Mutagenicity and NO formation from UVA irradiated N-nitrosoproline, and characterization of photoproduct formed in UVA-irradiated mixture of N-nitrosoproline with 2-′deoxyguanosine in neutral solution

Sakae Arimoto, Masaki Machida, Kayoko Sano, Shuhei Aoyama, Chiharu Asahi, Noriko Tanaka, Keinosuke Okamoto, Tomoe Negishi, Sachiko Kimura, Toshinori Suzuki

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Earlier studies in our laboratory showed that UVA-irradiated N-nitrosoproline (NPRO) could produce mutagenic compounds and strand breaks in treated DNA with the release of nitric oxide and active oxygen species. In the present study, we investigated the phosphate-dependence of photomutagenicity and solvent effects on nitric oxide release from irradiated NPRO. We also investigated the UVA-driven reaction of NPRO with 2′-deoxyguanosine (dG) in neutral solution, and identified the chemical structure of the photoproduct. A mixture of NPRO and dG dissolved in neutral solution was irradiated with UVA at 320-400 nm for 6 h, and the solution was then subjected to HPLC analysis. The photoproduct isolated from the NPRO and dG mixture in neutral buffer was identified as 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG). We propose a photoreaction mechanism involving the absorption of UVA photons by NPRO followed by UVA-driven photolysis of NPRO, and subsequent production of active oxygen radicals that generate 8-oxodG.

Original languageEnglish
Pages (from-to)47-53
Number of pages7
JournalGenes and Environment
Volume36
Issue number2
DOIs
Publication statusPublished - 2014

Fingerprint

Deoxyguanosine
mutagenicity
nitric oxide
oxygen
Reactive Oxygen Species
photolysis
phosphate
Nitric Oxide
DNA
Photolysis
nitrosoproline
Photons
Buffers
Phosphates
High Pressure Liquid Chromatography

Keywords

  • 8-oxo-deoxyguanosine
  • DNA adduct
  • N-nitrosamine
  • NO radical
  • Photoreaction

ASJC Scopus subject areas

  • Genetics
  • Environmental Science (miscellaneous)
  • Social Psychology

Cite this

Mutagenicity and NO formation from UVA irradiated N-nitrosoproline, and characterization of photoproduct formed in UVA-irradiated mixture of N-nitrosoproline with 2-′deoxyguanosine in neutral solution. / Arimoto, Sakae; Machida, Masaki; Sano, Kayoko; Aoyama, Shuhei; Asahi, Chiharu; Tanaka, Noriko; Okamoto, Keinosuke; Negishi, Tomoe; Kimura, Sachiko; Suzuki, Toshinori.

In: Genes and Environment, Vol. 36, No. 2, 2014, p. 47-53.

Research output: Contribution to journalArticle

Arimoto, Sakae ; Machida, Masaki ; Sano, Kayoko ; Aoyama, Shuhei ; Asahi, Chiharu ; Tanaka, Noriko ; Okamoto, Keinosuke ; Negishi, Tomoe ; Kimura, Sachiko ; Suzuki, Toshinori. / Mutagenicity and NO formation from UVA irradiated N-nitrosoproline, and characterization of photoproduct formed in UVA-irradiated mixture of N-nitrosoproline with 2-′deoxyguanosine in neutral solution. In: Genes and Environment. 2014 ; Vol. 36, No. 2. pp. 47-53.
@article{346935af33e34ceea143990a560164d1,
title = "Mutagenicity and NO formation from UVA irradiated N-nitrosoproline, and characterization of photoproduct formed in UVA-irradiated mixture of N-nitrosoproline with 2-′deoxyguanosine in neutral solution",
abstract = "Earlier studies in our laboratory showed that UVA-irradiated N-nitrosoproline (NPRO) could produce mutagenic compounds and strand breaks in treated DNA with the release of nitric oxide and active oxygen species. In the present study, we investigated the phosphate-dependence of photomutagenicity and solvent effects on nitric oxide release from irradiated NPRO. We also investigated the UVA-driven reaction of NPRO with 2′-deoxyguanosine (dG) in neutral solution, and identified the chemical structure of the photoproduct. A mixture of NPRO and dG dissolved in neutral solution was irradiated with UVA at 320-400 nm for 6 h, and the solution was then subjected to HPLC analysis. The photoproduct isolated from the NPRO and dG mixture in neutral buffer was identified as 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG). We propose a photoreaction mechanism involving the absorption of UVA photons by NPRO followed by UVA-driven photolysis of NPRO, and subsequent production of active oxygen radicals that generate 8-oxodG.",
keywords = "8-oxo-deoxyguanosine, DNA adduct, N-nitrosamine, NO radical, Photoreaction",
author = "Sakae Arimoto and Masaki Machida and Kayoko Sano and Shuhei Aoyama and Chiharu Asahi and Noriko Tanaka and Keinosuke Okamoto and Tomoe Negishi and Sachiko Kimura and Toshinori Suzuki",
year = "2014",
doi = "10.3123/jemsge.2014.004",
language = "English",
volume = "36",
pages = "47--53",
journal = "Genes and Environment",
issn = "1880-7046",
publisher = "The Japanese Environmental Mutagen Society",
number = "2",

}

TY - JOUR

T1 - Mutagenicity and NO formation from UVA irradiated N-nitrosoproline, and characterization of photoproduct formed in UVA-irradiated mixture of N-nitrosoproline with 2-′deoxyguanosine in neutral solution

AU - Arimoto, Sakae

AU - Machida, Masaki

AU - Sano, Kayoko

AU - Aoyama, Shuhei

AU - Asahi, Chiharu

AU - Tanaka, Noriko

AU - Okamoto, Keinosuke

AU - Negishi, Tomoe

AU - Kimura, Sachiko

AU - Suzuki, Toshinori

PY - 2014

Y1 - 2014

N2 - Earlier studies in our laboratory showed that UVA-irradiated N-nitrosoproline (NPRO) could produce mutagenic compounds and strand breaks in treated DNA with the release of nitric oxide and active oxygen species. In the present study, we investigated the phosphate-dependence of photomutagenicity and solvent effects on nitric oxide release from irradiated NPRO. We also investigated the UVA-driven reaction of NPRO with 2′-deoxyguanosine (dG) in neutral solution, and identified the chemical structure of the photoproduct. A mixture of NPRO and dG dissolved in neutral solution was irradiated with UVA at 320-400 nm for 6 h, and the solution was then subjected to HPLC analysis. The photoproduct isolated from the NPRO and dG mixture in neutral buffer was identified as 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG). We propose a photoreaction mechanism involving the absorption of UVA photons by NPRO followed by UVA-driven photolysis of NPRO, and subsequent production of active oxygen radicals that generate 8-oxodG.

AB - Earlier studies in our laboratory showed that UVA-irradiated N-nitrosoproline (NPRO) could produce mutagenic compounds and strand breaks in treated DNA with the release of nitric oxide and active oxygen species. In the present study, we investigated the phosphate-dependence of photomutagenicity and solvent effects on nitric oxide release from irradiated NPRO. We also investigated the UVA-driven reaction of NPRO with 2′-deoxyguanosine (dG) in neutral solution, and identified the chemical structure of the photoproduct. A mixture of NPRO and dG dissolved in neutral solution was irradiated with UVA at 320-400 nm for 6 h, and the solution was then subjected to HPLC analysis. The photoproduct isolated from the NPRO and dG mixture in neutral buffer was identified as 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG). We propose a photoreaction mechanism involving the absorption of UVA photons by NPRO followed by UVA-driven photolysis of NPRO, and subsequent production of active oxygen radicals that generate 8-oxodG.

KW - 8-oxo-deoxyguanosine

KW - DNA adduct

KW - N-nitrosamine

KW - NO radical

KW - Photoreaction

UR - http://www.scopus.com/inward/record.url?scp=84902153090&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84902153090&partnerID=8YFLogxK

U2 - 10.3123/jemsge.2014.004

DO - 10.3123/jemsge.2014.004

M3 - Article

AN - SCOPUS:84902153090

VL - 36

SP - 47

EP - 53

JO - Genes and Environment

JF - Genes and Environment

SN - 1880-7046

IS - 2

ER -