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AMP-PCP disodium

Alias: AMPPCP disodium; AMP PCP disodium
Cat No.:V39091 Purity: ≥98%
AMP-PCP disodium is an ATP analog that binds to the N-terminal domain of Hsp90 with Kd of 3.8 μM.
AMP-PCP disodium
AMP-PCP disodium Chemical Structure CAS No.: 7414-56-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of AMP-PCP disodium:

  • AMP-PCP
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Top Publications Citing lnvivochem Products
Product Description
AMP-PCP disodium is an ATP analog that binds to the N-terminal domain of Hsp90 with Kd of 3.8 μM. AMP-PCP disodium binding facilitates the formation of Hsp90 active homodimers.
AMP-PCP disodium (CAS 7414-56-4) is a non-hydrolyzable analog of adenosine monophosphate (AMP). In this analog, the phosphate group is replaced by a phosphonate group, which is resistant to hydrolysis by enzymes such as phosphatases. AMP-PCP disodium is used as a biochemical tool to study the role of AMP in various cellular processes. It is often used as a competitive inhibitor of AMP-dependent enzymes, such as AMP-activated protein kinase (AMPK) and adenylate kinase. The compound is also used in studies of nucleotide binding and signaling. AMP-PCP disodium is a valuable tool for investigating the functions of AMP in metabolism and signal transduction.
Biological Activity I Assay Protocols (From Reference)
Targets
AMP-PCP disodium targets AMP-dependent enzymes, such as AMP-activated protein kinase (AMPK) and adenylate kinase. AMPK is a key regulator of cellular energy homeostasis that is activated by an increase in the AMP/ATP ratio. AMP binds to the γ-subunit of AMPK, leading to its activation. AMP-PCP disodium is a non-hydrolyzable analog of AMP that can bind to AMPK and activate it, but it cannot be metabolized. This makes it a useful tool for studying the effects of AMPK activation. Adenylate kinase is an enzyme that catalyzes the interconversion of adenine nucleotides: ATP + AMP ↔ 2 ADP. AMP-PCP disodium can bind to adenylate kinase and inhibit its activity. By inhibiting adenylate kinase, the compound can affect the levels of ATP, ADP, and AMP.
ln Vitro
AMP-PCP disodium binding promotes the slow-motion distinctive conformational exchange of those residues in the surrounding area (A117-A141) and cap repair (A111-G135), which in turn promotes the creation of Hsp90 active homodimers. Using three labels, Hsp90 was able to fully identify 170 non-proline residues [1].
In vitro, AMP-PCP disodium is used to activate AMPK or inhibit adenylate kinase. The compound is typically used at concentrations in the micromolar range. The activation of AMPK is measured by assessing the phosphorylation of AMPK and its downstream targets, such as acetyl-CoA carboxylase (ACC). The inhibition of adenylate kinase is measured by assessing the enzyme's activity in a coupled assay. The compound is also used in studies of nucleotide binding to proteins, such as in surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC) experiments.
ln Vivo
Detailed in vivo activity data for AMP-PCP disodium is limited. As a charged molecule, it does not readily cross cell membranes and is not typically administered in vivo. It is primarily used as a tool for in vitro studies. However, its effects on AMPK activation and adenylate kinase inhibition can be studied in cell-based assays. The compound's in vivo effects, if any, would likely be limited by its poor cell permeability.
Enzyme Assay
The activity of AMP-PCP disodium is typically assessed in cell-free enzyme assays. For AMPK activation, the assay is performed using purified AMPK and a substrate, such as SAMS peptide (a synthetic peptide derived from ACC). The reaction mixture contains AMPK, the substrate, ATP, and varying concentrations of AMP-PCP disodium. The phosphorylation of the substrate is measured using a radioactive or a luminescent assay. For adenylate kinase inhibition, the assay is performed using purified adenylate kinase, ATP, and AMP. The production of ADP is measured using a coupled assay. These assays provide a measure of the compound's ability to activate AMPK or inhibit adenylate kinase.
Cell Assay
For in vitro cellular assays, AMP-PCP disodium is typically introduced into cells using electroporation or by using a cell-permeable derivative. Once inside the cell, the compound can activate AMPK or inhibit adenylate kinase. The effects on cellular metabolism and signaling are then assessed. For example, the activation of AMPK can be measured by assessing the phosphorylation of AMPK and ACC. The inhibition of adenylate kinase can be inferred by measuring changes in the levels of ATP, ADP, and AMP. These assays provide a measure of the compound's activity in a cellular context.
Animal Protocol
In vivo animal experiments involving AMP-PCP disodium are not typical, as the compound does not readily cross cell membranes. However, studies may involve the use of AMPK knockout mice or the use of other pharmacological tools to study the role of AMPK in vivo. The effects of AMPK activation on metabolism and physiology can be studied using these approaches.
ADME/Pharmacokinetics
Pharmacokinetic properties for AMP-PCP disodium are not applicable, as it is not a drug. It is a charged molecule that does not readily cross cell membranes. It is used as a tool for in vitro studies.
Toxicity/Toxicokinetics
AMP-PCP disodium is generally considered to be non-toxic, as it is used as a research tool. However, as a research chemical, standard safety precautions should be observed when handling this compound. No specific toxicity studies have been detailed in the public domain. The compound is not approved for clinical use.
References

[1]. A dynamic view of ATP-coupled functioning cycle of Hsp90 N-terminal domain. Sci Rep. 2015 Apr 13;5:9542.

Additional Infomation
AMP-PCP disodium is a research tool for studying AMP-dependent enzymes. It is a non-hydrolyzable AMP analog. It is not a drug.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H18N5NAO12P3
Molecular Weight
528.198
Exact Mass
548.98
CAS #
7414-56-4
Related CAS #
AMP-PCP;3469-78-1
PubChem CID
71308607
Appearance
White to off-white solid powder
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
16
Rotatable Bond Count
8
Heavy Atom Count
33
Complexity
790
Defined Atom Stereocenter Count
4
SMILES
O=P(OP(O)(CP(O)(O)=O)=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O)O.[Na+].[Na+]
InChi Key
KZCUOVRMGTZINH-LYYWGVPGSA-L
InChi Code
InChI=1S/C11H18N5O12P3.2Na/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-31(24,25)28-30(22,23)4-29(19,20)21;;/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21);;/q;2*+1/p-2/t5-,7-,8-,11-;;/m1../s1
Chemical Name
disodium;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-[[hydroxy(oxido)phosphoryl]methyl]phosphinate
Synonyms
AMPPCP disodium; AMP PCP disodium
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, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~182.09 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 50 mg/mL (91.05 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.8932 mL 9.4661 mL 18.9322 mL
5 mM 0.3786 mL 1.8932 mL 3.7864 mL
10 mM 0.1893 mL 0.9466 mL 1.8932 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.
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