Literature DB >> 17208007

Liquid chromatography-tandem mass spectrometry analysis of the DNA adducts of aristolochic acids.

Wan Chan1, Yufang Zheng, Zongwei Cai.   

Abstract

Electrophilic attack of aristolactam-nitrenium ion by the C7 position to the exocyclic amino group in the DNA bases led to the formation of the major adducts. In this study, liquid chromatography coupled with electrospray ionization tandem mass spectrometry was applied to the study of DNA adducts of aristolochic acid (AA). When DNA (bases and CT-DNA) was incubated with AA, dG-AAI, dG-AAII, dA-AAI, dA-AAII, dC-AAI, and dC-AAII were detected and characterized. The dC adducts of AA were identified for the first time. The soft ionization technology allowed detection of the intact DNA adducts. High-resolution MS and MS-MS capabilities of a quadrupole time-of-flight mass spectrometer were shown to be efficient for DNA adducts analysis. DNA-AA adducts showed characteristic fragmentation patterns in MS-MS analysis. The dissociative loss of 116 Da from the DNA-AA adducts, which resulted from internal hydrogen transfer and cleavage at the C-N glycosidic bond, provided a characteristic fragment for the structural elucidation.

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Year:  2007        PMID: 17208007     DOI: 10.1016/j.jasms.2006.11.010

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN: 1044-0305            Impact factor:   3.109


  33 in total

1.  [Aristolochic acids from Aristolochia manshuriensis (author's transl)].

Authors:  V G Rücker; B S Chung
Journal:  Planta Med       Date:  1975-02       Impact factor: 3.352

2.  Sequence-specific detection of aristolochic acid-DNA adducts in the human p53 gene by terminal transferase-dependent PCR.

Authors:  V M Arlt; H H Schmeiser; G P Pfeifer
Journal:  Carcinogenesis       Date:  2001-01       Impact factor: 4.944

3.  Investigation of the regio- and stereo-selectivity of deoxyguanosine linkage to deuterated 2-hydroxyestradiol by using liquid chromatography/ESI-ion trap mass spectrometry.

Authors:  L Debrauwer; E Rathahao; I Jouanin; A Paris; G Clodic; H Molines; O Convert; F Fournier; J C Tabet
Journal:  J Am Soc Mass Spectrom       Date:  2003-04       Impact factor: 3.109

4.  Pressurized liquid extraction of berberine and aristolochic acids in medicinal plants.

Authors:  E S Ong; S O Woo; Y L Yong
Journal:  J Chromatogr A       Date:  2000-12-22       Impact factor: 4.759

5.  32P-postlabelling analysis of the DNA adducts formed by aristolochic acid I and II.

Authors:  W Pfau; H H Schmeiser; M Wiessler
Journal:  Carcinogenesis       Date:  1990-09       Impact factor: 4.944

6.  32P-post-labelling analysis of DNA adducts formed by aristolochic acid in tissues from patients with Chinese herbs nephropathy.

Authors:  C A Bieler; M Stiborova; M Wiessler; J P Cosyns; C van Ypersele de Strihou; H H Schmeiser
Journal:  Carcinogenesis       Date:  1997-05       Impact factor: 4.944

7.  Comparison of DNA adduct formation by aristolochic acids in various in vitro activation systems by 32P-post-labelling: evidence for reductive activation by peroxidases.

Authors:  H H Schmeiser; E Frei; M Wiessler; M Stiborova
Journal:  Carcinogenesis       Date:  1997-05       Impact factor: 4.944

8.  Analyses of DNA adducts formed by ochratoxin A and aristolochic acid in patients with Chinese herbs nephropathy.

Authors:  V M Arlt; A Pfohl-Leszkowicz; J Cosyns; H H Schmeiser
Journal:  Mutat Res       Date:  2001-07-25       Impact factor: 2.433

9.  Analysis and quantification of DNA adducts of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in liver of rats by liquid chromatography/electrospray tandem mass spectrometry.

Authors:  Axel Paehler; Janique Richoz; John Soglia; Paul Vouros; Robert J Turesky
Journal:  Chem Res Toxicol       Date:  2002-04       Impact factor: 3.739

10.  Postlabeling methods for carcinogen-DNA adduct analysis.

Authors:  K Randerath; E Randerath; H P Agrawal; R C Gupta; M E Schurdak; M V Reddy
Journal:  Environ Health Perspect       Date:  1985-10       Impact factor: 9.031

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  3 in total

1.  Identification of a reduction product of aristolochic acid: implications for the metabolic activation of carcinogenic aristolochic acid.

Authors:  Horacio A Priestap; Carlos de los Santos; J Martin E Quirke
Journal:  J Nat Prod       Date:  2010-12-08       Impact factor: 4.050

2.  Biomonitoring of aristolactam-DNA adducts in human tissues using ultra-performance liquid chromatography/ion-trap mass spectrometry.

Authors:  Byeong Hwa Yun; Thomas A Rosenquist; Viktoriya Sidorenko; Charles R Iden; Chung-Hsin Chen; Yeong-Shiau Pu; Radha Bonala; Francis Johnson; Kathleen G Dickman; Arthur P Grollman; Robert J Turesky
Journal:  Chem Res Toxicol       Date:  2012-05-04       Impact factor: 3.739

3.  Comparative studies on the multi-component pharmacokinetics of Aristolochiae Fructus and honey-fried Aristolochiae Fructus extracts after oral administration in rats.

Authors:  Jinbin Yuan; Gang Ren; Jian Liang; Chong-Zhi Wang; Zhihong Yan; Qun Huang; Jiankang Li; Yang Chen; Yi Tang; Xiaofei Liu; Chun-Su Yuan
Journal:  BMC Complement Altern Med       Date:  2017-02-10       Impact factor: 3.659

  3 in total

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