Abacavir sulfate - ≥99%, used for Abacavir sulfate has been used as a compound to validate the P19C5 gastrulation in mouse. It has also been used to induces chromosomal double-strand breaks (DSBs) and kills adult T cell leukemia (ATL) cells.
Abacavir sulf, Human immunodeficiency virus type 1 reverse transcriptase inhibitor
Abacavir sulfate - ≥99%, used for Abacavir sulfate has been used as a compound to validate the P19C5 gastrulation in mouse. It has also been used to induces chromosomal double-strand breaks (DSBs) and kills adult T cell leukemia (ATL) cells.
Abacavir sulf, Human immunodeficiency virus type 1 reverse transcriptase inhibitor
Abacavir sulfate is a Nucleoside analog reverse transcriptase inhibitor (NRTI); guanosine analog used to treat HIV and AIDS;Abacavir sulfate is the sulfate form of abacavir, a nucleoside reverse transcriptase inhibitor (NRTI). NRTIs work by blocking HIV r
Aplicação
Abacavir sulfate has been used as a compound to validate the P19C5 gastrulation in mouse. It has also been used to induces chromosomal double-strand breaks (DSBs) and kills adult T cell leukemia (ATL) cells.
Abacavir sulfate has been used in the cytotoxic
Condições de armazenamento de armazenamento
Store at 2-8°C,Argon charged
Enviado em
Wet ice
Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.
Tipo de ação
INHIBITOR
Mecanismo de ação
Human immunodeficiency virus type 1 reverse transcriptase inhibitor
Nota
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
This compound belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
External Descriptors
azaheterocycle sulfate salt
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No item-specific, vendor-validated application protocols are provided for this product. The following general protocols are commonly used in research laboratories for small molecules of this class (guidance only):
Preparation of DMSO stock solution
Weigh compound quickly to minimize moisture uptake. Dissolve to 10–50 mM in anhydrous DMSO. Vortex and brief sonication may assist dissolution. Aliquot and store at 2–8°C or below; avoid repeated freeze–thaw.
Preparation of aqueous working solutions
From DMSO stock, dilute into buffer (e.g., 10–50 mM phosphate, pH 6.5–7.4) to a final DMSO content ≤1% v/v. If direct dissolution is preferred, dissolve the sulfate salt in sterile water or buffer, adjusting pH to 4–6 if needed to maintain solubility. Filter (0.2 µm) when sterility/clarity is required.
LC–MS reference standard use
Prepare a primary standard solution gravimetrically. Verify purity/assay from CoA and correct for counterion/hydrate. Prepare a calibration series in water:acetonitrile (1:1) with 0.1% formic acid. Store working standards cold and protected from light; remake periodically per stability studies.
In vitro enzyme assay setup (research-only)
Typical final concentrations: 0.1–100 µM, depending on enzyme/assay sensitivity. Include matched vehicle controls. Pre-equilibrate at assay temperature and monitor for precipitation.
Always validate concentration by an orthogonal method (e.g., UV or LC–MS) and confirm solution clarity before use.
Biological Roles
The following reflects general, literature-based biochemical information about the abacavir chemotype; it is provided for research context only and does not imply any medical or clinical use.
Structural class
Carbocyclic purine nucleoside analogue featuring a cyclopentenyl “sugar” mimetic linked to a 6-substituted purine core.
Cellular processing (literature)
In mammalian cells, nucleoside analogues of this class are taken up via equilibrative or concentrative nucleoside transporters and are subject to kinase-mediated phosphorylation to the mono-, di-, and triphosphate forms.
Triphosphate derivatives of purine analogues can interact with DNA/RNA polymerases and related enzymes due to structural mimicry of natural dNTPs.
Enzymology and metabolism (literature trends)
Phosphorylation typically proceeds via adenosine kinase or related nucleoside kinases (first step), followed by nucleotide monophosphate and diphosphate kinases.
Catabolic pathways may involve deamination, N-dealkylation, and conjugation; salt form (sulfate) affects solubility and transport but not the intrinsic aglycone chemistry.
Experimental implications
When studying kinase kinetics or transporter specificity, careful control of pH, ionic strength, and competing nucleoside concentrations is critical.
The sulfate counterion can influence ionic strength in vitro; account for it in buffer design when working at millimolar concentrations.
All biological work with this product must be conducted as basic research; no clinical, diagnostic, or in vivo human/animal use is implied or supported.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare buffer systems. However, it is frequently handled in buffered aqueous media for biochemical assays.
Practical notes for buffer use with this compound (general guidance)
Use mildly acidic to neutral buffers (e.g., 10–50 mM citrate-phosphate, acetate, MES, phosphate, or HEPES) to maintain the sulfate salt in solution. Avoid high pH where free-base precipitation may occur.
Include 0.1–1.0% DMSO if needed to maintain solubility after dilution from DMSO stocks; verify compatibility with the biological assay.
Filter-sterilize working solutions through 0.2 µm membranes when sterility or particulate-free solutions are required.
For actual buffer capacity, pH range, and recipes, consult the specific buffering reagent documentation; abacavir sulfate itself does not provide buffer capacity.
Green Alternatives
Abacavir sulfate is a target analyte/standard rather than a process solvent or reagent; “green alternative” considerations focus on solvent systems and handling practices used with this compound.
Greener solvent choices for handling
Prefer water or aqueous buffers where feasible; they provide the lowest environmental impact and best EHS profile for dissolution and dilutions.
When an organic co-solvent is required, consider ethanol or isopropanol over higher-toxicity solvents. DMSO is broadly acceptable in small volumes for stock solutions.
Example comparison (general guidance)
Water vs DMSO: Water is ideal for final assay media; DMSO enables high-concentration stocks but should be minimized in final dilutions (<1–2% v/v typical in biochemical assays).
Acetonitrile vs methanol (analytical LC): Methanol is generally greener but may alter selectivity; evaluate method performance before substitution.
Waste minimization and scale
Use micro-scale dissolution and serial dilution to reduce solvent consumption in screening workflows.
Collect aqueous/organic mixtures for appropriate disposal; avoid unnecessary basification/neutralization steps that generate sulfate-containing salts in waste streams.
Packaging and stability
Choose package sizes aligned with experimental throughput to limit repeated openings and potential material loss, which indirectly reduces waste.
These practices improve the overall sustainability of experiments involving abacavir sulfate without altering the compound itself.
Pharmaceutical Uses
No therapeutic or clinical claims are made for this catalog item. The following pertains to research and development contexts only.
Typical roles in pharmaceutical R&D (general)
Reference standard for analytical method development and validation (assay, impurity profiling, dissolution testing) in support of formulation studies involving carbocyclic nucleoside analogues.
System suitability and retention-time marker in LC–UV/LC–MS platforms; useful for establishing response factors and recovery in sample preparation workflows.
Excipient compatibility screening: evaluate stability in the presence of common formulation excipients (lactose, microcrystalline cellulose, povidone, etc.) under ICH stress conditions.
Regulatory compendia (literature context)
Abacavir sulfate is described in major pharmacopeias (e.g., USP/EP) as a drug substance; compendial monographs provide tests for identity, assay, related substances, water, and sulfate content. These monographs can guide analytical control strategies in research settings.
Formulation considerations for research
Salt form offers enhanced aqueous solubility; pH control reduces risk of precipitation during granulation or dissolution studies.
Hygroscopicity may warrant desiccated handling and rapid transfer to minimize moisture uptake during blend preparation in lab-scale studies.
All uses are for laboratory research and method-development purposes only.
Physical Properties
Only limited item-specific physical specifications are provided for this catalog entry. Where values are given below, they are literature descriptions for abacavir sulfate or the abacavir free base and are not specifications of this item.
Item-specific values
Appearance: 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.
Literature/general properties (for reference; not item specs)
Physical state: crystalline solid; sulfate salts are typically hygroscopic and freely water-soluble
Solubility: abacavir sulfate is highly soluble in water; the free base is sparingly soluble in water and soluble in polar organics such as DMSO and methanol (literature)
pKa: multiple basic centers; conjugate acid pKa values in the ~5–9 range have been reported for related purinyl amines (literature, method-dependent)
logP/logD: free base logP around 1–1.5; the sulfate salt exhibits much lower apparent logD in water (literature trends for ionic salts)
Melting behavior: salts often show decomposition on heating rather than a sharp boiling point; reported melting ranges vary with hydration state (literature)
Optical activity: chiral at the cyclopentene positions (literature stereochemistry typically (1S,4R))
Practical handling implications
Preference for aqueous or mixed aqueous/organic media due to salt form
Hygroscopicity can influence weighing accuracy; pre-equilibrate to room temperature in a desiccator before opening when possible
Avoid strong base if free base precipitation is undesired; pH strongly governs solubility.
Quality and Grades
Grade/purity
Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, water content, and counterion stoichiometry/hydration state.
What grade means for this class of material (general guidance)
Small-molecule library compounds are typically offered at research grade, with identity confirmed by orthogonal methods (e.g., NMR and/or LC–MS) and an assay suitable for screening and method development. Where applicable, salt form, hydrate level, and residual solvent content are documented on the CoA.
For analytical uses (bioanalytical standards, LC–MS method development), users often require tight limits on related substances and residual inorganic content; these are item-specific and should be confirmed on the CoA.
Stabilizers and additives
No stabilizer is indicated in the Product Data. If present, stabilizers or crystallization solvents will be disclosed on the CoA.
Practical notes for users
Verify the exact salt form (abacavir·H2SO4 vs hydrate) on receipt; this impacts molecular weight for solution preparation and dosing calculations.
For quantitative work, standardize by mass balance (assay-on-as-is basis) or correct for counterion and water of crystallization as specified on the CoA.
If UV-based detection is intended, assess UV cutoff and extinction coefficients empirically; item-specific UV specs are not provided here.
Reaction and Applications
This product is primarily intended as a research-grade small molecule for biochemical studies, reference standardization, and screening, rather than as a general-purpose synthetic reagent.
Research and analytical applications (general/literature)
Reference material for chromatographic method development (HPLC/UPLC–UV/MS) including retention behavior of carbocyclic nucleoside analogues; useful for system suitability and calibration in bioanalytical workflows.
In vitro biochemical studies on nucleoside phosphorylation pathways: stepwise phosphorylation by cellular kinases to mono/di/tri-phosphate can be assayed using enzyme panels in cell-free extracts (no clinical claims; research-only context).
Transport studies: probe interactions with nucleoside transporters in model systems (e.g., uptake assays in vesicles or overexpression cell lines).
Synthetic/derivatization notes (general)
Functional handles include a primary alcohol (amenable to esterification, carbonate formation, phosphorylation) and exocyclic amines (acylation, sulfonylation) for prodrug or analytical tagging studies.
Salt interconversion: sulfate ↔ free base via controlled basification/neutralization enables solubility tuning for different media.
Practical tips
Maintain acidic to neutral pH during aqueous handling to keep the compound in the soluble salt form.
For quantitative assays, determine extinction coefficients or MS response factors under your exact solvent/mobile phase conditions.
Minimize freeze–thaw cycles of concentrated aqueous or DMSO stocks to prevent potential degradation or adsorption losses.
Reaction Conditions
As supplied, abacavir sulfate is not primarily used as a reagent in named synthetic transformations. Nonetheless, for derivatization and analytical preparation, the following general, literature-based conditions are relevant:
Alcohol functionalization
Esterification: carboxylic acid (1.1–1.5 eq), DCC/DMAP or EDCI/DMAP, dry CH2Cl2 or DMF, 0–25°C, 2–16 h. Protect amines first (e.g., Boc) to control chemoselectivity.
Phosphorylation: POCl3 or phosphoramidite strategies under anhydrous conditions (e.g., pyridine/CH3CN, −20 to 0°C), followed by oxidation (mCPBA/I2-water) to afford phosphate esters.
Amine derivatization
Acylation: acyl chloride/anhydride (1.1 eq), base (NEt3 or DIPEA), DMF or CH2Cl2, 0–25°C, 1–4 h; monitor to avoid purine ring acylation.
Carbamate formation: chloroformates or CDI-activated carbonates, 0–25°C, aprotic solvents.
Salt interconversion
Free base generation: adjust aqueous solution to pH 9–10 with NaHCO3/Na2CO3, extract into suitable organic solvent, dry and handle under inert atmosphere; reconvert to sulfate by treatment with H2SO4 in alcohol/ether and recrystallization.
Stability considerations
Avoid strong base and prolonged heating; purine analogues can undergo N-dealkylation or ring degradation.
In aqueous solutions, maintain pH 3–7 and low temperatures during workup to limit decomposition.
All conditions above are general literature guidance for analogous nucleoside analogues; optimize and validate experimentally for your specific objectives.
Safety and Handling
Regulatory and classification
GHS classification: Not specified for this item; refer to SDS.
Signal word / hazard statements / pictograms: Not specified for this item; refer to SDS.
Research use restriction: For research use only (not for human or veterinary use; no clinical applications).
General hazards and precautions (literature-based/good lab practice)
May cause irritation to eyes, skin, and respiratory tract. Avoid dust generation and inhalation. Handle powders in a fume hood or ventilated enclosure.
Pharmaceutical actives and analogues should be treated as potentially bioactive. Minimize exposure via appropriate engineering controls.
PPE recommendations
Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use a particulate respirator if dusts/aerosols may be generated and adequate ventilation is not assured.
Storage and incompatibilities
Storage (item-specific): Store at 2–8°C. Shipped on wet ice.
Protect from moisture; keep container tightly closed. Avoid strong oxidizers and strong bases/acids that can alter salt state or cause degradation.
First-aid overview (defer to SDS)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Always consult the product-specific SDS for authoritative safety, toxicological, and ecological information.
Solvent Selection
Abacavir sulfate is an ionic organic salt with high polarity and hydrogen-bonding capacity.
Polarity and miscibility (general/literature)
Preferentially soluble in water and aqueous buffers due to sulfate counterion.
Readily soluble in DMSO; often used to prepare concentrated stock solutions for screening and cell-free biochemical assays, then diluted into aqueous media.
Solubility in less polar organics (e.g., acetonitrile, ethanol, isopropanol) is moderate to low and strongly pH-dependent; free base solubility increases in protic/polar solvents.
Practical selection scenarios
Aqueous assay work: Prepare stocks in sterile water or buffer (pH 3–6 maintains salt form and solubility). Filter-sterilize through 0.2 µm when needed.
LC–MS method development: Water/DMSO stocks diluted into water/acetonitrile mobile phases with 0.1% formic acid or ammonium formate/ammonia for ionization control.
Organic synthesis or derivatization: Convert to free base to enhance solubility in aprotic organics (THF, DMF) if required; reconvert to sulfate after processing.
Comparison with alternatives (general)
Water: best for maximal solubility and biological compatibility.
DMSO: excellent for high-concentration stocks; mixability with water for serial dilutions.
Methanol/ethanol: convenient for analytical sample prep but may yield lower maximum concentrations vs water or DMSO.
Tips
Confirm pH after dilution; precipitation may occur if pH drifts basic (free-base formation).
Warm gently and sonicate to aid dissolution; avoid prolonged heating to prevent degradation.
Storage and Reconstitution
Storage conditions (item-specific)
Store at 2–8°C. Shipped on wet ice. Keep container tightly closed and protected from moisture.
Stability considerations
Hygroscopic salts can absorb water, altering mass and concentration. Where possible, store under desiccation and allow the container to equilibrate to room temperature before opening to minimize condensation.
Avoid prolonged exposure to elevated temperatures and strong light; prepare smaller aliquots to limit repeated openings.
Reconstitution guidelines (general)
Aqueous: Dissolve the sulfate salt directly in high-purity water or appropriate buffer. If needed, gently warm to room temperature and vortex/sonicate. Target pH 4–7 to maintain solubility.
Organic: For high-concentration stocks, dissolve in anhydrous DMSO. Verify complete dissolution visually and, if critical, by LC–MS or UV.
Concentration calculations: Confirm exact salt form, assay, and hydration state on the CoA. Adjust weighed mass to “free base equivalent” as needed for dosing or to “as-is basis” for analytical work.
Aliquoting and freeze–thaw
Prepare single-use aliquots in inert, low-bind vials. Minimize freeze–thaw; if freezing, avoid repeated cycles and thaw gently at 2–8°C.
Shelf life
Not specified for this item; refer to CoA/Spec Sheet. Users should perform periodic re-testing of stored solutions (e.g., LC–MS purity) to confirm ongoing suitability for use.
Structure and Identity
Abacavir sulfate is a carbocyclic purine nucleoside analogue presented as its sulfate salt for research use.
Item-specific identifiers (from Product Data)
SKU: A129792
CAS: 188062-50-2
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identifiers and composition (for reference only; not item specifications)
Fused bicyclic purine ring (6-5 imidazo-pyrimidine) with exocyclic amino groups at C-2 and N-6 substitution by a cyclopropylamino moiety (literature)
Carbocyclic “nucleoside” scaffold: a cyclopent-2-en-1-yl methanol side chain attached at N-9 of the purine (literature)
Functional groups: primary alcohol, primary amine(s), secondary amine (as cyclopropylamino substituent), heteroaromatic nitrogen atoms capable of protonation; sulfate counterion provides overall salt form
Stereochemistry (literature): typically reported as (1S,4R) on the cyclopentene ring for the marketed form
2D structure in words
A purine nucleus bearing at N-9 a substituted cyclopentenylmethyl group that carries a benzylic-like primary alcohol, with a cyclopropylamino substituent on the 6-position of the purine and an exocyclic amino at the 2-position; formulated as the sulfate salt for improved aqueous handling.
Synthetic Utility
Although primarily supplied as a research small molecule/standard, abacavir sulfate contains functional elements that enable selective derivatization and mechanistic studies.
Functional group reactivity (general)
Primary alcohol: amenable to esterification (acyl/activated carbonate), phosphorylation (to model nucleotide prodrugs), or oxidation to the corresponding aldehyde/acid for metabolite mimics.
Exocyclic amines on the purine core: acylation, sulfonylation, or urea/carbamate formation; N-alkylation under carefully controlled conditions.
Heteroaromatic nitrogens: protonation state can be tuned; N-oxide formation is not applicable to purines but electrophilic substitution at C-6 is influenced by amino substituents.
Salt interconversion and protection
Conversion to the free base facilitates reactions in aprotic solvents (DMF, THF), whereas the sulfate salt is advantageous for aqueous-phase chemistry.
Standard protecting groups for alcohols (e.g., TBDMS, benzyl) and amines (Boc, CBz) may be applied, with attention to purine ring stability.
Retrosynthetic perspective (literature)
The carbocyclic nucleoside scaffold arises from cyclopentene precursors (e.g., enantioenriched cyclopentene epoxides) coupled at N-9 with purine derivatives, followed by introduction of the cyclopropylamino substituent at C-6.
Analytical derivatization
Isotopic labeling (2H, 13C, 15N) on the purine or side chain can generate internal standards for LC–MS quantitation.
These utilities support probe development, prodrug exploration, and analytical standard preparation in a research setting.
Target Specificity
Not applicable. This product is a small-molecule compound, not a biological macromolecule or antibody. No antigen, epitope, clone, isotype, or species reactivity information applies.
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