Actinonin | CAS#13434-13-4 | MedKoo Biosciences

MedKoo Cat#: 406221 | Name: Actinonin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Actinonin is a naturally occurring antibacterial agent that has demonstrated anti-tumor activity. Actinonin is also an antibiotic and CD13/aminopeptidase N (APN) inhibitor, has been shown to be cytotoxic to tumor cell lines in vitro. Actinonin inhibited growth of NB4 and HL60 human cell lines and AKR mouse leukemia cells in vitro with an IC50 of about 2-5 micrograms/ml. Actinonin induces a G1 arrest in HL60 and NB4 cells; apoptosis was observed in 20-35% of the cells. Actinonin showed dose-dependent antitumor effects on AKR leukemia in vivo, resulting in a survival advantage.

Chemical Structure

Actinonin

CAS#13434-13-4

Theoretical Analysis

MedKoo Cat#: 406221

Name: Actinonin

CAS#: 13434-13-4

Chemical Formula: C19H35N3O5

Exact Mass: 385.2577

Molecular Weight: 385.50

Elemental Analysis: C, 59.20; H, 9.15; N, 10.90; O, 20.75

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 580.00	2 Weeks

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Related CAS #

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Synonym

Actinonin.

IUPAC/Chemical Name

(R)-N4-hydroxy-N1-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-pentylsuccinamide

InChi Key

XJLATMLVMSFZBN-VYDXJSESSA-N

InChi Code

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

SMILES Code

O=C(N[C@@H](C(C)C)C(N1[C@H](CO)CCC1)=O)[C@H](CCCCC)CC(NO)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 385.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Fang EF, Hou Y, Palikaras K, Adriaanse BA, Kerr JS, Yang B, Lautrup S, Hasan- Olive MM, Caponio D, Dan X, Rocktäschel P, Croteau DL, Akbari M, Greig NH, Fladby T, Nilsen H, Cader MZ, Mattson MP, Tavernarakis N, Bohr VA. Mitophagy inhibits amyloid-β and tau pathology and reverses cognitive deficits in models of Alzheimer's disease. Nat Neurosci. 2019 Mar;22(3):401-412. doi: 10.1038/s41593-018-0332-9. Epub 2019 Feb 11. PMID: 30742114; PMCID: PMC6693625. 2: Jung D, Yum SJ, Jeong HG. Characterization and evaluation of antimicrobial activity of actinonin against foodborne pathogens. Food Sci Biotechnol. 2017 Sep 6;26(6):1649-1657. doi: 10.1007/s10068-017-0190-3. PMID: 30263702; PMCID: PMC6049706. 3: Ahlawat P, Phutela K, Bal A, Singh N, Sharma S. Therapeutic potential of human serum albumin nanoparticles encapsulated actinonin in murine model of lung adenocarcinoma. Drug Deliv. 2022 Dec;29(1):2403-2413. doi: 10.1080/10717544.2022.2067600. PMID: 35892161; PMCID: PMC9336490. 4: Goodman CD, Uddin T, Spillman NJ, McFadden GI. A single point mutation in the Plasmodium falciparum FtsH1 metalloprotease confers actinonin resistance. Elife. 2020 Jul 17;9:e58629. doi: 10.7554/eLife.58629. PMID: 32678064; PMCID: PMC7386903. 5: Wolf F, Leipoldt F, Kulik A, Wibberg D, Kalinowski J, Kaysser L. Characterization of the Actinonin Biosynthetic Gene Cluster. Chembiochem. 2018 Mar 30. doi: 10.1002/cbic.201800116. Epub ahead of print. PMID: 29600569. 6: Wang Z, Herzog C, Kaushal GP, Gokden N, Mayeux PR. Actinonin, a meprin A inhibitor, protects the renal microcirculation during sepsis. Shock. 2011 Feb;35(2):141-7. doi: 10.1097/SHK.0b013e3181ec39cc. PMID: 20577148; PMCID: PMC3265793. 7: Lan B, Zhao H, He Y, Zhao Z, Wang N, Gao Y. Inhibition of human peptide deformylase by actinonin sensitizes glioblastoma cells to temozolomide chemotherapy. Exp Cell Res. 2022 Nov 15;420(2):113358. doi: 10.1016/j.yexcr.2022.113358. Epub 2022 Sep 15. PMID: 36116558. 8: Kousalová J, Šírová M, Kostka L, Šubr V, Kovářová J, Běhalová K, Studenovský M, Kovář M, Etrych T. Metastatic spread inhibition of cancer cells through stimuli-sensitive HPMA copolymer-bound actinonin nanomedicines. Nanomedicine. 2022 Aug;44:102578. doi: 10.1016/j.nano.2022.102578. Epub 2022 Jun 29. PMID: 35779856. 9: Pradeepkiran JA, Hindle A, Kshirsagar S, Reddy PH. Are mitophagy enhancers therapeutic targets for Alzheimer's disease? Biomed Pharmacother. 2022 May;149:112918. doi: 10.1016/j.biopha.2022.112918. Epub 2022 Apr 4. PMID: 35585708; PMCID: PMC9148418. 10: Yang N, Sun C. The Inhibition and Resistance Mechanisms of Actinonin, Isolated from Marine Streptomyces sp. NHF165, against Vibrio anguillarum. Front Microbiol. 2016 Sep 13;7:1467. doi: 10.3389/fmicb.2016.01467. PMID: 27679625; PMCID: PMC5020083. 11: Grujic M, Zavasnik-Bergant T, Pejler G, Renko M. Actinonin induces apoptosis in U937 leukemia cells. Cancer Lett. 2005 Jun 8;223(2):211-8. doi: 10.1016/j.canlet.2004.10.048. Epub 2004 Dec 13. PMID: 15896455. 12: Hu L, Cai X, Dong S, Zhen Y, Hu J, Wang S, Jiang J, Huang J, Han Y, Qian Y, Yuan Y, Hu W. Synthesis and Anticancer Activity of Novel Actinonin Derivatives as HsPDF Inhibitors. J Med Chem. 2020 Jul 9;63(13):6959-6978. doi: 10.1021/acs.jmedchem.0c00079. Epub 2020 Jun 26. PMID: 32551649. 13: Takayama J, Takaoka M, Yamamoto S, Nohara A, Ohkita M, Matsumura Y. Actinonin, a meprin inhibitor, protects ischemic acute kidney injury in male but not in female rats. Eur J Pharmacol. 2008 Feb 26;581(1-2):157-63. doi: 10.1016/j.ejphar.2007.11.044. Epub 2007 Nov 28. PMID: 18093581. 14: Chen DZ, Patel DV, Hackbarth CJ, Wang W, Dreyer G, Young DC, Margolis PS, Wu C, Ni ZJ, Trias J, White RJ, Yuan Z. Actinonin, a naturally occurring antibacterial agent, is a potent deformylase inhibitor. Biochemistry. 2000 Feb 15;39(6):1256-62. doi: 10.1021/bi992245y. PMID: 10684604. 15: GORDON JJ, KELLY BK, MILLER GA. Actinonin: an antibiotic substance produced by an actinomycete. Nature. 1962 Aug 18;195:701-2. doi: 10.1038/195701b0. PMID: 13900478. 16: Kshirsagar S, Sawant N, Morton H, Reddy AP, Reddy PH. Mitophagy enhancers against phosphorylated Tau-induced mitochondrial and synaptic toxicities in Alzheimer disease. Pharmacol Res. 2021 Dec;174:105973. doi: 10.1016/j.phrs.2021.105973. Epub 2021 Nov 8. PMID: 34763094; PMCID: PMC8670983. 17: Sina A, Lord-Dufour S, Annabi B. Cell-based evidence for aminopeptidase N/CD13 inhibitor actinonin targeting of MT1-MMP-mediated proMMP-2 activation. Cancer Lett. 2009 Jul 8;279(2):171-6. doi: 10.1016/j.canlet.2009.01.032. Epub 2009 Mar 4. PMID: 19264392. 18: Hachisu M, Hiranuma T, Murata S, Aoyagi T, Umezawa H. Analgesic effect of actinonin, a new potent inhibitor of multiple enkephalin degrading enzymes. Life Sci. 1987 Jul 13;41(2):235-40. doi: 10.1016/0024-3205(87)90498-x. PMID: 3298909. 19: Chepurnova DA, Samoilova EV, Fesenko АG, Korotaeva АА. Reduced Expression of Extracellular Matrix Proteins in the Heart and Kidneys of Rats with Endotoxemia under the Effect of Actinonin. Bull Exp Biol Med. 2021 Apr;170(6):744-747. doi: 10.1007/s10517-021-05146-y. Epub 2021 Apr 24. PMID: 33893962. 20: Xu Y, Lai LT, Gabrilove JL, Scheinberg DA. Antitumor activity of actinonin in vitro and in vivo. Clin Cancer Res. 1998 Jan;4(1):171-6. PMID: 9516967.