Identification of Adducts Formed in the Reaction of the Bacterial Mutagen 3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone with Cytidine

Pluskota-Karwatka, D.; Munter, T.; Le Curieux, F.; Sjöholm, R.; Koroniak, H.; Kronberg, L.

Artykuł - szczegóły

Tytuł artykułu

Identification of Adducts Formed in the Reaction of the Bacterial Mutagen 3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone with Cytidine

Autorzy

Pluskota-Karwatka D. , Munter T. , Le Curieux F. , Sjöholm R. , Koroniak H. , Kronberg L.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF), a strong bacterial mutagen reacts with cytidine in buffered aqueous solutions. The reaction products were separated by preparative HPLC C18 column chromatography and were structurally characterized by UV absorbance, 1H NMR and 13C NMR spectroscopy, and mass spectrometry. The main products were identified as 7-(-D-ribofuranosyl)-4-carboxy-6- oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (cM1FA-Cyd), and 7-(beta-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (M1FA-Cyd). The highest yields of cM1FA-Cyd andM1FA-Cyd, being 12 and 1mol%respectively, were obtained in the reaction performed at pH 4.6 and 37 graduateC for 7 days. M1FA-Cyd and cM1FA-Cyd are structurally related to pfA-dR, the adduct previously identified in the reaction of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) or 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF) with 2'-deoxyadenosine.

Słowa kluczowe

DNA adducts chlorohydroxyfuranones structural characterization

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2007

Tom

Vol. 81, nr 5-6

Strony

1145--1157

Opis fizyczny

Bibliogr. 35 poz., rys.

Twórcy

autor

Pluskota-Karwatka D.

autor

Munter T.

autor

Le Curieux F.

autor

Sjöholm R.

autor

Koroniak H.

autor

Kronberg L.

Laboratory of Organic Chemistry, Abo Akademi University, Biskopsgatan 8, FIN-20500 Turku/Abo, Finland, leif.kronberg@abo.fi

Bibliografia

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Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ5-0014-0070