37819-60-6

Basic information

• Product Name: N-(deoxyguanosin-8-yl)acetylaminofluorene
• Synonyms: N-(deoxyguanosin-8-yl)acetylaminofluorene;N-(deoxyguanosin-8-yl)-2-acetylaminofluorene
• CAS NO: 37819-60-6
• Molecular Formula: C₂₅H₂₄N₆O₅
• Molecular Weight: 488.5
• Mol File: 37819-60-6.mol

Chemical Properties

• Boiling Point: 849.9±75.0 °C(Predicted)
• Appearance: /
• Density: 1.68±0.1 g/cm3(Predicted)
• PKA: 14.44±0.10(Predicted)
• CAS DataBase Reference: N-(deoxyguanosin-8-yl)acetylaminofluorene(CAS DataBase Reference)
• NIST Chemistry Reference: N-(deoxyguanosin-8-yl)acetylaminofluorene(37819-60-6)
• EPA Substance Registry System: N-(deoxyguanosin-8-yl)acetylaminofluorene(37819-60-6)

Safety Data

• Hazardous Substances Data: 37819-60-6(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology Research:
N-(deoxyguanosin-8-yl)acetylaminofluorene is used as a molecular probe for studying the interactions between carcinogenic compounds and DNA. Its formation upon exposure to certain chemicals can help researchers understand the mechanisms of DNA damage and repair, as well as the role of specific DNA adducts in the development of cancer.
Used in Cancer Research:
In cancer research, N-(deoxyguanosin-8-yl)acetylaminofluorene is utilized as a model compound to investigate the mutagenic and carcinogenic potential of various agents. By studying the effects of N-(deoxyguanosin-8-yl)acetylaminofluorene on cellular processes, researchers can gain insights into the molecular pathways involved in cancer initiation and progression.
Used in Drug Development:
N-(deoxyguanosin-8-yl)acetylaminofluorene can be employed as a reference compound in the development of new drugs targeting DNA repair mechanisms or cancer treatment. Understanding its interactions with DNA and cellular processes can guide the design of novel therapeutic agents that interfere with or counteract the effects of similar DNA adducts.
Used in Analytical Chemistry:
N-(deoxyguanosin-8-yl)acetylaminofluorene can also be used as a reference material in analytical chemistry for the development and validation of methods to detect and quantify DNA adducts. Accurate measurement of such adducts is crucial for assessing the genotoxic potential of environmental and occupational exposures to carcinogens.
Used in Toxicology:
In toxicology, N-(deoxyguanosin-8-yl)acetylaminofluorene serves as a biomarker for exposure to certain carcinogens. By measuring the levels of N-(deoxyguanosin-8-yl)acetylaminofluorene in biological samples, researchers can evaluate the extent of DNA damage caused by specific toxicants and assess the risk of developing cancer in exposed populations.

Upstream product

• 6098-44-8 NA-AAF 
• 961-07-9 2'-deoxyguanosine 
• 53-95-2 N-Hydroxy-2-acetylaminofluoren 
• 479408-24-7 8-(N-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2'-deoxyguanosine 
• 479408-36-1 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine 
• 479408-40-7 N-[6-benzyloxy-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-(9H-fluoren-2-ylamino)-9H-purin-2-yl]-2-(4-isopropyl-phenoxy)-acetamide 
• 479408-23-6 O⁶-benzyl-8-bromo-3′,5′-O-bis(tert-butyldimethylsilyl)-N²-dimethoxytrityl-2′-deoxyguanosine 
• 479408-42-9 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine 
• 479408-35-0 8-(N-acetyl-2-amino-fluorene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 
• 479408-22-5 O⁶-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 
• 479408-21-4 3',5'-O,O'-bis(tert-butyldimethylsilyl)-8-bromo-2'-deoxyguanosine 
• 13389-03-2 8-bromo-2'-deoxyguanosine 
• 153-78-6 2-aminofluorene 
• 479408-38-3 8-(N-acetyl-2-amino-fluorene)-N²-(p-isopropylphenoxyacetyl)-2'-deoxyguanosine 

Downstream Products

• 1137726-82-9 C₅₈H₆₄N₉O₈P 
• 73051-69-1 N-(deoxyguanosin-8-yl)-2-aminofluorene 
• 152685-32-0 N-<5'-Dimethoxytrityl-N²-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl>-2-(acetylamino)fluorene 
• 153875-52-6 N-<3',5'-Bis(dimethoxytrityl)-N²-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl>-2-(acetylamino)fluorene 
• 73051-69-1 2-fluoren 
• 127999-39-7 N'-(9H-Fluoren-2-yl)-N-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-N-(2-imino-5-oxo-imidazolidin-4-yl)-guanidine 
• 127999-35-3 2-[(E)-9H-Fluoren-2-ylimino]-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7-imino-1,3,6,8-tetraaza-spiro[4.4]nonane-4,9-dione 
• 961-07-9 2'-Deoxyguanosine 
• 5744-03-6 dodecahydrofluorene 
• 14490-85-8 8->guanine 

Relevant articles and documents

Synthesis of the Ultimate Hepatocarcinogen, 2-Acetylaminofluorene N-Sulphate

Reaction of N-hydroxy-2-acetylaminofluorene with dicyclohexylcarbodi-imide and H2SO4 yields 2-acetylaminofluorenone N-sulphate, the presumed ultimate form of the hepatocarcinogen 2-acetylaminofluorene.

Synthesis of site-specific damaged DNA strands by 8-(acetylarylamino)- 2′-deoxyguanosine adducts and effects on various DNA polymerases

Beside the predominately found 8-(arylamino)-2′-dG, 8-(acetylarylamino) damages within DNA-strands may also play an important role in the induction of chemical carcinogenesis. A synthesis pathway leading to these 8-(acetylarylamino)-dG adducts using different aromatic amines has been optimized. The 8-modified dGs were converted into the corresponding phosphoramidites and site-specifically incorporated into different oligonucleotides leading to DNA strands. Lesion-bearing hybrids of these damaged DNA-strands with complementary oligonucleotides were used to study their melting properties and their circular dichroism spectra. It was shown that no EcoRI restriction took place with the damage inside the cleavage site. Finally, three different DNA polymerases were used for primer extension studies. C8-NAc-Arylamine adducts of 2′-deoxyguanosine with various aromatic amines were synthesized by using cross-coupling reactions and converted into 3′-phosphoramidites. Site-specific damaged NarI-, EcoRI- and 20mer-oligonucleotides were prepared by automated DNA-synthesis. Biophysical properties, restriction endonuclease studies and DNA-polymerase assays were performed. Copyright

Preparation of C8-amine and acetylamine adducts of 2′-deoxyguanosine suitably protected for DNA synthesis

(Equation presented) C8-Amine and acetylamine adducts of 2′-deoxyguanosine were synthesized. Our approach provides solutions for the coupling of aromatic amines to a protected 8-bromo-2′-deoxyguanosine derivative, for the selective acetylation of the coup

Reactivity of the 4-biphenylyl and 2-fluorenylnitrenium ions with heterocyclic and carbon nucleophiles

The carcinogens 4-aminobiphenyl, 2-aminofluorene and their N-acetyl derivatives form DNA adducts in vivo with the aryl nitrogen attached at C-8 of guanine. These adducts are proposed to arise through the reaction with the DNA base of a nitrenium ion obtai

Interaction and Reactivity of Carcinogenic N-Acetyl-N-(acyloxy)-2-aminofluorene with Deoxyguanosine. An Intramolecular Approach

Solvolysis of 3 in water-acetone mixtures yields the "adduct" 4 (65percent in water) with product and rate data consistent with the hypothesis that hydrophobic guanine-fluorene stacking, similar to that which occurs when the carcinogenic animofluorene metabolite is intercalated in DNA, is responsible for selective binding of the carcinogen at the C-8 guanine center.

Substituent effects on the bioactivation of 2-(N-hydroxyacetamido)fluorenes by N-arylhydroxamic acid N,O-cyltransferase

A series of 7-substituted analogues of 2-(N-hydroxyacetamido)fluorene (1) was subjected to bioactivation by a partially purified preparation of hamster hepatic AHAT, and the rates of methylthio adduct formation resulting from the reaction of the activated intermediates with N-acetylmethionine were determined. Electronegative substituents enhanced the amount of adduct formed; this finding contrasted with the results of a previous study in which it was found that electron-donating substituents facilitated the mechanism-based inactivation of AHAT by analogues of 1. The structures of the adducts formed from reaction of the activated forms of several of the 7-substituted compounds with N-acetylmethionine and with 2'-deoxyguanosine were determined; the types of adducts formed were similar to those formed with electrophiles generated by the AHAT-catalyzed activation of 1. Electronegative substituents enhanced the amount of adducts formed in the reaction with 2'-deoxyguanosine as well as with N-acetylmethionine.