STEARDA

Endogenous inhibitor of 5-lipoxygenase CAS# 105955-10-0

STEARDA

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STEARDA

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Chemical Properties of STEARDA

Cas No. 105955-10-0 SDF Download SDF
PubChem ID 10025103 Appearance Powder
Formula C26H45NO3 M.Wt 419.64
Type of Compound N/A Storage Desiccate at -20°C
Synonyms <em>N</em>-Stearoyldopamine
Solubility Soluble to 5 mM in ethanol with gentle warming
Chemical Name N-[2-(3,4-dihydroxyphenyl)ethyl]octadecanamide
SMILES CCCCCCCCCCCCCCCCCC(=O)NCCC1=CC(=C(C=C1)O)O
Standard InChIKey KOCSVLPLQCBIGW-UHFFFAOYSA-N
Standard InChI InChI=1S/C26H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h18-19,22,28-29H,2-17,20-21H2,1H3,(H,27,30)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of STEARDA

DescriptionEndogenous fatty acid dopamide that displays 'entourage' effects on endovanilloids NADA and anandamide. Inactive at TRPV1 and CB1 receptors (at concentrations up to 5 μM) and does not inhibit AMT or FAAH (IC50 > 25 μM). However, potentiates TRPV1-mediated effects of NADA in vitro and in vivo; enhances effects on intracellular Ca2+ (EC50 lowered 3-fold) and nociception. Also inhibits arachidonate 5-lipoxygenase (IC50 = 16 nM).

STEARDA Dilution Calculator

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Preparing Stock Solutions of STEARDA

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.383 mL 11.915 mL 23.8299 mL 47.6599 mL 59.5749 mL
5 mM 0.4766 mL 2.383 mL 4.766 mL 9.532 mL 11.915 mL
10 mM 0.2383 mL 1.1915 mL 2.383 mL 4.766 mL 5.9575 mL
50 mM 0.0477 mL 0.2383 mL 0.4766 mL 0.9532 mL 1.1915 mL
100 mM 0.0238 mL 0.1191 mL 0.2383 mL 0.4766 mL 0.5957 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on STEARDA

Modulation of inhibitory neurotransmission by the vanilloid receptor type 1 (TRPV1) in organotypically cultured mouse substantia gelatinosa neurons.[Pubmed:20451324]

Pain. 2010 Jul;150(1):128-40.

The vanilloid receptor type 1 (TRPV1) plays a pivotal role in modulating thermal, chemical, and inflammatory pain. TRPV1s are expressed in some dorsal horn (DH) neurons, but their contribution, if any, to central pain processing still remains unclear. We studied the effects of 2microM capsaicin-induced TRPV1 activation in organotypically cultured substantia gelatinosa neurons from post-natal (8-12) mice. Capsaicin affected sIPSC frequency (272+/-60% of control, n=14, P<0.02), but not amplitude (131+/-12% of control, n=14, P>0.05) in patch clamp recordings, also in the presence of 50microM AP-5 (frequency: 265+/-69% of control; n=8, P<0.05; amplitude: 156+/-28% of control; n=8, P>0.05). The frequency increase was reduced by TTX (181+/-21% of control; n=12, P<0.05). Pre-administration of I-RTX (1microM), a TRPV1 antagonist, prevented the capsaicin effect (frequency: 149+/-28% of control, P>0.05, n=12; amplitude: 97+/-4% of control, P>0.05, n=12). NADA (1microM), an endovanilloid/endocannabinoid agonist of TRPV1, induced a significant increase of sISPC frequency (191+/-40% of control; n=8, P<0.05) without affecting the amplitude (102+/-6% of control; n=8, P>0.05), and the co-application of two naturally occurring N-acyldopamines, PALDA (5microM) and STEARDA (5microM) that facilitate the effect of TRPV1 agonists, also induced a significant increase of sIPSC frequency (278+/-67% of control, n=6, P<0.05). The presence of TRPV1 protein and mRNA in DH neurons was confirmed by histological (immunocytochemistry, in situ PCR) and biochemical (Western blotting, PCR) procedures. These data show that TRPV1 modulates inhibitory neurotransmission in cultured substantia gelatinosa neurons, and suggest that endogenous agonists can activate the spinal receptors in vivo.

Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels.[Pubmed:15289293]

Br J Pharmacol. 2004 Sep;143(2):251-6.

Four long-chain, linear fatty acid dopamides (N-acyldopamines) have been identified in nervous bovine and rat tissues. Two unsaturated members of this family of lipids, N-arachidonoyl-dopamine (NADA) and N-oleoyl-dopamine, were shown to potently activate the transient receptor potential channel type V1 (TRPV1), also known as the vanilloid receptor type 1 for capsaicin. However, the other two congeners, N-palmitoyl- and N-stearoyl-dopamine (PALDA and STEARDA), are inactive on TRPV1. We have investigated here the possibility that the two compounds act by enhancing the effect of NADA on TRPV1 ('entourage' effect). When pre-incubated for 5 min with cells, both compounds dose-dependently enhanced NADA's TRPV1-mediated effect on intracellular Ca(2+) in human embryonic kidney cells overexpressing the human TRPV1. In the presence of either PALDA or STEARDA (0.1-10 microm), the EC(50) of NADA was lowered from approximately 90 to approximately 30 nm. The effect on intracellular Ca(2+) by another endovanilloid, N-arachidonoyl-ethanolamine (anandamide, 50 nm), was also enhanced dose-dependently by both PALDA and STEARDA. PALDA and STEARDA also acted in synergy with low pH (6.0-6.7) to enhance intracellular Ca(2+) via TRPV1. When co-injected with NADA (0.5 micrograms) in rat hind paws, STEARDA (5 micrograms) potentiated NADA's TRPV1-mediated nociceptive effect by significantly shortening the withdrawal latencies from a radiant heat source. STEARDA (1 and 10 micrograms) also enhanced the nocifensive behavior induced by carrageenan in a typical test of inflammatory pain. These data indicate that, despite their inactivity per se on TRPV1, PALDA and STEARDA may play a role as 'entourage' compounds on chemicophysical agents that interact with these receptors, with possible implications in inflammatory and neuropathic pain.

N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia.[Pubmed:12569099]

J Biol Chem. 2003 Apr 18;278(16):13633-9.

N-Arachidonoyldopamine (NADA) was recently identified as an endogenous ligand for the vanilloid type 1 receptor (VR1). Further analysis of the bovine striatal extract from which NADA was isolated indicated the existence of substances corresponding in molecular mass to N-oleoyldopamine (OLDA), N-palmitoyldopamine (PALDA), and N-stearoyldopamine (STEARDA). Quadrupole time-of-flight mass spectrometric analysis of bovine striatal extracts revealed the existence of OLDA, PALDA, and STEARDA as endogenous compounds in the mammalian brain. PALDA and STEARDA failed to affect calcium influx in VR1-transfected human embryonic kidney (HEK) 293 cells or paw withdrawal latencies from a radiant heat source, and there was no evidence of spontaneous pain behavior. By contrast, OLDA induced calcium influx (EC(50) = 36 nm), reduced the latency of paw withdrawal from a radiant heat source in a dose-dependent manner (EC(50) = 0.72 microg), and produced nocifensive behavior. These effects were blocked by co-administration of the VR1 antagonist iodo-resiniferatoxin (10 nm for HEK cells and 1 microg/50 micro;l for pain behavior). These findings demonstrate the existence of an endogenous compound in the brain that is similar to capsaicin and NADA in its chemical structure and activity on VR1. Unlike NADA, OLDA was only a weak ligand for rat CB1 receptors; but like NADA, it was recognized by the anandamide membrane transporter while being a poor substrate for fatty-acid amide hydrolase. Analysis of the activity of six additional synthetic and potentially endogenous N-acyldopamine indicated the requirement of a long unsaturated fatty acid chain for an optimal functional interaction with VR1 receptors.

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