MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 563183 | Name: DHMEQ
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

DHMEQ is an NF-kB inhibitor that acts by inducing apoptosis and cell-cycle arrest in human hepatoma cells.

Chemical Structure

DHMEQ
CAS#287194-40-5

Theoretical Analysis

MedKoo Cat#: 563183

Name: DHMEQ

CAS#: 287194-40-5

Chemical Formula: C13H11NO5

Exact Mass: 261.0637

Molecular Weight: 261.23

Elemental Analysis: C, 59.77; H, 4.24; N, 5.36; O, 30.62

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Dehydroxymethylepoxyquinomicin; DHMEQ; (-)-DHMEQ; DHMEQ cpd
IUPAC/Chemical Name
2-Hydroxy-N-[(1S,2S,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
InChi Key
IUOMATKBBPCLFR-TUAOUCFPSA-N
InChi Code
InChI=1S/C13H11NO5/c15-8-4-2-1-3-6(8)13(18)14-7-5-9(16)11-12(19-11)10(7)17/h1-5,10-12,15,17H,(H,14,18)/t10-,11+,12-/m0/s1
SMILES Code
O=C(NC([C@H](O)[C@]1([H])O[C@]21[H])=CC2=O)C3=CC=CC=C3O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 261.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Lampiasi N, Umezawa K, Montalto G, Cervello M. Corrigendum to "poly (ADP-ribose) polymerase inhibition synergizes with the NF-κB inhibitor DHMEQ to kill hepatocellular carcinoma cells" [Biochim. Biophys. Acta 1853(12)(2015) 3224-3234]. Biochim Biophys Acta. 2018 Jul;1865(7):1023. doi: 10.1016/j.bbamcr.2018.04.004. Epub 2018 Apr 21. PubMed PMID: 29685431. 2: Lin Y, Ukaji T, Koide N, Umezawa K. Inhibition of Late and Early Phases of Cancer Metastasis by the NF-κB Inhibitor DHMEQ Derived from Microbial Bioactive Metabolite Epoxyquinomicin: A Review. Int J Mol Sci. 2018 Mar 3;19(3). pii: E729. doi: 10.3390/ijms19030729. Review. PubMed PMID: 29510517; PubMed Central PMCID: PMC5877590. 3: Ramos PMM, Pezuk JA, Castro-Gamero AM, Oliveira HF, Scrideli CA, Umezawa K, Tone LG. Antineoplastic effects of NF-κB inhibition by DHMEQ (Dehydroxymethylepoxyquinomicin) alone and in co-treatment with radio-and chemotherapy in medulloblastoma cell lines. Anticancer Agents Med Chem. 2017 Nov 13. doi: 10.2174/1871520617666171113151335. [Epub ahead of print] PubMed PMID: 29141555. 4: Simon-Gabriel CP, Foerster K, Saleem S, Bleckmann D, Benkisser-Petersen M, Thornton N, Umezawa K, Decker S, Burger M, Veelken H, Claus R, Dierks C, Duyster J, Zirlik K. Microenvironmental stromal cells abrogate NF-κB inhibitor-induced apoptosis in chronic lymphocytic leukemia. Haematologica. 2018 Jan;103(1):136-147. doi: 10.3324/haematol.2017.165381. Epub 2017 Nov 9. PubMed PMID: 29122993; PubMed Central PMCID: PMC5777201. 5: Jiang X, Lan Y, Wei B, Dai C, Gu Y, Ma J, Liu X, Umezawa K, Zhang Y. External application of NF-κB inhibitor DHMEQ suppresses development of atopic dermatitis-like lesions induced with DNCB/OX in BALB/c mice. Immunopharmacol Immunotoxicol. 2017 Jun;39(3):157-164. doi: 10.1080/08923973.2017.1312436. PubMed PMID: 28418286. 6: El-Salhy M, Umezawa K, Hatlebakk JG, Gilja OH. Abnormal differentiation of stem cells into enteroendocrine cells in rats with DSS-induced colitis. Mol Med Rep. 2017 Apr;15(4):2106-2112. doi: 10.3892/mmr.2017.6266. Epub 2017 Mar 1. PubMed PMID: 28259987; PubMed Central PMCID: PMC5364957. 7: Ukaji T, Lin Y, Okada S, Umezawa K. Inhibition of MMP-2-mediated cellular invasion by NF-κB inhibitor DHMEQ in 3D culture of breast carcinoma MDA-MB-231 cells: A model for early phase of metastasis. Biochem Biophys Res Commun. 2017 Mar 25;485(1):76-81. doi: 10.1016/j.bbrc.2017.02.022. Epub 2017 Feb 8. PubMed PMID: 28188787. 8: Pires BR, Mencalha AL, Ferreira GM, de Souza WF, Morgado-Díaz JA, Maia AM, Corrêa S, Abdelhay ES. NF-kappaB Is Involved in the Regulation of EMT Genes in Breast Cancer Cells. PLoS One. 2017 Jan 20;12(1):e0169622. doi: 10.1371/journal.pone.0169622. eCollection 2017. PubMed PMID: 28107418; PubMed Central PMCID: PMC5249109. 9: Sosińska P, Baum E, Maćkowiak B, Staniszewski R, Jasinski T, Umezawa K, Bręborowicz A. Inhibition of NF-kappaB with Dehydroxymethylepoxyquinomicin modifies the function of human peritoneal mesothelial cells. Am J Transl Res. 2016 Dec 15;8(12):5756-5765. eCollection 2016. PubMed PMID: 28078047; PubMed Central PMCID: PMC5209527. 10: Guarneri C, Bevelacqua V, Polesel J, Falzone L, Cannavò PS, Spandidos DA, Malaponte G, Libra M. NF κB inhibition is associated with OPN/MMP 9 downregulation in cutaneous melanoma. Oncol Rep. 2017 Feb;37(2):737-746. doi: 10.3892/or.2017.5362. Epub 2017 Jan 10. PubMed PMID: 28075446; PubMed Central PMCID: PMC5355753. 11: Sidthipong K, Ma J, Yu WL, Wang YF, Kobayashi S, Kishino S, Koide N, Yokochi T, Kato K, Okada S, Umezawa K. Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor. Bioorg Med Chem Lett. 2017 Feb 1;27(3):562-566. doi: 10.1016/j.bmcl.2016.12.017. Epub 2016 Dec 8. PubMed PMID: 28003138. 12: Burgess JT, Bolderson E, Adams MN, Baird AM, Zhang SD, Gately KA, Umezawa K, O'Byrne KJ, Richard DJ. Activation and cleavage of SASH1 by caspase-3 mediates an apoptotic response. Cell Death Dis. 2016 Nov 10;7(11):e2469. doi: 10.1038/cddis.2016.364. PubMed PMID: 27831555; PubMed Central PMCID: PMC5260870. 13: El-Salhy M, Mazzawi T, Umezawa K, Gilja OH. Enteroendocrine cells, stem cells and differentiation progenitors in rats with TNBS-induced colitis. Int J Mol Med. 2016 Dec;38(6):1743-1751. doi: 10.3892/ijmm.2016.2787. Epub 2016 Oct 24. PubMed PMID: 27779708; PubMed Central PMCID: PMC5117771. 14: Kawaguchi M, Yamamoto K, Kanemaru A, Tanaka H, Umezawa K, Fukushima T, Kataoka H. Inhibition of nuclear factor-κB signaling suppresses Spint1-deletion-induced tumor susceptibility in the ApcMin/+ model. Oncotarget. 2016 Oct 18;7(42):68614-68622. doi: 10.18632/oncotarget.11863. PubMed PMID: 27612426; PubMed Central PMCID: PMC5356577. 15: Pordanjani SM, Hosseinimehr SJ. The Role of NF-kB Inhibitors in Cell Response to Radiation. Curr Med Chem. 2016;23(34):3951-3963. Review. PubMed PMID: 27554808. 16: El-Salhy M, Umezawa K. Effects of AP 1 and NF κB inhibitors on colonic endocrine cells in rats with TNBS induced colitis. Mol Med Rep. 2016 Aug;14(2):1515-22. doi: 10.3892/mmr.2016.5444. Epub 2016 Jun 27. PubMed PMID: 27357734; PubMed Central PMCID: PMC4940105. 17: El-Salhy M, Umezawa K. Anti-inflammatory effects of novel AP-1 and NF-κB inhibitors in dextran-sulfate-sodium-induced colitis in rats. Int J Mol Med. 2016 Jun;37(6):1457-64. doi: 10.3892/ijmm.2016.2560. Epub 2016 Apr 12. PubMed PMID: 27082818; PubMed Central PMCID: PMC4866953. 18: Seubwai W, Vaeteewoottacharn K, Kraiklang R, Umezawa K, Okada S, Wongkham S. Inhibition of NF-κB Activity Enhances Sensitivity to Anticancer Drugs in Cholangiocarcinoma Cells. Oncol Res. 2016;23(1-2):21-8. doi: 10.3727/096504015X14424348426071. PubMed PMID: 26802647. 19: Labbozzetta M, Poma P, Vivona N, Gulino A, D'Alessandro N, Notarbartolo M. Epigenetic changes and nuclear factor-κB activation, but not microRNA-224, downregulate Raf-1 kinase inhibitor protein in triple-negative breast cancer SUM 159 cells. Oncol Lett. 2015 Dec;10(6):3807-3815. Epub 2015 Oct 9. PubMed PMID: 26788213; PubMed Central PMCID: PMC4665334. 20: Seubwai W, Vaeteewoottacharn K, Kraiklang R, Umezawa K, Okada S, Wongkham S. Inhibition of NF-κB Activity Enhances Sensitivity to Anticancer Drugs in Cholangiocarcinoma Cells. Oncol Res. 2016 Jan 21;23(1):21-28. doi: 10.3727/096504015X14424348426071. PubMed PMID: 29021017.