CevipabulinAnti-microtubule agent CAS# 849550-05-6 |
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Quality Control & MSDS
3D structure
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| Cas No. | 849550-05-6 | SDF | Download SDF |
| PubChem ID | 11488110 | Appearance | Powder |
| Formula | C18H18ClF5N6O | M.Wt | 464.82 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | TTI-237 | ||
| Solubility | DMSO : 16.67 mg/mL (35.86 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble) | ||
| Chemical Name | 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-N-[(2S)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine | ||
| SMILES | CC(C(F)(F)F)NC1=C(C(=NC2=NC=NN12)Cl)C3=C(C=C(C=C3F)OCCCNC)F | ||
| Standard InChIKey | ZUZPCOQWSYNWLU-VIFPVBQESA-N | ||
| Standard InChI | InChI=1S/C18H18ClF5N6O/c1-9(18(22,23)24)28-16-14(15(19)29-17-26-8-27-30(16)17)13-11(20)6-10(7-12(13)21)31-5-3-4-25-2/h6-9,25,28H,3-5H2,1-2H3/t9-/m0/s1 | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | Cevipabulin(TTI-237) is a novel, potent, synthetic small molecule, inhibits binding of vinblastine at the Vinca alkaloid site of the αβ-tubulin heterodimer.
IC50 value:
Target: Antimicrotubule agent
in vitro: TTI-237 inhibited the binding of [(3)H]vinblastine to tubulin, but it caused a marked increase in turbidity development that more closely resembled the effect observed with docetaxel than that observed with vincristine. When applied to cultured human tumor cells at concentrations near its IC(50) value for cytotoxicity (34 nmol/L), TTI-237 induced multiple spindle poles and multinuclear cells, as did paclitaxel, but not vincristine or colchicine. Flow cytometry experiments revealed that, at low concentrations (20-40 nmol/L), TTI-237 produced sub-G(1) nuclei and, at concentrations above 50 nmol/L, it caused a strong G(2)-M block. The compound was a weak substrate of multidrug resistance 1 (multidrug resistance transporter or P-glycoprotein). In a cell line expressing a high level of P-glycoprotein, the IC(50) of TTI-237 increased 25-fold whereas those of paclitaxel and vincristine increased 806-fold and 925-fold, respectively. TTI-237 was not recognized by the MRP or MXR transporters [1]. TTI-237 inhibited the exchange of [(3)H]GTP at the exchangeable nucleotide site of the tubulin heterodimer, and was similar to vincristine in its effects on the phosphorylation of eight intracellular proteins in HeLa cells [3].
in vivo: TTI-237 was active in vivo in several nude mouse xenograft models of human cancer, including LoVo human colon carcinoma and U87-MG human glioblastoma, when dosed i.v. or p.o [1]. References: | |||||
Cevipabulin Dilution Calculator
Cevipabulin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1514 mL | 10.7569 mL | 21.5137 mL | 43.0274 mL | 53.7843 mL |
| 5 mM | 0.4303 mL | 2.1514 mL | 4.3027 mL | 8.6055 mL | 10.7569 mL |
| 10 mM | 0.2151 mL | 1.0757 mL | 2.1514 mL | 4.3027 mL | 5.3784 mL |
| 50 mM | 0.043 mL | 0.2151 mL | 0.4303 mL | 0.8605 mL | 1.0757 mL |
| 100 mM | 0.0215 mL | 0.1076 mL | 0.2151 mL | 0.4303 mL | 0.5378 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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Cevipabulin (TTI-237) is a new anti-microtubule agent [1][2][3][4].
Microtubules are a component of the cytoskeleton that participate in many crucial cellular functions, include maintaining the structure of the cell, forming the cytoskeleton and chromosome separation.
Cevipabulin (TTI-237) is a new anti-microtubule agent with antitumor activity. In COLO 205 cells, TTI-237 inhibited cell proliferation with IC50 value of 31 nM [1]. At low ratios of TTI-237: tubulin heterodimer (about 1:30), TTI-237 increased depolymerization kinetics in response to low temperature, but stabilized the aggregates at high ratios (about 1:4). TTI-237 inhibited the exchange of [3H]GTP at the exchangeable nucleotide site of the tubulin heterodimer [2]. Cevipabulin (TTI-237) increased tubulin polymerization. Cevipabulin was stable and water-soluble, and could be administered i.v. or p.o. in saline [3]. TTI-237 inhibited the binding of [3H]vinblastine to tubulin, but significantly increased turbidity development that more closely resembled the effect of docetaxel. In Hela cells, TTI-237 (34 nmol/L) induced multiple spindle poles and multi-nuclear cells. At 20-40 nmol/L, TTI-237 produced sub-G1 nuclei, while at > 50 nmol/L, TTI-237 induced G2-M block.
In athymic mice bearing LoVo human colon adenocarcinoma, TTI-237 exhibited good antitumor activity in a dose-dependent way. In mice bearing U87-MG human glioblastoma, TTI-237 (25 mg/kg) given both i.v. and p.o. were equally effective [4].
References:
[1]. Zhang N, Ayral-Kaloustian S, Nguyen T, et al. 2-cyanoaminopyrimidines as a class of antitumor agents that promote tubulin polymerization. Bioorg Med Chem Lett, 2007, 17(11): 3003-3005.
[2]. Beyer CF, Zhang N, Hernandez R, et al. The microtubule-active antitumor compound TTI-237 has both paclitaxel-like and vincristine-like properties. Cancer Chemother Pharmacol, 2009, 64(4): 681-689.
[3]. Ayral-Kaloustian S, Zhang N, Beyer C. Cevipabulin (TTI-237): preclinical and clinical results for a novel antimicrotubule agent. Methods Find Exp Clin Pharmacol, 2009, 31(7): 443-447.
[4]. Beyer CF, Zhang N, Hernandez R, et al. TTI-237: a novel microtubule-active compound with in vivo antitumor activity. Cancer Res, 2008, 68(7): 2292-2300.
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Cevipabulin (TTI-237): preclinical and clinical results for a novel antimicrotubule agent.[Pubmed:19907719]
Methods Find Exp Clin Pharmacol. 2009 Sep;31(7):443-7.
Antimitotic agents are among the most effective drugs for the treatment of solid tumors and metastatic cancer. These drugs promote cell death by interfering with the crucial structural and regulatory function of microtubules in cells. Most of the agents of clinical relevance are natural products or semisynthetic derivatives thereof, and they fall into two major classes: microtubule stabilizers such as the taxanes, which enhance tubulin polymerization, and microtubule destabilizers such as the Vinca alkaloids, which lead to the depolymerization of existing microtubules. While these drugs are effective in inhibiting the progression of certain types of tumors, their utility is limited in part by incomplete tumor responses and/or significant side effects. In addition, inherent resistance is encountered in many tumor types, or acquired resistance may occur as a result of multiple cycles of therapy. Cevipabulin (TTI-237) is a novel, small synthetic molecule with an unusual biological mode of action. It appears to bind at the vinca site, but exhibits some properties similar to those of taxane-site ligands, such as enhancing tubulin polymerization. The compound works against a variety of tumors, including those resistant to paclitaxel and vincristine. Furthermore, Cevipabulin is stable and water-soluble, and can be administered i.v. or p.o. in saline. It can be synthesized in bulk quantities efficiently. Based on these properties, Cevipabulin was selected for clinical development.
