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dc.contributor.authorShen, Li-Chingen_US
dc.contributor.authorChiang, Su-Yinen_US
dc.contributor.authorLin, Ming-Huanen_US
dc.contributor.authorChung, Wen-Shengen_US
dc.contributor.authorWu, Kuen-Yuhen_US
dc.date.accessioned2014-12-08T15:24:15Z-
dc.date.available2014-12-08T15:24:15Z-
dc.date.issued2012-09-18en_US
dc.identifier.issn0378-4274en_US
dc.identifier.urihttp://dx.doi.org/10.1016/j.toxlet.2012.07.006en_US
dc.identifier.urihttp://hdl.handle.net/11536/16847-
dc.description.abstractSafrole, a naturally occurring product derived from spices and herbs, has been shown to be associated with the development of hepatocellular carcinoma in rodents. Safrole 2',3'-oxide (SFO), an electrophilic metabolite of safrole, was shown to react with DNA bases to form detectable DNA adducts in vitro, but not detected in vivo. Therefore, the objective of this study was to investigate the formation of N7-(3-benzo[1,3] dioxol-5-yl-2-hydroxypropyl) guanine ( N7 gamma-SFO-Gua) resulting from the reaction of SFO with the most nucleophilic site of guanine in vitro and in vivo with a newly developed isotope-dilution high performance liquid chromatography electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) method. N7 gamma-SFO-Gua and [N-15(5)]-N7-(3-benzo[1,3] dioxol-5-yl-2-hydroxypropyl) guanine ([N-15(5)]-N7 gamma-SFO-Gua) were first synthesized, purified, and characterized. The HPLC-ESI-MS/MS method was developed to measure N7 gamma-SFO-Gua in calf thymus DNA treated with 60 mu mol of SFO for 72 h and in urine samples of mice treated with a single dose of SFO (30 mg/kg body weight, intraperitoneally). In calf thymus DNA, the level of N7 gamma-SFO-Gua was 2670 adducts per 106 nucleotides. In urine of SFO-treated mice, the levels of N7 gamma- SFO-Gua were 1.02 +/- 0.14 ng/mg creatinine (n = 4) on day 1, 0.73 +/- 0.68 ng/mg creatinine (n = 4) on day 2, and below the limit of quantitation on day 3. These results suggest that SFO can cause in vivo formation of N7 gamma-SFO-Gua, which may then be rapidly depurinated from the DNA backbone and excreted through urine. (c) 2012 Elsevier Ireland Ltd. All rights reserved.en_US
dc.language.isoen_USen_US
dc.subjectSafrole 2 ',3 '-oxideen_US
dc.subjectN7-(3-Benzo[1,3] dioxol-5-yl-2-hydroxypropyl)guanineen_US
dc.subject(N7 gamma-SFO-Gua)en_US
dc.subjectHigh performance liquid chromatographyen_US
dc.subjectelectrospray ionization tandem massen_US
dc.subjectspectrometry (HPLC-ESI-MS/MS)en_US
dc.titleIn vivo formation of N7- guanine DNA adduct by safrole 2 ',3 '-oxide in miceen_US
dc.typeArticleen_US
dc.identifier.doi10.1016/j.toxlet.2012.07.006en_US
dc.identifier.journalTOXICOLOGY LETTERSen_US
dc.citation.volume213en_US
dc.citation.issue3en_US
dc.citation.spage309en_US
dc.citation.epage315en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000309170300002-
dc.citation.woscount3-
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