Laccaic acid A

Modify Date: 2024-01-02 18:47:34

Laccaic acid A Structure
Laccaic acid A structure
Common Name Laccaic acid A
CAS Number 15979-35-8 Molecular Weight 537.42900
Density 1.715g/cm3 Boiling Point 995.3ºC at 760mmHg
Molecular Formula C26H19NO12 Melting Point N/A
MSDS N/A Flash Point 555.7ºC

 Use of Laccaic acid A


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].

 Names

Name 7-[5-(2-acetamidoethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid
Synonym More Synonyms

 Laccaic acid A 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
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

 Synonyms

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)