Sulbactam sodium - 10mM in DMSO , Bacterial beta-lactamase TEM inhibitor, CAS No.69388-84-7, Bacterial beta-lactamase TEM inhibitor

CAS: 69388-84-7 Cat. No.: S409112 Summenformel: C₈H₁₀NO₅S·Na Molekulargewicht: 255.22 EG-Nummer: 273-984-4

GRADE & PURITY 10mM in DMSO

Synonyms

CP-45899-2 | 3,3-dimethyl-7-oxo-4,4-dioxide-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, sodium salt (1:1)

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Übersicht

Information

Sulbactam sodium Sulbactam sodium (Unasyn, CP-45899-2) is an irreversible β-lactamase inhibitor.
In vitro

In vivo

Cell Data

cell lines：Human breast cancer cells MCF-7

Concentrations：

Incubation Time：

Powder Purity:≥98%

Specifications

Synonyme

CP-45899-2 | 3,3-dimethyl-7-oxo-4,4-dioxide-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, sodium salt (1:1)

Spezifikationen & Reinheit

10mM in DMSO

Biochemische und physiologische Mechanismen

Sulbactam sodium (Unasyn, CP-45899-2) is an irreversible β-lactamase inhibitor.

Storage

Store at -80°C

Verschickt in

Dry ice packs + Cold packs

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

Aktionsart

INHIBITOR

Mechanismus der Wirkung

Bacterial beta-lactamase TEM inhibitor

Namen und Kennungen

Isomere SMILES

CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])C.[Na+]

Molekulargewicht

255.22

Reaxy-Rn

1137390

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1137390&ln=

Application Protocols

• Not specified for this item; no tested application protocols or recommended dilutions are provided in the Product Data.
• For laboratory use, consult peer-reviewed literature and internal SOPs to develop assay-specific protocols using sulbactam sodium as a biochemical tool compound.

Biological Roles

• Role (literature; not a product claim): Sulbactam is a mechanism-based β-lactamase inhibitor (penicillanic acid sulfone). It acylates the active-site serine of class A β-lactamases, forming a stable acyl–enzyme that slows hydrolysis and protects companion β-lactam substrates in vitro.
• Enzymology context:
  • More effective against many class A enzymes; limited activity against most metallo-β-lactamases and some class C/D enzymes (literature generalization).
  • Undergoes rearrangements after acylation; the sulfone enhances electrophilicity and stabilizes the inhibitory intermediate.
• Physicochemical/biochemical implications:
  • As a sodium carboxylate, it is well-suited for aqueous assay systems; ionic strength and pH modulate activity and stability.
  • Susceptible to hydrolysis outside of optimal conditions; freshly prepared solutions improve reproducibility in kinetic measurements.
• Research uses (non-clinical):
  • Tool compound for dissecting β-lactamase contributions to bacterial resistance mechanisms in vitro.
  • Benchmark comparator in structure–activity studies of β-lactamase inhibitors.
• Note: No therapeutic or clinical performance claims are made here; this product is supplied strictly for research use only (Product Data).

Buffer Applications

• This compound is not a buffer component; it does not form a conventional buffering system. As an active small molecule, it is typically dissolved in pre-made buffers for biochemical or microbiological assays.
• Practical guidance (general):
  • Use near-neutral buffers (e.g., phosphate, HEPES, or MOPS, pH ~7.0–7.5) to balance stability of the β-lactam ring with enzyme compatibility.
  • Avoid strong alkaline or acidic buffers that can accelerate ring opening.
  • Consider ionic strength: added Na+ from the salt contributes to total ionic strength; adjust buffer composition accordingly for sensitive enzymatic assays.
• For specific recipes, consult assay protocols relevant to your enzyme or organism of interest. No item-specific buffer recipes are provided.

Green Alternatives

• Context: Sulbactam sodium is an active research chemical rather than a solvent or process reagent; “green alternatives” pertain mainly to solvent choice and handling during analytical or biochemical workflows.
• Greener handling options (general):
  • Prefer aqueous buffers over organic solvents whenever compatible with your assay.
  • Use water–ethanol or water–acetonitrile in the lowest feasible organic percentage for HPLC sample prep.
  • Avoid chlorinated solvents; they offer no advantage for this ionic compound and pose higher environmental burdens.
• Process considerations:
  • Prepare concentrated aqueous stocks to minimize solvent volumes and waste.
  • Employ microscale assay formats (96/384-well plates) to reduce chemical usage and waste.
  • Dispose of β-lactam–containing waste according to institutional guidelines to prevent environmental release of bioactive compounds.
• Comparison table (general):
  • Aqueous buffer (pH ~7): highest compatibility; lowest environmental impact; may require cold storage to limit hydrolysis.
  • Water–acetonitrile: good for LC methods; moderate environmental impact; volatile organic component.
  • DMSO: useful for small-volume stocks when solubility allows; persistent solvent; minimize final assay %.
• No item-specific environmental certifications or solvent recommendations are provided for this product.

Pharmaceutical Uses

• Scope: Information below concerns general formulation and analytical concepts from literature; it does not constitute clinical or therapeutic claims for this catalog item.
• General roles in development/QC (literature):
  • Used as a reference standard in analytical methods (e.g., HPLC, LC–MS) for β-lactamase inhibitors.
  • Studied in formulation science for compatibility, stability, and admixture behavior with β-lactam antibiotics in aqueous media (e.g., pH, ionic strength, diluent effects) in a research setting.
• Excipient status: Not an excipient; it is an active small molecule. Any pharmacopeial monographs or compliance aspects, if applicable, are outside the scope of this listing.
• Manufacturing/QC considerations (general):
  • Assess solution stability under intended storage/handling (light, temperature, pH) due to potential β-lactam hydrolysis.
  • Validate impurity and degradant methods (stress testing) per ICH guidance in development studies.
• For regulated uses, consult the appropriate pharmacopeia and perform full method validation. This catalog item is supplied for research use only (Product Data).

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point/Decomposition: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: β-lactam sulfone salts often decompose on melting.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: sulbactam sodium is typically highly soluble in water; limited solubility in most nonpolar organics.
• pKa(s): Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: carboxylate pKa for related β-lactams is acidic; sulfone reduces basicity of ring nitrogens.
• LogP/Partitioning: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: expected to be hydrophilic due to ionic carboxylate and sulfone.
• Density/Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Hygroscopicity: Not specified for this item; refer to CoA/Spec Sheet.
  • Practical note (general): sodium β-lactam salts can be moisture-sensitive; handle promptly to avoid uptake of water.
• UV/Vis: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: β-lactams typically have weak UV absorption above 250–280 nm; check CoA for chromatographic UV cutoff if relevant.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• What to look for in quality (general guidance for sulbactam sodium):
  • Identity confirmation by HPLC/LC–MS and NMR consistent with sulbactam sodium; verify counterion content (Na+) and degree of hydration if applicable.
  • Assay (content %) on anhydrous basis; check for related substances (ring-opened products, degradants) often monitored by gradient RP-HPLC.
  • Residual solvents, water (Karl Fischer), and inorganic content (Na) where applicable. Limits are method- and grade-dependent; not specified for this item.
• Stabilization: No stabilizer information is provided for this item.
• Documentation: Each lot’s CoA/Spec Sheet should be consulted for assay, impurity profile, chromatographic conditions, and recommended analytical methods for incoming QC.
• Suitability by application:
  • Analytical/reference use: prioritize lots with detailed chromatographic purity and tight related-substances profiles.
  • Microbiology/enzyme studies: confirm low endotoxin/bioburden if relevant to your assay; not specified for this item.

Reaction and Applications

• This compound is primarily a biochemical tool (β-lactamase inhibitor) rather than a synthetic reagent. It is not typically used as a substrate or catalyst in standard organic reactions.
• Research applications (general, literature-based):
  • Evaluation of β-lactamase inhibition in enzymology assays (e.g., clavulanate/sulbactam/tazobactam comparisons).
  • Microbiological research to study synergy with β-lactam antibiotics in vitro (e.g., checkerboard assays, time–kill curves). No clinical claims; research use only.
  • Analytical reference standard for developing/validating chromatographic methods (HPLC/LC–MS) for β-lactamase inhibitors.
• Practical notes:
  • β-Lactam ring integrity is crucial; minimize exposure to strong base or acid and elevated temperatures during solution prep.
  • For kinetic assays, prepare fresh aqueous stocks, keep on ice, and use buffered conditions (pH ~7) to reduce non-enzymatic hydrolysis (literature guidance).
  • Include controls for potential salt effects (Na+) in enzyme assays; ionic strength can modulate enzyme activity.
• Not commonly involved in named synthetic transformations; if chemical modification is desired (e.g., derivatization for analytical tagging), proceed under mild conditions to avoid ring opening.

Reaction Conditions

• This compound is not generally used to run transformations; however, conditions below refer to typical handling in biochemical/analytical contexts (literature/guidance):
• Solution preparation:
  • Dissolve in cold water or buffered saline (pH 6.5–7.5). Concentrations for assay stocks commonly range from low millimolar to tens of millimolar; select based on your assay design.
  • Filter sterilize if sterility is required (0.22 µm PES/RC). Work on ice and protect from prolonged exposure to light/heat.
• Stability considerations:
  • β-Lactam ring is susceptible to hydrolysis; avoid pH > 8 or < 5 for extended periods. Store aliquots at low temperature.
• Chromatography (analytical):
  • Reverse-phase HPLC/UPLC with aqueous buffer (volatile salts for MS as needed) and acetonitrile/methanol gradients is common. Monitor at low-UV wavelengths if sensitivity is required. Optimize pH to balance retention and stability.
• Enzymology assays:
  • Maintain controlled ionic strength (Na+, buffer counterions) as these can influence enzyme kinetics.
• Yields/times: Not applicable; no synthetic reactions are prescribed for this item.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
• General hazard information (literature/practice; not product-specific):
  • β-Lactam derivatives may cause allergic sensitization in susceptible individuals; avoid skin contact and inhalation of dust/aerosol.
  • May cause eye/skin/respiratory irritation. Handle as a potentially harmful substance.
• Recommended PPE: laboratory coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood or ventilated enclosure when handling powders/solutions.
• Storage incompatibilities (general): avoid strong oxidizers and strong acids/bases that can promote β-lactam ring opening; avoid prolonged exposure to moisture and elevated temperature.
• Thermal/chemical stability (general): β-lactam ring can hydrolyze under basic or strongly acidic conditions; sulfone is oxidized state and typically stable to mild oxidants, but overall molecule is hydrolytically sensitive.
• First-aid overview (general):
  • Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Always consult the product-specific SDS for authoritative safety information.

Solvent Selection

• Polarity and ionic character: as a sodium carboxylate, sulbactam sodium is strongly hydrophilic and typically dissolves readily in water and aqueous buffers (literature). It is poorly soluble in most nonpolar organic solvents.
• Practical choices:
  • Water / aqueous buffers (pH ~6–8): preferred for preparing stock solutions for biochemical assays. Avoid strong acid/base to minimize β-lactam hydrolysis.
  • Mixed solvents: If needed for chromatographic or analytical work, water–acetonitrile or water–methanol mixtures can be used; maintain moderate pH and low temperature.
  • Anhydrous polar aprotics (e.g., DMSO): limited use; the ionic nature may limit solubility unless converted to the free acid or a different salt (literature). When using DMSO, prepare concentrated stocks to minimize final DMSO percentage in assays.
• Comparison (general):
  • Sulbactam free acid is less water-soluble at neutral pH but more amenable to some organic media; the sodium salt prioritizes aqueous handling and biological assay readiness.
• Tips:
  • Filter sterilize aqueous stocks (0.22 µm) when sterility is required.
  • Prepare fresh solutions or store aliquots at low temperature to reduce hydrolysis.

Storage and Reconstitution

• Storage conditions (Product Data): Store at -80°C.
  • Shipped on dry ice packs + cold packs to maintain low temperature.
• Handling on receipt:
  • Keep container closed. Minimize time at ambient temperature. If frequent use is expected, consider preparing aliquots to avoid repeated freeze–thaw cycles.
• Reconstitution (general guidance; not item-specific):
  • Solvent: cold sterile water or suitable buffer (e.g., phosphate, HEPES) at pH ~7.0–7.5 to limit β-lactam hydrolysis.
  • Concentration: prepare assay-appropriate stocks (e.g., millimolar range). Filter sterilize when required (0.22 µm). Record exact solvent, pH, and concentration on the vial.
• Short-term storage of solutions (general):
  • Keep on ice during use. For longer storage, freeze single-use aliquots at ≤ -20°C or -80°C depending on stability requirements. Avoid repeated freeze–thaw.
• Light/moisture sensitivity: protect from moisture ingress and prolonged light/heat exposure.
• Shelf-life: Not specified for this item; refer to CoA/Spec Sheet. Always check solutions for discoloration or precipitate before use.
• Research Use Note: For research use only (Product Data).

Structure and Identity

• Item name: Sulbactam sodium (sodium salt of sulbactam; β-lactamase inhibitor)
• CAS: 69388-84-7 (Product Data)
• CID: 23663973 (Product Data)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: sodium salt of sulbactam (penicillanic acid sulfone monoanionic form)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: the sodium salt has a higher MW than sulbactam free acid by ~22.99 Da due to Na+ counterion
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature: corresponds to the sodium salt of penicillanic acid 1,1-dioxide (sulfone)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general description; literature):
  • Bicyclic β-lactam framework: an azetidin-2-one (β-lactam) fused to a thiazolidine-type ring.
  • Sulfone (–SO2–) on the thiazolidine sulfur (penicillanic acid sulfone), which imparts strong electron-withdrawing character.
  • Carboxylate anion neutralized by Na+ (sodium salt), typically existing as a zwitterion/carb anion sodium complex in the solid state.
  • Multiple heteroatoms (O, N, S) enabling hydrogen bonding; no stereochemistry specified here, but sulbactam is known to be chiral (literature).

Synthetic Utility

• Chemical functionality overview (general, literature):
  • β-Lactam (azetidin-2-one): electrophilic, prone to nucleophilic ring opening under basic or nucleophilic conditions.
  • Sulfone (–SO2–): strong electron-withdrawing group that enhances the β-lactam’s susceptibility to nucleophilic attack and participates in enzyme-inhibition mechanisms.
  • Carboxylate (sodium salt): increases water solubility but reduces solubility in many organic media; the free acid or protected derivatives are more common for synthetic manipulations.
• Synthetic relevance:
  • Sulbactam sodium itself is not widely employed as a building block due to instability of the β-lactam under many reaction conditions.
  • Derivatization efforts (literature) typically target protected or activated forms, or are conducted under mild, neutral conditions to preserve the β-lactam ring.
  • Useful as a benchmark inhibitor in mechanistic organic chemistry studies of acylation/deacylation of serine active sites.
• Retrosynthetic note:
  • Access to sulbactam frameworks often involves β-lactam formation (e.g., Staudinger ketene–imine routes) followed by oxidation to the sulfone, and careful control of stereochemistry; such routes are beyond the scope of routine lab modification of the sodium salt.

Target Specificity

• Not specified for this item; no target specificity metadata is provided in the Product Data.
• Note: While sulbactam is known in literature as a β-lactamase inhibitor, this section only reports product-specific target information, which is not provided here.