287194-40-5

中文名称 287194-40-5

英文名称 DEHYDROXYMETHYLEPOXYQUINOMICIN

CAS 287194-40-5

分子式 C13H11NO5

分子量 261.23

MOL 文件 287194-40-5.mol

287194-40-5 结构式

基本信息物理化学性质安全数据常见问题列表

基本信息

中文别名

(-)-DHMEQ
NF-ΚB抑制剂((+)-DHMEQ)
2-羟基-N-(((1S,2S,6S)-2-羟基-5-氧代-7-氧杂双环[4.1.0]庚-3-烯-3-基)苯甲酰胺

英文别名

DHMEQ
DHM2EQ
DEHYDROXYMETHYLEPOXYQUINOMICIN
Dehydroxymethylepoxyquinomicin (DHMEQ)
(-)-DHMEQ?(dehydroxymethylepoxyquinomicin)
2-hydroxy-N-[(1S,2S,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzaMide
Benzamide, 2-hydroxy-N-[(1S,2S,6S)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-

物理化学性质

熔点187 °C

沸点617.2±55.0 °C(Predicted)

密度1.58±0.1 g/cm3(Predicted)

储存条件-20°C储存

溶解度DMSO : ≥ 32 mg/mL (122.50 mM)

酸度系数(pKa)8.43±0.30(Predicted)

形态Solid

颜色Off-white to gray

安全数据

危险性符号(GHS)

GHS07

警示词警告

危险性描述H302-H315-H319-H335

防范说明P261-P305+P351+P338

常见问题列表

生物活性

(-)-DHMEQ (Dehydroxymethylepoxyquinomicin) 是一种有效，选择性且不可逆的 NF-κB 抑制剂，与半胱氨酸残基共价结合。(-)-DHMEQ 抑制 NF-κB 的核易位，并显示抗炎和抗癌活性。

靶点

RelA

RelB

体外研究

(-)-DHMEQ (Dehydroxymethylepoxyquinomicin; 2-10 μg/mL; 12-48 hours) treatment significantly reduces the viability of all cell lines in a dose- and time-dependent manner, whereas the effect is not significant in a control cell line K562 without constitutive NF-κB activity.
(-)-DHMEQ (10 μg/mL; 0-48 hours; TL-Om1, MT-1 and K562 cells) treatment significantly increases the Annexin V-positive cells in MT-1 and TL-Om1 cell lines.
(-)-DHMEQ (10 μg/mL; 4-16 hours; MT-1 cells) treatment down-regulates Bcl-xL, Bcl-2, c-myc, cyclin D1, Rb, and p53, and up-regulates proapoptotic genes such as caspase-3, -8, and-9.
(-)-DHMEQ treatment increases cells in G0 /G1 phase in a time-dependent manner, demonstrating antiproliferative effects of (-)-DHMEQ.
(-)-DHMEQ binds to p65, cRel, RelB, and p50, but not to p52 at specific cysteine residues. (-)-DHMEQ inhibits not only DNA-binding of RelB, but also its interaction to importin. (-)-DHMEQ also induces instability of RelB.

Cell Proliferation Assay

Cell Line:	TL-Om1, MT-1, KK-1, ST-1 and K562 cells
Concentration:	2 μg/mL, 5 μg/mL, 10 μg/mL
Incubation Time:	12 hours, 24 hours, 48 hours
Result:	Significantly reduced the viability of all cell lines in a dose- and time-dependent manner.

Apoptosis Analysis

Cell Line:	TL-Om1, MT-1 and K562 cells
Concentration:	10 μg/mL
Incubation Time:	0 hours, 24 hours, 48 hours
Result:	Annexin V-positive cells were significantly increased after 24 to 48 hours.

Western Blot Analysis

Cell Line:	MT-1 cells
Concentration:	10 μg/mL
Incubation Time:	4 hours, 8 hours, 16 hours
Result:	Annexin V-positive cells were significantly increased after 24 to 48 hours.

体内研究

(-)-DHMEQ (Dehydroxymethylepoxyquinomicin; 4 mg/kg or 12 mg/kg; intraperitoneal injection; on day 0 and 3 times a week; for one month; SCID mice) treatment shows a significant increase in the survival rate in mice.

Animal Model:	Male C.B17-scid/scid (5 weeks old) mice injected with MT-2 cells
Dosage:	4 mg/kg or 12 mg/kg
Administration:	Intraperitoneal injection; on day 0 and 3 times a week; for one month
Result:	Showed a significant increase in the survival rate in mice.