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Merck
CN

SML3977

proTAME

≥90% (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
NACRES:
NA.21
Assay:
≥90% (HPLC)
Form:
(Powder or solid or crytals or semi-solid)
Quality level:
Storage condition:
desiccated
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Quality Level

assay

≥90% (HPLC)

form

(Powder or solid or crytals or semi-solid)

storage condition

desiccated

color

colorless to yellow

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

O=C(CC1=CC=CC=C1)OCOC(/N=C(NC(OCOC(CC2=CC=CC=C2)=O)=O)\NCCC[C@H](NS(C3=CC=C(C=C3)C)(=O)=O)C(OC)=O)=O

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.

Disclaimer

Hygroscopic


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Global Trade Item Number

SKUGTIN
SML3977-1MG04065271065222
SML3977-5MG04065271065239