BTZ043 - Moligand™, 10 mM in DMSO , CAS No.1161233-85-7

CAS: 1161233-85-7 Cat. No.: B1496431 Formula: C₁₇H₁₆F₃N₃O₅S Molecular Weight: 431.39

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

BTZ043 is an inhibitor of decaprenyl-phosphoribose-epimerase (DprE1) , with MICs of of 2.3 nM and 9.2 nM for M. tuberculosis H37Rv and Mycobacterium smegmatis , respectively.

Specifications

Specifications & Purity

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Names and Identifiers

• Isomeric SMILES: C[C@H]1COC2(O1)CCN(CC2)C3=NC(=O)C4=C(S3)C(=CC(=C4)C(F)(F)F)[N+](=O)[O-]
• Alternate CAS: 1161233-85-7
• MeSH Entry Terms: 2-(2-methyl-1,4-dioxa-8-azaspiro(4.5)dec-8-yl)-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one;BTZ 043;BTZ038;BTZ043
• Molecular Weight: 431.39
• Reaxy-Rn: 13034878
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13034878&ln=

Application Protocols

Not specified for this item; refer to CoA/Spec Sheet.

General guidance (non-validated, literature-style) is intentionally omitted here because application conditions can vary widely by assay format (biochemical enzyme assay, whole-cell microbiology, biophysical binding). Please consult primary literature for BTZ043 and validate protocols under your laboratory’s QA practices.

Biological Roles

Scope: For research use only. The following summarizes literature-reported biochemical roles of the benzothiazinone class relevant to BTZ043 without implying clinical utility.

• Putative molecular target (literature): The BTZ chemotype is widely reported to act on the mycobacterial enzyme DprE1 (decaprenylphosphoryl-β-D-ribose 2′-epimerase A subunit), a FAD-dependent oxidoreductase involved in the biosynthesis of arabinan components of the mycobacterial cell wall. Covalent adduct formation at an active-site cysteine has been described upon bioactivation of the nitro group to a nitroso species (literature).
• Pathway context: Inhibition of DprE1 perturbs formation of decaprenylphosphoryl-D-arabinose, impacting arabinogalactan assembly and cell-envelope integrity in mycobacteria (literature).
• Mechanistic features: Nitro-dependent bioactivation followed by conjugate addition to a nucleophilic cysteine (mechanism proposed in multiple studies) underlies durable target engagement, a common motif for benzothiazinones (literature).
• Resistance studies: Target-site mutations (e.g., cysteine-to-serine substitution) and redox alterations in bacteria have been used to map engagement and resistance liabilities for BTZ-class compounds (literature).
• Assay modalities: Biochemical turnover assays for DprE1, whole-cell MIC determinations in model mycobacteria, and proteomic covalent-adduct profiling have been utilized to characterize this class (literature).

Note: Exact potency, selectivity, and off-target profiles for BTZ043 should be sourced from primary publications and the CoA/Spec Sheet; none are specified for this item.

Buffer Applications

Not typically applicable. BTZ043 is a hydrophobic small molecule used as a research ligand and is not a buffering agent.

Practical notes for assay buffers (general):

• Use standard biological buffers (e.g., HEPES, Tris, or phosphate) compatible with your enzyme or cell system; maintain low final DMSO (≤0.5–1%) when introducing BTZ043 from stock solutions.
• Include carrier protein (e.g., 0.01–0.1% BSA) or small amounts of non-ionic surfactant (e.g., 0.01% Tween-20) only if needed to mitigate nonspecific adsorption or precipitation; validate these additives do not interfere with readouts.

No buffer recipes or pH ranges are specified for this item.

Green Alternatives

As a small-molecule research ligand, BTZ043 itself is not substituted by a “greener reagent” in the traditional solvent/reagent sense. Green chemistry considerations primarily pertain to the choice of dissolution and handling media in assays.

Greener solvent considerations for preparing stocks and dilutions (general):

• Prefer minimal DMSO: While DMSO is relatively benign compared to many aprotic solvents, maintain the lowest feasible final DMSO concentration in aqueous systems to reduce environmental and biological impact.
• Ethanol vs DMF: If assay-compatible, ethanol can sometimes replace DMF as a less problematic organic co-solvent, though achievable solubility may be lower for hydrophobic heteroaromatics.

Comparison (general guidance):

• DMSO: High solvency, miscible with water; broadly acceptable in green chemistry frameworks; minimize volume where possible.
• Ethanol: Renewable sources available; good EHS profile; limited solvency for BTZ-class compounds.
• DMF/NMP: Powerful solvents but with more significant EHS concerns; avoid if DMSO or ethanol suffice.

Operational greener practices:

• Use microvolumes and high-concentration stocks to reduce solvent waste.
• Employ sealed microplates to limit evaporative losses.
• Consolidate solvent waste streams for proper recycling/disposal.

Note: The intrinsic structure of BTZ043 (aromatic nitro-heterocycle) dictates its solubility; “greener” alternatives relate to formulation and workflow rather than replacing the compound itself.

Pharmaceutical Uses

This product is supplied strictly for research use only. No clinical, diagnostic, or therapeutic applications are claimed or supported.

Context for discovery and development workflows (general):

• Role as a reference tool compound: BTZ-class molecules are frequently used in drug discovery to benchmark target engagement, to validate assays for enzymes in mycobacterial cell-wall biosynthesis, and to compare structure–activity relationships (SAR) across analog series.
• Formulation R&D: In preformulation-style laboratory studies, researchers may explore solubilization strategies (e.g., DMSO cosolvent systems, cyclodextrin inclusion, or micellar vehicles) purely to enable in vitro testing; such approaches remain research procedures and are not product specifications.
• Pharmacopeial status: Not a pharmacopoeial article. No compendial monograph is implied.

Any use in human or veterinary applications is prohibited. Refer to your institution’s policies and local regulations before employing this compound outside in vitro experimental settings.

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.

Literature/general physicochemical characteristics for benzothiazinone chemotypes (context only; not product specifications):

• Physical state: Typically isolated as a crystalline solid or amorphous powder.
• Solubility profile: Low aqueous solubility expected for aromatic heterocycles of this class; readily soluble in polar aprotic organic solvents such as DMSO and DMF; limited solubility in methanol/ethanol; poorly soluble in water and nonpolar hydrocarbons.
• Partitioning: Moderately lipophilic due to fused aromatic system and heteroatoms; logP/logD values in the mid-range are reported for related BTZs (literature), supporting membrane permeability in bacterial systems.
• UV–vis: Conjugated heteroaromatic systems typically show strong UV absorbance in the 230–320 nm region (literature), useful for HPLC-UV monitoring.
• Thermal behavior: Aromatic heterocyclic solids commonly show decomposition rather than clean boiling; melting points for related BTZ compounds are in the mid-to-high °C range (literature). Exact item MP/BP is not specified here.
• Stability: Stable under dry, dark, low-temperature storage; sensitive to prolonged exposure to light/heat and strong nucleophiles/bases that can open or react with the thiazinone core (literature).

Important: Where exact numeric values are required (mp, solubility at given T, logP, refractive index), consult the product’s CoA/Spec Sheet or primary literature for BTZ043. No numeric physical constants are specified for this item.

Quality & Grades

• Supplied grade: Moligand™

What Moligand™ denotes (general):

• Moligand™ products are intended for ligand screening, chemical biology, and discovery research. This typically emphasizes identity confirmation and suitability for biochemical/biophysical assays over bulk process impurities control. The focus is on small-molecule library quality appropriate for target engagement studies, in vitro profiling, or mechanistic enzymology.

What this means in practice:

• Identity and integrity: Expect analytical verification (e.g., NMR/LC–MS/HPLC) appropriate to a research ligand offering. Exact test items and acceptance criteria may vary; consult the CoA/Spec Sheet for this SKU for the current batch.
• Purity reporting: Specific purity percentage, residual solvents, water content, inorganic impurities, or stabilizers are Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoffs/metal content/peroxide levels: Not specified for this item; refer to CoA/Spec Sheet.

Selecting this item vs other grades:

• Choose Moligand™ when your application is target screening, mechanistic assays, or reference control studies requiring a characterized small molecule rather than bulk synthetic precursor grade.
• For regulated uses, GMP manufacturing, or quantitative bioanalysis requiring pharmacopoeial alignment, this research-only grade is not appropriate.

Documentation:

• Please review the batch CoA for analytical data, handling notes, and any lot-specific storage observations before initiating sensitive assays.

Reaction & Applications

This product is offered as a research ligand (Moligand™) rather than as a synthetic reagent; consequently, it is not typically employed as a stoichiometric reagent, catalyst, or solvent in organic reactions.

Research applications (literature/general for BTZ chemotype):

• Target engagement studies: Employed as a reference compound in biochemical assays interrogating mycobacterial arabinogalactan biosynthesis enzymes. The benzothiazinone core is associated in the literature with covalent trapping of flavin-dependent oxidoreductases following nitro-group bioactivation.
• Microbial pathway probing: Used to perturb cell-wall precursor processing in mycobacterial systems in vitro to dissect enzyme function and resistance mechanisms, e.g., site-directed mutagenesis of target cysteines and SAR comparisons.
• Biophysical profiling: Suitable for thermal shift assays (DSF), surface-based binding formats, and activity-based readouts when combined with appropriate reductants/cofactors.

Practical considerations:

• Solution preparation: Prepare concentrated DMSO stocks; verify solubility at intended assay temperature and ionic strength.
• Adsorption: Hydrophobic heteroaromatics can adsorb to plastics; prefer low-bind polypropylene or glass for low-nanomolar work.
• Controls: Include vehicle and inactivity controls (e.g., analogs lacking the nitro or with ring modifications) to benchmark specificity.

Note: If your intent is chemical synthesis using this molecule as a starting material or intermediate, consult specialized literature for benzothiazinone functionalization; this is not a common role for BTZ043 in routine synthetic chemistry.

Reaction Conditions

Because BTZ043 is supplied as a finished research ligand rather than a reagent, there are no item-specific reaction conditions to recommend.

General literature guidance relevant to assay preparation and handling:

• Stock solutions: Prepare at 10–50 mM in anhydrous DMSO under subdued light. Vortex and, if needed, warm gently (≤37 °C) to fully dissolve. Avoid prolonged heating.
• Dilution into assay: Add DMSO stocks to buffered systems with vigorous mixing; maintain final DMSO ≤0.5–1% unless your assay validates higher.
• Adsorption mitigation: For low-nanomolar assays, precondition plasticware with buffer or add minimal carrier protein (e.g., 0.01% BSA) if compatible, to limit non-specific binding.

If you intend to synthesize BTZ analogs (literature/general):

• Cyclization to form benzothiazinone cores often proceeds in polar aprotic solvents (e.g., DMF or acetonitrile) at 60–120 °C with acid or base catalysis; reaction times range from 1–16 h depending on precursors.
• Nitration or electrophilic substitutions on the aromatic ring should be done with careful temperature control due to exothermicity and to avoid over-substitution.

Important: None of the above constitutes item specifications. Consult primary literature for BTZ043-specific synthetic or assay conditions and adapt to your laboratory’s safety protocols.

Safety & Handling

Authoritative safety classification for this specific item:

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

General laboratory safety guidance (literature/general):

• Potential hazards: Aromatic nitro-containing heterocycles and activated electrophiles may present hazards of skin/eye irritation and organ toxicity upon prolonged exposure. Avoid inhalation of dust/particles and contact with skin or eyes.
• PPE: Use lab coat, safety goggles, and chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to minimize aerosolization.
• Incompatibilities: Avoid strong bases, strong nucleophiles, and reducing agents that may undesirably transform nitro-activated systems. Keep away from strong oxidants until compatibility is established.
• First aid (overview; defer to SDS): In case of eye/skin contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested or upon any exposure concern, seek medical attention and provide SDS to responders.
• Spill response: Avoid raising dust; collect mechanically and dispose of in accordance with local regulations. Decontaminate surfaces with appropriate organic solvent followed by detergent and water, per institutional practice.
• Waste: Dispose as organic hazardous waste. Avoid drain disposal.

Always consult the product-specific SDS for definitive hazard, exposure limits, and emergency measures.

Solvent Selection

Context: BTZ043 is a hydrophobic heteroaromatic small molecule used predominantly in biochemical and microbiological research assays rather than as a process solvent.

Solubility and solvent choices (literature/general):

• Primary stock solvent: DMSO is the standard choice for preparing concentrated stocks (e.g., 10–50 mM) due to high solubilizing power for benzothiazinone scaffolds and compatibility with most in vitro assays at low final DMSO percentages (≤0.5–1%).
• Alternative solvents: DMF can be used where DMSO is incompatible with a readout. Ethanol (absolute) may dissolve limited amounts but often at lower concentrations. Aqueous buffers typically require co-solvent (DMSO) or surfactant to avoid precipitation.
• Miscibility/compatibility: DMSO is miscible with water and buffers; titrate stocks into pre-warmed media with vigorous mixing to prevent local supersaturation.

Practical recommendations:

• Filter sterilization: If sterility is required, use 0.22 μm PTFE filters on diluted working solutions (avoid filtering highly concentrated DMSO stocks to protect membranes).
• Precipitation watch: On dilution into high-protein media or salt-rich buffers, monitor for haze/precipitate; adjust DMSO fraction or reduce final concentration.
• Light sensitivity: Prepare and dispense under subdued light to minimize potential photolysis of nitroaromatic motifs (general precaution). Store aliquots to minimize freeze–thaw.

Comparison snapshot (general):

• DMSO: Highest solubilization; broadly assay-compatible.
• DMF: Good solubility; less preferred in biological assays due to cytotoxicity concerns.
• Ethanol: Moderate solubility; volatile; often limited achievable stock molarity.

Storage & Reconstitution

Item-specific instructions:

• Storage conditions: Store at -80°C.
• Shipped in: Dry ice packs + Cold packs.
• Research use note: For research use only.

General handling and reconstitution guidance (non-spec; align with best practice):

• Upon receipt: Verify container integrity. Minimize time at ambient temperature; transfer immediately to -80°C storage.
• Aliquoting: If supplied as a solid, consider subdividing into single-use aliquots in an inert, dry environment to avoid repeated freeze–thaw and moisture uptake. If supplied as a solution, aliquot under low-light conditions.
• Stock preparation: Dissolve in anhydrous DMSO to prepare a concentrated stock (e.g., 10–50 mM). Mix thoroughly; gentle warming (≤37°C) may assist dissolution. Record final concentration and date.
• Working solutions: Dilute stocks into assay buffer/media with vigorous mixing to the desired final concentration, keeping DMSO content as low as feasible (commonly ≤0.5–1%). Prepare fresh working solutions and use promptly to limit degradation.
• Stability considerations: Protect from light and moisture. Avoid repeated freeze–thaw cycles; store aliquots at -80°C tightly sealed. Discard solutions showing precipitation, discoloration, or unexpected assay behavior.

For definitive instructions (including any lot-specific stabilizers or form), always consult the CoA/Spec Sheet and the SDS for this SKU.

Structure & Identity

Brief overview: BTZ043 is a small-molecule benzothiazinone-class research ligand supplied in Aladdin’s Moligand™ format for screening and chemical biology.

• SKU: B1496431
• Product name: BTZ043
• CAS: 1161233-85-7
• PubChem CID: 42609849
• 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 (literature/general):

• Core scaffold: 1,3-benzothiazin-4-one (benzothiazinone) fused bicyclic system containing both sulfur and nitrogen within a six-membered thiazinone ring fused to a benzene ring.
• Electrophilic/nitro functionality: Members of this class typically bear an electron-withdrawing nitro substituent on the benzothiazinone ring system, which is implicated in bioactivation and covalent target engagement in mycobacterial enzymes (literature).
• Aromaticity: Polycyclic aromatic framework with heteroatoms (N, S, O) supporting conjugation and ring planarity (literature/general description).
• 2D description: A benzene ring fused to a heterocycle that contains sulfur and nitrogen; the heterocycle carries a carbonyl (lactam-like) at the 4-position (thiazinone). Substitution patterns on the aromatic ring are characteristic of the BTZ chemotype (literature).

Notes:

• Exact stereochemistry: BTZ043 is typically represented as an achiral small molecule (literature).
• For definitive identifiers (SMILES/InChIKey) used in your regulatory or informatics systems, please consult the item’s CoA/Spec Sheet or PubChem record (CID 42609849).

Synthetic Utility

Primary role: BTZ043 is offered as a screening ligand rather than a synthetic building block. Nonetheless, knowledge of benzothiazinone chemistry can aid in analog synthesis and mechanistic studies (literature/general):

• Functional group landscape: The 1,3-benzothiazin-4-one core features an activated carbonyl within a heterocycle and an electron-deficient aromatic system (often bearing a nitro group), enabling selective electrophilic behavior in biological contexts and guiding derivatization strategies.
• Typical transformations (for analog/SAR work):
  • Introduction or modification of substituents on the benzothiazinone ring via electrophilic aromatic substitution or modern cross-couplings when suitably functionalized.
  • Manipulation of the nitro handle (carefully, due to reactivity and safety) to probe bioactivation-dependent covalency.
  • Lactam/heterocycle formation strategies from thioamide/aminothiol precursors to assemble the benzothiazinone core.
• Retrosynthetic considerations: Construction of the thiazinone ring via intramolecular cyclizations (e.g., acylation/condensation of o-aminothiobenzamides) is documented for BTZ scaffolds (literature); side-chain diversity can be introduced prior to ring closure or via late-stage substitution.

Caveats:

• The compound is not commonly used as a reagent in transformations; it is typically the synthetic endpoint for biological evaluation.
• Any synthetic manipulation should consider potential sensitivity of the nitroaromatic and heterocyclic core to strong nucleophiles/bases or reductants.

Target Specificity

Not specified for this item; refer to CoA/Spec Sheet.

Note: This section typically applies to biological macromolecules (e.g., antibodies) where clone, epitope, and species reactivity are defined. For small molecules like BTZ043, specific target and selectivity data are not provided in the product data. Literature commonly discusses BTZ-class interactions with mycobacterial enzymes, but no item-certified target specificity is stated here.