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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:
Molecular Weight:
223.27
Beilstein:
2807677
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
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

Signal Word

Danger

Hazard Statements

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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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
Bu-Gao Zhou et al.
Frontiers in pharmacology, 9, 1165-1165 (2018-11-09)
It is known that excessive hepatocellular apoptosis is a typical characteristic of hepatic disease, and is regulated by the mammalian target of rapamycin (mTOR) signaling pathway. As the main active component of Kudzu (Pueraria lobata) roots, which is frequently used
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
Jung-Eun Yeo et al.
Chemical research in toxicology, 25(11), 2462-2468 (2012-10-24)
Nucleotide excision repair (NER) removes lesions caused by environmental mutagens or UV light from DNA. A hallmark of NER is the extraordinarily wide substrate specificity, raising the question of how one set of proteins is able to recognize structurally diverse
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

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

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