Hemopressin (rat)Bioactive substrate for endopeptidase 24.15, neurolysin and ACE CAS# 568588-77-2 |
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Quality Control & MSDS
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Chemical structure
3D structure
Cas No. | 568588-77-2 | SDF | Download SDF |
PubChem ID | 44560117 | Appearance | Powder |
Formula | C53H77N13O12 | M.Wt | 1088.27 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 2 mg/ml in 20% acetonitrile | ||
Sequence | PVNFKFLSH | ||
Chemical Name | (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-3-methyl-2-[[(2S)-pyrrolidine-2-carbonyl]amino]butanoyl]amino]-4-oxobutanoyl]amino]-3-phenylpropanoyl]amino]hexanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid | ||
SMILES | CC(C)CC(C(=O)NC(CO)C(=O)NC(CC1=CN=CN1)C(=O)O)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CCCCN)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CC(=O)N)NC(=O)C(C(C)C)NC(=O)C4CCCN4 | ||
Standard InChIKey | DUTLYPZZJJBEAJ-QISMNGAHSA-N | ||
Standard InChI | InChI=1S/C53H77N13O12/c1-30(2)22-37(47(71)65-42(28-67)51(75)64-41(53(77)78)25-34-27-56-29-58-34)60-49(73)39(24-33-16-9-6-10-17-33)61-46(70)36(18-11-12-20-54)59-48(72)38(23-32-14-7-5-8-15-32)62-50(74)40(26-43(55)68)63-52(76)44(31(3)4)66-45(69)35-19-13-21-57-35/h5-10,14-17,27,29-31,35-42,44,57,67H,11-13,18-26,28,54H2,1-4H3,(H2,55,68)(H,56,58)(H,59,72)(H,60,73)(H,61,70)(H,62,74)(H,63,76)(H,64,75)(H,65,71)(H,66,69)(H,77,78)/t35-,36-,37-,38-,39-,40-,41-,42-,44-/m0/s1 | ||
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. |
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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. |
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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. |
Description | Bioactive endogenous peptide substrate for endopeptidase 24.15 (ep24.15), neurolysin (ep24.16) and ACE. Ki values are 27.76, 3.43 and 1.87 μM respectively. Potent hypotensive in vivo. Also acts as a selective CB1 receptor inverse agonist. Displays antinociceptive activity and induces hypophagia in vivo. |
Hemopressin (rat) Dilution Calculator
Hemopressin (rat) Molarity Calculator
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Pharmacological characterization of rat VD-hemopressin(alpha), an alpha-hemoglobin-derived peptide exhibiting cannabinoid agonist-like effects in mice.[Pubmed:28010996]
Neuropeptides. 2017 Jun;63:83-90.
Hemopressin and related peptides have shown to function as the endogenous ligands or the regulator of cannabinoid receptors. Moreover, hemopressin and its truncated peptides were also reported to produce a slight modulatory effect on opioid system. In the present work, based on the amino acid sequence analyses of hemoglobin subunit alpha, rat VD-hemopressin(alpha) [(r)VD-Hpalpha] was predicted as a cannabinoid peptide derived from rat alpha-hemoglobin. Furthermore, (r)VD-Hpalpha was synthesized and characterized in a series of in vitro and in vivo assays. Our results demonstrated that (r)VD-Hpalpha induced neurite outgrowth in Neuro 2A cells via CB1 receptor. In the tail-flick assay, (r)VD-Hpalpha dose-dependently exerted central antinociception through CB1 receptor, but not CB2 and opioid receptors. In mice, supraspinal administration of (r)VD-Hpalpha produced dose-dependent hypothermia, which was partially reduced by the CB1 receptor antagonist AM251, but not by the antagonists of CB2 and opioid receptors. In addition, (r)VD-Hpalpha caused hypoactivity after intracerebroventricular injection, and this effect was insensitive to the antagonists of cannabinoid and opioid receptors. Further assessment of the side-effects demonstrated that (r)VD-Hpalpha evoked the limited effects on gastrointestinal transit at antinociceptive doses, but repeated i.c.v. injection of (r)VD-Hpalpha induced development of antinociceptive tolerance. Taken together, these data suggest that the predicted peptide (r)VD-Hpalpha produces antinociception, hypothermia and hypoactivity via different pharmacological mechanisms, at least partially, which may offer an attractive strategy for separating cannabinoid analgesia from hypoactivity. Moreover, it implies that (r)VD-Hpalpha has therapeutic potential in pain management with limited side-effects.
Hemopressin, a hemoglobin fragment, dilates the rat systemic vascular bed through release of nitric oxide.[Pubmed:16713023]
Peptides. 2006 Sep;27(9):2284-8.
The present study was undertaken to investigate the effects of intravenous (i.v.) administration of rat hemopressin (rHP), 30-1000 microg/kg, on systemic arterial pressure (SAP), cardiac output (CO) and systemic vascular resistance (SVR) in the anesthetized rat. Bolus i.v. injections of rHP produced mild decreases in SAP that were dose-dependent. Since CO was not altered, the decreases in SAP reflect reductions in SVR. The systemic vasodilator response to rHP was not subject to tachyphylaxis. The systemic vasodilator response to rHP was abolished by L-nitro-arginine methylester (L-NAME) but was not altered by meclofenamate. In addition, rHP lacked direct contractile and relaxant activity on isolated rat aortic rings (AA) and pulmonary arterial rings (PA). The present data suggest rHP dilates the rat systemic vascular bed through the endogenous release of nitric oxide (NO) independent of the formation of cyclooxygenase products including prostacyclin. It is possible rHP acts as an endogenous vasodilator substance to regulate local blood flow during clinical states of altered red cell turnover, microvascular disease and hemolysis.
The peptide hemopressin acts through CB1 cannabinoid receptors to reduce food intake in rats and mice.[Pubmed:20505104]
J Neurosci. 2010 May 26;30(21):7369-76.
Hemopressin is a short, nine amino acid peptide (H-Pro-Val-Asn-Phe-Lys-Leu-Leu-Ser-His-OH) isolated from rat brain that behaves as an inverse agonist at the cannabinoid receptor CB(1), and is shown here to inhibit agonist-induced receptor internalization in a heterologous cell model. Since this peptide occurs naturally in the rodent brain, we determined its effect on appetite, an established central target of cannabinoid signaling. Hemopressin dose-dependently decreases night-time food intake in normal male rats and mice, as well as in obese ob/ob male mice, when administered centrally or systemically, without causing any obvious adverse side effects. The normal, behavioral satiety sequence is maintained in male mice fasted overnight, though refeeding is attenuated. The anorectic effect is absent in CB(1) receptor null mutant male mice, and hemopressin can block CB(1) agonist-induced hyperphagia in male rats, providing strong evidence for antagonism of the CB(1) receptor in vivo. We speculate that hemopressin may act as an endogenous functional antagonist at CB(1) receptors and modulate the activity of appetite pathways in the brain.
Hemopressin is an inverse agonist of CB1 cannabinoid receptors.[Pubmed:18077343]
Proc Natl Acad Sci U S A. 2007 Dec 18;104(51):20588-93.
To date, the endogenous ligands described for cannabinoid receptors have been derived from membrane lipids. To identify a peptide ligand for CB(1) cannabinoid receptors, we used the recently described conformation-state sensitive antibodies and screened a panel of endogenous peptides from rodent brain or adipose tissue. This led to the identification of hemopressin (PVNFKFLSH) as a peptide ligand that selectively binds CB(1) cannabinoid receptors. We find that hemopressin is a CB(1) receptor-selective antagonist, because it is able to efficiently block signaling by CB(1) receptors but not by other members of family A G protein-coupled receptors (including the closely related CB(2) receptors). Hemopressin also behaves as an inverse agonist of CB(1) receptors, because it is able to block the constitutive activity of these receptors to the same extent as its well characterized antagonist, rimonabant. Finally, we examine the activity of hemopressin in vivo using different models of pain and find that it exhibits antinociceptive effects when administered by either intrathecal, intraplantar, or oral routes, underscoring hemopressin's therapeutic potential. These results represent a demonstration of a peptide ligand for CB(1) cannabinoid receptors that also exhibits analgesic properties. These findings are likely to have a profound impact on the development of novel therapeutics targeting CB(1) receptors.
Novel natural peptide substrates for endopeptidase 24.15, neurolysin, and angiotensin-converting enzyme.[Pubmed:12500972]
J Biol Chem. 2003 Mar 7;278(10):8547-55.
Endopeptidase 24.15 (EC; ep24.15), neurolysin (EC; ep24.16), and angiotensin-converting enzyme (EC; ACE) are metallopeptidases involved in neuropeptide metabolism in vertebrates. Using catalytically inactive forms of ep24.15 and ep24.16, we have identified new peptide substrates for these enzymes. The enzymatic activity of ep24.15 and ep24.16 was inactivated by site-directed mutagenesis of amino acid residues within their conserved HEXXH motifs, without disturbing their secondary structure or peptide binding ability, as shown by circular dichroism and binding assays. Fifteen of the peptides isolated were sequenced by electrospray ionization tandem mass spectrometry and shared homology with fragments of intracellular proteins such as hemoglobin. Three of these peptides (PVNFKFLSH, VVYPWTQRY, and LVVYPWTQRY) were synthesized and shown to interact with ep24.15, ep24.16, and ACE, with K(i) values ranging from 1.86 to 27.76 microm. The hemoglobin alpha-chain fragment PVNFKFLSH, which we have named hemopressin, produced dose-dependent hypotension in anesthetized rats, starting at 0.001 microg/kg. The hypotensive effect of the peptide was potentiated by enalapril only at the lowest peptide dose. These results suggest a role for hemopressin as a vasoactive substance in vivo. The identification of these putative intracellular substrates for ep24.15 and ep24.16 is an important step toward the elucidation of the role of these enzymes within cells.