1960
DOI: 10.1016/0006-2952(60)90017-4
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Synthesis of 5-chlorodeoxyuridine and a comparative study of 5-halodeoxyuridines in E. Coli

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Cited by 38 publications
(16 citation statements)
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“…The damaging agents include hydrogen peroxide and hypochlorous acid resulting in both oxidized and chlorinated bases. Among these damage products is 5-chlorouracil (ClU), which could arise by chlorination and deamination of cytosine residues in DNA and nucleotides or chlorination of uracil bases present in nucleotide precursor pools (610) as shown in Fig. 1.…”
Section: Introductionmentioning
confidence: 99%
“…The damaging agents include hydrogen peroxide and hypochlorous acid resulting in both oxidized and chlorinated bases. Among these damage products is 5-chlorouracil (ClU), which could arise by chlorination and deamination of cytosine residues in DNA and nucleotides or chlorination of uracil bases present in nucleotide precursor pools (610) as shown in Fig. 1.…”
Section: Introductionmentioning
confidence: 99%
“…[14] We chose chlorouracil (c) as the most promising candidate for DNAbase transliteration (see Figure S1b) because: 1) it closely resembles thymine in structural studies of synthetic DNA duplexes, which suggests that the stability of the A:c pair is close to that of A:T; [15] 2) it is readily converted into the chlorodeoxyuridine nucleoside and the dcMP, dcDP, and dcTP nucleotides by nucleoside phosphorylases, thymidine kinase, thymidylate kinase, and nucleoside diphosphate kinase, respectively; [2] 3) unlike fluorouracil, it is less liable to elevated tautomerism, which causes ambiguous pairing with guanine as well as adenine; [15] 4) unlike the bromo and iodo analogues, it is not reduced to uracil at the redox potential of the cytoplasm. [16] Chlorine is present in numerous natural compounds, especially secondary metabolites of marine organisms, and a number of enzymatic mechanisms that enable the formation of C À Cl bonds have been elucidated. [17] Apparently, it has not been reported to occur in any natural nucleic acid building block so far.…”
mentioning
confidence: 99%
“…The effects for both analogues have been described as very similar and encompass filamentation, cessation of growth, low mortality, and mutagenesis. [16,18] The strain THY1 that was subjected to 5-chlorouracil transliteration is a derivative of wild-type E. coli K12 strain MG1655. [19] Its construction involved consecutive deletions of the genes thyA and udp and the deoCABD operon from the MG1655 chromosome, and the insertion of a P15A plasmid carrying the Lactobacillus leichmannii gene ntd, which encodes nucleoside deoxyribosyltransferase (see Supporting Information).…”
mentioning
confidence: 99%
“…We observe that 10 µM concentration of CldU in the media does not alter cell division kinetics; however, the mole ratio of ClU to T in the DNA is 0.89 ± 0.02 when cells are grown for two cell doublings. Previously it has been shown that CldU is metabolized and incorporated into DNA using antibodies that bind selectively to DNA containing halogenated bases (2832). We have confirmed and extended these finding using a mass spectral method as reported here.…”
Section: Discussionmentioning
confidence: 99%
“…While it is known that 5-chloro-2’-deoxyuridine (CldU) added to culture media is metabolized and incorporated into DNA as shown by antibody binding (2832), CldU induces senescence, toxicity, and sister-chromatid exchanges by as yet unknown mechanisms (3336). …”
Section: Introductionmentioning
confidence: 99%