AICAR__Autophagy inducer TEPP-46
Product Name
AICAR
Description
Autophagy inducer
Purity
>99% (TLC), NMR conforms
CAS No.
2627-69-2
Molecular Formula
C9H14N4O5
Molecular Weight
258.2
Storage Temperature
-20ºC
Shipping Temperature
Shipped Ambient
Product Type
Inducer
Solubility
Soluble to 75 mM in water and to 75 mM in DMSO.
Source
Synthetic
Appearance
Off-white solid.
SMILES
[C@@H]2([N]1C(=C(C(N)=O)N=C1)N)O[[email protected]function(t,e,r,n,c,a,p){try{t=document.currentScript||function(){for(t=document.getElementsByTagName(_script_),e=t.length;e–;)if(t[e].getAttribute(_data-cfhash_))return t[e]}();if(t&&(c=t.previousSibling)){p=t.parentNode;if(a=c.getAttribute(_data-cfemail_)){for(e=__,r=_0x_+a.substr(0,2)|0,n=2;a.length-n;n+=2)e+=_%_+(_0_+(_0x_+a.substr(n,2)^r).toString(16)).slice(-2);p.replaceChild(document.createTextNode(decodeURIComponent(e)),c)}p.removeChild(t)}}catch(u){}}()/* ]]> */](CO)[[email protected]function(t,e,r,n,c,a,p){try{t=document.currentScript||function(){for(t=document.getElementsByTagName(_script_),e=t.length;e–;)if(t[e].getAttribute(_data-cfhash_))return t[e]}();if(t&&(c=t.previousSibling)){p=t.parentNode;if(a=c.getAttribute(_data-cfemail_)){for(e=__,r=_0x_+a.substr(0,2)|0,n=2;a.length-n;n+=2)e+=_%_+(_0_+(_0x_+a.substr(n,2)^r).toString(16)).slice(-2);p.replaceChild(document.createTextNode(decodeURIComponent(e)),c)}p.removeChild(t)}}catch(u){}}()/* ]]> */]([[email protected]function(t,e,r,n,c,a,p){try{t=document.currentScript||function(){for(t=document.getElementsByTagName(_script_),e=t.length;e–;)if(t[e].getAttribute(_data-cfhash_))return t[e]}();if(t&&(c=t.previousSibling)){p=t.parentNode;if(a=c.getAttribute(_data-cfemail_)){for(e=__,r=_0x_+a.substr(0,2)|0,n=2;a.length-n;n+=2)e+=_%_+(_0_+(_0x_+a.substr(n,2)^r).toString(16)).slice(-2);p.replaceChild(document.createTextNode(decodeURIComponent(e)),c)}p.removeChild(t)}}catch(u){}}()/* ]]> */]2O)O
InChI
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
InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N
Safety Phrases
Classification: D2B- Toxic Material Causing Other Toxic Effects, Moderate skin irritant, Moderate respiratory irritant, Moderate eye irritant
Safety Phrases:
S22 – Do not breathe dust.
S24/25 – Avoid contact with skin and eyes.
S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection.
Hazard statements:
H315- Causes skin irritation.
H319- Causes serious eye irritation.
H335- May cause respiratory irritation.
Precautionary statements:
P261- Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P264- Wash skin thoroughly after handling.
P271- Use only outdoors or in a well-ventilated area.
P280- Wear protective gloves/ eye protection/ face protection.
P302 + P352- IF ON SKIN: Wash with plenty of soap and water.
P304 + P340- IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338- IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312- Call a POISON CENTER or doctor/ physician if you feel unwell.
P321- Specific treatment (see supplemental first aid instructions on this label).
P332 + P313- If skin irritation occurs: Get medical advice/ attention.
P337 + P313- If eye irritation persists: Get medical advice/ attention.
P362- Take off contaminated clothing and wash before reuse.
P403 + P233- Store in a well-ventilated place. Keep container tightly closed.
P405- Store locked up.
P501- Dispose of contents/ container to an approved waste disposal plant.
Cite This Product
AICAR (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-402)
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/19112401
Alternative Names
N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide
Research Areas
Cancer, Autophagy
PubChem ID
17513
Scientific Background
AICAR is an adenosine analog that when phosphorylated forms 5-aminoimidazole-4-carboxamide-1-D-ribofuranosyl-5’-monophosphate (ZMP) which proceeds to activate adenosine monophosphate-activated protein kinase (AMPK). This process in turn stimulates glucose uptake by skeletal muscle in an insulin-dependent manner. Autophagy is initiated by the UNC-51-like kinase 1/2 complex (ULK1 and ULK2). Under basal conditions, autophagy is negatively regulated due to the phosphorylation of ULK1 at serine-757 by mTORC1. During starvation, autophagy is positively regulated by ULK1/2 when it is phosphorylated at serine-555 and serine-777 by AMPK. Therefore, the activation of AMPK by AICAR, in turn will induce autophagy.
References
1. Jhun B.S., et al. (2004) Biochem Biophys Res Commun. 318(2): 372-80.
2. Huang H., et al. (2013) Autophagy. 9(2): 175-95.
Autophagy inducer
Safety Phrases:
S22 – Do not breathe dust.
S24/25 – Avoid contact with skin and eyes.
S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection.
Hazard statements:
H315- Causes skin irritation.
H319- Causes serious eye irritation.
H335- May cause respiratory irritation.
Precautionary statements:
P261- Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P264- Wash skin thoroughly after handling.
P271- Use only outdoors or in a well-ventilated area.
P280- Wear protective gloves/ eye protection/ face protection.
P302 + P352- IF ON SKIN: Wash with plenty of soap and water.
P304 + P340- IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338- IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P312- Call a POISON CENTER or doctor/ physician if you feel unwell.
P321- Specific treatment (see supplemental first aid instructions on this label).
P332 + P313- If skin irritation occurs: Get medical advice/ attention.
P337 + P313- If eye irritation persists: Get medical advice/ attention.
P362- Take off contaminated clothing and wash before reuse.
P403 + P233- Store in a well-ventilated place. Keep container tightly closed.
P405- Store locked up.
P501- Dispose of contents/ container to an approved waste disposal plant.
2. Huang H., et al. (2013) Autophagy. 9(2): 175-95.