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Key Documents

SML3714

Sigma-Aldrich

SMIP004-7

≥98% (HPLC)

Synonym(s):

2-Methyl-4-butylaniline, 4-Butyl-2-methylaniline, 4-Butyl-2-methylbenzenamine

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About This Item

Empirical Formula (Hill Notation):
C11H17N
CAS Number:
Molecular Weight:
163.26
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

Assay

≥98% (HPLC)

form

(Oil or liquid)

color

colorless to brown

storage temp.

-10 to -25°C

Biochem/physiol Actions

SMIP004-7 is a cell penetrant, potent and selective ubiquinone uncompetitive inhibitor of mitochondrial Complex I (NADH:ubiquinone oxidoreductase). SMIP004-7 selectively binds to a distinct N-terminal region of Complex I catalytic subunit NDUFS2, which leads to rapid disassembly of Complex I. SMIP004-7 potently inhibits growth of triple-negative breast cancer xenografts in mice.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Metabolic targeting of cancer by a ubiquinone uncompetitive inhibitor of mitochondrial complex I
Cell Chemical Biology, 29(3), 436-450 (2022)
Gabriela Reyes-Castellanos et al.
Trends in pharmacological sciences, 43(9), 706-708 (2022-04-07)
Targeting metabolic reprogramming has proven successful in oncology, but this field requires better identification of drugs that inhibit mitochondrial metabolism in cancer cells. Recent work from Dr Wolf's group reveals that the primary target of the antitumor compound SMIP004-7 is
Elizabeth Rico-Bautista et al.
Oncotarget, 4(8), 1212-1229 (2013-08-02)
We previously identified SMIP004 (N-(4-butyl-2-methyl-phenyl) acetamide) as a novel inducer of cancer-cell selective apoptosis of human prostate cancer cells. SMIP004 decreased the levels of positive cell cycle regulators, upregulated cyclin-dependent kinase inhibitors, and resulted in G1 arrest, inhibition of colony

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