Effects of 5-hydroxymethyl-2′-deoxyuridine and 3-aminobenzamide on chromosome aberrations in cultured human lymphocytes

Zhang, A.; Lin, Mingen; Fujimoto, Atsuko

doi:10.1016/0165-7992(93)90062-z

Cited by 6 publications

(4 citation statements)

References 14 publications

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“…culture induces chromatid gaps, breaks, and exchanges (Zhang et al, 1993). We have constructed a seven-base-pair oligonucleotide duplex in which the central thymidine residue has been replaced by HMdU, forming an HMdU-A base pair in order to determine the structural consequences of HMdU in DNA.…”

mentioning

confidence: 99%

Structures of base pairs with 5-(hydroxymethyl)-2'-deoxyuridine in DNA determined by NMR spectroscopy

Mellac¹,

Fazakerley²,

Sowers³

1993

Biochemistry

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Base pairs with 5-(hydroxymethyl)-2'-deoxyuridine (HMdU) opposite either adenine or guanine in a seven-base oligonucleotide duplex have been studied by NMR spectroscopy. When paired with A, the HMdU-A base pair is in Watson-Crick geometry. The hydroxymethyl group maintains a fixed orientation in which the oxygen is on the 5' side of the base. The energy-minimized structure indicates the presence of a hydrogen bond between the hydroxymethyl group and the N7 of the 5' guanine residue. When paired with guanine, HMdU-G is in a wobble configuration at low pH. The hydroxymethyl group is on the 3' side of the base, positioned to form an intramolecular hydrogen bond with its own O4 carbonyl. With increasing pH, HMdU-G is observed to ionize with an apparent pK value of 9.7. The high-pH structure is in a Watson-Crick configuration, with the HMdU residue in a position similar to that observed for HMdU-A. It is proposed that interresidue hydrogen bonding of the HMdU residue may stabilize aberrant base-pair configurations.

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mentioning

confidence: 99%

Structures of base pairs with 5-(hydroxymethyl)-2'-deoxyuridine in DNA determined by NMR spectroscopy

Mellac¹,

Fazakerley²,

Sowers³

1993

Biochemistry

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“…This pyrimidine base analog, when incorporated into DNA, conferred cytotoxicity,5 genetic mutations,6 and antiviral as well as antibacterial activities 7. Chromatid breakage and exchanges were also observed in vitro upon administration of hmU into cells in culture 4, 8. Cellular accumulation of hmU, presumably due to a decrease in excision‐repair activity of hmU‐DNA glycosylase,9, 10 was suggested to be responsible for adult progeria (Werner's syndrome, a rare autosomal recessive disorder).…”

Section: Introductionmentioning

confidence: 99%

Specificity of hydroxylmethyluracil-containing DNA for transcription factor 1: Structural insights

Pasternack

Kearns

1999

Biopolymers

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The genomic materials from some Bacillus subtilis bacteriophages are found to contain 5‐(hydroxymethyl)‐2'‐deoxyuridine in place of thymine. Phage‐encoded proteins such as transcription factor 1 specifically and preferentially bind to the minor grooves of these hmU‐containing DNA but not to thymine‐containing DNA. Data from electrophoretic mobility shift assays suggest that the inherent, localized flexibility of hmU‐DNA, which is sequence‐specific, is responsible for its discriminative binding. We discuss here, from the NMR‐derived structural point of view, how differential DNA flexibility can contribute to specific binding of TF1 to hmU‐DNA. © 2000 John Wiley & Sons, Inc. Biopoly 52: 57–63, 1999

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“…3,4 This pyrimidine base analog, when incorporated into DNA, conferred cytotoxicity, 5 genetic mutations, 6 and antiviral as well as antibacterial activities. 4,8 Cellular accumulation of hmU, presumably due to a decrease in excision-repair activity of hmU-DNA glycosylase, 9,10 was suggested to be responsible for adult progeria (Werner's syndrome, a rare autosomal recessive disorder). 4,8 Cellular accumulation of hmU, presumably due to a decrease in excision-repair activity of hmU-DNA glycosylase, 9,10 was suggested to be responsible for adult progeria (Werner's syndrome, a rare autosomal recessive disorder).…”

Section: Introductionmentioning

confidence: 99%

Specificity of hydroxylmethyluracil‐containing DNA for transcription factor 1: Structural insights

Pasternack

Kearns

1999

Biopolymers

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The genomic materials from some Bacillus subtilis bacteriophages are found to contain 5-(hydroxymethyl)-2'-deoxyuridine in place of thymine. Phage-encoded proteins such as transcription factor 1 specifically and preferentially bind to the minor grooves of these hmU-containing DNA but not to thymine-containing DNA. Data from electrophoretic mobility shift assays suggest that the inherent, localized flexibility of hmU-DNA, which is sequence-specific, is responsible for its discriminative binding. We discuss here, from the NMR-derived structural point of view, how differential DNA flexibility can contribute to specific binding of TF1 to hmU-DNA.

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Effects of 5-hydroxymethyl-2′-deoxyuridine and 3-aminobenzamide on chromosome aberrations in cultured human lymphocytes

Cited by 6 publications

References 14 publications

Structures of base pairs with 5-(hydroxymethyl)-2'-deoxyuridine in DNA determined by NMR spectroscopy

Structures of base pairs with 5-(hydroxymethyl)-2'-deoxyuridine in DNA determined by NMR spectroscopy

Specificity of hydroxylmethyluracil-containing DNA for transcription factor 1: Structural insights

Specificity of hydroxylmethyluracil‐containing DNA for transcription factor 1: Structural insights

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