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| | ACTINONIN Basic information |
| Product Name: | ACTINONIN | | Synonyms: | (-)-ACTINONIN;ACTINONIN;3-[[1-[[2-(HYDROXYMETHYL)-1-PYRROLIDINYL]CARBONYL]-2-METHYL-PROPYL]CARBAMOYL]OCTANOHYDROXAMIC ACID;3-[[1-[[2-(HYDROXYMETHYL)-1-PYRROLIDINYL]-CARBONYL]-2-METHYLPROPYL]-CARBAMOYL]-OCTONOHYDROXAMIC ACID;N4-HYDROXY-N1-[(1S)-1[[(2S)-2-(HYDROXYMETHYL)-1-PYRROLDINYL]CARBONYL]-2-METHYLPROPYL]-2-PENTYL-,(2R)-(9CI);(R)-N4-Hydroxy-N1-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-pentylsuccinamide;hylpropyl)carbamoyl)-;octanohydroxamicacid,3-((1-((2-(hydroxymethyl)-1-pyrrolidinyl)carbonyl)-2-met | | CAS: | 13434-13-4 | | MF: | C19H35N3O5 | | MW: | 385.5 | | EINECS: | | | Product Categories: | All Inhibitors;Inhibitors;Antibiotic.;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 13434-13-4.mol |  |
| | ACTINONIN Chemical Properties |
| Melting point | 137-139°C | | density | 1.139±0.06 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml). | | pka | 9.19±0.20(Predicted) | | form | White to off-white powder. | | color | White | | biological source | synthetic (organic) | | BRN | 1555250 | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months. | | InChI | 1S/C19H35N3O5/c1-4-5-6-8-14(11-16(24)21-27)18(25)20-17(13(2)3)19(26)22-10-7-9-15(22)12-23/h13-15,17,23,27H,4-12H2,1-3H3,(H,20,25)(H,21,24) | | InChIKey | XJLATMLVMSFZBN-UHFFFAOYSA-N | | SMILES | CCCCCC(CC(=O)NO)C(=O)NC(C(C)C)C(=O)N1CCCC1CO | | CAS DataBase Reference | 13434-13-4(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | WGK Germany | 3 | | RTECS | RG9900700 | | Storage Class | 11 - Combustible Solids |
| | ACTINONIN Usage And Synthesis |
| Description | Actinonin (13434-13-4) is a potent hydroxamic acid inhibitor of aminopeptidases which displays analgesic effects by inhibiting enkephalin-degrading enzymes.1Actinonin also inhibits peptide deformylase.2Induces apoptosis and displays antitumor activity in vivo.3Inhibits neutrophil collagenase and other MMPs.4 Induces mitochondrial proteotoxicity.5 | | Chemical Properties | Off-White Solid | | Uses | (-)-Actinonin is a bioactive peptide and antibiotic that is a potent inhibitor of aminopeptidase M and leucine aminopeptidase. Actinonin has observed to be an inhibitor of peptide deformylase, meprin A, and thermolysin. Actinonin also inhibits tumor cell invasion and matrix degradation along with displayed antitumor activity in vitro and in vivo as well as acting as an apoptotic inducer. | | Uses | Actinonin has been used as a control to inhibit meprin-β activity in C57BL/6 mice. It has also been used to study the high-affinity interaction of EcPDF with actinonin by 15N NMR spectroscopy and isothermal titration. | | Uses | A potent in vivo inhibitor of collagenase | | General Description | Chemical structure: peptide | | Biochem/physiol Actions | Actinonin has inhibitory action against peptide deformylase (PDF). It is effective against Gram-positive and fastidious Gram-negative microorganisms. | | in vitro | actinonin showed an inhibitory effect in cell growth. the in vitro ic50 values of actinonin against nb4, hl6o human cell lines, akr mouse leukemia cells cd13-negative cell lines ra.ji and daudi human lymphoma were about 2-5 μg/ml. cell cycle analysis indicated that actinonin induced a g1 arrest in nb4 and hl6o cells. intracellular flow cytometry showed that actinonin could induce cell apoptosis in 20-35% of the cells [2]. actinonin dose-dependently inhibited the three forms (zn-, ni-, and fe-) of peptide deformylases from both s. aureus and e. coli bacteria. the ic50 values of actinonin were 90, 3, 0.8, and 11 nm for zn-pdf (e. coli), ni-pdf (e. coli), fe-pdf (e. coli), and ni-pdf (s. aureus), respectively [2]. actinonin is a tight binding inhibitor of e. coli ni-pdf with a ki of 0.3 nm [3]. | | in vivo | actinonin showed dose-dependent antitumor effects on akr leukemia, resulting in a survival advantage. in the syngeneic akr mouse leukemia model, treatment with 100 p.g actinonin daily for 3 days beginning at day 3 after transplantation showed significant antitumor effects [2]. | | storage | +4°C | | References | [1] MITSUGU HACHISU . Analgesic effect of actinonin, a new potent inhibitor of multiple enkephalin degrading enzymes[J]. Life sciences, 1987, 41 2: Pages 235-240. DOI:10.1016/0024-3205(87)90498-x
[2] MONA D LEE. Human mitochondrial peptide deformylase, a new anticancer target of actinonin-based antibiotics.[J]. Journal of Clinical Investigation, 2004, 114 8: 1107-1116. DOI:10.1172/jci22269
[3] Y XU. Antitumor activity of actinonin in vitro and in vivo.[J]. Clinical Cancer Research, 1998, 4 1: 171-176.
[4] ASMAA SINA Borhane A Simon Lord Dufour. Cell-based evidence for aminopeptidase N/CD13 inhibitor actinonin targeting of MT1-MMP-mediated proMMP-2 activation[J]. Cancer letters, 2009, 279 2: Pages 171-176. DOI:10.1016/j.canlet.2009.01.032
[5] JONATHON L BURMAN. Mitochondrial fission facilitates the selective mitophagy of protein aggregates.[J]. The Journal of Cell Biology, 2017: 3231-3247. DOI:10.1083/jcb.201612106 |
| | ACTINONIN Preparation Products And Raw materials |
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