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DAMNACANTHAL

DAMNACANTHAL

中文名稱DAMNACANTHAL
中文同義詞3-羥基-1-甲氧基-2-蒽醌甲醛;丹寧卡;丹拿堪索;丹寧卡【3-羥基-1-甲氧基-2-蒽醌甲醛】
英文名稱DAMNACANTHAL
英文同義詞DAMNACANTHAL;DAMNACANTAL;1-Methoxy-2-formyl-3-hydroxy-9,10-anthraquinone;1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde;3-HYDROXY-1-METHOXYANTHRAQUINONE-2-ALDEHYDE;1-Methoxy-3-hydroxy-9,10-dioxoanthracene-2-carbaldehyde;9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarbaldehyde;3-hydroxy-1-methoxy-9,10-dioxo-anthracene-2-carbaldehyde
CAS號(hào)477-84-9
分子式C16H10O5
分子量282.25
EINECS號(hào)
相關(guān)類別標(biāo)準(zhǔn)品;植物提取物;標(biāo)準(zhǔn)品 -對(duì)照藥材;其它天然產(chǎn)物
Mol文件477-84-9.mol
結(jié)構(gòu)式DAMNACANTHAL 結(jié)構(gòu)式

DAMNACANTHAL 性質(zhì)

熔點(diǎn)218~219℃
沸點(diǎn)531.9±50.0 °C(Predicted)
密度1.461±0.06 g/cm3(Predicted)
儲(chǔ)存條件-20°C
溶解度溶于DMSO(高達(dá)7mg/ml)
酸度系數(shù)(pKa)5.26±0.20(Predicted)
形態(tài)淡橙色固體。
顏色粘黃色
穩(wěn)定性可在-20°C下的DMSO溶液保存長(zhǎng)達(dá)1個(gè)月。
InChI1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3
InChIKeyIPDMWUNUULAXLU-UHFFFAOYSA-N
SMILESO(C)c1c2c(cc(c1C=O)O)C(=O)c3c(cccc3)C2=O

DAMNACANTHAL 用途與合成方法

Damnacanthal 是從 Morinda citrifolia 的根中分離出來(lái)的蒽醌。Damnacanthal 是一種強(qiáng)效選擇性的 p56lck 酪氨酸激酶活性的抑制劑。天然的 Damnacanthal 抑制 p56lck 的自磷酸化和外源底物的磷酸化,IC50 分別為 46 nM 和 220 nM。Damnacanthal 是一種具有抗癌活性的有效凋亡誘導(dǎo)劑。Damnacanthal 在小鼠中也具有鎮(zhèn)痛,抗炎作用,并且對(duì)白色念珠菌具有抗真菌活性。

IC50: 46 nM (p56 lck autophosphorylation) and 220 nM (phosphorylation of exogenous substrates by p56 lck );
Apoptosis;
Candida albicans

Damnacanthal has > 100-fold selectivity for p56 lck over the serine/threonine kinases, protein kinase A and protein kinase C, and > 40-fold selectivity for p56 lck over four receptor tyrosine kinases. Damnacanthal also demonstrates modest (7-20-fold), but highly statistically significant, selectivity for p56 lck over the homologous enzymes p60 src and p59 fyn .
Damnacanthal (0.1-100 μM; 1-4 days; HCT-116 and SW480 cells) treatment results in a significant reduction of cell proliferation in a concentration- and time-dependent manner.
Damnacanthal (1-50 μM; 72 hours; HCT-116 cells) treatment results in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM.
Damnacanthal (10 μM; 24 hours; HCT-116 cells) treatment significantly increases caspase 3/7 activity. Damnacanthal-induced apoptosis.
Damnacanthal (0.1-10 μM; 24 hours; HCT-116 cells) treatment induces NAG-1 expression in HCT-116 cells. Cyclin D1 expression is reduced at 10 μM of Damnacanthal, whereas p21 and p53 does not alter their expression. PARP cleavage is seen at 10 μM Damnacanthal treatment only in HCT-116 cells, where NAG-1 is induced.
Damnacanthal treatment for 2 weeks shows significant decreasing colony number in HCT-116 cells in a concentration-dependent manner. Damnacanthal-treated cells show a dramatic inhibition of clonogenic capacity. Damnacanthal-treated (1-50 μM; 48 hours) cells significantly inhibits the migration of HCT-116 cells in a concentration-dependent manner.

Cell Proliferation Assay

Cell Line: HCT-116 and SW480 cells
Concentration: 0.1 μM, 1 μM, 10 μM, 100 μM
Incubation Time: 1, 2, and 4 days
Result: Resulted in a significant reduction of cell proliferation in a concentration- and time-dependent manner.

Cell Cycle Analysis

Cell Line: HCT-116 cells
Concentration: 1 μM, 10 μM and 50 μM
Incubation Time: 72 hours
Result: Resulted in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM.

Apoptosis Analysis

Cell Line: HCT-116 cells
Concentration: 10 μM
Incubation Time: 24 hours
Result: Significantly increased caspase 3/7 activity.

Western Blot Analysis

Cell Line: HCT-116 cells
Concentration: 0.1 μM, 1 μM and 10 μM
Incubation Time: 24 hours
Result: NAG-1 was induced in HCT-116 cells in a dose- and time-dependent manner. Cyclin D1 expression was reduced at 10 μM.

Damnacanthal (10-100 mg/kg; oral administration; for 10-300 minutes; male ddY mice) treatment exhibits a significant antinociceptive effect in a dose-dependent manner in the formalin test. Administration of damnacanthal (100 mg/kg) shows significant inhibition of histamine-induced paw edema.

Animal Model: Male ddY mice (5-6 weeks) injected with formalin or Histamine
Dosage: 10 mg/kg, 30 mg/kg and 100 mg/kg
Administration: Oral administration; for 10 minutes, 30 minutes, 60 minutes or 300 minutes
Result: Significantly reduced the growth of human lung tumor without acute toxicity.

安全信息

WGK GermanyWGK 1
存儲(chǔ)類別11 - 可燃固體

MSDS信息

更新日期產(chǎn)品編號(hào)產(chǎn)品名稱CAS號(hào)包裝價(jià)格
2025/12/22HY-108485Damnacanthal477-84-91 mg3733元
2024/08/19HY-108485DAMNACANTHAL
Damnacanthal
477-84-95 mg9800元

DAMNACANTHAL 上下游產(chǎn)品信息

"DAMNACANTHAL"相關(guān)產(chǎn)品信息
疏螺旋體素 (β,β-二甲基丙烯?;?紫草素 大黃素-1-O-葡萄糖苷 蘭雪醌 大黃素-8-Β-D-吡喃葡萄糖苷 大黃酚 羥基茜草素 大黃酚-8-O-葡萄糖苷 大黃酚-1-葡萄糖苷 橙黃決明素 淫羊藿 1-甲氧基蒽醌 甲基異茜草素 虎刺素
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