2-アセチルアミノフルオレン

関: 2-acetylaminofluorene、acetylaminofluorene

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the 1st letter of the Roman alphabet (同)a
the blood group whose red cells carry the A antigen (同)type_A, group A

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アルコール中毒患者更生会
(映画で)14歳以下の児童観賞禁止の表示 / 14歳以下観賞禁止の
Automobile Association(英国の)自動車協会
answer / ampere

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/04/20 05:55:19」(JST)

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[Wiki en表示]

2-Acetylaminofluorene (AAF,^[4] 2-AAF) is a carcinogenic and mutagenic derivative of fluorene. It is used as a biochemical tool in the study of carcinogenesis. It induces tumors in a number of species in the liver, bladder and kidney. The metabolism of this compound in the body by means of biotransformation reactions is the key to its carcinogenicity. 2-AAF is a substrate for cytochrome P-450 (CYP) enzyme, which is a part of a super family found in almost all organisms. This reaction results in the formation of N-hydroxy-2-acetylaminofluorene which is a proximal carcinogen and is more potent than the parent molecule. The N-hydroxy metabolite undergoes several enzymatic and non-enzymatic rearrangements. It can be O-acetylated by cytosolic N-acetyltransferase enzyme to yield N-acetyl-N-acetoxyaminofluorene. This intermediate can spontaneously rearrange to form the arylamidonium ion and a carbonium ion which can interact directly with DNA to produce DNA adducts. In addition to esterification by acetylation, the N-hydroxy derivative can be O-sulfated by cytosolic sulfur transferase enzyme giving rise to the N-acetyl-N-sulfoxy product.

In addition, the cytosolic N,O-aryl hydroxamic acid acyltransferase enzyme catalyzes the transfer of the acetyl group from the N atom of the N-OH-2-AAF to the O atom of the N-OH group to produce N-acetoxy-2-aminofluorene (N-OH-2-AF). This reactive metabolite spontaneously decomposes to form a nitrenium ion which will also react with DNA. However, the product of this latter reaction is the deacetylated aminofluorene adduct. The interconversion of amide and amine metabolites of 2-AAF can further occur via the microsomal enzyme deacetylase producing the N-hydroxy metabolite of the amine derivative. Subsequent esterification of the aryl hydroxylamine by sulfur transferase yields the sulfate ester which also spontaneously decompose to form nitrenium ion. The reactive nitrenium, carbonium and arylamidonium ion metabolites of 2-AAF react with the nucleophilic groups in DNA, proteins and endogenous thiols like glutathione. Other metabolites such as the N,O-glucuronide, although not directly activated products, can be important in the carcinogenic process because they are capable of degradation to proximal N-hydroxy metabolites. This metabolite is presumed to be involved in formation of bladder tumors. The mechanism for this is thought to involve degradation of glucuronide in the bladder due to acidic pH of urine.

References

^ ^a ^b "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevnetion.
^ ^a ^b ^c "NIOSH Pocket Guide to Chemical Hazards #0007". National Institute for Occupational Safety and Health (NIOSH).
^ "2-Acetylaminofluorene - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. Descriptors Computed from Structure.
^ Logan, Carolynn M.; Rice, M. Katherine (1987). Logan's Medical and Scientific Abbreviations. Philadelphia: J. B. Lippincott Company. p. 3. ISBN 0-397-54589-4.

UpToDate Contents

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1. 病原性大腸菌 pathogenic escherichia coli

English Journal

A disintegrin and metalloprotease with thrombospondin type I motif 7: a new protease for connective tissue growth factor in hepatic progenitor/oval cell niche.

Pi L1, Jorgensen M2, Oh SH2, Protopapadakis Y2, Gjymishka A2, Brown A2, Robinson P2, Liu C3, Scott EW4, Schultz GS5, Petersen BE2.
The American journal of pathology.Am J Pathol.2015 Jun;185(6):1552-63. doi: 10.1016/j.ajpath.2015.02.008. Epub 2015 Apr 2.
Hepatic progenitor/oval cell (OC) activation occurs when hepatocyte proliferation is inhibited and is tightly associated with the fibrogenic response during severe liver damage. Connective tissue growth factor (CTGF) is important for OC activation and contributes to the pathogenesis of liver fibrosi
PMID 25843683
PMID 25862958

Induction of an altered lipid phenotype by two cancer promoting treatments in rat liver.

Riedel S1, Abel S2, Swanevelder S3, Gelderblom WC4.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.Food Chem Toxicol.2015 Apr;78:96-104. doi: 10.1016/j.fct.2015.01.023. Epub 2015 Feb 2.
Changes in lipid metabolism have been associated with tumor promotion in rat liver. Similarities and differences of lipid parameters were investigated using the mycotoxin fumonisin B1 (FB1) and the 2-acetylaminofluorene/partial hepatectomy (AAF/PH) treatments as cancer promoters in rat liver. A typi
PMID 25656646

Japanese Journal

Annexin A3-Expressing Cellular Phenotypes Emerge from Necrotic Lesion in the Pericentral Area in 2-Acetylaminofluoren/Carbon Tetrachloride-Treated Rat Livers

ITO Yoshimasa,WATANABE Takenori,NAGATOMO Shunsuke,SEKI Taiichiro,NIIMI Shingo,ARIGA Toyohiko
Bioscience, biotechnology, and biochemistry 71(12), 3082-3089, 2007-12-23
… Here we describe the results of an in vivo demonstration of AnxA3-expressing cellular phenotypes in the liver with 2-acetylaminofluoren (2-AAF)/carbon tetrachloride (CCl4)-injury. …
NAID 10027522436

Lack of Initiating Activity of Kojic Acid on Hepatocarcinogenesis in F344 Rats

WATANABE Takao,MORI Taeko,KITAMURA Yasuki,UMEMURA Takashi,OKAMURA Miwa,KASHIDA Yoko,NISHIKAWA Akiyoshi,HIROSE Masao,MITSUMORI Kunitoshi
Journal of toxicologic pathology 18(2), 79-84, 2005-06-30
… In the present experiments, in order to investigate possible liver initiation activity, partially hepatectomized male F344 rats received a single oral dose of 0, 1000 and 2000 mg/kg body weight of KA followed by dietary administration of 0.015% of N-2-acetylaminofluorene (2-AAF) for 2 weeks and a single 0.8 mL/kg body weight dose of CCl4. …
NAID 10025852850

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★リンクテーブル★

リンク元	「N-2-フルオレニルアセタミド」「2-アセチルアミノフルオレン」「2-acetylaminofluorene」「acetylaminofluorene」
関連記事	「AA」「A」「AAF」

「N-2-フルオレニルアセタミド」

2-Acetylaminofluorene
Names
	Systematic IUPAC name N-(9H-fluoren-2-yl)acetamide
	Other names 2-Acetaminofluorene; N-2-Fluorenylacetamide; N-Acetyl-2-aminofluorene
Identifiers
Abbreviations	2-AAF
Beilstein Reference	2807677
CAS Registry Number	53-96-3
ChEBI	CHEBI:17356
ChEMBL	ChEMBL311469
ChemSpider	5686
EC number	200-188-6
	InChI 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) ; Key: CZIHNRWJTSTCEX-UHFFFAOYSA-N ; InChI=1/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); Key: CZIHNRWJTSTCEX-UHFFFAOYAF ;
Jmol-3D images	Image; Image
KEGG	C02778
MeSH	2-Acetylaminofluorene
PubChem	5897
RTECS number	AB9450000
	SMILES CC(=O)Nc1ccc2c(Cc3ccccc23)c1 ; CC(=O)NC1=CC=C2C(CC3=C2C=CC=C3)=C1 ;
UN number	3077
Properties
Molecular formula	C15H13NO
Molar mass	223.27 g·mol−1
Appearance	Vivid, light brown, opaque crystals
Melting point	192 °C (378 °F; 465 K)
log P	3.264
Hazards
Main hazards	potential occupational carcinogen
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H302, H350
GHS precautionary statements	P201, P308+313
EU classification	T N
R-phrases	R45, R22, R51/53
S-phrases	S53, S36/37/39, S45
	US health exposure limits (NIOSH):
PEL (Permissible)	[OSHA-Regulated Carcinogen]
	Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	verify (what is: /?)
	Infobox references

　　[★]

英: N-2-fluorenylacetamide
同: 2-アセチルアミノフルオレン 2-acetylaminofluorene 2-AAF

「2-アセチルアミノフルオレン」

　　[★]

英: 2-acetylaminofluorene、2-AAF
関: アセチルアミノフルオレン

「2-acetylaminofluorene」

　　[★]

2-アセチルアミノフルオレン

関: 2-AAF、acetylaminofluorene

「acetylaminofluorene」

　　[★]

アセチルアミノフルオレン

関: 2-AAF、2-acetylaminofluorene

「AA」

　　[★]

「A」

　　[★]

「AAF」

　　[★]

同: aggregative adherence fimbriae

[pocket-1] "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevnetion.

[NIOSH-2] "NIOSH Pocket Guide to Chemical Hazards #0007". National Institute for Occupational Safety and Health (NIOSH).

[3] "2-Acetylaminofluorene - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. Descriptors Computed from Structure.

[loganabbrev-4] Logan, Carolynn M.; Rice, M. Katherine (1987). Logan's Medical and Scientific Abbreviations. Philadelphia: J. B. Lippincott Company. p. 3. ISBN 0-397-54589-4.

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案内

2-AAF