16611-84-0 Usage
Description
6-Pentadecylsalicylic acid, also known as Anacardic acid, is a compound isolated from cashew shells and other medicinal plants. It belongs to a family of four different 6-alkyl salicyclic acids with varying degrees of unsaturation in the 15-carbon alkyl chain. 6-Pentadecylsalicylic acid is recognized for its anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activities. The completely-saturated compound in this family is specifically referred to as 6-pentadecyl salicylic acid. It has the ability to inhibit the histone acetyltransferase (HAT) activity of transcription co-activators p300 and PCAF, and also suppresses NF-κB activation, among other biological effects.
Uses
1. Used in Neurobiology Research:
6-Pentadecylsalicylic acid is used as a histone acetylase (HAT) inhibitor to study its effects on rat cortical neurons, providing insights into the regulation of gene expression and neuronal function.
2. Used in Cellular and Molecular Biology:
It serves as a positive control in acetylation assays in vitro, helping researchers understand the role of protein acetylation in various cellular processes.
3. Used in Agricultural Applications:
6-Pentadecylsalicylic acid is used to treat agriculture from various fruit insects, showcasing its potential as a natural pesticide.
4. Used in Enzyme Research:
The derivative of this molecule has been shown to be a potent activator of human 5-lipoxygenases (5-LOX), which are enzymes involved in the production of inflammatory mediators.
5. Used in Pharmaceutical Research:
As an inhibitor of protein SUMO modification, 6-Pentadecylsalicylic acid is used to study the role of SUMOylation in cellular processes by selectively targeting the SUMO-activating enzyme E1.
6. Used in the Development of Drug Delivery Systems:
6-Pentadecylsalicylic acid is explored for its potential in enhancing the delivery, bioavailability, and therapeutic outcomes of various drugs, particularly in the context of cancer treatment.
7. Used in the Inhibition of Specific Enzymes:
It has been reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, which are important for various physiological and pathological processes.
8. Used in the Study of Kinase Activity:
6-Pentadecylsalicylic acid enhances Aurora kinase A autophosphorylation and kinase activity by inducing a conformational change and enhancing ATP binding, which is crucial for understanding the regulation of cell division and other cellular processes.
Biochem/physiol Actions
Target IC50: 5 μM against HAT; 8.5 μM against PCAF; 2.2 μM inhibiting protein SUMO modification using RanGAP1-C2 as substrate
in vitro
lncap, a classical metastatic prostate adenocarcinoma cell line, was adopted to study the effect of aa on cell growth, cycles and apoptosis. it was found that 125 m aa significantly inhibited lncap cell proliferation. in addition, the g1/s cell cycles arrest and the apoptosis of lncap cell was induced. further mechanistic study suggested that aa induced cell apoptosis via suppressing p300. [1]
in vivo
diesel exhaust particle- (dep-) induced lung inflammation model was established to study the effect of aa on inflammation in mice. ten days before dep-instillation stimulation, mice were orally pretreated with 50, 150, or 250 mg/kg of aa for thirty days. all doses of aa ameliorated activities of oxidative enzymes. moreover, 50 mg/kg of aa significantly decreased the expression level of tumor necrosis factor in lung. [2]
IC 50
noncompetitively inhibit histone acetyltransferase (hat) activity in prostate cancer with an ic50 value of about 5.0 m.
References
1) Balasubramanyam et al. (2003), Small molecule modulators of histone acetyltransferase p300; J. Biol. Chem. 278 19134
2) Sun et al. (2006), Inhibition of histone acetyltransferase activity by anacardic acid sensitizes tumor cells to ionizing radiation; FEBS Lett. 580 4353
3) Wu et al. (2011), Anacardic acid (6-Pentadecylsalicylic acid) Inhibits Tumor Angiogenesis by Targeting Src/FAK/Rho GTPases Signaling Pathway; J. Pharmacol. Exp. Ther. 339 403
4) Omanakuttan et al. (2012), Anacardic acid Inhibits the Catalytic Activity of Matrix Metalloproteinase-2 and Matrix Metalloproteinase-9; Mol. Pharmacol. 82 614
5) Sung et al. (2008), Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-kB- regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-kBα kinase, leading to potentiation of apoptosis; Blood 111 4880
Check Digit Verification of cas no
The CAS Registry Mumber 16611-84-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,6,1 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 16611-84:
(7*1)+(6*6)+(5*6)+(4*1)+(3*1)+(2*8)+(1*4)=100
100 % 10 = 0
So 16611-84-0 is a valid CAS Registry Number.
InChI:InChI=1/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h15,17-18,23H,2-14,16H2,1H3,(H,24,25)
16611-84-0Relevant articles and documents
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Izzo,Dawson
, p. 1039,1046 (1949)
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Phenolic Lipids Derived from Cashew Nut Shell Liquid to Treat Metabolic Diseases
Sahin, Cigdem,Magomedova, Lilia,Ferreira, Thais A. M.,Liu, Jiabao,Tiefenbach, Jens,Alves, Priscilla S.,Queiroz, Fellipe J. G.,Oliveira, Andressa S. De,Bhattacharyya, Mousumi,Grouleff, Julie,Nogueira, Patrícia C. N.,Silveira, Edilberto R.,Moreira, Daniel C.,Leite, José Roberto Souza De Almeida,Brand, Guilherme D.,Uehling, David,Poda, Gennady,Krause, Henry,Cummins, Carolyn L.,Romeiro, Luiz A. S.
, p. 1961 - 1978 (2022/02/14)
Metabolic diseases are increasing at staggering rates globally. The peroxisome proliferator-activated receptors (PPARα/γ/δ) are fatty acid sensors that help mitigate imbalances between energy uptake and utilization. Herein, we report compounds derived from phenolic lipids present in cashew nut shell liquid (CNSL), an abundant waste byproduct, in an effort to create effective, accessible, and sustainable drugs. Derivatives of anacardic acid and cardanol were tested for PPAR activity in HEK293 cell co-transfection assays, primary hepatocytes, and 3T3-L1 adipocytes. In vivo studies using PPAR-expressing zebrafish embryos identified CNSL derivatives with varying tissue-specific activities. LDT409 (23) is an analogue of cardanol with partial agonist activity for PPARα and PPARγ. Pharmacokinetic profiling showed that 23 is orally bioavailable with a half-life of 4 h in mice. CNSL derivatives represent a sustainable source of selective PPAR modulators with balanced intermediate affinities (EC50 ～100 nM to 10 μM) that provide distinct and favorable gene activation profiles for the treatment of diabetes and obesity.
Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor
Swamy, Mahadeva M. M.,Murai, Yuta,Ohno, Yusuke,Jojima, Keisuke,Kihara, Akio,Mitsutake, Susumu,Igarashi, Yasuyuki,Yu, Jian,Yao, Min,Suga, Yoshiko,Anetai, Masaki,Monde, Kenji
supporting information, p. 12758 - 12761 (2018/12/01)
Ginkgolic acid obtained as a sphingomyelin synthase inhibitor from a plant extract library inspired the concept of sphingolipid mimics. Ginkgolic acid-derived N-acyl anilines and ginkgolic acid 2-phosphate (GA2P) respectively mimic ceramide and sphingosine 1-phosphate (S1P) in structure and function. The GA2P-induced phosphorylation of ERK and internalization of S1P receptor 1 (S1P1) indicated potent agonist activity. Docking studies revealed that GA2P adopts a similar binding conformation to the bound ligand ML5, which is a strong antagonist of S1P1.
Synthesis and antibacterial activity of anacardic acid derivatives
Nallamillia, Subhakara Reddy,Kumara, V. Ravi,Himabindub,Rama,Aalapati, Srinivas Rao
experimental part, p. 626 - 632 (2012/05/05)
New anacardic acid derivatives (6a -6u) were prepared from commercially available anacardic acid and tested for Gram positive and Gram negative activities. Most compounds were found to be active compared to ampicillin.
