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A6671

Sigma-Aldrich

Actinonin

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C19H35N3O5
CAS-Nummer:
13434-13-4
Molekulargewicht:
385.50
Beilstein:
1555250
MDL-Nummer:
MFCD00080257
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278232
NACRES:
NA.77

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Assay

≥98% (TLC)

Form

powder

Löslichkeit

ethanol: 50 mg/mL, clear, colorless

Wirkungsspektrum von Antibiotika

Gram-negative bacteria
Gram-positive bacteria

Wirkungsweise

enzyme | inhibits

Lagertemp.

−20°C

SMILES String

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)

InChIKey

XJLATMLVMSFZBN-UHFFFAOYSA-N

Angaben zum Gen

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

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Allgemeine Beschreibung

Chemical structure: peptide

Anwendung

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.

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Sigma-Aldrich

CC10

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Apicidin ≥98% (HPLC), from microbial

Sigma-Aldrich

A8851

Apicidin

Azaserin ≥98% (TLC)

Sigma-Aldrich

A4142

Azaserin

Actinomycin D from Streptomyces sp., ≥95% (HPLC)

Sigma-Aldrich

A4262

Actinomycin D

Bestatin -hydrochlorid ≥98% (HPLC)

Sigma-Aldrich

B8385

Bestatin -hydrochlorid

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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