Antioxidant activity assessed as DPPH radical scavenging activity2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.
AID1460230Chemical stability in PBS at 100 ug/ml up to 12 hrs at 37 degC by HPLC analysis2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor.
AID363447Binding affinity to NF-kappaB p65 (1-325) Rel subunit at 100 uM by surface plasmon resonance analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID363451Inhibition of DNA binding activity of NF-kappaB p65 (1-325) C120S mutant by MALDI-TOF MS analysis2008Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18
Inactivation of NF-kappaB components by covalent binding of (-)-dehydroxymethylepoxyquinomicin to specific cysteine residues.
AID449282Inhibition of NF-kappaB transcriptional activity in LPS-stimulated mouse RAW264.7 cells treated for 1 hr before LPS challenge measured after 6 hrs by luciferase reporter gene assay2009Bioorganic & medicinal chemistry letters, Sep-15, Volume: 19, Issue:18
Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (151)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's62 (41.06)29.6817
2010's80 (52.98)24.3611
2020's9 (5.96)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.05

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 Index17.05 (24.57)
Research Supply Index5.04 (2.92)
Research Growth Index6.91 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.05)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews16 (10.46%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (0.65%)0.25%
Other136 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]