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Seco Rapamycin Sale

(Synonyms: 依维莫司杂质DCP,Secorapamycin A) 目录号 : GC37615

A degradation product of rapamycin

Seco Rapamycin Chemical Structure

Cas No.:147438-27-5

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥5,098.00
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1mg
¥1,431.00
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5mg
¥3,150.00
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10mg
¥4,950.00
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25mg
¥10,800.00
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50mg
¥18,900.00
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产品描述

Rapamycin is a natural macrolide immunosuppressant that activates mTORC1. Seco rapamycin (sodium salt) is a nonenzyme-dependent degradation product of rapamycin resulting from ester hydration followed by dehydration.1 It has less than 4% of the potency of rapamycin in a thymocyte proliferation assay.1 Rapamycin quickly degrades to two ring-opened products, including seco rapamycin, in the cytoplasm or in homogenates of Caco-2 cells.2 Like rapamycin, seco rapamycin is secreted from cells by P-glycoprotein and metabolized to a common dihydro species.3 While seco rapamycin poorly activates mTOR, it mimics rapamycin in its ability to inhibit the proteasome.4

1.Wang, C.P., Chan, K.W., Schiksnis, R.A., et al.High performance liquid chromatographic isolation, spectroscopic characterization, and immunosuppressive activities of two rapamycin degradation productsJ. Liq. Chromatogr.17(16)3383-3392(1994) 2.Paine, M.F., Leung, L.Y., Lim, H.K., et al.Identification of a novel route of extraction of sirolimus in human small intestine: Roles of metabolism and secretionJ. Pharmacol. Exp. Ther.301(1)174-186(2002) 3.Paine, M.F., Leung, L.Y., and Watkins, P.B.New insights into drug absorption: Studies with sirolimusTher. Drug Monit.26(5)463-467(2004) 4.Osmulski, P.A., and Gaczynska, M.Rapamycin allosterically inhibits the proteasomeMol. Pharmacol.84(1)104-113(2013)

Chemical Properties

Cas No. 147438-27-5 SDF
别名 依维莫司杂质DCP,Secorapamycin A
Canonical SMILES O=C([C@H]1N(C(C([C@@]2(O)[C@H](C)CC[C@@H](C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C([C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(/C=C/[C@H](C)C[C@H]3C[C@@H](OC)[C@H](O)CC3)=O)=O)O2)=O)=O)CCCC1)O
分子式 C51H79NO13 分子量 914.17
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 1.0939 mL 5.4694 mL 10.9389 mL
5 mM 0.2188 mL 1.0939 mL 2.1878 mL
10 mM 0.1094 mL 0.5469 mL 1.0939 mL
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Research Update

Rapamycin allosterically inhibits the proteasome

Mol Pharmacol 2013 Jul;84(1):104-13.PMID:23619386DOI:10.1124/mol.112.083873.

Rapamycin is a canonical allosteric inhibitor of the mammalian tarpet of rapamycin (mTOR) kinase with immunosuppressive and proapoptotic activities. We found that in vitro rapamycin also regulates the proteasome, which is an essential intracellular protease of the ubiquitin-proteasome pathway. Rapamycin inhibits proteinase and selected peptidase activities of the catalytic core proteasome at low micromolar concentrations. Moreover, the drug interferes with binding of the 19S cap essential for processing of polyubiquitinylated substrates and with the PA200 proteasome activator to the 20S catalytic core proteasome. These protein complexes are known to bind to specific grooves on the α face region of the 20S core. Treatment with rapamycin affects the conformational dynamics of the proteasomal gate, which is centrally positioned within the α face and allosterically regulated element responsible for the intake of substrates. We showed that rapamycin shares all the proteasome targeting properties not only with other two-domain, closed-ring analogs (rapalogs) but also with its single domain mimics and Seco-Rapamycin, which is the first in vivo open-ring metabolite of rapamycin that does not affect mTOR. We hypothesize that rapamycin and related compounds bind to the α face and allosterically impact proteasome function. This article discusses the implications of our findings for the mechanism of in vivo actions of rapamycin and for the design of novel allosteric drugs targeting the proteasome.