Sp-cAMPS-AM , CAS No.152218-24-1

CAS: 152218-24-1 Cat. No.: S1452843 Summenformel: C₁₃H₁₆N₅O₇PS Molekulargewicht: 417.33

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Sp-cAMPS-AM is an analog of cAMP. Sp-cAMPS-AM acts as the inducer of PKA activation and CREB phosphorylation, through entrance into the cell and release of its parent polar structure Sp-cAMPS.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Molekulargewicht

417.33

Application Protocols

No manufacturer-validated application protocols are provided for this item. The following is generalized, literature-based guidance for cell-based use; adjust per your system.

Example protocol (cell loading of Sp-cAMPS-AM)

1. Stock: Dissolve powder in anhydrous DMSO to 10–50 mM. Aliquot and store at −20°C, desiccated.
2. Preparation: Immediately before dosing, dilute stock into pre-warmed culture medium to the desired final concentration (e.g., 1–50 µM). Keep final DMSO constant across all conditions (≤0.1–0.5% v/v).
3. Dosing: Add to cells and incubate at 37°C for 10–60 min (optimize per readout). Longer incubations (up to several hours) may be used for transcriptional endpoints.
4. Controls: Include vehicle (DMSO) control and, if relevant, an Rp-cAMPS antagonist or PKA inhibitor (e.g., H-89) to confirm pathway specificity.
5. Readouts: Assess PKA activation via phospho-CREB Western blot, PKA substrate phosphorylation assays, or reporter gene assays.
6. Washout (optional): For transient activation studies, wash cells and replace with fresh medium; monitor decay kinetics.

Notes

• For cell-free assays, use the deprotected Sp-cAMPS salt instead of the AM-ester for defined concentrations in aqueous buffer.
• Sterile technique: If sterility is critical, prepare stocks using sterile, dry DMSO and handle under aseptic conditions.

Biological Roles

Context (literature)

• Cyclic adenosine monophosphate (cAMP) is a ubiquitous second messenger regulating metabolism, gene expression, ion channel activity, and synaptic plasticity. Its principal effector is PKA, with additional effectors including Epac and cyclic nucleotide–gated channels.

Role of Sp-cAMPS and the AM prodrug

• Sp-cAMPS is a stereospecific, thiophosphate analog of cAMP that functions as a PKA agonist (the Sp diastereomer promotes activation). The sulfur substitution increases resistance to hydrolysis by many phosphodiesterases, extending intracellular lifetime relative to cAMP.
• The AM-ester (Sp-cAMPS-AM) masks negative charges on the phosphate, greatly enhancing passive membrane diffusion. Once inside cells, carboxylesterases and phosphodiesterases unmask the thiophosphate to release active Sp-cAMPS, elevating PKA activity.

Selectivity considerations

• PKA vs Epac: Sp-cAMPS preferentially activates PKA; it is generally less potent at Epac compared with certain 2′-O-modified cAMP analogs. Researchers exploit this to dissect PKA-dependent signaling from Epac-mediated pathways.

Typical experimental use (literature)

• Concentration range: Often effective at 1–50 µM in cell-based assays; optimal dosing depends on cell type, expression of esterases, and assay duration.
• Readouts: CREB phosphorylation, PKA substrate phosphorylation profiles, transcriptional reporters (CRE-luc), electrophysiological modulation, metabolic shifts.

Note: These roles reflect typical research findings and are provided for informational purposes only. This product is for research use only.

Buffer Applications

This product is a bioactive small molecule, not a buffering agent. It is not used to establish or maintain pH in typical biochemical buffer systems.

Practical note

• When preparing working solutions, dilute DMSO stocks into neutral physiological buffers (e.g., PBS, HBSS, or culture media) immediately before dosing to cells. Maintain consistent buffer composition and DMSO percentage across controls and treatments for rigorous comparisons.

Green Alternatives

Perspective

• As a specialized bioactive probe, direct “green” replacements are limited; however, choices in solvent, delivery format, and analog selection can improve environmental, safety, and waste profiles.

Options (general, literature)

• Use aqueous delivery of the active salt (Sp-cAMPS sodium) when membrane permeability is not required (e.g., permeabilized cells, cell-free assays) to avoid DMSO use and reduce organic solvent waste.
• Consider dibutyryl-cAMP (db-cAMP) or 8-Br-cAMP for certain applications; they are also membrane-permeant but have different metabolism and target profiles. Selection should be based on specificity for PKA vs Epac, hydrolysis rates, and cytotoxicity.
• Minimize DMSO volumes (final ≤0.1% v/v) and prepare small aliquots to reduce waste from expired solutions.

Comparison (illustrative; literature-based, not item-specific)

• Sp-cAMPS-AM: High PKA selectivity (Sp), PDE-resistant; requires DMSO stocks; AM-ester waste considerations.
• Sp-cAMPS (salt): Aqueous compatible; not cell-permeant; ideal for in vitro enzyme assays; reduced solvent hazards.
• 8-pCPT-2′-O-Me-cAMP-AM: Preferential Epac activator; similar AM-ester handling; choose only if Epac, not PKA, activation is desired.

Green practices

• Use water-based buffers whenever possible for working solutions and promptly use to avoid degradation.
• Collect DMSO waste separately; avoid chlorinated solvents entirely in routine handling of this product.
• Adopt microscale experiments to minimize chemical footprint without compromising data quality.

Pharmaceutical Uses

This product is supplied strictly for research use only. It is not formulated or certified for use as a pharmaceutical ingredient, excipient, or diagnostic.

General context (non-clinical)

• AM-ester cAMP analogs like Sp-cAMPS-AM are commonly used as tool compounds in preclinical research to modulate intracellular signaling for mechanistic studies and assay development.
• They may serve as positive controls in high-content or high-throughput screening of cAMP/PKA pathway modulators.

Compliance note

• No pharmacopeial status, dosage form guidance, or GMP information is provided. For any translational or manufacturing activities, a different sourcing and qualification pathway would be required.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General/literature characteristics (for context; not item specifications)

• Physical form: Typically supplied as a solid (often off-white) or as a dry film; hygroscopic and moisture-sensitive due to AM esters.
• Solubility/use: Commonly dissolved in anhydrous DMSO to prepare concentrated stocks (e.g., 10–50 mM), then diluted into aqueous buffers immediately before use. The unmasked active form (Sp-cAMPS) is water-soluble as an anionic salt.
• Partitioning: AM-ester masking transiently increases lipophilicity to facilitate cell loading; upon hydrolysis, lipophilicity decreases sharply as the charged thiophosphate is revealed.
• Stability: AM esters are susceptible to hydrolysis by moisture and base; solutions in dry, oxygen-free DMSO at low temperature are more stable than aqueous solutions. Aqueous working solutions are typically used promptly to minimize premature de-esterification before cell exposure.
• pH sensitivity: Hydrolysis to the active thiophosphate accelerates with increasing pH; neutral pH buffers are generally used for biological application to balance stability and activation.

Always consult the product CoA and SDS for item-specific physico-chemical data and handling constraints.

Quality and Grades

Item-specific quality data

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and implications (general)

• Research grade vs. bioactive grade: For signaling probes like Sp-cAMPS-AM, high chemical purity and low residual solvents/salts are important to minimize off-target cellular effects. Vendors often control identity by NMR/HRMS and purity by HPLC; UV traces can reveal degradation (e.g., de-esterified species).
• Diastereomeric integrity: The Sp diastereomer is critical for PKA activation; quality documentation should specify diastereomeric purity at phosphorus (if determined). Mixed Sp/Rp content can confound biological results.
• Counter-ions and residuals: AM-ester forms are typically neutral; residual acids/bases from synthesis may affect cell viability at high concentrations. CoA/SDS should list residual solvents if applicable.
• Stabilizers: None are typically added to AM-ester nucleotides; if any stabilizer is used, it should be disclosed on the CoA. Absence/presence of stabilizer can affect long-term stability in solution.

Recommendations

• Verify identity and purity on receipt (e.g., analytical HPLC and MS, if critical to your study).
• Use freshly prepared DMSO stocks; monitor by HPLC if experiments are highly time-sensitive to AM hydrolysis.
• For quantitative biology, request the latest CoA/Spec Sheet for exact assay purity, residuals, and diastereomeric ratio.

Reaction and Applications

This product is primarily a biological tool compound rather than a synthetic reagent. Accordingly, its “applications” are in modulating intracellular signaling rather than driving chemical reactions.

Biological/assay applications (literature)

• PKA activation: The Sp diastereomer of cAMPS is a well-established agonist of cAMP-dependent protein kinase (PKA). The AM-ester increases membrane permeability, allowing intracellular release of Sp-cAMPS by esterases.
• PDE resistance: The phosphorothioate confers resistance to many phosphodiesterases relative to native cAMP, prolonging signaling.
• Experimental paradigms: Commonly used to acutely elevate PKA signaling in cells or tissues to probe cAMP-dependent pathways (e.g., transcriptional regulation via CREB phosphorylation, ion channel modulation, synaptic plasticity assays). Also used as a positive control alongside forskolin/IBMX in pathway validation.

Practical notes

• Prepare concentrated, anhydrous DMSO stocks; dilute into pre-warmed buffer or medium immediately before dosing to cells.
• Typical working concentrations reported in the literature: low micromolar to tens of micromolar (e.g., 1–50 µM), with exposure times from minutes to hours depending on the readout. Optimize per system.
• Include vehicle controls matched for DMSO content and time course. Consider time-dependent activation kinetics due to intracellular de-esterification.

For chemical reaction chemistry (synthesis), this compound is not commonly used; see “Synthetic Utility” for limited relevant notes.

Reaction Conditions

Conventional synthetic “reaction conditions” are not typically applicable because Sp-cAMPS-AM is used as a biological probe rather than as a reagent. However, practical conditions relevant to its activation and use are noted below (literature/general):

• Stock preparation: Dissolve in anhydrous DMSO under dry, inert atmosphere if possible. Typical stock concentrations: 10–50 mM. Filter sterilize (0.22 µm PTFE) only if necessary and compatible with solvent.
• Working solutions: Dilute DMSO stock into physiological buffer or cell culture medium immediately before dosing. Maintain final DMSO at ≤0.1–0.5% v/v to limit solvent effects.
• Activation kinetics: AM-ester deprotection occurs via spontaneous hydrolysis and intracellular carboxylesterases; effective intracellular activation can occur within minutes. In purely aqueous buffer without cells, hydrolysis to the active thiophosphate proceeds over minutes to hours depending on pH and temperature (faster at higher pH and temperature).
• Temperature: Handle stocks on ice/cold block to slow hydrolysis; perform cell dosing at 20–37°C according to assay requirements.
• Light/oxygen: Protect from strong light and air moisture; while not highly photosensitive, minimizing light exposure is prudent for nucleotide analogs.

These guidelines are for planning purposes only. Optimize conditions empirically for your specific system and consult primary literature for comparable assay formats.

Safety and Handling

Item-specific safety data from Product Data

• GHS classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-phrases): Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety guidance (literature/practice; not a substitute for the SDS)

• Likely hazards: May cause skin/eye/respiratory irritation. AM-ester prodrugs are moisture-sensitive and can release small-molecule byproducts upon hydrolysis; handle in a fume hood to minimize inhalation exposure.
• PPE: Lab coat, gloves (nitrile), safety glasses; change gloves frequently when working with DMSO solutions due to dermal transport potential.
• Engineering controls: Use a certified chemical fume hood for weighing and solution preparation. Avoid aerosol generation.
• Incompatibilities: Avoid strong bases/acids (can accelerate uncontrolled ester cleavage), strong oxidizers, and prolonged exposure to moisture. Do not mix with amines or nucleophiles in stock form.
• First aid (overview): If on skin/eyes, rinse with water for ≥15 min; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention in all cases. Provide SDS to responders.
• Spills: Absorb liquids with inert material; collect solids by gentle sweeping while minimizing dust. Dispose of waste per institutional and local regulations.
• Stability/handling tips: Keep container tightly closed, desiccated, and cold. Prepare small aliquots to avoid repeated freeze–thaw. Use freshly prepared aqueous working solutions.

Authoritative information is in the product SDS; always consult it before use.

Solvent Selection

Role and polarity (general)

• Sp-cAMPS-AM is a neutral, lipophilized prodrug that is typically handled as a DMSO stock due to its improved solubility in polar aprotic solvents. After AM hydrolysis (in cells or in buffer), the active Sp-cAMPS is an anionic, water-soluble thiophosphate nucleotide.

Typical solvent choices (literature-guided)

• Primary: Anhydrous DMSO (stock preparation at 10–50 mM); miscible with water and buffers for final dilution.
• Alternatives: Dry DMF or acetonitrile for intermediate processing; ethanol is sometimes usable but can reduce shelf stability of AM esters. Aqueous buffers are suitable only immediately prior to use due to rapid AM cleavage.

Practical tips

• Use high-quality, anhydrous DMSO; dry over molecular sieves if needed. Minimize water content to prevent premature de-esterification.
• Upon dilution into aqueous media (HBSS, PBS, culture medium), deliver promptly to cells; typical final DMSO ≤0.1–0.5% v/v to limit solvent cytotoxicity (literature guidance).

Comparison (general)

• DMSO vs water: DMSO affords stability and high stock concentration; water triggers activation via AM cleavage but at the cost of rapid degradation of the prodrug form.
• DMSO vs ethanol: DMSO provides broader solubility and better chemical stability for AM esters; ethanol may be acceptable for low concentration, immediate-use preparations but is less preferred for long-term stocks.

Storage and Reconstitution

Item-specific conditions (from Product Data)

• Storage: Store at −20°C.
• Shipping: Shipped in an ice chest with ice pads.

General handling and reconstitution (literature/practice; not item-specific specifications)

• Upon receipt: Allow container to equilibrate to room temperature in a desiccator before opening to prevent moisture condensation. Reseal promptly under dry atmosphere.
• Reconstitution: Dissolve in anhydrous DMSO to prepare concentrated stock (e.g., 10–50 mM). Vortex gently to avoid foaming; if needed, sonicate briefly in a room-temperature water bath to aid dissolution.
• Aliquoting: Dispense into single-use, low-dead-volume vials or tubes to avoid repeated freeze–thaw and moisture ingress. Backfill with dry inert gas if possible.
• Storage of stocks: Keep at −20°C, desiccated, and protected from light. Avoid multiple freeze–thaw cycles; thaw on ice and use promptly.
• Working solutions: Prepare in aqueous buffer or cell culture medium immediately before use; do not store aqueous solutions due to rapid AM ester hydrolysis.
• Stability monitoring: For critical studies, periodically assess stock integrity by analytical HPLC.

Research use note

• For research use only. Not for human or veterinary use. Refer to the CoA/Spec Sheet and SDS for definitive, item-specific guidance.

Structure and Identity

Sp-cAMPS-AM is a membrane-permeant, AM-ester prodrug of the cyclic nucleotide analog Sp-adenosine-3′,5′-cyclic monophosphorothioate (Sp-cAMPS), widely used as a PKA-activating, phosphodiesterase-resistant cAMP mimetic in research.

• SKU: S1452843
• Product name: Sp-cAMPS-AM
• CAS: 152218-24-1
• Category: Small molecules and compound libraries (research use only)

Item-specific identifiers from Product Data

• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature)

• Core nucleoside: Adenosine (adenine base linked to ribofuranose).
• Cyclic phosphate: 3′,5′-cyclic phosphate ring bearing a sulfur atom (phosphorothioate) at phosphorus.
• Stereochemistry: Sp configuration at the thiophosphate center; this diastereomer activates PKA (contrast: Rp is generally antagonistic).
• Prodrug masking: The phosphate oxygens are protected as acetoxymethyl (AM) esters to neutralize charge and enhance membrane permeability; intracellular esterases/hydrolases liberate the active, anionic Sp-cAMPS.

2D description in words (general)

• A fused six–five ring purine (adenine) attached to a ribose; the ribose bears a cyclic 3′→5′ phosphorothioate bridging the 3′ and 5′ positions. The phosphate bears AM-ester masking groups. No chiral centers in the base; sugar has the natural ribofuranose stereochemistry; phosphorus is stereogenic with Sp configuration.

Synthetic Utility

Sp-cAMPS-AM is not typically employed as a building block or reagent in synthetic organic chemistry. Its value lies in biological modulation rather than chemical transformation.

General chemistry perspective (literature)

• Functional groups: Adenosine nucleoside, cyclic phosphorothioate (P=S), and acetoxymethyl ester protecting groups on phosphate oxygens.
• Reactivity: The AM esters are labile to hydrolysis (base- or enzyme-catalyzed). The thiophosphate is nucleophilic/soft relative to phosphate and can engage in coordination, but under biological conditions it primarily serves as a stable mimic.
• Stability considerations: Avoid strong nucleophiles and bases that can saponify AM esters; avoid oxidants that can convert P=S to P=O, changing biological properties.

If chemical modification is desired (custom probe development), transformations are more commonly executed on precursors (e.g., protected nucleosides or phosphoramidites) rather than on the final AM-prodrug due to its lability and complexity.

Target Specificity

This product is a small-molecule research tool, not an antibody or affinity reagent. Antigen/epitope specificity, clone, isotype, and species reactivity are not applicable.

Biochemical targeting context (literature)

• Primary functional target: cAMP-dependent protein kinase (PKA), activated by Sp-cAMPS.
• Secondary considerations: Lower activity at Epac relative to certain tailored cAMP analogs; relative resistance to phosphodiesterases compared to native cAMP.

Note: These are functional selectivity notes from the literature and are not item-specific assay claims.

Häufig gestellte Fragen

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 152218-24-1, the molecular formula is C13H16N5O7PS, and the molecular weight is 417.33 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.