1. Product Overview
Sanguinarine chloride (CAS 135096-78-5), systematically named 13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride, is a quaternary benzophenanthridine alkaloid derived from plants of the Papaveraceae and Fumariaceae families (e.g., Sanguinaria canadensis, Chelidonium majus). With the molecular formula C₂₀H₁₄ClNO₄ and a molecular weight of 367.78 g/mol (free base MW 332.33), it appears as an orange-red to reddish-brown crystalline powder. Sanguinarine chloride is a potent inhibitor of nuclear factor-kappa B (NF-κB) DNA binding and translocation (IC₅₀ ~1–5 µM), inhibits topoisomerase II (catenation/decatenation), and intercalates into DNA (preferentially GC-rich sequences). It induces reactive oxygen species (ROS), causes mitochondrial depolarization, and triggers apoptosis in various cancer cell lines. Additionally, it exhibits antimicrobial and anti-inflammatory properties at sub-cytotoxic concentrations. This product is supplied exclusively for laboratory research use and is not intended for clinical, diagnostic, veterinary, food (though historically used in oral care), or cosmetic applications.
2. Key Features and Advantages
• Potent NF-κB inhibition: Blocks IκBα phosphorylation and subsequent p65 nuclear translocation; inhibits NF-κB–dependent luciferase reporter activity (IC₅₀ ~1–3 µM in cells).
• Dual topoisomerase II & DNA intercalation: Inhibits topo II catalytic activity and intercalates into DNA (binding constant K ~10⁴–10⁵ M⁻¹), useful for studying DNA damage response and cell cycle arrest (G2/M).
• Pro-apoptotic & ROS-inducing: Triggers caspase-3/7 activation, PARP cleavage, Bax/Bak upregulation, and mitochondrial cytochrome c release in a concentration- and time-dependent manner.
• Antimicrobial & anti-inflammatory: Active against Gram-positive bacteria (including MRSA at 2–8 µg/mL) and inhibits pro-inflammatory cytokine (TNF-α, IL-6, iNOS) production in macrophages.
• High purity: Typically ≥98% by HPLC (suppliers offer 98–99%+), suitable for MTT/XTT viability, Annexin V/PI flow, Western blot (NF-κB p65, IκBα, cleaved caspase-3), and DNA binding assays (EB/AO, DAPI displacement).
• Good solubility in mild acid: Soluble in water (~1–2 mg/mL with slight yellow fluorescence), DMSO (≥10 mg/mL; prepare fresh 5–10 mM stock, protect from light), ethanol; solutions are photosensitive and pH-sensitive (converts to sanguinarine free base at alkaline pH, changing color from orange-red to yellow-brown).
3. Main Applications
• NF-κB signaling research: Evaluating inhibition of TNF-α– or LPS-induced NF-κB activation, IκBα degradation, and downstream target gene expression (COX-2, cyclin D1, Bcl-2) in cancer and immune cells.
• Antitumor mechanism studies: Assessing apoptosis induction, G2/M arrest, ROS generation (DCFDA), mitochondrial membrane potential (JC-1/Rh123), and DNA damage (γH2AX, comet assay) in HeLa, MCF-7, A549, etc.
• Antimicrobial & anti-biofilm assays: Testing bactericidal/fungicidal activity (MIC determination), biofilm disruption in Staphylococcus aureus and Candida spp.
• DNA–small molecule interaction: Spectroscopic studies of intercalation (hypochromicity, red-shift in UV-vis), thermal denaturation (ΔTm), and competition assays with ethidium bromide.
• Traditional medicine & natural product research: Quantification in plant extracts by HPLC, studying alkaloid metabolism, and comparing biological activities among benzophenanthridine alkaloids (chelerythrine, berberine, sanguinarine).
4. Technical Specifications
5. Storage and Handling
• Store the powdered compound sealed with desiccant, strictly protected from light (amber vial or foil-wrapped); recommended storage at -20°C (long term 2 years) or 4°C (short term ≤6 months). For DMSO or aqueous stock solutions, prepare fresh when possible; if storing, aliquot and keep at -20°C wrapped in foil (3–6 months stable); avoid repeated freeze–thaw cycles. Typical working stocks are 5–10 mM in DMSO or PBS (pH 5.5–7.0), protected from light.
• Before opening, allow the sealed vial to warm to room temperature to prevent moisture condensation. Keep container tightly closed and wrapped in aluminum foil when not in use. Note the color change with pH—orange-red indicates protonated/cationic form (active); yellow-brown indicates free base (less active/neutral form at high pH).
• Handle in a well-ventilated area or fume hood. Use personal protective equipment including safety glasses, nitrile gloves, and a lab coat. Avoid inhalation of dust and contact with skin or eyes. Sanguinarine is a potent bioactive alkaloid—wash hands thoroughly after handling. Solutions may stain surfaces and plastics orange-red.
• Intended exclusively for laboratory research by qualified personnel; not for human or veterinary use, food additive, or oral care product formulation (despite historical use in dentifrices—this material is research-grade only).
6. Safety Overview
• Sanguinarine chloride is a potent bioactive plant alkaloid with cytotoxicity (IC₅₀ 0.5–5 µM in many cancer lines), mutagenic potential in bacterial assays (Ames test mixed results—frame-shift mutagenic in TA98 with S9), and genotoxic effects reported in high-dose animal studies. Treat as hazardous: may cause severe irritation to eyes, skin, and respiratory system; suspected carcinogen/mutagen at high exposure levels.
• In case of eye contact, rinse immediately with plenty of running water for at least 15 minutes and seek immediate medical attention. In case of skin contact, wash thoroughly with soap and water for several minutes.
• If inhaled, move the person to fresh air and keep at rest in a position comfortable for breathing; seek medical advice promptly. If ingested, rinse mouth and seek emergency medical attention—do not induce vomiting.
• Use appropriate engineering controls (fume hood, closed handling) and personal protective equipment (safety goggles, nitrile gloves, double gloving recommended for powder, lab coat, face shield if weighing). Avoid generating dust; work under reduced light if possible due to photosensitivity.
• Dispose of in accordance with local regulations for hazardous chemical and cytotoxic/natural toxin waste. Do not discharge into drains, waterways, or soil.
• For detailed safety information, refer to the applicable Safety Data Sheet (SDS) prior to handling; many institutions require special authorization for benzophenanthridine alkaloid work.
