| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Source | Plant — Rutaceae Murraya tetramera C. C. Huang |
| Molecular weight | |
| Molecular formula | C14H13NO |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Murrayafoline A is a carbazole alkaloid that can be extracted from Murraya tetramera. It targets Specificity protein 1 (Sp1) directly, thereby inhibiting the NF-κB and MAPK signaling pathways, and it induces G0/G1-phase arrest in platelet-derived growth factor (PDGF)-stimulated vascular smooth muscle cells. The compound attenuates the Wnt/β-catenin pathway by promoting degradation of intracellular β-catenin protein, enhances contraction of rat ventricular myocytes and the L-type calcium current through activation of protein kinase C, and inhibits LPS-induced neuroinflammation in vivo; it can therefore be applied to the study of inflammation, vascular complications and colon cancer[1][2][3][4]. It is supplied as a white to light yellow solid (C14H13NO, MW 211.26) at 99.73% purity.
Physical & Chemical Properties
| CAS Number | 4532-33-6 |
|---|---|
| Molecular Formula | C14H13NO |
| Molecular Weight | 211.26 g/mol |
| Purity | 99.73% |
| Appearance | Solid |
| Color | White to light yellow |
| Structure Classification | Alkaloids Carbazole Alkaloids |
| SMILES | CC1=CC2=C(C(=C1)OC)NC3=CC=CC=C23 |
| Signaling Pathway | NF-κB; MAPK/ERK Pathway; Immunology/Inflammation; Stem Cell/Wnt |
| Initial Source | Plant — Rutaceae Murraya tetramera C. C. Huang |
| Solubility | In Vitro: DMSO: 100 mg/mL (473.35 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) H2O: < 0.1 mg/mL (insoluble) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 6 months; -20°C, 1 month. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (473.35 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
| H2O | < 0.1 mg/mL | insoluble |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | ≥ 2.5 mg/mL (11.83 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Protocol 2
| Composition | 10% DMSO + 90% Corn Oil |
|---|---|
| Result | ≥ 2.5 mg/mL (11.83 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). Use with caution if continuous dosing will exceed two weeks. For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL corn oil. |
Data provided by the manufacturer.
In Vitro
In LPS-induced BV-2 microglial cells, Murrayafoline A (5-20 μM, 24 h) potently suppresses production of the neuroinflammation mediators nitric oxide (NO), TNF-α, IL-6 and IL-1β, and Sp1 knockdown can significantly antagonize this effect[1]. Murrayafoline A (20 μM, 2 h) interacts directly with Sp1 in BV-2 cells, as confirmed by surface plasmon resonance (SPR), with a dissociation constant (KD) of 11.34 pM[1]. In LPS-induced BV-2 cells, Murrayafoline A (20 μM) inhibits the IKKβ/NF-κB and p38/JNK MAPKs pathways, and Sp1 knockdown can markedly reverse this inhibition[1]. Murrayafoline A (1-5 μM, 24 h) inhibits PDGF-BB-stimulated proliferation and DNA synthesis in vascular smooth muscle cells (VSMCs) and induces a G0/G1-phase arrest[2]. In PDGF-BB-stimulated VSMCs, Murrayafoline A (1-5 μM) lowers expression of cyclin D1, cyclin E, CDK2, CDK4, and PCNA and inhibits pRb phosphorylation[2]. In HEK293 reporter cells, Murrayafoline A (5-40 μM, 15 h) reduces LiCl- and Wnt3a-CM-induced TOPFlash reporter activity and SEAP activity in a dose-dependent manner, with no effect on FOPFlash activity[3]. Murrayafoline A (20-40 μM, 15 h) lowers the cytosolic β-catenin level in LiCl- and Wnt3a-CM-treated HEK293 reporter cells[3]. In SW480 and HCT-116 colon cancer cells, Murrayafoline A (10-80 μM, 15-48 h) lowers cytosolic β-catenin, cyclin D1 and c-myc levels, and it inhibits proliferation of SW480, DLD-1, HCT-116 and LS174T colon cancer cells in a dose-dependent manner[3]. In rat ventricular myocytes, Murrayafoline A (25 μM, 2 min) increases cell shortening, L-type Ca2+ current, and PKC phosphorylation, and enhances the rate of contraction[4].
Cell Cycle Analysis[2]
| Cell Line | Vascular smooth muscle cells (VSMCs) |
|---|---|
| Concentration | 1, 3, 5 μM |
| Incubation Time | 24 h |
| Result | Increased the cell population in G0/G1phase. Decreased the S, G2, and M phases. |
Cell Cycle Analysis[3]
| Cell Line | SW480, DLD-1, HCT-116 and LS174T colon cancer cells |
|---|---|
| Concentration | 5, 10, 20, 40, 80 μM |
| Incubation Time | 48 h |
| Result | Inhibited the proliferation of SW480, DLD-1, HCT-116 and LS174T colon cancer cells. |
In Vivo
In mice with LPS-induced neuroinflammation, Murrayafoline A (10-50 mg/kg, 1h pretreatment, single dose) shows excellent anti-neuroinflammatory efficacy[1].
| Animal Model | LPS (1.5 mg/kg) was used to induce neuroinflammation in 6-7-week-old male Balb/c mice[1] |
|---|---|
| Dosage | 10, 50 mg/kg |
| Administration | 1h pretreatment for a single dose |
| Result | Reduced the expression of Iba-1, TNF-α, and IL-6 in the brains of LPS-induced male Balb/c mice. Increased the number of Nissl bodies in the brains of LPS-induced male Balb/c mice. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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