Vinaxanthone

SKU: orb1738525

Description

Vinaxanthone (SM-345431) is a natural product from Penicillium chrysogenum that acts as a selective inhibitor of semaphorin3A and the bacterial enoyl-ACP reductase (FabI). It demonstrates potent in vitro antimicrobial activity against Staphylococcus aureus by disrupting fatty acid biosynthesis. This compound is a valuable tool for researching bacterial pathogenesis and host-pathogen interactions.

Research Area

Infectious Disease & Virology, Metabolism Research

Key Properties

• CAS Number: 133293-89-7
• MW: 576.42
• Purity: >99.99% (May vary between batches)
• Formula: C₂₈H₁₆O₁₄
• SMILES: C(C)(=O)C=1C(=C(C(C)=O)C=C2C1OC=3C(C2=O)=C(C(O)=O)C(O)=C(O)C3)C=4C(=O)C=5C(OC4)=CC(O)=C(O)C5C(O)=O
• Target: Phospholipase,Antibacterial
• Solubility: DMSO:80 mg/mL (138.79 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:3.3 mg/mL (5.72 mM)

Bioactivity

• Target IC50:
  PA:9.3 μM (mouse colon 26 adenocarcinoma)|PA:44 μM (NIH3T3 cell)|PA:5.4 μM (Rat brain)
• In Vivo:
  Vinaxanthone (SM-345431), administered by subconjunctival injection at a concentration of 0.1 mg/mL every two days for 3 weeks, accelerates peripheral nerve regeneration and functional recovery in a mouse corneal transplantation model.Vinaxanthone (SEMA3A-I), given by intraperitoneal injection at a dose of 20 µg, protects against podocyte injury induced by Adriamycin in a mouse model through an anti-apoptotic mechanism.
• In Vitro:
  Vinaxanthone exhibits selective inhibitory activity against phospholipase C (PLC) in rat brain, mouse colon 26 adenocarcinoma, and mouse fibroblast NIH3T3 cells, with IC50 values of 5.4, 9.3, and 44 μM, respectively.At a concentration of 0.1 mg/mL for 24 hours, Vinaxanthone enhances peripheral nerve regeneration and induces limited neovascularization in the cornea.At a concentration of 0.5 μM for 20 minutes, Vinaxanthone may protect against Doxorubicin-induced apoptosis in foot cells.In the range of 0.1-1 μM for 24 hours, Vinaxanthone improves the changes in renal tubular cell characteristics induced by TGF-β1.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Antibacterial, PLC, enoyl-acyl carrier protein reductase (FabI), SM345431, SM-345431, SM 345431, Vinaxanthone

Compound Identifiers

PubChem CID

5487402