E3330 - 10mM in DMSO , DNA-(apurinic or apyrimidinic site) lyase inhibitor, CAS No.136164-66-4, DNA-(apurinic or apyrimidinic site) lyase inhibitor

CAS: 136164-66-4 Cat. No.: E421373 Formula: C21H30O6 Molecular Weight: 378.46 EC Number: 693-030-4
AVAILABLE TO ORDER
GRADE & PURITY 10mM in DMSO
Synonyms
E3330 | E-3330 | EX-A2212 | Undecanoic acid, 2-((4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene)-, (E)- | (2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]undecanoic acid | (2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-d
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
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Size
Germany (EU)
USA*
Price
Qty
1ml
E421373-1ml
Made to order · 8–12 wks
€209.91
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Why this grade

10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

📚

Literature proof

Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

Information

E3330 E3330 (APX-3330) is a potent and selective APE1(Ref-1) inhibitor, which suppressed NF-kappa B DNA-binding activity.

Targets

NF-κB ; APE1(Ref-1)

In vitro

E3330 affects hemangioblast development in vitro via inhibition of Ape1 redox activity. E3330 inhibits the growth of human pancreatic cancer cell line PANC1, XPA1, MIAPACA, BxPC3, and PK9. E3330 also promotes exit of cell cycle in PANC1 cells, inhibits the DNA-Binding activity of HIF-1α and migration of pancreatic cancer cells. In JHH6 cells, E3330 prevents the functional activation of NF-κB via the alteration of APE1 subcellular trafficking and reduces IL-6 and IL-8 expression induced by TNF-α and FAs accumulation through blockage of the redox-mediated activation of NF-κB.

In vivo

In mice with endotoxin-mediated hepatitis, E3330 (300 mg/kg, p.o.) attenuates the elevation of plasma tumor necrosis factor activity and protectes mice from liver injury. In Rat model, E3330 (100 mg/kg, p.o.) also protectes rats from severe liver injury induced with endotoxin plus galactosamine.

Cell Research(from reference)

Cell lines:PANC1 cells 

Concentrations:~30 μM 

Incubation Time:72 hours 

Specifications

Synonyms
E3330 | E-3330 | EX-A2212 | Undecanoic acid, 2-((4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene)-, (E)- | (2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]undecanoic acid | (2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-d
Specifications & Purity
10mM in DMSO
Biochemical and Physiological Mechanisms
E3330 (APX-3330) is a potent and selective APE1(Ref-1) inhibitor, which suppressed NF-kappa B DNA-binding activity.
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.
Action Type
INHIBITOR
Mechanism of action
DNA-(apurinic or apyrimidinic site) lyase inhibitor
Product Properties
alogp
5.3
Names and Identifiers
Canonical Smiles
CCCCCCCCCC(=CC1=C(C(=O)C(=C(C1=O)OC)OC)C)C(=O)O
IUPAC Name
(2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid
InChIKey
AALSSIXXBDPENJ-FYWRMAATSA-N
INCHI
1S/C21H30O6/c1-5-6-7-8-9-10-11-12-15(21(24)25)13-16-14(2)17(22)19(26-3)20(27-4)18(16)23/h13H,5-12H2,1-4H3,(H,24,25)/b15-13+
Isomeric SMILES
CCCCCCCCC/C(=C\C1=C(C(=O)C(=C(C1=O)OC)OC)C)/C(=O)O
Molecular Weight
378.46
Reaxy-Rn
24609616
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24609616&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassQuinone and hydroquinone lipids
Intermediate Tree Nodes Prenylquinones
Direct ParentUbiquinones
Alternative Parents P-benzoquinones  Medium-chain fatty acids  Methyl-branched fatty acids  Unsaturated fatty acids  Vinylogous esters  Monocarboxylic acids and derivatives  Carboxylic acids  Organic oxides  Hydrocarbon derivatives  
Molecular FrameworkAliphatic homomonocyclic compounds
Substituents Ubiquinone skeleton - P-benzoquinone - Quinone - Medium-chain fatty acid - Branched fatty acid - Methyl-branched fatty acid - Fatty acyl - Fatty acid - Unsaturated fatty acid - Vinylogous ester - Ketone - Cyclic ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Carbonyl group - Organic oxygen compound - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).
External Descriptors Not available
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
Molecular Weight378.500 g/mol
XLogP35.300
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count12
Exact Mass378.204 Da
Monoisotopic Mass378.204 Da
Topological Polar Surface Area89.900 Ų
Heavy Atom Count27
Formal Charge0
Complexity666.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds1
Covalently-Bonded Unit Count1
Solution Calculators
Reviews

Customer Reviews

Application Protocols
  • Tested applications, recommended concentrations/dilutions, and positive controls: Not specified for this item; refer to CoA/Spec Sheet.

  • General research practice notes (not product‑validated protocols):

    • Establish vehicle controls matching final solvent content.
    • Begin with a concentration range-finding study (e.g., low μM to tens of μM) and include cytotoxicity counterscreens.
    • Confirm reproducibility across biological replicates and, where relevant, include orthogonal assays to support conclusions.
Biological Roles
  • Literature context (not item specification):

    • E3330 (also known as APX‑3330) is frequently reported as a small‑molecule modulator of APE1/Ref‑1 redox function. APE1/Ref‑1 is a bifunctional protein with (i) DNA base excision repair endonuclease activity and (ii) redox regulation of transcription factors via reduction of critical cysteines.
    • Through modulation of APE1/Ref‑1 redox activity, E3330 has been used to study the redox-dependent regulation of transcription factors such as NF‑κB, HIF‑1, STAT3, and AP‑1 in various cellular models.
    • Importantly, literature often distinguishes redox modulation from inhibition of APE1 endonuclease activity, allowing selective interrogation of signaling versus DNA-repair roles.
  • Research implications:

    • Tool for dissecting redox signaling pathways, oxidative stress responses, and gene expression programs influenced by APE1/Ref‑1.
    • Employed in studies exploring cellular adaptation to hypoxia, inflammation, and metabolic stress, where thiol redox state affects transcriptional networks.
  • Experimental considerations (general):

    • Validate target engagement with orthogonal assays (e.g., redox Westerns, transcription factor DNA‑binding assays, cellular ROS probes) and consider potential off‑target redox effects.
    • Titrate concentrations to separate on‑target signaling effects from nonspecific oxidative stress or cytotoxicity; include appropriate vehicle controls and, where possible, genetic controls (siRNA/CRISPR knockdown of APE1/Ref‑1).

No medical or clinical claims are made. Use is for research only.

Buffer Applications
  • This compound is not a buffering agent and is not typically used to prepare pH buffer systems.
  • For experimental use, it may be diluted into biological buffers (e.g., PBS, HBSS, culture media) from an organic stock solution. Match vehicle controls to the final solvent concentration to maintain constant buffer composition.
Green Alternatives
  • As a bioactive tool compound, the concept of a “green alternative” pertains more to formulation and handling than to replacing the active itself.

  • Greener solvent/formulation choices (general guidance):

    • Prefer water-based systems with minimal DMSO by using co-solubilizers (cyclodextrins), low percentages of biocompatible surfactants, or buffered cosolvent blends.
    • When organic stock solutions are necessary, minimize solvent volume and select lower-toxicity options (DMSO over DMF; ethanol over chlorinated solvents) consistent with assay requirements.
  • Process considerations:

    • Reduce waste by preparing small, single-use aliquots to avoid disposal of degraded material.
    • Use amber vials and cold-chain logistics to extend solution stability, thereby avoiding repeated synthesis/purchase and reducing environmental footprint.
  • Comparison of common dissolution vehicles (general):

    • DMSO: High solvency, low volatility; accepted for bioassays at low v/v but consider aquatic toxicity in waste streams.
    • Ethanol: Renewable feedstock potential; higher volatility eases removal but may limit achievable concentrations.
    • PEG‑400 or HP‑β‑cyclodextrin: Enable aqueous delivery; assess biological compatibility and potential assay interference.
  • Note: No item-specific green certifications or solvent recommendations are provided; consult institutional green-chemistry guidelines.

Pharmaceutical Uses
  • Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

  • Context (general; non-clinical):

    • In research settings, small-molecule tools like E3330 are formulated for in vitro and in vivo studies using standard vehicles (e.g., DMSO, PEG‑based cosolvents, cyclodextrins) to evaluate pharmacology. This catalog item is designated for research use only.
    • No therapeutic, diagnostic, or clinical use is claimed or supported by this listing. Any formulation discussion is provided solely to aid laboratory research design.
Physical Properties
  • Item-specific physicochemical data:

    • Melting point, boiling point, density, solubility, logP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
  • Practical handling observations (general for bioactive small molecules; not specifications):

    • Many hydrophobic tool compounds similar to E3330 are readily dissolved in anhydrous DMSO to prepare concentrated stocks (e.g., 10–50 mM) and then diluted into aqueous media immediately before use.
    • Aqueous solubility is often limited without co-solvent; gentle warming (room temperature to 37 °C) and vortexing/sonication can assist dissolution. Avoid prolonged heating or high pH unless validated.
    • Light sensitivity is possible for conjugated systems; protect solutions from light when feasible.
  • Literature notes (where applicable):

    • Detailed physical constants for APX‑3330 (E3330) vary by source and form; consult primary literature or the manufacturer CoA for definitive values prior to method development.
Quality and Grades
  • Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

  • Interpreting common grades (general guidance):

    • Research grade: Suitable for discovery biology and chemical research; purity typically verified by HPLC/LC–MS and/or NMR.
    • High-purity/assay grade (if provided on CoA): Supports quantitative bioassays where impurities may confound readouts; low residual solvents and defined potency.
    • Stabilizers/salt form: If the CoA indicates a particular solvate/salt or stabilizer, note the effective molecular weight for molarity calculations and any effects on solubility or assay background.
  • Identity and purity confirmation (recommended practice):

    • Verify by independent analytical methods as appropriate for your workflow: HPLC/UPLC purity, HRMS, NMR, and water/volatile content by KF/GC.
    • For potency-critical work, consider system-suitability tests (e.g., reference control curves in your assay) to detect degradation or adsorption losses.
  • Documentation: Use the batch-specific CoA for exact assay purity, residual solvent profile, counter-ion/solvate content, and any stabilizers.

Reaction and Applications
  • This product is primarily used as a bioactive reference compound in research, rather than as a synthetic reagent. Consequently, it is not typically employed to drive organic reactions (e.g., coupling, reductions, etc.).

  • Research application context (literature, general):

    • E3330 (APX‑3330) is widely described as a modulator of APE1/Ref‑1 redox signaling. It has been used in biochemical and cell-based studies investigating redox-dependent activation of transcription factors.
    • Typical use-cases include target engagement studies, pathway validation, and phenotypic assays where redox signaling is implicated.
  • Practical assay considerations (general guidance):

    • Establish solvent controls matched to the final DMSO/ethanol content.
    • Include time-course and washout designs to distinguish reversible target modulation from cytotoxic or off-target effects.
    • Consider orthogonal readouts (e.g., reporter assays, EMSA, redox-sensitive fluorescent probes) to confirm on-pathway effects.
  • For synthetic chemists: If you intend to derivatize or use this scaffold for SAR, consult primary structural literature and ensure you have the necessary analytical confirmation; no reaction-specific data are provided for this catalog item.

Reaction Conditions
  • Not applicable as a synthetic reagent: No item-specific reaction conditions (solvent, temperature, catalysts) are provided for promoting chemical transformations.

  • Solution preparation for assays (general lab guidance; not specification):

    • Prepare concentrated anhydrous DMSO stock (e.g., 10–50 mM). Mix thoroughly by vortexing and, if needed, brief sonication at room temperature. Protect from light if the compound is photosensitive (verify on CoA/SDS).
    • For aqueous dilution, add the organic stock slowly into vigorously stirred buffer/media to minimize precipitation. Maintain final DMSO at ≤0.1–0.5% v/v for delicate cell systems.
    • For sterile applications, pass through 0.22 μm PTFE/PES filters. Avoid adsorptive plastics when possible; use low‑binding tubes and glass vials.
  • Stability (general):

    • Aliquot and store frozen to avoid repeated freeze–thaw. Track solution age; many small‑molecule solutions are best used within days to a few weeks depending on storage conditions. Confirm stability by LC–MS/HPLC as appropriate.
Safety and Handling
  • GHS and hazard information (item-specific):

    • Signal Word: Not specified for this item; refer to SDS.
    • H‑Statements: Not specified for this item; refer to SDS.
    • GHS Classification/Pictograms: Not specified for this item; refer to SDS.
  • General laboratory precautions (good practice; defer to SDS for authority):

    • Handle in a chemical fume hood and avoid inhalation, ingestion, and skin/eye contact. Wear appropriate PPE: lab coat, safety glasses, and chemically resistant gloves.
    • Prevent dust or aerosol generation. Use closed containers for weighing and solution prep. Wash hands and decontaminate benches after use.
    • Avoid incompatible conditions common to organic small molecules: strong oxidizers or reducers, strong acids/bases, and excessive heat or UV exposure unless compatibility is documented.
    • For bioassay use, prepare solutions fresh or from frozen aliquots using sterile technique if sterility is required for cell culture.
  • First-aid overview (general):

    • Skin/eye contact: Rinse with water for at least 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; seek medical attention. Do not induce vomiting unless directed by medical personnel.
  • Spills/waste: Absorb small spills with inert material, place in chemical waste. Dispose of according to institutional and local regulations.

Always consult the product-specific SDS for authoritative hazard classification and response measures.

Solvent Selection
  • Item-specific solubility: Not specified for this item; refer to CoA/Spec Sheet.

  • General solvent guidance for small-molecule bioactives (literature/practice):

    • Primary stock solvent: Anhydrous DMSO is commonly used due to high solvating power and compatibility with biological assays at low final percentages (≤0.1–0.5% v/v).
    • Secondary co-solvents: Ethanol or DMF can be used where DMSO is undesirable, with careful consideration of cell compatibility and final solvent percentage.
    • Aqueous formulation aids: Surfactants (e.g., 0.01–0.05% Tween‑20), cyclodextrins, or serum/albumin may reduce precipitation upon dilution; validate for your assay to avoid confounding effects.
  • Practical tips:

    • Prepare concentrated DMSO stocks (e.g., 10–50 mM) and perform serial dilutions to minimize precipitation. Add stock slowly to vigorously mixed buffer/media.
    • Filter sterilize through 0.22 μm PTFE/PES if sterility is required and the compound is compatible. Avoid nylon if the compound adsorbs to polyamides.
    • Minimize freeze–thaw and exposure to moisture; use anhydrous solvent and nitrogen blanket where feasible.
  • Comparison (general):

    • DMSO: Highest solubilizing power; widely accepted in cell assays but may affect membrane integrity at >0.5–1%.
    • Ethanol: Lower solvency; volatile; often limited to ≤0.1–0.5% in sensitive systems.
    • PEG‑400/propylene glycol: Useful for in vivo formulation research; viscosity and assay interference must be considered.
Storage and Reconstitution
  • Item-specific conditions (from Product Data):

    • Storage temperature: Store at −80 °C.
    • Shipping: Dry ice packs + Cold packs.
  • Reconstitution (general guidance; verify with CoA):

    • Allow the container to equilibrate to room temperature in a desiccated environment before opening to avoid moisture condensation.
    • Prepare a concentrated stock in anhydrous DMSO (e.g., 10–50 mM) or another suitable solvent validated for your assay. Mix thoroughly. If sterility is required, filter through 0.22 μm PTFE/PES.
    • Aliquot into low‑binding, amber vials to minimize adsorption and light exposure. Flush headspace with inert gas if long-term storage is anticipated.
  • Storage of solutions (general):

    • Store aliquots at −80 °C. Avoid repeated freeze–thaw cycles; thaw once, use immediately, and discard leftovers or keep a strict usage log.
    • Protect from light and moisture. Periodically assess integrity by HPLC/LC‑MS, especially for solutions older than 1–2 weeks at 4 °C or −20 °C.
  • Stability note: No item-specific shelf-life or stability data are provided; consult the batch CoA and perform in‑house verification for critical applications.

Structure and Identity
  • Item-specific identifiers (from Product Data):

    • SKU: E421373
    • Product Name: E3330
    • CAS: 136164-66-4
    • InChIKey: 320 (as provided; appears incomplete — verify against CoA/SDS)
    • 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.
  • Common literature naming/context (for scientific orientation; not item specification):

    • E3330 is widely referenced in the literature as APX‑3330, a small-molecule modulator of APE1/Ref‑1 redox signaling. Confirm exact structure and identifiers on the CoA before use.
  • Structural features (literature, general):

    • Reported as an aromatic-containing small molecule with heteroatoms consistent with redox activity; often discussed in the context of interacting with redox-sensitive cysteines of APE1/Ref‑1. For structural drawings and stereochemistry, consult primary literature and the CoA.
  • 2D structure description (general):

    • Typically depicted as a rigid, polycyclic/aryl-bearing framework with conjugation and polar functional groups enabling protein interaction; exact ring systems and substituents must be confirmed from the official specification sheet for this catalog item.
Synthetic Utility
  • This product is supplied as a discrete bioactive small molecule and is not typically employed as a general synthetic reagent or building block.

  • For medicinal or synthetic chemistry efforts (general guidance):

    • Researchers may use the reported scaffold of E3330 (APX‑3330, literature) to design analogs for SAR around APE1/Ref‑1 redox modulation. However, this requires independent synthesis and full analytical verification; no derivative chemistry guidance is provided for this catalog item.
    • If derivatization is attempted, ensure compatibility of any functional groups with standard coupling, protection/deprotection, and oxidation/reduction steps; confirm stability under the planned conditions.
  • Bottom line: Treat this compound as a reference standard/tool compound rather than a reagent for promoting transformations.

Target Specificity
  • Item-specific, experimentally verified target information: Not specified for this item; refer to CoA/Spec Sheet and any provided validation data.

  • Note: While E3330 is discussed in the literature as a modulator of APE1/Ref‑1 redox signaling, no target-binding data or specificity metrics are provided in this product listing. Users should validate target engagement within their own assay systems.

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