Investigation of the adducts formed by reaction of butenedioic acids with adenosine

Robert Franzén; Masatoshi Morita; Kiyoshi Tanabe; Hiroo Takagi; Yasuyuki Shibata

doi:10.1021/tx970036d

Investigation of the adducts formed by reaction of butenedioic acids with adenosine

Robert Franzén^*, Masatoshi Morita, Kiyoshi Tanabe, Hiroo Takagi, Yasuyuki Shibata

^*Corresponding author for this work

Not published at Aalto University

National Institute for Environmental Studies of Japan

Research output: Contribution to journal › Article › Scientific › peer-review

1 Citation (Scopus)

Abstract

Several genotoxic butenedioic acids present in chlorine-disinfected drinking water were allowed to react with adenosine, guanosine, and cytidine in aqueous solution. HPLC analyses, with detection at 254 and 310 nm, showed that clearly detectable products were formed only in the reactions with adenosine. The major products from the reactions between either 2-chloro-3- methyl-2-butenedioic acid (ox-MCF) or 2-chloro-3-(chloromethyl)-2- butenedioic acid (ox-CMCF) and adenosine were the same. This substance was isolated by C18 column chromatography and characterized by UV absorbance, ¹H and ¹³C NMR spectroscopy, and mass spectrometry. It was identified as 3-(β-D-ribofuranosyl)-7-carboxy-7-formyl-8-[9'-(β-D-ribofuranosyl)-N⁶- adenosinyl]-1,N⁶-ethanoadenosine (cfεA,A). The yields of cfεA,A in reactions performed at pH 7.4 and 37 °C were 0.7% and 0.3% with ox-MCF and ox-CMCF, respectively.

Original language	English
Pages (from-to)	1186-1191
Number of pages	6
Journal	Chemical Research in Toxicology
Volume	10
Issue number	10
DOIs	https://doi.org/10.1021/tx970036d
Publication status	Published - Oct 1997
MoE publication type	A1 Journal article-refereed

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title = "Investigation of the adducts formed by reaction of butenedioic acids with adenosine",

abstract = "Several genotoxic butenedioic acids present in chlorine-disinfected drinking water were allowed to react with adenosine, guanosine, and cytidine in aqueous solution. HPLC analyses, with detection at 254 and 310 nm, showed that clearly detectable products were formed only in the reactions with adenosine. The major products from the reactions between either 2-chloro-3- methyl-2-butenedioic acid (ox-MCF) or 2-chloro-3-(chloromethyl)-2- butenedioic acid (ox-CMCF) and adenosine were the same. This substance was isolated by C18 column chromatography and characterized by UV absorbance, 1H and 13C NMR spectroscopy, and mass spectrometry. It was identified as 3-(β-D-ribofuranosyl)-7-carboxy-7-formyl-8-[9'-(β-D-ribofuranosyl)-N6- adenosinyl]-1,N6-ethanoadenosine (cfεA,A). The yields of cfεA,A in reactions performed at pH 7.4 and 37 °C were 0.7% and 0.3% with ox-MCF and ox-CMCF, respectively.",

author = "Robert Franz{\'e}n and Masatoshi Morita and Kiyoshi Tanabe and Hiroo Takagi and Yasuyuki Shibata",

year = "1997",

month = oct,

doi = "10.1021/tx970036d",

language = "English",

volume = "10",

pages = "1186--1191",

journal = "Chemical Research in Toxicology",

issn = "0893-228X",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Investigation of the adducts formed by reaction of butenedioic acids with adenosine

AU - Franzén, Robert

AU - Morita, Masatoshi

AU - Tanabe, Kiyoshi

AU - Takagi, Hiroo

AU - Shibata, Yasuyuki

PY - 1997/10

Y1 - 1997/10

N2 - Several genotoxic butenedioic acids present in chlorine-disinfected drinking water were allowed to react with adenosine, guanosine, and cytidine in aqueous solution. HPLC analyses, with detection at 254 and 310 nm, showed that clearly detectable products were formed only in the reactions with adenosine. The major products from the reactions between either 2-chloro-3- methyl-2-butenedioic acid (ox-MCF) or 2-chloro-3-(chloromethyl)-2- butenedioic acid (ox-CMCF) and adenosine were the same. This substance was isolated by C18 column chromatography and characterized by UV absorbance, 1H and 13C NMR spectroscopy, and mass spectrometry. It was identified as 3-(β-D-ribofuranosyl)-7-carboxy-7-formyl-8-[9'-(β-D-ribofuranosyl)-N6- adenosinyl]-1,N6-ethanoadenosine (cfεA,A). The yields of cfεA,A in reactions performed at pH 7.4 and 37 °C were 0.7% and 0.3% with ox-MCF and ox-CMCF, respectively.

AB - Several genotoxic butenedioic acids present in chlorine-disinfected drinking water were allowed to react with adenosine, guanosine, and cytidine in aqueous solution. HPLC analyses, with detection at 254 and 310 nm, showed that clearly detectable products were formed only in the reactions with adenosine. The major products from the reactions between either 2-chloro-3- methyl-2-butenedioic acid (ox-MCF) or 2-chloro-3-(chloromethyl)-2- butenedioic acid (ox-CMCF) and adenosine were the same. This substance was isolated by C18 column chromatography and characterized by UV absorbance, 1H and 13C NMR spectroscopy, and mass spectrometry. It was identified as 3-(β-D-ribofuranosyl)-7-carboxy-7-formyl-8-[9'-(β-D-ribofuranosyl)-N6- adenosinyl]-1,N6-ethanoadenosine (cfεA,A). The yields of cfεA,A in reactions performed at pH 7.4 and 37 °C were 0.7% and 0.3% with ox-MCF and ox-CMCF, respectively.

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U2 - 10.1021/tx970036d

DO - 10.1021/tx970036d

M3 - Article

C2 - 9348442

AN - SCOPUS:0030778905

SN - 0893-228X

VL - 10

SP - 1186

EP - 1191

JO - Chemical Research in Toxicology

JF - Chemical Research in Toxicology

IS - 10

ER -

Investigation of the adducts formed by reaction of butenedioic acids with adenosine

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