anacardic acid

Names

[ Name ]:
anacardic acid

[Synonym ]:
2-Hydroxy-6-pentadecyl-benzoic acid
2-pentadecyl-6-hydroxybenzoic acid
Benzoic acid, 2-hydroxy-6-pentadecyl-
22:0-Anacardic acid
6-(pentadecenyl)salicylic acid
6-n-pentadecylsalicylic acid
(15:0)-Anacardic acid
ANACARDIC ACID
6-pentadecylsalicylic acid
Anarcadic Acid
Pentadecylsalicylic acid, 6-
Cyclogallipharic acid
2-Hydroxy-6-pentadecylbenzoic acid
salicylic acid, 6-pentadecyl-
22:0-Anacardic acid,2-Hydroxy-6-pentadecylbenzoic acid,6-Pentadecylsalicylic acid

Biological Activity

[Description]:

Anacardic Acid, extracted from cashew nut shell liquid, is a histone acetyltransferase inhibitor, inhibits HAT activity of p300 and PCAF, with IC50s of ∼8.5 μM and ∼5 μM, respectively.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> Epigenetic Reader Domain

Signaling Pathways >> Epigenetics >> Histone Acetyltransferase

Natural Products >> Acids and Aldehydes

Research Areas >> Cancer

[Target]

p300:8.5 μM (IC50)

[In Vitro]

Anacardic Acid is a histone acetyltransferase, inhibits HAT activity of p300 and PCAF, with IC50s of ∼8.5 μM and ∼5 μM, respectively[1]. Anacardic Acid (300 μM) inhibits mycelial growth. Anacardic Acid (50 μM) induces apoptosis-like characteristics in M. oryzae, and the effect is caspase independent. Anacardic Acid (1-80 μM) leads to loss of mitochondrial potential. Anacardic Acid (1-60 μM) also exhibits antioxidant activity in M. oryzae[3].

[In Vivo]

Anacardic acid (5 mg/kg, i.p.) attenuates the binding of HATs to the promoter of MEF2A and reverse hyperacetylation of H3K9ac caused by phenylephrine in C57BL/6 mice. Anacardic acid inhibits the level of transcription on MEF2A and cardiac development-related downstream genes, attenuates the protein overexpression of cardiac downstream genes caused by phenylephrine, reverses and attenuates cardiac hypertrophy in the hearts of mice exposed to phenylephrine, and attenuates the left ventricular pressure and improves cardiac function in the cardiac hypertrophy mice[2].

[Kinase Assay]

Briefly, indicated amounts of proteins/peptide are incubated in HAT assay buffer containing 50 mM Tris-HCl, pH 8.0, 10% (v/v) glycerol, 1 mM dithiothreitol, 1 mM phenylmethyl sulfonyl fluoride, 0.1 mM EDTA, pH 8.0, 10 mM sodium butyrate at 30°C for 10 min in the presence or absence of compound followed by the addition of 1 μL of 6.2 Ci/mmol [3H]acetyl coenzyme A (acetyl-CoA) and are further incubated for another 10 min. The final reaction volume is 30 μL. The reaction mixture is then blotted onto P-81 filter papers, and radioactive counts are recorded on a Wallac 1409 liquid scintillation counter. To characterize the inhibition kinetics of anacardic acid, filter binding assays are done using a constant amount of HeLa core histones in the presence or absence of AA with increasing concentrations of [3H]acetyl-CoA[1].

[Cell Assay]

Mycelial cell death assay is performed to evaluate the number of colony-forming units in treated and untreated samples. M. oryzae conidia (106 conidia/mL) are allowed to germinate in 100-mL flasks with 20 mL complete medium broth (CM) at 28°C in a rotary shaker (200 rpm) for 12 h. The cultures are exposed to different concentrations of anacardic acid for 2 h. The germinated conidia are washed with sterile water, diluted to 104 conidia/mL, and plated on oat meal agar and incubated at 28°C for 3 days. Colony-forming units (CFUs) are counted in each of the three ndividual experiments performed, and values are plotted in the graph as average of three replicates. The data in each sample is expressed as the percentage of the total number of CFUs observed in untreated or 0.1 % DMSO treated control[3].

[Animal admin]

Pathogen-free male and female 11-13 week-old C57BL/6 mice (18-20 g) are randomly selected to inject phenylephrine (20 mg/kg) (control groups receive equivalent normal saline). In some cases, phenylephrine-treated C57BL/6 mice are administered with a Chinese herbal extract anacardic acid (5 mg/kg). Anacardic acid is dissolved in sterile DMSO at a concentration of 1 mg/ml and stored at 4°C. Phenylephrine is administered by a subcutaneous injection at a dose of 20 mg per kg per day continuously for 30 days. Moreover, anacardic acid is administered by an intraperitoneal injection at a dose of 5 mg/kg every 3rd day intraperitoneal injection at a dose of 5 mg/kg every 3rd day. After modeling, mice are euthanized using 20% carbon dioxide in an anesthesia chamber until they are unresponsive to nose pinch and the hearts are isolated[2].

[References]

[1]. Balasubramanyam K, et al. Small molecule modulators of histone acetyltransferase p300. J Biol Chem. 2003 May 23;278(21):19134-40. Epub 2003 Mar 6.

[2]. Peng C, et al. Phenylephrine-induced cardiac hypertrophy is attenuated by a histone acetylase inhibitor anacardic acid in mice. Mol Biosyst. 2017 Mar 28;13(4):714-724.

[3]. Muzaffar S, et al. Anacardic acid induces apoptosis-like cell death in the rice blast fungus Magnaporthe oryzae. Appl Microbiol Biotechnol. 2016 Jan;100(1):323-35.

[Related Small Molecules]

(+)-JQ1 | GSK126 | Tazemetostat (EPZ-6438) | Birabresib (OTX015) | A 485 | Curcumin | ARV-771 | ARV-825 | I-BET762 | BI 2536 | GSK343 | C646 | 3-Deazaneplanocin A (hydrochloride) | I-BET151 | 666-15

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
474.8±33.0 °C at 760 mmHg

[ Melting Point ]:
90-91℃

[ Molecular Formula ]:
C₂₂H₃₆O₃

[ Molecular Weight ]:
348.519

[ Flash Point ]:
255.1±21.9 °C

[ Exact Mass ]:
348.266449

[ PSA ]:
57.53000

[ LogP ]:
9.96

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.515

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: ≥20mg/mL

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2918290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

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