For research use only. Not for therapeutic Use.
(-)-Actinonin（Cat No.:R000760）is a natural hydroxamic acid derivative and a potent inhibitor of metalloproteases, including peptide deformylase (PDF), which plays a critical role in bacterial protein maturation. Its broad-spectrum antibacterial activity makes it a valuable tool in antimicrobial research, particularly for studying bacterial growth and protein synthesis mechanisms. Additionally, (-)-Actinonin is explored for its anticancer potential due to its ability to inhibit metalloproteases involved in tumor progression. Its unique properties contribute to advancements in drug discovery and the development of novel therapeutics targeting infectious diseases and cancer.
| Catalog Number | R000760 |
| CAS Number | 13434-13-4 |
| Synonyms | (2R)-N4-Hydroxy-N1-[(1S)-1-[[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]carbonyl]-2-methylpropyl]-2-pentyl-butanediamide; Actinonine; 3-[[1-[[2-(Hydroxymethyl)-1-pyrrolidinyl]carbonyl]-2-methylpropyl]carbamoyl]octanohydroxamic Acid; Actinonin; CONA 57; Ro |
| Molecular Formula | C19H35N3O5 |
| Purity | ≥95% |
| Target | Metabolic Enzyme/Protease |
| Storage | -20°C |
| IUPAC Name | (2R)-N'-hydroxy-N-[(2S)-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-pentylbutanediamide |
| InChI | 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)/t14-,15+,17+/m1/s1 |
| InChIKey | XJLATMLVMSFZBN-VYDXJSESSA-N |
| SMILES | CCCCC[C@H](CC(=O)NO)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1CO |
| Reference | </br>1:The Inhibition and Resistance Mechanisms of Actinonin, Isolated from Marine Streptomyces sp. NHF165, against Vibrio anguillarum. Yang N, Sun C.Front Microbiol. 2016 Sep 13;7:1467. doi: 10.3389/fmicb.2016.01467. eCollection 2016. PMID: 27679625 Free PMC Article</br>2:Crystal Structures of Peptide Deformylase from Rice Pathogen Xanthomonas oryzae pv. oryzae in Complex with Substrate Peptides, Actinonin, and Fragment Chemical Compounds. Ngo HP, Ho TH, Lee I, Tran HT, Sur B, Kim S, Kim JG, Ahn YJ, Cha SS, Kang LW.J Agric Food Chem. 2016 Oct 5;64(39):7307-7314. Epub 2016 Sep 21. PMID: 27616570 </br>3:Structural basis for the inhibition of M1 family aminopeptidases by the natural product actinonin: Crystal structure in complex with E. coli aminopeptidase N. Ganji RJ, Reddi R, Gumpena R, Marapaka AK, Arya T, Sankoju P, Bhukya S, Addlagatta A.Protein Sci. 2015 May;24(5):823-31. doi: 10.1002/pro.2653. Epub 2015 Apr 8. PMID: 25644575 Free PMC Article</br>4:Peptide deformylase inhibitor actinonin reduces celastrol/’s HSP70 induction while synergizing proliferation inhibition in tumor cells. Peng B, Zhang X, Cao F, Wang Y, Xu L, Cao L, Yang C, Li M, Uzan G, Zhang D.BMC Cancer. 2014 Mar 4;14:146. doi: 10.1186/1471-2407-14-146. PMID: 24589236 Free PMC Article</br>5:Over-expression of peptide deformylase in chloroplasts confers actinonin resistance, but is not a suitable selective marker system for plastid transformation. Fernández-San Millán A, Obregón P, Veramendi J.Transgenic Res. 2011 Jun;20(3):613-24. doi: 10.1007/s11248-010-9447-9. Epub 2010 Oct 9. PMID: 20936344 </br>6:Actinonin, a meprin A inhibitor, protects the renal microcirculation during sepsis. Wang Z, Herzog C, Kaushal GP, Gokden N, Mayeux PR.Shock. 2011 Feb;35(2):141-7. doi: 10.1097/SHK.0b013e3181ec39cc. PMID: 20577148 Free PMC Article</br>7:1H, 13C and 15N NMR assignments of the E. coli peptide deformylase in complex with a natural inhibitor called actinonin. Larue V, Seijo B, Tisne C, Dardel F.Biomol NMR Assign. 2009 Jun;3(1):153-5. doi: 10.1007/s12104-009-9164-6. Epub 2009 May 7. PMID: 19636969 </br>8:Cell-based evidence for aminopeptidase N/CD13 inhibitor actinonin targeting of MT1-MMP-mediated proMMP-2 activation. Sina A, Lord-Dufour S, Annabi B.Cancer Lett. 2009 Jul 8;279(2):171-6. doi: 10.1016/j.canlet.2009.01.032. Epub 2009 Mar 4. PMID: 19264392 </br>9:Delineation of alternative conformational states in Escherichia coli peptide deformylase via thermodynamic studies for the binding of actinonin. Berg AK, Srivastava DK.Biochemistry. 2009 Feb 24;48(7):1584-94. doi: 10.1021/bi8019542. PMID: 19191548 Free PMC Article</br>10:Design, synthesis and antibacterial activity of novel actinonin derivatives containing benzimidazole heterocycles. Zhang D, Wang Z, Xu W, Sun F, Tang L, Wang J.Eur J Med Chem. 2009 May;44(5):2202-10. doi: 10.1016/j.ejmech.2008.05.009. Epub 2008 May 23. PMID: 18617291 |
