Ac2-12Annexin/lipocortin 1-mimetic; inhibits leukocyte extravasation CAS# 256447-08-2 |
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Chemical structure
3D structure
Cas No. | 256447-08-2 | SDF | Download SDF |
PubChem ID | 90488718 | Appearance | Powder |
Formula | C63H94N14O17S | M.Wt | 1351.58 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 1 mg/ml in 20% acetonitrile / water | ||
Sequence | AMVSEFLKQAW (Modifications: Ala-1 = N-terminal Ac) | ||
Chemical Name | (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamidopropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxypropanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-oxopentanoic acid | ||
SMILES | CC(C)CC(C(=O)NC(CCCCN)C(=O)NC(CCC(=O)N)C(=O)NC(C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(C)NC(=O)C | ||
Standard InChIKey | SUDAISORCUBKHK-RCVXMRHOSA-N | ||
Standard InChI | InChI=1S/C63H94N14O17S/c1-33(2)28-46(59(89)70-42(20-14-15-26-64)56(86)71-43(21-23-50(65)80)55(85)68-36(6)54(84)75-48(63(93)94)30-39-31-66-41-19-13-12-18-40(39)41)73-60(90)47(29-38-16-10-9-11-17-38)74-57(87)44(22-24-51(81)82)72-61(91)49(32-78)76-62(92)52(34(3)4)77-58(88)45(25-27-95-8)69-53(83)35(5)67-37(7)79/h9-13,16-19,31,33-36,42-49,52,66,78H,14-15,20-30,32,64H2,1-8H3,(H2,65,80)(H,67,79)(H,68,85)(H,69,83)(H,70,89)(H,71,86)(H,72,91)(H,73,90)(H,74,87)(H,75,84)(H,76,92)(H,77,88)(H,81,82)(H,93,94)/t35-,36-,42-,43-,44-,45-,46-,47-,48-,49-,52-/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 | Annexin/lipocortin 1-mimetic peptide; inhibits leukocyte extravasation. Reduces neutrophil adhesion and emigration, and promotes detachment of neutrophils from activated mesenteric endothelium in mice in vivo. |
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Involvement of the receptor for formylated peptides in the in vivo anti-migratory actions of annexin 1 and its mimetics.[Pubmed:11395373]
Am J Pathol. 2001 Jun;158(6):1969-73.
An innovative avenue for anti-inflammatory therapy is inhibition of neutrophil extravasation by potentiating the action of endogenous anti-inflammatory mediators. The glucocorticoid-inducible protein annexin 1 and derived peptides are effective in inhibiting neutrophil extravasation. Here we tested the hypothesis that an interaction with the receptor for formylated peptide (FPR), so far reported only in vitro, could be the mechanism for this in vivo action. In a model of mouse peritonitis, FPR antagonists abrogated the anti-migratory effects of peptides Ac2-26 and Ac2-12, with a partial reduction in annexin 1 effects. A similar result was obtained in FPR (knock-out) KO mice. Binding of annexin 1 to circulating leukocytes was reduced (>50%) in FPR KO mice. In vitro, annexin binding to peritoneal macrophages was also markedly reduced in FPR KO mice. Finally, evidence of direct annexin 1 binding to murine FPR was obtained with HEK-293 cells transfected with the receptor. Overall, these results indicate a functional role for FPR in the anti-migratory effect of annexin 1 and derived peptides.
Promoting detachment of neutrophils adherent to murine postcapillary venules to control inflammation: effect of lipocortin 1.[Pubmed:9826735]
Proc Natl Acad Sci U S A. 1998 Nov 24;95(24):14535-9.
In this study we investigated, using intravital microscopy, how neutrophil extravasation across mouse mesenteric postcapillary venules is inhibited by the glucocorticoid-regulated protein lipocortin (LC; also termed annexin) 1. Intraperitoneal injection of 1 mg of zymosan into mice induced neutrophil rolling on the activated mesenteric endothelium followed by adhesion (maximal at 2 hr: 5-6 cells per 100-micrometers of vessel length) and emigration (maximal at 4 hr: 8-10 cells per high-powered field). Treatment of mice with human recombinant LC1 (2 mg/kg s.c.) or its mimetic peptide Ac2-26 (13 mg/kg s.c.) did not modify cell rolling but markedly reduced (>/=50%) the degree of neutrophil adhesion and emigration (P < 0.05). Intravenous treatment with peptide Ac2-26 (13 mg/kg) or recombinant human LC1 (0.7-2 mg/kg) promoted detachment of neutrophils adherent to the endothelium 2 hr after zymosan administration, with adherent cells detaching within 4.12 +/- 0.75 min and 2.36 +/- 0.31 min, respectively (n = 20-25 cells). Recruitment of newly adherent cells to the endothelium was unaffected. The structurally related protein LC5 was inactive in this assay, whereas a chimeric molecule constructed from the N terminus of LC1 (49 aa) attached to the core region of LC5 produced cell detachment with kinetics similar to LC1. Removal of adherent neutrophils from activated postcapillary endothelium is a novel pharmacological action, and it is at this site where LC1 and its mimetics operate to down-regulate this aspect of the host inflammatory response.