13434-13-4 Usage
Description
Actinonin (13434-13-4) is a potent hydroxamic acid inhibitor of aminopeptidases which displays analgesic effects by inhibiting enkephalin-degrading enzymes.1?Actinonin also inhibits peptide deformylase.2?Induces apoptosis and displays antitumor activity in vivo.3?Inhibits neutrophil collagenase and other MMPs.4 Induces mitochondrial proteotoxicity.5
Chemical Properties
Off-White Solid
Uses
Different sources of media describe the Uses of 13434-13-4 differently. You can refer to the following data:
1. (-)-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.
2. 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.
3. 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].
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
Check Digit Verification of cas no
The CAS Registry Mumber 13434-13-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,4,3 and 4 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 13434-13:
(7*1)+(6*3)+(5*4)+(4*3)+(3*4)+(2*1)+(1*3)=74
74 % 10 = 4
So 13434-13-4 is a valid CAS Registry Number.
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
13434-13-4Relevant articles and documents
Preparation method of actinonin
-
, (2017/09/05)
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
Analogs and derivatives of (S,S,R)-(-)-actinonin and uses therefor
-
, (2008/06/13)
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 (-)-Actinonin and (-)-epi-Actinonin
Bashiardes, George,Bodwell, Graham J.,Davies, Stephen G.
, p. 459 - 470 (2007/10/02)
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
