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A6671

Actinonin

Name: Actinonin
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₃₅N₃O₅

CAS Number:

13434-13-4

Molecular Weight:

385.50

NACRES:

NA.77

PubChem Substance ID:

24278232

UNSPSC Code:

12352200

MDL number:

MFCD00080257

Beilstein/REAXYS Number:

1555250

Assay:

≥98% (TLC)

Form:

powder

Quality level:

200

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Product Name

Actinonin,

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (TLC)

form

powder

solubility

ethanol: 50 mg/mL, clear, colorless

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

enzyme | inhibits

storage temp.

−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)

InChI key

XJLATMLVMSFZBN-UHFFFAOYSA-N

Gene Information

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

General description

Chemical structure: peptide

Application

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 Actions

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.

Features and Benefits

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000548798

0000520969

0000520970

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Ectodomain shedding of CD99 within highly conserved regions is mediated by the metalloprotease meprin $\beta$ and promotes transendothelial cell migration

Bedau T, et al.

Faseb Journal, 31(3), 1226-1237 (2016)

Actinonin, a naturally occurring antibacterial agent, is a potent deformylase inhibitor

Chen DZ, et al.

Biochemistry, 39(6), 1256-1262 (2000)

Protease Inhibition Improves Healing of The Vaginal Wall after Obstetrical Injury: Results from a Preclinical Animal Model.

Jennifer Hamner et al.

Scientific reports, 10(1), 6358-6358 (2020-04-15)

Vaginal delivery with obstetrical trauma is a risk factor for pelvic organ prolapse later in life. Loss of fibulin-5 (FBLN5), an elastogenesis-promoting cellular matrix protein, results in prolapse in mice. Here, we evaluated effects of pregnancy, parturition, and obstetrical injury

A single point mutation in the Plasmodium falciparum FtsH1 metalloprotease confers actinonin resistance.

Christopher D Goodman et al.

eLife, 9 (2020-07-18)

The antibiotic actinonin kills malaria parasites (Plasmodium falciparum) by interfering with apicoplast function. Early evidence suggested that actinonin inhibited prokaryote-like post-translational modification in the apicoplast; mimicking its activity against bacteria. However, Amberg Johnson et al. (2017) identified the metalloprotease TgFtsH1

Ligand-induced changes in the structure and dynamics of Escherichia coli peptide deformylase

Amero CD, et al.

Biochemistry, 48(32), 7595-7607 (2009)

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Global Trade Item Number

SKU	GTIN
A6671-25MG	04061833382646
A6671-10MG	04061833258477

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