(-)-DHMEQ (Dehydroxymethylepoxyquinomicin) is a potent, selective, and irreversible inhibitor of NF-κB that covalently binds to a cysteine residue. (-)-DHMEQ inhibits the nuclear translocation of NF-κB and displays anti~inflammatory and anticancer activities.

Physicochemical Properties

Molecular Formula	C13H11NO5
Molecular Weight	261.2301
Exact Mass	261.064
CAS #	287194-40-5
PubChem CID	9881652
Appearance	Off-white to gray solid powder
LogP	0.291
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Heavy Atom Count	19
Complexity	446
Defined Atom Stereocenter Count	3
SMILES	C1=CC=C(C(=C1)C(=O)NC2=CC(=O)[C@@H]3[C@H]([C@H]2O)O3)O
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
Chemical Name	2-Hydroxy-N-[(1S,2S,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
Synonyms	DHMEQ Dehydroxymethylepoxyquinomicin
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Treatment with (-)-DHMEQ (Dehydroxymethylepoxyquinomicin; 2–10 μg/mL; 12-48 hours) dramatically lowers all cell lines' survival in a time- and dose-dependent manner; however, the impact is not statistically significant in the control cell line K562, which lacks constitutive NF-κB activity[2]. In MT-1 and TL-Om1 cell lines, (-)-DHMEQ (10 μg/mL; 0-48 hours; TL-Om1, MT-1, and K562 cells) treatment dramatically increases the Annexin V-positive cells[2]. Under (-)-DHMEQ (10 μg/mL; 4–16 hours; MT-1 cells) treatment, proapoptotic genes such caspase-3, -8, and-9 are up-regulated and Bcl-xL, Bcl-2, c-myc, cyclin D1, Rb, and p53 are down-regulated.Reference [2]. Treatment with (-)-DHMEQ results in a time-dependent increase in cells in the G0 /G1 phase, indicating (-)-DHMEQ's antiproliferative properties[2]. At particular cysteine residues, (-)-DHMEQ binds to p65, cRel, RelB, and p50 but not p52. RelB's DNA binding and interaction with importin are both inhibited by (-)-DHMEQ. RelB becomes unstable as well due to (-)-DHMEQ[1].
ln Vivo	The intraperitoneal injection of (-)-DHMEQ (4 mg/kg or 12 mg/kg) given to SCID mice on day 0 and three times a week for a month significantly increases the mice's survival rate[2].
Cell Assay	Cell Proliferation Assay[2] Cell Types: TL-Om1, MT-1, KK-1, ST-1 and K562 cells Tested Concentrations: 2 μg/mL, 5 μg/mL, 10 μg/mL Incubation Duration: 12 hrs (hours), 24 hrs (hours), 48 hrs (hours) Experimental Results: Dramatically decreased the viability of all cell lines in a dose- and time- dependent manner. Apoptosis Analysis[2] Cell Types: TL-Om1, MT-1 and K562 cells Tested Concentrations: 10 μg/mL Incubation Duration: 0 hrs (hours), 24 hrs (hours), 48 hrs (hours) Experimental Results: Annexin V-positive cells were Dramatically increased after 24 to 48 hrs (hours). Western Blot Analysis[2] Cell Types: MT-1 cells Tested Concentrations: 10 μg/mL Incubation Duration: 4 hrs (hours), 8 hrs (hours), 16 hrs (hours) Experimental Results: Annexin V-positive cells were Dramatically increased after 24 to 48 hrs (hours).
Animal Protocol	Animal/Disease Models: Male C.B17-scid/scid (5 weeks old) mice injected with MT-2 cells[2] Doses: 4 mg/kg or 12 mg/kg Route of Administration: intraperitoneal (ip)injection; on day 0 and 3 times a week ; for one month Experimental Results: demonstrated a significant increase in the survival rate in mice.
References	[1]. Inhibition of Late and Early Phases of Cancer Metastasis by the NF-κB Inhibitor DHMEQ Derived from Microbial Bioactive Metabolite Epoxyquinomicin: A Review. [2]. Dual targeting of transformed and untransformed HTLV-1-infected T cells by DHMEQ, a potent and selective inhibitor of NF-kappaB, as a strategy for chemoprevention and therapy of adult T-cell leukemia. Blood. 2005 Oct 1;106(7):2462-71. [3]. Eudesmane-Type Sesquiterpene Lactones Inhibit Nuclear Translocation of the Nuclear Factor κB Subunit RelB in Response to a Lymphotoxin β Stimulation. Biol Pharm Bull. 2017;40(10):1669-1677.

Solubility Data

Solubility (In Vitro)

DMSO : ~95 mg/mL (~363.66 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 5 mg/mL (19.14 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.8280 mL	19.1402 mL	38.2804 mL
	5 mM	0.7656 mL	3.8280 mL	7.6561 mL
	10 mM	0.3828 mL	1.9140 mL	3.8280 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.