MPC-3100Hsp90 inhibitor CAS# 958025-66-6 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 958025-66-6 | SDF | Download SDF |
PubChem ID | 57336747 | Appearance | Powder |
Formula | C22H25BrN6O4S | M.Wt | 549.4 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | DMSO | ||
Chemical Name | (2S)-1-[4-[2-[6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]-2-hydroxypropan-1-one | ||
SMILES | CC(C(=O)N1CCC(CC1)CCN2C3=C(C(=NC=N3)N)N=C2SC4=C(C=C5C(=C4)OCO5)Br)O | ||
Standard InChIKey | CVBWTNHDKVVFMI-LBPRGKRZSA-N | ||
Standard InChI | InChI=1S/C22H25BrN6O4S/c1-12(30)21(31)28-5-2-13(3-6-28)4-7-29-20-18(19(24)25-10-26-20)27-22(29)34-17-9-16-15(8-14(17)23)32-11-33-16/h8-10,12-13,30H,2-7,11H2,1H3,(H2,24,25,26)/t12-/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. |
MPC-3100 Dilution Calculator
MPC-3100 Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 1.8202 mL | 9.1008 mL | 18.2017 mL | 36.4033 mL | 45.5042 mL |
5 mM | 0.364 mL | 1.8202 mL | 3.6403 mL | 7.2807 mL | 9.1008 mL |
10 mM | 0.182 mL | 0.9101 mL | 1.8202 mL | 3.6403 mL | 4.5504 mL |
50 mM | 0.0364 mL | 0.182 mL | 0.364 mL | 0.7281 mL | 0.9101 mL |
100 mM | 0.0182 mL | 0.091 mL | 0.182 mL | 0.364 mL | 0.455 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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MPC-3100 is a purine-based inhibitor of Hsp90 with IC50 value of 60nM [1].
MPC-3100 targets the N-terminal ATP-binding site of Hsp90 and blocks the activity of ATPase. In the Her2-luciferase degradation assay, MPC-3100 reduces this client protein of Hsp90 with IC50 value of 60nM. In HCT-116 cell lines, MPC-3100 inhibits cell proliferation with IC50 value of 540nM. Besides that, MPC-3100 shows a broad spectrum anti-proliferative activity against various cancer cell lines, such as NCI-N87 and DU-145. MPC-3100 also inhibits tumor growth in the NCI-N87 gastric cancer xenograft mode. Moreover, PK studies show that MPC-3100 displays a superior oral PK profile, good overall exposure and a reasonable hepatic clearance rate. Phase I clinical studies demonstrate MPC-3100 is safe and tolerated when administered at doses below 600 mg per day [1].
References:
[1] Kim SH, Bajji A, Tangallapally R, Markovitz B, Trovato R, Shenderovich M, Baichwal V, Bartel P, Cimbora D, McKinnon R, Robinson R, Papac D, Wettstein D, Carlson R, Yager KM. Discovery of (2S)-1-[4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9H-purin-9-yl}ethyl)piperidin-1-yl]-2-hydroxypropan-1-one (MPC-3100), a purine-based Hsp90 inhibitor. J Med Chem. 2012 Sep 13;55(17):7480-501.
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Discovery of (2S)-1-[4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9H-purin-9-yl}et hyl)piperidin-1-yl]-2-hydroxypropan-1-one (MPC-3100), a purine-based Hsp90 inhibitor.[Pubmed:22913511]
J Med Chem. 2012 Sep 13;55(17):7480-501.
Modulation of Hsp90 (heat shock protein 90) function has been recognized as an attractive approach for cancer treatment, since many cancer cells depend on Hsp90 to maintain cellular homeostasis. This has spurred the search for small-molecule Hsp90 inhibitors. Here we describe our lead optimization studies centered on the purine-based Hsp90 inhibitor 28a containing a piperidine moiety at the purine N9 position. In this study, key SAR was established for the piperidine N-substituent and for the congeners of the 1,3-benzodioxole at C8. These efforts led to the identification of orally bioavailable 28g that exhibits good in vitro profiles and a characteristic molecular biomarker signature of Hsp90 inhibition both in vitro and in vivo. Favorable pharmacokinetic properties along with significant antitumor effects in multiple human cancer xenograft models led to the selection of 28g (MPC-3100) as a clinical candidate.
Discovery of an L-alanine ester prodrug of the Hsp90 inhibitor, MPC-3100.[Pubmed:26483201]
Bioorg Med Chem Lett. 2015 Nov 15;25(22):5254-7.
Various types of Hsp90 inhibitors have been and continue to undergo clinical investigation. One development candidate is the purine-based, synthetic Hsp90 inhibitor 1 (MPC-3100), which successfully completed a phase I clinical study. However, further clinical development of 1 was hindered by poor solubility and consequent formulation issues and promoted development of a more water soluble prodrug. Towards this end, numerous pro-moieties were explored in vitro and in vivo. These studies resulted in identification of L-alanine ester mesylate, 2i (MPC-0767), which exhibited improved aqueous solubility, adequate chemical stability, and rapid bioconversion without the need for solubilizing excipients. Based on improved physical characteristics and favorable PK and PD profiles, 2i mesylate was selected for further development. A convergent, scalable, chromatography-free synthesis for 2i mesylate was developed to support further clinical evaluation.