SML1131

Fosbretabulin disodium

≥98% (HPLC)

• Synonym(s): 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl disodium phosphate, CA4P, Combretastatin A4 phosphate disodium
• Empirical Formula (Hill Notation): C₁₈H₁₉O₈P · 2Na
• CAS Number: 168555-66-6
• Molecular Weight: 440.29
• MDL number: MFCD00943911
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825668

Properties

• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: H₂O: 5 mg/mL, clear
• storage temp.: −20°C
• SMILES string: [O-]P(OC1=CC(/C=C\C2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC)([O-])=O.[Na+].[Na+]
• InChI: 1S/C18H21O8P.2Na/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3;;/h5-11H,1-4H3,(H2,19,20,21);;/q;2*+1/p-2/b6-5-;;
• InChI key: VXNQMUVMEIGUJW-XNOMRPDFSA-L
• Gene Information: human ... TUBA1A(7846) , TUBA1B(10376) , TUBA1C(84790) , TUBA3C(7278) , TUBA3E(112714) , TUBA4A(7277) , TUBB(203068) , TUBB1(81027) , TUBB2A(7280) , TUBB2B(347733) , TUBB3(10381) , TUBB4A(10382) , TUBB4B(10383) , TUBB6(84617) , TUBB8(347688)

Description

Biochem/physiol Actions

Fosbretabulin disodium (Combretastatin A4 phosphate, CA4P) is a potent vascular-disrupting agent (VDA). Fosbretabulin disodium is a prodrug that is converted to combretastatin A (Sigma Cat No. C7744) inside the endothelial cells that line blood vessels, where it binds to tubulin dimers and prevents microtubule polymerization, resulting in mitotic arrest and apoptosis in endothelial cells. Fosbretabulin disodium is a potent anti-cancer agent that exhibits antivascular effects on tumor vasculature, inducing a rapid reduction in tumor blood flow and a concomitant increase of cellular necrosis. Some of its activity is believed to involve interference with vascular endothelial-cadherin signaling in addition to its microtubule-disrupting activity.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable