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A6671

Sigma-Aldrich

Actinonin

≥98% (TLC), powder, leucine aminopeptidase inhibitor

Sinonimo/i:

3-[[1-[(2-(Hydroxymethyl)-1-pyrrolidinyl)carbonyl]-2-methylpropyl]carbamoyl]octanohydroxamic acid

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About This Item

Formula empirica (notazione di Hill):
C19H35N3O5
Numero CAS:
13434-13-4
Peso molecolare:
385.50
Beilstein:
1555250
Numero MDL:
MFCD00080257
Codice UNSPSC:
12352200
ID PubChem:
24278232
NACRES:
NA.77

Nome del prodotto

Actinonin,

Origine biologica

synthetic (organic)

Saggio

≥98% (TLC)

Stato

powder

Solubilità

ethanol: 50 mg/mL, clear, colorless

Spettro attività antibiotica

Gram-negative bacteria
Gram-positive bacteria

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

−20°C

Stringa SMILE

CCCCCC(CC(=O)NO)C(=O)NC(C(C)C)C(=O)N1CCCC1CO

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)
XJLATMLVMSFZBN-UHFFFAOYSA-N

Informazioni sul gene

human ... ANPEP(290) , DPP4(1803) , ECE1(1889) , LAP3(51056)

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Descrizione generale

Chemical structure: peptide

Applicazioni

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.

Azioni biochim/fisiol

Actinonin has inhibitory action against peptide deformylase (PDF). It is effective against Gram-positive and fastidious Gram-negative microorganisms.
Actinonin is an inhibitor of leucine aminopeptidase. Actinonin has also been used to improve antibacterial activity and antiobesity therapeutics.

Caratteristiche e vantaggi

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
0000275654
0000275655
0000275655
0000275654
SLCH8526

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Sonia Fieulaine et al.
PLoS biology, 9(5), e1001066-e1001066 (2011-06-02)
For several decades, molecular recognition has been considered one of the most fundamental processes in biochemistry. For enzymes, substrate binding is often coupled to conformational changes that alter the local environment of the active site to align the reactive groups
Ligand-induced changes in the structure and dynamics of Escherichia coli peptide deformylase
Amero CD, et al.
Biochemistry, 48(32), 7595-7607 (2009)
Diana Mader et al.
Microbes and infection, 12(5), 415-419 (2010-02-17)
The biosynthesis of proteins with N-terminal formylated methionine residues and subsequent protein deformylation are unique and invariant bacterial processes. They are exploited by the capacity of the human innate immune system to sense formylated peptides (FPs) and targeted by the
Asmaa Sina et al.
Cancer letters, 279(2), 171-176 (2009-03-07)
Recent profiling has identified the aminopeptidase N/CD13 inhibitor actinonin as a selective soluble secreted matrix metalloproteinase (MMP) inhibitor. Given that actinonin's effects against membrane-bound MMPs remain unknown and that MT1-MMP has been linked to chemo- and radio-therapy resistance in brain
Actinonin, a naturally occurring antibacterial agent, is a potent deformylase inhibitor
Chen DZ, et al.
Biochemistry, 39(6), 1256-1262 (2000)
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