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AICA Ribonucleotide Sale

(Synonyms: 5-氨基咪唑-4-甲酰胺-1-Β-D-呋喃核糖苷5-一磷酸盐) 目录号 : GC49110

An AMPK activator

AICA Ribonucleotide Chemical Structure

Cas No.:3031-94-5

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1 mg
¥378.00
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5 mg
¥1,421.00
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10 mg
¥2,465.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

AICA ribonucleotide is a cell-permeable activator of AMP-activated protein kinase (AMPK).1 It activates AMPK in a cell-free assay when used at concentrations ranging from 1 to 500 µM. AICA ribonucleotide (100-500 µM) inhibits lipolysis and lipogenesis in primary rat adipocytes. In vivo, AICA ribonucleotide (0.5 mg/kg) increases insulin sensitivity and prevents pancreatic β-cell damage in Zucker diabetic fatty rats.2 AICA ribonucleotide (0.5 mg/kg) induces cardiac mobilization and myofibroblast differentiation of endogenous CD44+CD45- mesenchymal stem cells (MSCs), as well as decreases cardiac scar formation, in an aged mouse model of myocardial infarction induced by left anterior descending artery (LAD) occlusion.3 Formulations containing AICA ribonucleotide have been used in the treatment and prevention of cardiac ischemic injury.

1.Sullivan, J.E., Brocklehurst, K.J., Marley, A.E., et al.Inhibition of lipolysis and lipogenesis in isolated rat adipocytes with AICAR, a cell-permeable activator of AMP-activated protein kinaseFEBS Lett.353(1)33-36(1994) 2.Pold, R., Jensen, L.S., Jessen, N., et al.Long-term AICAR administration and exercise prevents diabetes in ZDF ratsDiabetes54(4)928-934(2005) 3.Cieslik, K.A., Taffet, G.E., Crawford, J.R., et al.AICAR-dependent AMPK activation improves scar formation in the aged heart in a murine model of reperfused myocardial infarctionJ. Mol. Cell. Cardiol.6326-36(2013)

Chemical Properties

Cas No. 3031-94-5 SDF
别名 5-氨基咪唑-4-甲酰胺-1-Β-D-呋喃核糖苷5-一磷酸盐
Canonical SMILES O[C@@H]1[C@@H](COP(O)(O)=O)O[C@@]([H])(N2C=NC(C(N)=O)=C2N)[C@@H]1O
分子式 C9H15N4O8P 分子量 338.2
溶解度 : ,PBS (pH 7.2): 1 mg/ml 储存条件 -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.9568 mL 14.7842 mL 29.5683 mL
5 mM 0.5914 mL 2.9568 mL 5.9137 mL
10 mM 0.2957 mL 1.4784 mL 2.9568 mL
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Research Update

A Multi-enzyme Cascade for the Biosynthesis of AICA Ribonucleoside Di- and Triphosphate

Chembiochem 2022 Feb 4;23(3):e202100596.PMID:34859954DOI:10.1002/cbic.202100596.

AICA (5'-aminoimidazole-4-carboxamide) ribonucleotides with different phosphorylation levels are the pharmaceutically active metabolites of AICA nucleoside-based drugs. The chemical synthesis of AICA ribonucleotides with defined phosphorylation is challenging and expensive. In this study, we describe two enzymatic cascades to synthesize AICA derivatives with defined phosphorylation levels from the corresponding nucleobase and the co-substrate phosphoribosyl pyrophosphate. The cascades are composed of an adenine phosphoribosyltransferase from Escherichia coli (EcAPT) and different polyphosphate kinases: polyphosphate kinase from Acinetobacter johnsonii (AjPPK), and polyphosphate kinase from Meiothermus ruber (MrPPK). The role of the EcAPT is to bind the nucleobase to the sugar moiety, while the kinases are responsible for further phosphorylation of the nucleotide to produce the desired phosphorylated AICA Ribonucleotide. The selected enzymes were characterized, and conditions were established for two enzymatic cascades. The diphosphorylated AICA Ribonucleotide derivative ZDP, synthesized from the cascade EcAPT/AjPPK, was produced with a conversion up to 91 %. The EcAPT/MrPPK cascade yielded ZTP with conversion up to 65 % with ZDP as a side product.

MicroRNA modulation induced by AICA Ribonucleotide in J1 mouse ES cells

PLoS One 2014 Jul 31;9(7):e103724.PMID:25078608DOI:10.1371/journal.pone.0103724.

ES cells can propagate indefinitely, maintain self-renewal, and differentiate into almost any cell type of the body. These properties make them valuable in the research of embryonic development, regenerative medicine, and organ transplantation. MicroRNAs (miRNAs) are considered to have essential functions in the maintenance and differentiation of embryonic stem cells (ES cells). It was reported that, strong external stimuli, such as a transient low-pH and hypoxia stress, were conducive to the formation of induced pluripotent stem cells (iPS cells). AICA Ribonucleotide (AICAR) is an AMP-activated protein kinase activator, which can let cells in the state of energy stress. We have demonstrated that AICAR can maintain the pluripotency of J1 mouse ES cells through modulating protein expression in our previous research, but its effects on ES cell miRNA expression remain unknown. In this study, we conducted small RNA high-throughput sequencing to investigate AICAR influence on J1 mouse ES cells by comparing the miRNA expression patterns of the AICAR-treated cells and those without treatment. The result showed that AICAR can significantly modulate the expression of multiple miRNAs, including those have crucial functions in ES cell development. Some differentially expressed miRNAs were selected and confirmed by real-time PCR. For the differently expressed miRNAs identified, further study was conducted regarding the pluripotency and differentiation associated miRNAs with their targets. Moreover, miR-134 was significantly down-regulated after AICAR treatment, and this was suggested to be directly associated with the up-regulated pluripotency markers, Nanog and Sox2. Lastly, Myc was significantly down-regulated after AICAR treatment; therefore, we predicted miRNAs that may target Myc and identified that AICAR induced up-regulation of miR-34a, 34b, and 34c can repress Myc expression in J1 mouse ES cells. Taken together, our study provide a new mechanism for AICAR in ES cells pluripotency maintenance and give insight for its usage in iPS cells generation.