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Key Documents

A9978

Sigma-Aldrich

AICAR

≥98% (HPLC), powder, AMPK activator

Sinônimo(s):

5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside, Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide

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About This Item

Fórmula empírica (Notação de Hill):
C9H14N4O5
Número CAS:
Peso molecular:
258.23
Número CE:
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

product name

AICAR, ≥98% (HPLC), powder

Nível de qualidade

Ensaio

≥98% (HPLC)

forma

powder

cor

tan

pf

214-215 °C

solubilidade

H2O: >7 mg/mL

Condições de expedição

dry ice

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N

InChI

1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1

chave InChI

RTRQQBHATOEIAF-UUOKFMHZSA-N

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Descrição geral

Adenosine monophosphate protein kinase (AMPK) activator 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) modulates cellular energy. It regulates lipid and glucose metabolism, pro-inflammatory responses, cytokine production, cell proliferation and apoptosis. AICAR improves ischemia or reperfusion injury and kidney fibrosis in rats. It provides protection against acute tubular necrosis.

Aplicação

AICAR has been used to provide protection against cisplatin-induced acute kidney injury through the JAK (tyrosine-protein kinase )/STAT (signal transducer and activator of transcription )/SOCS (suppressor of cytokine signaling) pathway. It also has been used in the assay of FapR (malonyl-CoA responsive bacterial transcriptional factor )-NLuc (nanoLuciferase) biosensor activity.

Ações bioquímicas/fisiológicas

AICAR is a cell permeable activator of AMP-activated protein kinase (AMPK), a metabolic master regulator that is activated in times of reduced energy availability (high cellular AMP:ATP ratios) and serves to inhibit anabolic processes. In vivo, pharmacologic activation of AMPK with AICAR mimics exercise and triggers insulin-independent glucose uptake by skeletal muscle.

Características e benefícios

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


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Hiroaki Sunaga et al.
Scientific reports, 9(1), 11841-11841 (2019-08-16)
Fibroblast growth factor 21 (FGF21) is a metabolic hormone having anti-oxidative and anti-hypertrophic effects. However, the regulation of FGF21 expression during acute myocardial infarction (AMI) remains unclear. We tested blood samples from 50 patients with AMI and 43 patients with
AICAR, an AMPK activator, protects against cisplatin-induced acute kidney injury through the JAK/STAT/SOCS pathway
Tsogbadrakh B, et al.
Biochemical and Biophysical Research Communications (2019)
Genetically-encoded FapR-NLuc as a biosensor to determine malonyl-CoA in situ at subcellular scales
Du Y, et al.
Bioconjugate Chemistry (2019)
Ai Ushiyama et al.
Biology of reproduction, 100(6), 1482-1491 (2019-02-06)
Despite knowledge that glucose metabolism is essential for the regulation of signaling cascades in the sperm that are pre-assembled into specific areas and function at multistage for fertilization, the physiological roles of glucose in avian sperm are poorly understood. Accumulated
Hongshun Wang et al.
Cell death & disease, 10(9), 627-627 (2019-08-21)
Oxysterol-binding protein like 2 (OSBPL2) was identified as a novel causal gene for autosomal dominant nonsyndromic hearing loss. However, the pathogenesis of OSBPL2 deficits in ADNSHL was still unclear. The function of OSBPL2 as a lipid-sensing regulator in multiple cellular

Artigos

We present an article about how proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication.

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