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Key Documents

SML3977

proTAME

new

≥95% (HPLC)

Synonym(s):

(2S)-2-[[(4-Methylphenyl)sulfonyl]amino]-9,13-dioxo-14-phenyl-7-[[[[(2-phenylacetyl)oxy]methoxy]carbonyl]amino]-10,12-dioxa-6,8-diazatetradec-6-enoic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C34H38N4O12S
CAS Number:
Molecular Weight:
726.75
UNSPSC Code:
12352200

Quality Level

Assay

≥95% (HPLC)

form

(Powder or solid or crytals or semi-solid)

color

colorless to yellow

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Biochem/physiol Actions

Cell-permeable N,N′-bis(acyloxymethyl carbamate) prodrug of the anaphase-promoting complex (APC) inhibitor Nα-p-Tosyl-L-arginine methyl ester (TAME).
proTAME is a cell-permeable N,N′-bis(acyloxymethyl carbamate) prodrug of the anaphase-promoting complex (APC) inhibitor Nα-p-Tosyl-L-arginine methyl ester (TAME). Upon entering cells, proTAME (12 μM) is effectively converted by cellular esterases to TAME, which in turn inactivates the spindle assembly checkpoint (SAC) by blocking APC-dependent proteolysis, causing prolonged mitotic duration at low doses (780 nM - 3 μM in HeLa cells, 6 μM in hTERT-RPE1 cells) or mitotic arrest and cell death at high doses (12 μM in HeLa cells). Note: proTAME is not active in some cells (e.g. MCF10A, due to the lack of esterase activity required for proTAME activation.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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