13434-13-4

Basic information

• Product Name: ACTINONIN
• Synonyms: N4-HYDROXY-N1-[(1S)-1[[(2S)-2-(HYDROXYMETHYL)-1-PYRROLDINYL]CARBONYL]-2-METHYLPROPYL]-2-PENTYL-,(2R)-(9CI);(-)-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;hylpropyl)carbamoyl)-;octanohydroxamicacid,3-((1-((2-(hydroxymethyl)-1-pyrrolidinyl)carbonyl)-2-met;Butanediamide, N4-hydroxy-N1-(1S)-1-(2S)-2-(hydroxymethyl)-1-pyrrolidinylcarbonyl-2-methylpropyl-2-pentyl-, (2R)-
• CAS NO: 13434-13-4
• Molecular Formula: C₁₉H₃₅N₃O₅
• Molecular Weight: 385.5
• Product Categories: All Inhibitors;Inhibitors;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Antibiotic.;Chiral Reagents
• Mol File: 13434-13-4.mol

Chemical Properties

• Melting Point: 137-139°C
• Appearance: Off-white solid
• Density: 1.14 g/cm³
• Refractive Index: 1.513
• 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)
• 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.
• BRN: 1555250
• CAS DataBase Reference: ACTINONIN(CAS DataBase Reference)
• NIST Chemistry Reference: ACTINONIN(13434-13-4)
• EPA Substance Registry System: ACTINONIN(13434-13-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: RG9900700
• Hazardous Substances Data: 13434-13-4(Hazardous Substances Data)

Usage

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].

References

1) Hachisu et al. (1987), Analgesic effect of actinonin, a new potent inhibitor of multiple encephalin degrading enzymes; Life Sci., 41 235 2) Lee et al. (2004), Human mitochondrial peptide deformylase, a new anticancer target of actinonin-based antibiotics; J. Clin. Invest., 114 1107 3) Xu et al. (1998), Antitumor activity of actinonin in vitro and in vivo; Clin. Cancer Res., 4 171 4) Sina et al. (2009), Cell-based evidence for aminopeptidase N/CD13 inhibitor actinonin targeting of MT1-MMP-mediated pro-MMP-2 activation; Cancer Lett., 279 171 5) Burman et al. (2017) Mitochondrial fission facilitate the selective mitophagy of protein aggregates; J. Cell Biol., 216 3231

InChI:InChI=1/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

Upstream product

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• 122501-60-4 (R)-(+)-tert-Butyl 2-(N-benzyl-N-benzyloxycarbamoylmethyl)heptanoate 
• 122501-59-1 2-benzyloxymethyl-N-(N-tert-butoxycarbonyl-L-valinyl)pyrrolidine 
• 122501-61-5 (R)-(+)-2-(N-Benzyl-N-benzyloxycarbamoylmethyl)heptanoic acid 
• 122501-58-0 N-(N-Boc-L-valyl)-L-prolinol 
• 122519-30-6 (S)-2-Amino-1-((R)-2-benzyloxymethyl-pyrrolidin-1-yl)-3-methyl-butan-1-one 
• 41120-72-3 N-Boc-L-valine o-nitrophenyl ester 
• 122501-62-6 tribenzyl-actinonin 
• 130603-36-0 tert-butyl (S)-2-((benzyloxy)methyl)pyrrolidine-1-carboxylate 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 460754-33-0 C₃₃H₄₇N₃O₅ 
• 54124-60-6 L-Valyl-L-prolinol 
• 1321530-43-1 (1'S,2''S)-N-benzyloxy-N'-{1-[(2-hydroxymethyl)pyrrolidinylcarbonyl]-2-methylpropyl}-3-[(E)-pentylidene]succinamide 
• 1321530-38-4 (1'S,2''S)-N-benzyloxy-N'-{1-[(2-benzyloxymethyl)pyrrolidinylcarbonyl]-2-methylpropyl}-3-[(E)-pentylidene]succinamide 

Downstream Products

• 3507-62-8 monoamyl succinic acid 
• 3975-91-5 (R)-(+)-2-pentylsuccinic acid 

Relevant articles and documents

Preparation method of actinonin

The invention discloses a preparation method of actinonin. The preparation method includes: taking N-Boc-L prolinol as a raw material; firstly, protecting hydroxyl, and then removing Boc protection base of amino; condensing with N-Boc-L-valine to obtain d

Synthesis of (-)-actinonin

Synthesis of (-)-actinonin in 17% overall yield was accomplished in seven steps via the formation of an isoimide derivative as the key intermediate. The synthesis was carried out using commercially available dimethyl maleate without the use of a highly expensive reagent. Georg Thieme Verlag Stuttgart - New York.

Analogs and derivatives of (S,S,R)-(-)-actinonin and uses therefor

The present invention provides analog and derivative compounds of (S,S,R)-(?)-actinonin and methods of asymmetric synthesis thereof having a structure: where R1 is hydrogen, C(O)R6 or R1 in combination with N is 2-oxomorph

Asymmetric synthesis of (S,S,R)-(-)-actinonin and its analogs and uses therefor

The present invention provides methods for the asymmetric synthesis of (S,S,R)-(?)-actinonin and its analogs and the compounds thereby synthesized having a structural formula: 1 where R1 is an optionally substituted or halogenated alkyl, aryl, heteroalkyl

Asymmetric Synthesis of (-)-Actinonin and (-)-epi-Actinonin

The highly asymmetric induction imparted by the iron chiral auxiliary 5-C5H5)Fe(CO)(PPh3)> is exploited in the preparation of homochiral (R)- and (S)-α-pentylsuccinates.Their application in the synthesis of (-)-actinonin and (-)-epi-actinoni

THE ASYMMETRIC SYNTHESIS OF (-)-ACTINONIN USING THE IRON CHIRAL AUXILIARY 5-C5H5)Fe(CO)(PPh3)>

The asymmetric synthesis of the α-pentyl succinate fragment of (-)-Actinonin is achived using the chiral ironacetyl S-(+)-5-C5H5)-Fe(CO)(PPh3)COCH3> and subsequently converted to (-)-Actinonin in an overall yield of 41percent.