High impact information on alpha-Acetoxy-N-nitrosopyrrolidine

• This report describes the isolation and characterization of DNA adducts formed in vitro from alpha-acetoxy-N-nitrosopyrrolidine and in rats treated with the hepatocarcinogen N-nitrosopyrrolidine [1].
• Esterase-catalyzed hydrolysis of alpha-acetoxy-N-nitrosopyrrolidine in the presence of DNA also produced the exocyclic 1,N2-propanodeoxyguanosine Adducts 4a and 4b which we have previously described [1].
• Detection of exocyclic guanine adducts in hydrolysates of hepatic DNA of rats treated with N-nitrosopyrrolidine and in calf thymus DNA reacted with alpha-acetoxy-N-nitrosopyrrolidine [1].
• Both alpha-hydroxynitrosopyrrolidine and 3-formyl-1-propanediazohydroxide, which are unstable intermediates resulting from alpha hydroxylation of nitrosopyrrolidine, were generated inaqueous solution from the stable precursors alpha-acetoxynitrosopyrrolidine and 4-(N-carbethoxy-N-nitrosamino)butanal [2].
• alpha-Acetoxy-N-nitrosopyrrolidine (AcO-NPYR), in the presence of esterase, was reacted with the plasmid pBR322 [3].

Biological context of alpha-Acetoxy-N-nitrosopyrrolidine

• Differential effects of thiols on DNA modifications via alkylation and Michael addition by alpha-acetoxy-N-nitrosopyrrolidine [4].
• As a mutagen, Compound III was approximately as active as N-nitroso compounds not requiring metabolic activation, more active than alpha-acetoxy dialkylnitrosamines and less active than the cyclic alpha-acetoxynitrosopyrrolidine [5].

Gene context of alpha-Acetoxy-N-nitrosopyrrolidine

• alpha-Acetoxy-N-nitrosopyrrolidine (alpha-acetoxyNPYR) is a stable precursor to alpha-hydroxyNPYR, the initial product of metabolism and proposed proximate carcinogen of NPYR [6].

Analytical, diagnostic and therapeutic context of alpha-Acetoxy-N-nitrosopyrrolidine

• The six adduct standards were used to develop HPLC systems for their analysis as products of the reaction of alpha-acetoxy-N-nitrosopyrrolidine with DNA [7].

References