MPC 6827 hydrochloride

Potent microtubule inhibitor CAS# 917369-31-4

MPC 6827 hydrochloride

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Chemical structure

MPC 6827 hydrochloride

3D structure

Chemical Properties of MPC 6827 hydrochloride

Cas No. 917369-31-4 SDF Download SDF
PubChem ID 11638255 Appearance Powder
Formula C17H18ClN3O M.Wt 315.8
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in water and to 100 mM in DMSO
Chemical Name N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine;hydrochloride
SMILES CC1=NC2=CC=CC=C2C(=N1)N(C)C3=CC=C(C=C3)OC.Cl
Standard InChIKey VYUWDIKZJLOZJL-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H17N3O.ClH/c1-12-18-16-7-5-4-6-15(16)17(19-12)20(2)13-8-10-14(21-3)11-9-13;/h4-11H,1-3H3;1H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of MPC 6827 hydrochloride

DescriptionPotent inhibitor of microtubule formation (IC50 = 1.5 - 3.4 nM); inhibits polymerization of tubulin in vitro and disrupts microtubule formation in several cancer cell lines. Inhibits tumor growth in vitro and in vivo; exhibits pro-apoptotic characteristics. Brain penetrant.

MPC 6827 hydrochloride Dilution Calculator

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MPC 6827 hydrochloride Molarity Calculator

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Preparing Stock Solutions of MPC 6827 hydrochloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1666 mL 15.8328 mL 31.6656 mL 63.3312 mL 79.164 mL
5 mM 0.6333 mL 3.1666 mL 6.3331 mL 12.6662 mL 15.8328 mL
10 mM 0.3167 mL 1.5833 mL 3.1666 mL 6.3331 mL 7.9164 mL
50 mM 0.0633 mL 0.3167 mL 0.6333 mL 1.2666 mL 1.5833 mL
100 mM 0.0317 mL 0.1583 mL 0.3167 mL 0.6333 mL 0.7916 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on MPC 6827 hydrochloride

MPC-6827 (Azixa) is a small-molecule microtubule-destabilizing agent that binds to the same (or nearby) sites on β-tubulin as colchicine.[1]

Tubulin is a heterodimer consisting of an αand βmonomer, it can be covalently labeled with [3H] colchicine by near UV irradiation. Most of the label appears in β tubulin. Colchicine binds to tubulin with a stoichiometry of one and inhibits microtubule assembly substoichiometrically. Colchicine binding to tubulin exhibits pseudoirreversible kinetics; it displays a fast step followed by a slow step involving conformational changes of both ligand and tubulin. The tubulin, in turn, promotes fluorescence characteristic of the tropolone moiety of colchicine. [2]

MPC-6827 is a small-molecule microtubule-destabilizing agent that causes mitotic arrest and cell death. MPC-6827 interfere with microtubule dynamics, leading to arrest of dividing cells in the G2-M phase of the cell cycle, which eventually results in apoptotic cell death.[1]

In vivo, MPC-6827 significantly inhibits the growth of various subcutaneously implanted tumor lines. MPC-6827 has also been shown to be a vascular-disrupting agent (VDA) in a human ovarian carcinoma xenograft model. It also has shown synergism with carboplatin in a mouse xenograft model. Furthermore, MPC-6827 has been shown to inhibit the growth of human glioblastoma tumor cell line (D-54) implanted intracranially in athymic nude mice. [1]

References:
[1] Tsimberidou AM1, Akerley W, Schabel MC, etal. , Phase I clinical trial of MPC-6827 (Azixa), a microtubule destabilizing agent, in patients with advanced cancer. Mol Cancer Ther. 2010 Dec;9(12):3410-9.
[2] Uppuluri S, Knipling L, Sackett DL, Wolff J.   Localization of the colchicine-binding site of tubulin. Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11598-602.

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References on MPC 6827 hydrochloride

Effects of the tumor-vasculature-disrupting agent verubulin and two heteroaryl analogues on cancer cells, endothelial cells, and blood vessels.[Pubmed:24678059]

ChemMedChem. 2014 Apr;9(4):847-54.

Two analogues of the discontinued tumor vascular-disrupting agent verubulin (Azixa(R), MPC-6827, 1) featuring benzo-1,4-dioxan-6-yl (compound 5 a) and N-methylindol-5-yl (compound 10) residues instead of the para-anisyl group on the 4-(methylamino)-2-methylquinazoline pharmacophore, were prepared and found to exceed the antitumor efficacy of the lead compound. They were antiproliferative with single-digit nanomolar IC50 values against a panel of nine tumor cell lines, while not affecting nonmalignant fibroblasts. Indole 10 surpassed verubulin in seven tumor cell lines including colon, breast, ovarian, and germ cell cancer cell lines. In line with docking studies indicating that compound 10 may bind the colchicine binding site of tubulin more tightly (Ebind =-9.8 kcal mol(-1) ) than verubulin (Ebind =-8.3 kcal mol(-1) ), 10 suppressed the formation of vessel-like tubes in endothelial cells and destroyed the blood vessels in the chorioallantoic membrane of fertilized chicken eggs at nanomolar concentrations. When applied to nude mice bearing a highly vascularized 1411HP germ cell xenograft tumor, compound 10 displayed pronounced vascular-disrupting effects that led to hemorrhages and extensive central necrosis in the tumor.

Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier penetration.[Pubmed:19296653]

J Med Chem. 2009 Apr 23;52(8):2341-51.

As a continuation of our structure-activity relationship (SAR) studies on 4-anilinoquinazolines as potent apoptosis inducers and to identify anticancer development candidates, we explored the replacement of the 2-Cl group in our lead compound 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine (6b, EP128265, MPI-0441138) by other functional groups. This SAR study and lead optimization resulted in the identification of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine (6h, EP128495, MPC-6827) as an anticancer clinical candidate. Compound 6h was found to be a potent apoptosis inducer with EC(50) of 2 nM in our cell-based apoptosis induction assay. It also has excellent blood brain barrier penetration, and is highly efficacious in human MX-1 breast and other mouse xenograft cancer models.

MPC-6827: a small-molecule inhibitor of microtubule formation that is not a substrate for multidrug resistance pumps.[Pubmed:17575155]

Cancer Res. 2007 Jun 15;67(12):5865-71.

A novel series of 4-arylaminoquinazolines were identified from a cell-based screening assay as potent apoptosis inducers. Through structure-activity relationship studies, MPC-6827 and its close structural analogue, MPI-0441138, were discovered as proapoptotic molecules and mitotic inhibitors with potencies at low nanomolar concentrations in multiple tumor cell lines. Photoaffinity and radiolabeled analogues of MPC-6827 were found to bind a 55-kDa protein, and this binding was competed by MPC-6827, paclitaxel, and colchicine, but not vinblastine. MPC-6827 effectively inhibited the polymerization of tubulin in vitro, competed with colchicine binding, and disrupted the formation of microtubules in a variety of tumor cell lines, which together showed the molecular target as tubulin. Treatment of MCF-7 breast carcinoma or Jurkat leukemia cells with MPC-6827 led to pronounced G2-M cell cycle arrest followed by apoptosis. Apoptosis, as determined by terminal deoxyribonucleotidyl transferase-mediated dUTP nick end labeling assay, was preceded by loss of mitochondrial membrane potential, cytochrome c translocation from mitochondria to nuclei, activation of caspase-3, and cleavage of poly(ADP-ribose) polymerase. MPC-6827 was equipotent in an in vitro growth inhibition assay in several cancer cell lines regardless of the expression levels of the multidrug resistance ABC transporters MDR-1 (Pgp-1), MRP-1, and BCRP-1. In B16-F1 allografts and in OVCAR-3, MIAPaCa-2, MCF-7, HT-29, MDA-MB-435, and MX-1 xenografts, statistically significant tumor growth inhibition was observed with MPC-6827. These studies show that MPC-6827 is a microtubule-disrupting agent with potent and broad-spectrum in vitro and in vivo cytotoxic activities and, therefore, MPC-6827 is a promising candidate for development as a novel therapeutic for multiple cancer types.

Description

Verubulin hydrochloride (MPC-6827 hydrochloride) is a blood brain barrier permeable microtubule-disrupting agent, with potent and broad-spectrum in vitro and in vivo cytotoxic activities. Verubulin hydrochloride (MPC-6827 hydrochloride) exhibits potent anticancer activity in human MX-1 breast and other mouse xenograft cancer models. Verubulin hydrochloride (MPC 6827 hydrochloride) is a promising candidate for the treatment of multiple cancer types.

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