Combretastatin A4 - CAS 117048-59-6
Catalog number: 117048-59-6
Category: Inhibitor
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Molecular Formula:
C18H20O5
Molecular Weight:
316.35
COA:
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Targets:
Microtubule/Tubulin
Description:
Combretastatin A4, under the IUPAC name 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol, inhibits tubulin polymerization (IC50= 2.2 μM). It has demonstrable antineoplastic activity (inhibit IMR32 (neuroblastoma): IC50= 2.16nM, Hs746T (gastric carcinoma) IC50=5.20nM, CFPAC-1 (pancreatic carcinoma)IC50=3.46nM, and MCF-7 (breast cancer)IC50=18.47nM
Brife Description:
Inhibits tubulin polymerization (IC50= 2.2 μM)
Appearance:
Solid powder
Synonyms:
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol; 1-(3,4,5-trimethoxyphenyl)-2-(3'-hydroxy-4'-methoxyphenyl)ethene; D-64131; 74588-78-6; (5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE; CHEMBL140220; C16H13NO2; (5-methoxy-1H-indol-2-yl)-phenylmethanone; (5-Methoxy-1H-indol-2-yl)(phenyl)methanone; (5-Methoxy-1H-indol-2-yl)-phenyl-methanone; NCGC00025243-01; Tocris-1643; AC1N0QCR; 2-Benzoyl-5-methoxyindole; SCHEMBL5828518; CTK8F8930; DTXSID30397970; ICMIJSRDISNKOC-UHFFFAOYSA-N; HMS3268K07; ZINC2526466; 3570AH; BDBM50107658; AKOS022507157; CS-1008; 2-BENZOYL-5-METHOXY-1H-INDOLE; NCGC00025243-02; AN-25376; HE053371; HE187776; HY-15482; LS-83224; QC-11710; AB0165802; KB-208742; D64131; W-5310; BRD-K26997899-001-01-4; D-64131|(5-Methoxy-1H-indol-2-yl)phenylmethanone
Solubility:
Soluble to 100 mM in ethanol and to 100 mM in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -53℃ for long term (months to years).
MSDS:
Inquire
Melting Point:
84.5-85.5ºC
Density:
1.184 g/cm3
InChIKey:
HVXBOLULGPECHP-WAYWQWQTSA-N
InChI:
1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
Canonical SMILES:
COC1=C(C=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O
1.Combretastatins: more than just vascular targeting agents?
Greene LM1, Meegan MJ2, Zisterer DM2. J Pharmacol Exp Ther. 2015 Nov;355(2):212-27. doi: 10.1124/jpet.115.226225. Epub 2015 Sep 9.
Several prodrugs of the naturally occurring combretastatins have undergone extensive clinical evaluation as vascular targeting agents (VTAs). Their increased selectivity toward endothelial cells together with their innate ability to rapidly induce vascular shutdown and inhibit tumor growth at doses up to 10-fold less than the maximum tolerated dose led to the clinical evaluation of combretastatins as VTAs. Tubulin is well established as the molecular target of the combretastatins and the vast majority of its synthetic derivatives. Furthermore, tubulin is a highly validated molecular target of many direct anticancer agents routinely used as front-line chemotherapeutics. The unique vascular targeting properties of the combretastatins have somewhat overshadowed their development as direct anticancer agents and the delineation of the various cell death pathways and anticancer properties associated with such chemotherapeutics. Moreover, the ongoing clinical trial of OXi4503 (combretastatin-A1 diphosphate) together with preliminary preclinical evaluation for the treatment of refractory acute myelogenous leukemia has successfully highlighted both the indirect and direct anticancer properties of combretastatins.
2.Stepwise pH-responsive nanoparticles containing charge-reversible pullulan-based shells and poly(β-amino ester)/poly(lactic-co-glycolic acid) cores as carriers of anticancer drugs for combination therapy on hepatocellular carcinoma.
Zhang C1, An T1, Wang D1, Wan G1, Zhang M2, Wang H1, Zhang S1, Li R1, Yang X1, Wang Y3. J Control Release. 2016 Mar 28;226:193-204. doi: 10.1016/j.jconrel.2016.02.030. Epub 2016 Feb 16.
Stepwise pH-responsive nanoparticle system containing charge reversible pullulan-based (CAPL) shell and poly(β-amino ester) (PBAE)/poly(lactic-co-glycolic acid) (PLAG) core is designed to be used as carriers of paclitaxel (PTX) and combretastatin A4 (CA4) for combining antiangiogenesis and chemotherapy to treat hepatocellular carcinoma (HCC). CAPL-coated PBAE/PLGA (CAPL/PBAE/PLGA) nanoparticles displayed step-by-step responses to weakly acidic tumor microenvironment (pH ≈6.5) and endo/lysosome (pH ≈5.5) respectively through the cleavage of β-carboxylic amide bond in CAPL and the "proton-sponge" effect of PBAE, thus realized the efficient and orderly releases of CA4 and PTX. In human HCC HepG2 cells and human umbilical vein endothelial cells, CAPL/PBAE/PLGA nanoparticles significantly enhanced synergistic effects of PTX and CA4 on cell proliferation and cell migration. In HepG2 tumor-bearing mice, CAPL/PBAE/PLGA nanoparticles showed excellent tumor-targeting capability and remarkably increased inhibitory effects of PTX and CA4 on tumor growth and angiogenesis.
3.Combretastatin A-4 Conjugated Antiangiogenic Micellar Drug Delivery Systems Using Dendron-Polymer Conjugates.
Sumer Bolu B1, Manavoglu Gecici E1, Sanyal R1,2. Mol Pharm. 2016 Apr 14. [Epub ahead of print]
Employment of polymeric nanomaterials in cancer therapeutics is actively pursued since they often enable drug administration with increased efficacy along with reduced toxic side effects. In this study, drug conjugated micellar constructs are fabricated using triblock dendron-linear polymer conjugates where a hydrophilic linear polyethylene glycol (PEG) chain is flanked by well-defined hydrophobic biodegradable polyester dendrons bearing an antiangiogenic drug, combretastatin-A4 (CA4). Variation in dendron generation is utilized to obtain a library of micellar constructs with varying sizes and drug loadings. In particular, a family of drug appended dendron-polymer conjugates based on polyester dendrons of generations ranging from G1 to G3 and 10 kDa linear PEG were obtained using [3 + 2] Huisgen type "click" chemistry. The final constructs benefit from PEG's hydrophilicity and antibiofouling character, as well as biodegradable nature of the hydrophobic polyester dendrons.
4.Synthesis and Evaluation of 131I-Skyrin as a Necrosis Avid Agent for Potential Targeted Radionuclide Therapy of Solid Tumors.
Wang C1,2, Jin Q2, Yang S2, Zhang D2, Wang Q2,3, Li J1,2, Song S4, Sun Z5, Ni Y6, Zhang J2, Yin Z1. Mol Pharm. 2015 Dec 17. [Epub ahead of print]
An innovative anticancer approach targeted to necrotic tissues, which serves as a noncancerous and generic anchor, may present a breakthrough. Necrosis avid agents with a flat conjugate aromatic structure selectively accumulate in necrotic tissues, but they easily form aggregates that undesirably distribute to normal tissues. In this study, skyrin, a dianthraquinone compound with smaller and distorted π-cores and thus decreased aggregates as compared with hypericin (Hyp), was designed to target necrosis for tumor therapy. Aggregation studies of skyrin by UV/vis spectroscopy showed a smaller self-association constant with skyrin than with Hyp. Skyrin was labeled by iodine-131 with a radiochemical purity of 98% and exhibited good stability in rat serum for 72 h. In vitro cell uptake studies showed significant difference in the uptake of 131I-skyrin by necrotic cells compared to normal cells (P < 0.05). Compared in rats with liver and muscle necrosis, radiobiodistribution, whole-body autoradiography, and SPECT/CT studies revealed higher accumulation of 131I-skyrin in necrotic liver and muscle (p < 0.
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CAS 117048-59-6 Combretastatin A4

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