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A7015

Sigma-Aldrich

N-(2-Fluorenyl)acetamide

≥98% (HPLC)

Synonym(s):

2-AAF, 2-Acetamidofluorene, N-Acetyl-2-aminofluorene

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About This Item

Empirical Formula (Hill Notation):
C15H13NO
CAS Number:
53-96-3
Molecular Weight:
223.27
Beilstein:
2807677
EC Number:
200-188-6
MDL number:
MFCD00001116
UNSPSC Code:
12352103
PubChem Substance ID:
24891166
NACRES:
NA.25

Assay

≥98% (HPLC)

form

powder

mp

192-196 °C (lit.)

SMILES string

CC(=O)Nc1ccc-2c(Cc3ccccc-23)c1

InChI

1S/C15H13NO/c1-10(17)16-13-6-7-15-12(9-13)8-11-4-2-3-5-14(11)15/h2-7,9H,8H2,1H3,(H,16,17)

InChI key

CZIHNRWJTSTCEX-UHFFFAOYSA-N

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Application

N-(2-Fluorenyl)acetamide (2-Acetamidofluorene, 2-AAF), a genotoxic carcinogen, is used to induce liver cancer in animal models such as the 2-AAF/partial hepatectomy rat. 2-AAF may be used to study the mechanism of liver carcinogenesis and as a reference material during its identification or quantitation.

Biochem/physiol Actions

A genotoxic carcinogen that is used to model liver carcinogenesis in rat. When N-hydroxylated by cytochrome CYP1A2 in the liver, 2-AAF forms adducts with DNA and is tumorigenic in liver and bladder.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H350

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCD1839
SLBS9794
SLBT5494
SLBT5333
SLBS9801

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Shuai Xiang et al.
PloS one, 7(4), e35180-e35180 (2012-04-20)
Macrophages are known to play an important role in hepatocyte mediated liver regeneration by secreting inflammatory mediators. However, there is little information available on the role of resident macrophages in oval cell mediated liver regeneration. In the present study we
Samrat Chakraborty et al.
Molecular therapy. Nucleic acids, 20, 34-49 (2020-03-09)
Site-specific delivery of chemotherapeutics specifically to neoplastic hepatocytes without affecting normal hepatocytes should be a focus for potential therapeutic management of hepatocellular carcinoma (HCC). The aptamer TLS 9a with phosphorothioate backbone modifications (L5) has not been explored so far for
Mohammed A El-Magd et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 114, 108732-108732 (2019-03-30)
Pretreatment of mesenchymal stem cells (MSCs) with melatonin (Mel) improves their potential therapeutic effect on chronic diseases and cancers. However, this preconditioning strategy may direct the effect of Mel toward MSCs alone and deprive cancer cells of the oncostatic effect
Sana Javaid Awan et al.
Cell biology international, 41(1), 51-61 (2016-11-03)
Hepatic oval cells are likely to be activated during advanced stage of liver fibrosis to reconstruct damaged hepatic tissue. However, their scarcity, difficulties in isolation, and in vitro expansion hampered their transplantation in fibrotic liver. This study was aimed to
Hong Mu et al.
Nucleic acids research, 40(19), 9675-9690 (2012-08-21)
Nucleotide excision repair (NER) efficiencies of DNA lesions can vary by orders of magnitude, for reasons that remain unclear. An example is the pair of N-(2'-deoxyguanosin-8-yl)-2-aminofluorene (dG-C8-AF) and N-(2'-deoxyguanosin-8-yl)-2-acetylaminofluorene (dG-C8-AAF) adducts that differ by a single acetyl group. The NER
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