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Application Protocols
No tested applications, recommended dilutions, or protocols are provided in the Product Data for this item.
Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature; not item-specific):
Prepare sterile, nuclease-free aqueous stock (e.g., 1–10 mM) and store in single-use aliquots at −20 °C or below.
For cellular assays, select an appropriate delivery method (lipid-based transfection, electroporation, or permeabilization reagents) and titrate concentration over several logs to establish response curves, monitoring for cytotoxicity of vehicle or delivery system.
Include positive controls (known STING agonists) and negative controls (vehicle) as appropriate.
Users should validate any protocol under their specific laboratory conditions.
Biological Roles
Literature context (not item-specific):
Endogenous signaling molecule: 2′,3′-cGAMP is synthesized by cyclic GMP–AMP synthase (cGAS) from ATP and GTP upon recognition of cytosolic DNA. It functions as a second messenger.
Primary molecular target: stimulator of interferon genes (STING), an ER-associated adaptor protein. Binding of 2′,3′-cGAMP induces conformational changes that promote downstream signaling, including TBK1 recruitment and IRF3 activation in the innate immune pathway.
Specificity: 2′,3′ linkages confer distinct binding and species selectivity compared with bacterial 3′,3′-CDNs (e.g., c-di-GMP). Mammalian STING shows high affinity for 2′,3′-cGAMP.
Catabolism and transport: extracellular 2′,3′-cGAMP can be degraded by ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1). Gap junctions and specific transporters may mediate intercellular transfer (reported in literature), enabling paracrine signaling.
Experimental utility: used as a positive control ligand for STING activation, as a substrate/control in phosphodiesterase assays, and as a calibration standard in analytical workflows quantifying cellular CDN levels.
Important note: This product is provided strictly for research use only. Do not use in humans or for diagnostic/therapeutic applications. For species- or isoform-specific binding data, consult primary literature and confirm with your assay conditions.
Buffer Applications
This compound is not a pH buffer; however, its performance depends strongly on the buffer system chosen.
Recommended media (general practice; not item-specific):
Nuclease-free water for stock preparation.
HEPES (10–50 mM, pH 7.2–7.6), Tris (10–50 mM, pH 7.5–8.0), or PBS for biological assays. Maintain near-neutral pH to minimize phosphodiester hydrolysis.
Include physiological ionic strength (e.g., 100–150 mM NaCl) as required by your assay. Avoid strong acids/bases and prolonged exposure to >37 °C.
Additives and compatibility:
Mg2+ can affect binding/enzymatic processes; include or chelate (EDTA) according to assay design. For stability-only stocks, Mg2+-free buffers are commonly used.
For cell work, sterile-filter (0.22 μm) and use low-endotoxin, nuclease-free reagents.
Practical tips:
Prepare small aliquots (e.g., 10–100 μL) at convenient concentrations (commonly 1–10 mM in water or buffer, literature practice) and store at −20 °C or −80 °C.
Minimize freeze–thaw by single-use aliquoting; thaw on ice and keep cold during setup.
Item-specific buffer composition guidance is not provided in the Product Data; adjust buffer identity, pH, and ionic strength to your assay’s requirements and validate by pilot runs.
Green Alternatives
Although 2′,3′-cGAMP-dammonium is itself a polar biomolecule commonly used in water, thoughtful choices can further reduce environmental footprint.
Preferred media (greener practice):
Use aqueous buffers (HEPES, PBS, Tris) as primary solvents. Avoid unnecessary organic co-solvents. Prepare concentrated aqueous stocks when solubility permits.
For sterilization, sterile filtration (0.22 μm) is a low-energy alternative to heat sterilization, which can degrade nucleotides.
Comparison of vehicles (general; not item-specific):
Water/buffer: renewable, nonflammable, minimal hazard; ideal for most bioassays.
DMSO: effective co-solvent but has higher environmental persistence; limit volumes and segregate waste.
DMF/other aprotics: generally unnecessary for this analyte and best avoided.
Operational considerations:
Prepare only the amounts needed to reduce expired stock disposal.
Store in small single-use aliquots to minimize freeze–thaw cycles and waste.
Alternative tool compounds (biological context, not a green chemistry substitution): other CDNs such as c-di-GMP or c-di-AMP can answer related biological questions, but selection should be based on mechanistic relevance (STING vs other targets), not solely on green metrics.
Overall, the greenest approach for this material is strictly aqueous handling, right-sized preparation, and proper cold-chain storage to maximize lifetime and minimize waste.
Pharmaceutical Uses
No pharmaceutical or clinical uses are claimed or supported for this item. It is supplied strictly for research use only, as stated in the Product Data.
Formulation/excipient status: Not applicable. This product is not presented with pharmacopeial compliance (e.g., USP/EP) or GMP status in the provided data.
Research/manufacturing context (general; not item-specific):
In preclinical research, 2′,3′-cGAMP is commonly used as a reference standard or tool compound to interrogate the STING pathway, to develop bioassays, or to qualify analytical methods (e.g., LC–MS quantification of cyclic dinucleotides).
For any work requiring defined excipient or drug-substance quality attributes (endotoxin, bioburden, residual solvents, elemental impurities), obtain and review the lot-specific CoA/Specification Sheet or source a GMP-grade material.
No therapeutic claims are made. Do not use for diagnostic procedures, in humans, or in foods/cosmetics.
Physical Properties
Only limited item-specific physico-chemical specifications are provided for this SKU.
Item-specific values from Product Data:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight (item): Not specified for this item; refer to CoA/Spec Sheet.
General/literature properties for 2′,3′-cGAMP (free acid; not item-specific):
Molecular formula (free acid, literature): C20H24N10O13P2.
Molecular weight (free acid, literature): ~674.4 g/mol. Diammonium salt adds two NH4+ counter-ions; reported salt MWs vary by hydration and counter-ion content in specific lots (consult CoA for this item).
Physical state: typically supplied as a solid (often lyophilized) or as an aqueous stock solution for biochemical use (literature practice).
Solubility: highly polar; generally readily soluble in water and common biological buffers at neutral pH; limited solubility in organic solvents (literature). If organic co-solvent is required, small percentages of DMSO are commonly used in bioassays.
pKa: phosphate diesters display multiple acidic pKa values; net dianionic at physiological pH (literature qualitative note).
Properties not provided for this item (do not infer): melting point, boiling point, density, refractive index, UV cutoff/ε, water content, residual solvent, and metal limits. For any specification-grade details relevant to your application, refer to the item’s CoA/Specification Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grade for cyclic dinucleotides (general guidance; not item-specific):
Bioactive reagent or “research grade” typically indicates material suitable for biochemical assays, pathway modulation, and cell-based studies, but not certified for clinical or diagnostic use.
High-purity nucleotide salts often list HPLC purity (e.g., ≥95–98% by RP-HPLC) and low levels of related impurities such as linear di-nucleotides, mono-nucleotides, residual solvents, and inorganic salts. UV purity alone is insufficient—chromatographic purity is preferred.
Residual water/solvent, counter-ion content, and hydration state can influence concentration calculations from mass; CoA provides the necessary correction factors.
Endotoxin/bioburden: for sensitive cell assays, some suppliers specify low endotoxin. If your application is endotoxin-sensitive, verify limits on the CoA.
Identity confirmation by HRMS and/or NMR where stated on the CoA.
For solution formats: exact concentration, pH, and buffer components.
If a particular analytical grade (e.g., “HPLC grade,” “cell culture tested,” “NMR grade”) is required for your work, request the lot-specific Specification Sheet before use.
Reaction and Applications
This product is a bioactive cyclic dinucleotide tool compound rather than a typical organic reagent.
Research applications (literature; not item-specific):
Chemical biology studies of the cGAS–STING pathway: 2′,3′-cGAMP is the endogenous second messenger generated by cGAS upon dsDNA sensing and is a high-affinity agonist of STING across multiple species.
Positive control ligand in binding assays (e.g., MST, ITC), thermal shift, and fluorescence polarization assays with STING.
Cellular pathway activation studies, innate immune signaling mapping, and structure–activity relationship comparisons against c-di-GMP, c-di-AMP, and synthetic CDNs.
Biophysical standard in LC–MS or HPLC method development for CDN quantification and in enzymology assays involving ENPP1 or phosphodiesterases that catabolize 2′,3′-cGAMP.
Practical tips (general, not item-specific):
Prepare and handle solutions using nuclease-free, low-bind plastics or silanized glassware to minimize adsorption and degradation.
Control pH near neutrality (pH 7.0–7.5) to limit phosphodiester hydrolysis; avoid prolonged heating.
For cellular delivery, consider permeabilization/transfection aids (e.g., lipofection, electroporation) as free 2′,3′-cGAMP has limited passive membrane permeability.
Include appropriate negative (vehicle) and orthogonal controls (other CDNs) in assay design.
Note: No item-specific application claims are provided in the Product Data; ensure compatibility with your system by small-scale pilot experiments.
Reaction Conditions
This product is not intended for use as a reagent in traditional synthetic organic reactions; therefore, standard reaction condition guidance (solvent, temperature, catalysts) is not applicable.
Assay/handling conditions (literature; not item-specific):
Stock preparation: typically in nuclease-free water or neutral buffer (e.g., HEPES, Tris) at 1–10 mM; filter-sterilize when needed.
Stability: best maintained at ≤4 °C short-term and −20 to −80 °C long-term; avoid strong acids/bases and prolonged exposure to >37 °C.
Enzymology assays (e.g., ENPP1-mediated hydrolysis): commonly run at pH 7.4–8.5, 25–37 °C, with controlled Mg2+/Zn2+ as required by the enzyme; monitor by HPLC/LC–MS.
STING binding/activation in cell systems: dose and exposure time vary widely by cell type and delivery method; start with literature precedents and titrate empirically.
No item-specific reaction or assay parameters are provided in the Product Data. Optimize conditions for your particular biological system and verify with small-scale pilot experiments.
Safety and Handling
GHS/SDS information from Product Data:
Signal Word: Not specified for this item; refer to SDS.
Hazard Statements (H-codes): Not specified for this item; refer to SDS.
GHS Classification and Pictograms: Not specified for this item; refer to SDS.
General safety guidance for cyclic dinucleotides (literature/good laboratory practice; not item-specific):
Expected to be of low acute toxicity; handle with standard laboratory PPE: lab coat, safety glasses, and appropriate gloves (e.g., nitrile).
Avoid inhalation of powders/aerosols and contact with eyes/skin. Use in a clean area to minimize microbial/nuclease contamination.
First aid (general): upon skin/eye contact, rinse with water for several minutes; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention if irritation persists. Always follow your institutional protocols.
Incompatibilities: strong acids/bases may hydrolyze phosphodiester bonds; avoid prolonged exposure to elevated temperature, light, and nucleases. Oxidizing agents can degrade nucleobases.
Special risks: aqueous solutions may be prone to microbial growth; prepare using nuclease-free reagents and sterile technique. Minimize repeated freeze–thaw cycles to avoid degradation.
Waste disposal: dispose of aqueous nucleotide-containing waste according to local regulations for non-hazardous biochemical waste, unless contaminated with hazardous materials.
Consult the official SDS for authoritative hazard classification, exposure limits, and emergency procedures for this specific product/lot.
Solvent Selection
2′,3′-cGAMP-dammonium is a highly polar, ionic cyclic dinucleotide salt primarily handled in aqueous media.
Polarity/miscibility (literature, not item-specific):
Strongly hydrophilic; readily soluble in water and common biological buffers at neutral pH.
Poor solubility in nonpolar and moderately polar aprotic solvents. Small amounts of DMSO can be used as co-solvent for stock solutions when water solubility limits experimental design.
Recommended vehicles (practical use):
Nuclease-free water (ddH2O), PBS, HEPES, or Tris buffers at pH ~7–8 for stock and working solutions.
For intracellular delivery studies, mix with transfection reagents or permeabilization agents as appropriate for your assay (see your in-house protocols). Avoid extreme pH that may promote phosphodiester hydrolysis.
Comparison/selection tips (general):
For in vitro enzyme assays (e.g., STING binding or cGAS control reactions), buffered aqueous systems with Mg2+ control are typical. Include chelators only if specifically required since divalent metals can influence nucleotide interactions.
For cell culture, sterile, endotoxin- and nuclease-free aqueous stocks reduce variability. DMSO stocks can be convenient but keep final assay DMSO ≤0.1–0.5% v/v to minimize cellular effects (literature practice).
Not applicable: selection among organic reaction solvents is generally irrelevant for this biomolecule; prioritize buffer composition and ionic strength rather than organic solvent polarity.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data):
Reconstitution (general guidance; not item-specific):
Use nuclease-free water or neutral buffer (e.g., HEPES, Tris, PBS) to prepare stock solutions. If sterility is required, filter through 0.22 μm PVDF/nylon filters under aseptic conditions.
Typical working stock concentrations used in literature are in the 1–10 mM range; adjust based on assay needs. Accurately determine concentration by mass with counter-ion/hydration corrections from the CoA, or by UV if an extinction coefficient is validated for your system.
Aliquot into single-use volumes to avoid repeated freeze–thaw cycles. Store aliquots at −20 °C to −80 °C. Protect from light and moisture.
Stability considerations (general):
Aqueous solutions are generally stable for short periods at 2–8 °C; for longer-term storage, keep frozen. Avoid strong acids or bases that can hydrolyze phosphodiester linkages.
If precipitate forms upon thawing (rare in aqueous buffers), warm gently to room temperature and mix to redissolve; do not overheat.
For lot-specific instructions (e.g., exact concentration if supplied as solution, buffer composition, counter-ion content), consult the CoA/Specification Sheet accompanying this item.
Structure and Identity
Research-grade 2',3'-cGAMP-dammonium is the diammonium salt of the endogenous cyclic dinucleotide 2',3'-cyclic GMP-AMP (cGAMP).
Item-specific identifiers from Product Data:
CAS: C1440159 (catalog/internal identifier)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (literature description; not item-specific):
2',3'-cGAMP is a cyclic dinucleotide composed of one guanosine monophosphate (GMP) and one adenosine monophosphate (AMP) joined by mixed phosphodiester linkages: a 2′-5′ linkage from guanosine to adenosine and a 3′-5′ linkage from adenosine to guanosine, forming a bicyclic phosphate diester ring system.
Functional groups: two phosphate diesters (overall dianionic at neutral pH), multiple ribose hydroxyls, purine bases (adenine and guanine) with exocyclic amine on adenine and keto/exocyclic amine on guanine.
Salt form: diammonium counter-ions neutralize the phosphate charges; actual protonation state depends on pH.
Common synonyms (literature): 2′,3′-cGAMP; c[G(2′,5′)pA(3′,5′)p]; 2′3′-cyclic GMP-AMP; cGAMP (2′–3′).
2D structure in words: a rigid, bicyclic phosphate backbone in which the 3′-OH of adenosine and the 2′-OH of guanosine each form phosphodiester bonds that close a macrocyclic ring connecting the two ribose sugars; adenine and guanine bases project outward from the ribose ring system.
Synthetic Utility
As a cyclic dinucleotide, 2′,3′-cGAMP-dammonium is primarily a bioactive tool, not a general synthetic reagent. Its main value in synthesis-oriented laboratories is analytical and as a reference standard.
Utility in synthesis workflow (general; not item-specific):
Reference standard for calibrating HPLC/LC–MS methods used to monitor enzymatic synthesis of 2′,3′-cGAMP from ATP/GTP by cGAS or for tracking degradation by ENPP1 or other phosphodiesterases.
Benchmark for method validation: retention factors in ion-pair or HILIC chromatography, MS/MS fragmentation patterns of CDN standards.
Positive control in binding assays that support structure-based design of CDN analogs or non-nucleotide STING modulators.
Not typically used as a reagent in bond-forming reactions. The molecule is sensitive to conditions that promote phosphodiester cleavage; harsh acidic/basic conditions or strong nucleophiles should be avoided during any handling.
Retrosynthetic context (literature): chemical synthesis of 2′,3′-cGAMP involves selective protection of ribose hydroxyls, phosphoramidite coupling to form 2′–5′ and 3′–5′ linkages, cyclization, and global deprotection, or alternatively, enzymatic synthesis via cGAS followed by purification.
For general organic transformations or materials synthesis, this compound offers limited direct synthetic utility.
Target Specificity
Item-specific target data are not provided in the Product Data for this SKU.
Not specified for this item; refer to CoA/Spec Sheet.
General literature context (not item-specific): 2′,3′-cGAMP is a high-affinity agonist of the adaptor protein STING. Species variants of STING can display differing sensitivity to cyclic dinucleotides; confirm specificity and potency in your assay system.
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