Synthesis of para-benzoquinone and 1,3-bis(2-chloroethyl)nitrosourea adducts and their incorporation into oligonucleotides.

A. Chenna, H. Maruenda, B. Singer

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

8 Citas (Scopus)


Benzene is a widely known carcinogen and a cause of bone-marrow toxicity and leukaemia in humans. para-Benzoquinone is a stable metabolite of benzene. Its reaction with deoxycytidine, deoxyadenosine and deoxyguanosine produces the major stable exocyclic compounds (3-hydroxy)-1,N4-benzetheno-2'-deoxycytidine, (9-hydroxy)-1,N6-benzetheno-2'-deoxyadenosine and (7-hydroxy)-1,N2-benzetheno-2'-deoxyguanosine, respectively, on a large scale and at high yield. The desired products were identified by fast atom bombardment-mass spectrometry, proton nuclear magnetic resonance and UV spectroscopy. These adducts were converted to the fully protected phosphoramidites and incorporated site-specifically into a series of oligonucleotides. 1,N6-Ethano-2'-deoxyadenosine is one of the exocyclic adducts formed during DNA reaction with the antitumour agent, 1,3-bis(2-chloroethyl)nitrosourea. This compound was synthesized on a large scale with a high yield (62%) and then was converted to the phosphoramidite and incorporated site-specifically into oligonucleotides. The coupling efficiency of the incorporation of all these adducts was high (> or = 93%). After de-protection and purification of these oligomers, enzymatic hydrolysis and analysis by high-performance liquid chromatography confirmed the presence of the adduct in the oligomers. These oligomers are being used to investigate the biochemical and physical properties of these adducts.

Idioma originalInglés
Páginas (desde-hasta)89-101
Número de páginas13
PublicaciónIARC scientific publications
EstadoPublicada - 1999
Publicado de forma externa


Profundice en los temas de investigación de 'Synthesis of para-benzoquinone and 1,3-bis(2-chloroethyl)nitrosourea adducts and their incorporation into oligonucleotides.'. En conjunto forman una huella única.

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