methyl (2S)-5-carbamimidamido-2-(4-methylbenzenesulfonamido)pentanoate

• ChemBase编号: 73088
• 分子式: C14H22N4O4S
• 平均质量: 342.41388
• 单一同位素质量: 342.1361762
• SMILES: c1c(ccc(c1)S(=O)(=O)N[C@H](C(=O)OC)CCCNC(=N)N)C
• Canonical SMILES: COC(=O)[C@@H](NS(=O)(=O)c1ccc(cc1)C)CCCNC(=N)N
• InChI: InChI=1S/C14H22N4O4S/c1-10-5-7-11(8-6-10)23(20,21)18-12(13(19)22-2)4-3-9-17-14(15)16/h5-8,12,18H,3-4,9H2,1-2H3,(H4,15,16,17)/t12-/m0/s1
• InChIKey: FKMJXALNHKIDOD-LBPRGKRZSA-N

名称和登记号

名称

• IUPAC标准名: methyl (2S)-5-carbamimidamido-2-(4-methylbenzenesulfonamido)pentanoate
• IUPAC传统名: methyl (2S)-5-carbamimidamido-2-(4-methylbenzenesulfonamido)pentanoate; TAME
• 别名: TAME; p-TOLUENESULFONYL-L-ARGININE METHYL ESTER HYDROCHLORIDE

登记号

• CAS号: 901-47-3
• PubChem SID: 162038008
• PubChem CID: 1550286

理论计算性质

• Acid pKa: 10.354648
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -1.8157995
• LogD (pH = 7.4): -1.7515968
• Log P: 0.23181371
• 摩尔折射率: 96.9272 cm^3
• 极化性: 34.102673 Å^3
• 极化表面积: 134.37 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 147°C

安全信息

• 保存条件: -20°C

药理学性质

• 作用靶点: APC

产品相关信息

• 成盐信息: Free Base

详细说明

MP Biomedicals - 05218728

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2225

Biological Activity

• Description: Tosyl-L-Arginine Methyl Ester (TAME) is an APC inhibitor.
• Targets: APC
• In Vitro: TAME inhibits cyclin proteolysis in mitotic Xenopus egg extract with IC50 of 12 μM. TAME at concentration of 1-200 μM arrests interphase extract treated with recombinant cyclin B1/Cdc2 complex in mitosis, with stable cyclin B1 and phosphorylated Cdc27. TAME at concentration of 200 μM dramaticly inhibits the ubiquitin ligase activity of the Anaphase-Promoting Complex (APC), accompanied by reduced binding of Cdh1 to APC. TAME addition to interphase extract reduces Cdc20 association with the APC in a dose-dependent manner partly by binding directly to APC, and the contribution motif is the C-terminal isoleucine-arginine (IR) tail on APC. ^[1] TAME is hydrolysed by trypsin with K_m of 0.328 mM. ^[2] TAME accelerates the ATP hydrolysis process about 12-fold. ^[3] TAME interacts with β and γ phosphate and the adenine ring of ATP by the guanidinium group and the aromatic ring. ^[4] TAME at concentration of 50 mM inhibits nutrient-induced germination and pressure-induced germination at 600 MPa in Bacillus subtilis. ^[5] TAME induces a concentration dependent contractile response on ileal strips with EC50 of 4.3 x 10^3 M. ^[6]

Protocol

• Protocol: Kinase Assay ^[1]
• 3H-TAME binding assay: ^3H-TAME (200 nM; 15 Ci/mmol) is added to 100 μl interphase Xenopus extract or HeLa cell lysate. APC is immunoprecipitated with Cdc27 antibody coupled to affiprep beads. The beads are washed with XB and radioactivity measured by scintillation counting. Alternatively, ^3H-TAME is added and Cdc27 immunoprecipitation is performed after one or two rounds of APC immunodepletion. Specific binding is calculated as the difference between counts associated with Cdc27 antibody beads compared to beads lacking antibody (mock IP)

References

• References: [1] Zeng X, et al. Cancer Cell, 2010, 18(4), 382-395.
• References: [2] Khantaphant S, et al. Food Chem, 2010, 120(3), 658-664.
• References: [3] Ma YQ, et al. J Inorg Organomet P, 2008, 18(4), 435-440.
• References: [4] Ma Y, et al. Dalton Trans, 2008, 28(8), 1081-1086.
• References: [5] Wuytack EY, et al. Appl Environ Microbiol, 2000, 66(1), 257-261.
• References: [6] Subratty AH, et al. Indian J Exp Biol, 1998, 36(6), 618-621.

参考文献

• Zeng X, et al. Cancer Cell, 2010, 18(4), 382-395.
• Khantaphant S, et al. Food Chem, 2010, 120(3), 658-664.
• Ma YQ, et al. J Inorg Organomet P, 2008, 18(4), 435-440.
• Ma Y, et al. Dalton Trans, 2008, 28(8), 1081-1086.
• Wuytack EY, et al. Appl Environ Microbiol, 2000, 66(1), 257-261.
• Subratty AH, et al. Indian J Exp Biol, 1998, 36(6), 618-621.