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SML0176

Sigma-Aldrich

Z36

≥98% (HPLC)

Synonym(s):

(Z)-5-Fluoro-1-(3′-dimethylamino)propyl-3-[(5′-methoxyindol-3-ylidene)methyl]-indolin-2-one, 1-[3-(dimethylamino)propyl]-5-fluoro-1,3-dihydro-3-[(5-methoxy-1H-indol-3-yl)methylene]-2H-Indol-2-one

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About This Item

Empirical Formula (Hill Notation):
C23H24FN3O2
CAS Number:
1243148-19-7
Molecular Weight:
393.45
UNSPSC Code:
12352200
PubChem Substance ID:
329825205
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

light yellow to dark yellow

solubility

DMSO: ≥15 mg/mL

storage temp.

−20°C

SMILES string

COc1ccc2[nH]cc(\C=C3/C(=O)N(CCCN(C)C)c4ccc(F)cc34)c2c1

InChI

1S/C23H24FN3O2/c1-26(2)9-4-10-27-22-8-5-16(24)12-19(22)20(23(27)28)11-15-14-25-21-7-6-17(29-3)13-18(15)21/h5-8,11-14,25H,4,9-10H2,1-3H3/b20-11-

InChI key

CQNOITUXWKRVMB-JAIQZWGSSA-N

Application

Z36 may be used to study cell signaling that results in autophagy.

Biochem/physiol Actions

Z36 inhibits cell proliferation and induces death in HeLa cells. The cell death induced is via autophagy and autophagic flux.
Z36 is a Bcl-XL inhibitor that induces autophagic cell death independent of apoptosis which distinguishes it from other Bcl-XL and Bcl-2 inhibitors that induce cancer cell death mainly through apoptosis. Z36 binds to the BH3 binding groove of BCL-XL where it is thought to induce autophagy through blocking the interaction between Bcl-XL/Bcl2 and Beclin 1.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
101M4606V

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Jian Lin et al.
Autophagy, 5(3), 314-320 (2009-02-27)
Inhibition of Bcl2 family proteins Bcl-X(L) and Bcl-2 represents a promising drug development strategy for cancer treatment by triggering apoptosis in cancer cells. Here we report a novel Bcl-X(L) inhibitor, Z36, which unexpectedly induces only autophagic cell death, but not

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