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Laccaic acid A

Names

[ CAS No. ]:
15979-35-8

[ Name ]:
Laccaic acid A

[Synonym ]:
Laccacid Acid A
Laccaic acid A
7-{5-[2-(acetylamino)ethyl]2-hydroxyphenyl}-9,10-dihydro-3,5,6,8-tetrahydroxy-9,10-1,2-anthracenedicarboxylic acid
3-[3-(2-acetamidoethyl)-6-hydroxyphenyl]-1,2,4,7-tetrahydroxyanthraquinone-5,6-dicarboxylic acid
3-<3-(2-Acetamidoethyl)-6-hydroxy-phenyl>-1.2.4.7-tetrahydroxy-anthrachinon-dicarbonsaeure-(5.6),Lacaeure-A(1)
3-<3-(2-Acetamidoethyl)-6-hydroxy-phenyl>-1.2.4.7-tetrahydroxy-anthrachinon-dicarbonsaeure-(5.6)

Biological Activity

[Description]:

Laccaic acid A is a orally active and DNA-competitive inhibitor of DNA methyltransferase 1 (Dnmt1) (Ki=310 nM; IC50=650 nM). Laccaic acid A has stronger Dnmt1 inhibitory effect than SG-1027 (HY-13962). Laccaic acid A combined with Phenethyl isothiocyanate has a strong synergistic effect on colorectal cancer[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Epigenetics >> DNA Methyltransferase

[Target]

DNMT1:650 nM (IC50)

DNMT1:310 nM (Ki)


[In Vitro]

Laccaic acid A (200 μM) 与 0.5 μM Decitabine (HY-A0004) 协同改变 MCF-7 乳腺癌细胞中甲基化基因的表达[1]。 Laccaic acid A (0.01-100 μM; 24 h, 48 h, and 72 h) 抑制人直肠癌细胞 HT29 的生长，处理 72 h 时，IC50 为 6.08 μM[2]。 Laccaic acid A (6.08 μM) 诱导 HT29 细胞凋亡，并将细胞周期阻滞在亚 G1 期[2]。

[In Vivo]

Laccaic acid A (50 mg/kg，100 mg/kg，200 mg/kg; 口服; 每天 1 次，共 21 天) 对大鼠直肠癌模型具有改善效果[2]。 Animal Model: Healthy Sprague Dawley rats[2] Dosage: 50 mg/kg, 100 mg/kg, and 200 mg/kg Administration: Oral gavage; once daily for 21 days Result: Significantly reduced the tissue levels of Dnmt1, HDAC1, and cytokines IL-6 and TNF-alpha at 200 mg/kg dose.

[References]

[1]. Fagan RL, et al. Laccaic acid A is a direct, DNA-competitive inhibitor of DNA methyltransferase 1. J Biol Chem. 2013 Aug 16;288(33):23858-67.  

[2]. Gupta R, et al. Potent antitumor activity of Laccaic acid and Phenethyl isothiocyanate combination in colorectal cancer via dual inhibition of DNA methyltransferase-1 and Histone deacetylase-1. Toxicol Appl Pharmacol. 2019 Aug 15;377:114631.  

Chemical & Physical Properties

[ Density]:
1.715g/cm3

[ Boiling Point ]:
995.3ºC at 760mmHg

[ Molecular Formula ]:
C26H19NO12

[ Molecular Weight ]:
537.42900

[ Flash Point ]:
555.7ºC

[ Exact Mass ]:
537.09100

[ PSA ]:
238.99000

[ LogP ]:
2.12290

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.76

Related Compounds