TOS-ARG-OME.HCL

Names

[ Name ]:
TOS-ARG-OME.HCL

[Synonym ]:
Nalpha-4-Tosyl-L-arginine methyl ester hydrochloride
Na-p-Tosyl-L-arginine methyl ester hydrochloride
(S)-Methyl 5-guanidino-2-(4-methylphenylsulfonamido)pentanoate hydrochloride
Nα-p-Toluenesulfonyl-L-arginine Methyl Ester Hydrochloride
N-4-Tosyl-L-arginine methyl ester hydrochloride
Tos-Arg-OMe.HCl
Tos-Arg-Ome·Hcl
EINECS 217-235-1
TAME hydrochloride
Imino{[(4S)-5-methoxy-4-{[(4-methylphenyl)sulfonyl]amino}-5-oxopentyl]amino}methanaminium chloride
MFCD00012578
L-Ornithine, N-(diaminomethylene)-N-[(4-methylphenyl)sulfonyl]-, methyl ester, hydrochloride (1:1)
Nα-p-Tosyl-L-arginine methyl ester hydrochloride
Methyl N2-((p-tolyl)sulphonyl)-L-argininate monohydrochloride
Nalpha-Tosyl-L-arginine Methyl Ester Hydrochloride
TOS-ARG-OME HCL
Methyl N-(diaminomethylene)-N-[(4-methylphenyl)sulfonyl]-L-ornithinate hydrochloride (1:1)
Nα-Tosyl-L-arginine Methyl Ester Hydrochloride
Nalpha-p-Toluenesulfonyl-L-Arginine Methyl Ester Hydrochloride

Biological Activity

[Description]:

TAME hydrochloride is an inhibitor of anaphase-promoting complex (APC), which prevents its activation by Cdc20 and Cdh1.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> APC

Research Areas >> Cancer

[Target]

APC [1].

[In Vitro]

TAME shows inhibitory effect on APC activation when added to mitotic Xenopus extract. TAME (1-200 μM) inhibits Cdc20 association with mitotic APC and also inhibits Cdh1 association with interphase APC. TAME significantly inhibits crosslinking of the IR peptide to Cdc27 and Cdc16 but only slightly reduces crosslinking to Cdc23 and Apc7 at 20 µM; TAME strongly inhibits crosslinking to all APC subunits at 200 µM. TAME also inhibits binding of wild type Cdc20 to the APC, but not binding of a ΔIR mutant[1]. TAME (200 μM) induces Cdc20 dissociation from the APC in mitotic Xenopus extract calls for APC-dependent ubiquitination. TAME induces Cdc20 dissociation from the APC by promoting Cdc20 ubiquitination, but the dissociation can be suppresses by Cyclin B1. TAME terminates cyclin B1 ubiquitination prematurely[2]. TAME interacts with ATP by β and γ phosphate and the adenine ring of ATP. TAME in combination with the Mg(II) ion accelerates the ATP hydrolysis process[3].

[References]

[1]. Zeng X, et al. Pharmacologic inhibition of the anaphase-promoting complex induces a spindle checkpoint-dependent mitotic arrest in the absence of spindle damage. Cancer Cell. 2010 Oct 19;18(4):382-95.

[2]. Zeng X, et al. An APC/C inhibitor stabilizes cyclin B1 by prematurely terminating ubiquitination. Nat Chem Biol. 2012 Feb 26;8(4):383-92.

[3]. Ma Y, et al. Differential effects of Mg(ii) and N(alpha)-4-tosyl-l-arginine methyl ester hydrochloride on the recognition and catalysis in ATP hydrolysis. Dalton Trans. 2008 Feb 28;(8):1081-6.

[Related Small Molecules]

TAME

Chemical & Physical Properties

[ Boiling Point ]:
544.1ºC at 760mmHg

[ Melting Point ]:
145-147(lit.)

[ Molecular Formula ]:
C₁₄H₂₃ClN₄O₄S

[ Molecular Weight ]:
378.875

[ Flash Point ]:
282.9ºC

[ Exact Mass ]:
378.112854

[ PSA ]:
142.75000

[ LogP ]:
3.54280

[ Vapour Pressure ]:
6.73E-12mmHg at 25°C

[ Index of Refraction ]:
-14 ° (C=4, H2O)

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles

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A novel thiol-ene "click" strategy for the preparation of monolithic trypsin microreactor was proposed. The hybrid organic-inorganic monolithic capillary column with ene-functionality was fabricated b...

Rabbit plasminogen and plasmin isozymes.

Meth. Enzymol. 45 , 273, (1976)

A modified spectrophotometric determination of chymotrypsin, trypsin, and thrombin.

Can. J. Biochem. Physiol. 37 , 1393, (1959)