| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
Purity: ≥98%
SAICAR (Succino-AICAR) is a novel intermediate used in the de novo synthesis of purine nucleotides. It activates pyruvate kinase isoform M2 (PKM2) in an isozyme-selective manner, with an EC50 of 0.3 mM. SAICAR stimulates PKM2 and promotes cancer cell survival in glucose-limited conditions. SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. SAICAR induces protein kinase activity of PKM2 that is necessary for sustained proliferative signaling of cancer cells. SAICAR-mediated PKM2 protein kinase activity is necessary for EGF-induced cancer cell proliferation.
| ln Vitro |
PKM2 is nuclear localized upon SAICAR accumulation. PKM2-SAICAR increases PKM2's susceptibility to SAICAR binding via phosphorylating and activating Erk1/2. Furthermore, to cause mitogen-induced cell proliferation and persistent Erk1/2 activation, PKM2-SAICAR was required. Inducing H3 T11 and Erk1/2 phosphorylation requires and is satisfied by SAICAR-PKM2 interaction[2]. When cells are starved of glucose, the amount of SAICAR within them rises oscillatorily, which in turn causes cancer cells to activate PKM2. Additionally, in glucose-limited conditions, the SAICAR-PKM2 connection increases the survival of cancer cells. Adsl-kd cells and cells overexpressing PAICS fare better under glucose limitation, however paics-kd cells perished sooner than control-kd cells. Under glucose-restricted environments, SAICAR increases cancer cell survival1.
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| References |
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| Additional Infomation |
SAICAR is a 1-(phosphoribosyl)imidazolecarboxamide resulting from the formal condesation of the darboxy group of 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid with the amino group of L-aspartic acid. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a succinic acid. It is a conjugate acid of a SAICAR(4-).
SAICAR is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Saicar has been reported in Homo sapiens, Schizosaccharomyces pombe, and Apis cerana with data available. SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. The appearance of succinylaminoimidazolecarboxamide riboside (SAICAriboside) and succinyladenosine (S-Ado) in cerebrospinal fluid, urine, and to a lesser extent in plasma is characteristic of a heritable deficiency Adenylosuccinate lyase deficiency. . SAICAR is a metabolite found in or produced by Saccharomyces cerevisiae. |
| Molecular Formula |
C13H19N4O12P
|
|---|---|
| Molecular Weight |
454.28336
|
| Exact Mass |
454.074
|
| CAS # |
3031-95-6
|
| Related CAS # |
3031-95-6
|
| PubChem CID |
160666
|
| Appearance |
Purple to purplish red solid powder
|
| LogP |
-4.3
|
| Hydrogen Bond Donor Count |
8
|
| Hydrogen Bond Acceptor Count |
14
|
| Rotatable Bond Count |
9
|
| Heavy Atom Count |
30
|
| Complexity |
718
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
OC(C[C@H](NC(C1N=CN([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=1N)=O)C(=O)O)=O
|
| InChi Key |
NAQGHJTUZRHGAC-ZZZDFHIKSA-N
|
| InChi Code |
InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1
|
| Chemical Name |
N-((5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazol-4-yl)carbonyl)-L-aspartic acid
|
| Synonyms |
SAICAR Succino-AICAR.
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~220 mg/mL (~484.28 mM)
H2O : ~100 mg/mL (~220.13 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5.5 mg/mL (12.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 55.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5.5 mg/mL (12.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 55.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 5.5 mg/mL (12.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2013 mL | 11.0064 mL | 22.0129 mL | |
| 5 mM | 0.4403 mL | 2.2013 mL | 4.4026 mL | |
| 10 mM | 0.2201 mL | 1.1006 mL | 2.2013 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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