Determination of in Vitro- and in Vivo-Formed DNA Adducts of 2-Amino-3-methylimidazo[4,5-<i>f</i>]quinoline by Capillary Liquid Chromatography/Microelectrospray Mass Spectrometry

Gangl, Eric; Turesky, Robert J.; Vouros, Paul

doi:10.1021/tx990060m

Cited by 50 publications

(69 citation statements)

References 42 publications

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“…The chromatographic peak observed at RT ϭ 20.2 min in Figure 4a represents the major and the less polar adduct, which could fit dG-C8-IQ properties [21,22]. This peak corresponds to an ion with an accurate mass of 464.17904, in agreement with the expected molecular formula of the dG-IQ adduct as indicated in Table 2.…”

Section: Iq-deoxynucleoside Adductssupporting

confidence: 75%

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSⁿ and accurate mass measurement of fragment ions

Jamin

Arquier

Canlet

et al. 2007

J. Am. Soc. Mass Spectrom.

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The formation of adducts by reaction of active metabolites of two heterocyclic aromatic amines (NHOH-PhIP and NHOH-IQ) at nucleophilic sites of deoxynucleosides has been studied by LC-MS n analyses of the obtained reaction mixtures. Sequential MS 3 experiments were carried out on an ion trap mass spectrometer to gain extensive structural information on each adduct detected in the first MS step. Attribution of ions was supported by accurate mass measurements performed on an Orbitrap mass analyzer. Particular attention was given to ions diagnostic of the linking between the heterocyclic aromatic amine (HAA) and the deoxynucleoside. By this way, the structures of five adducts have been characterized in this study, among which two are new compounds: dG-N7-IQ and dA-N 6 -IQ. No depurinating adduct was found in the reactions investigated therein. As expected, the C8 and N 2 p p atoms of dG were found as the most reactive sites of deoxynucleosides, resulting in the formation of two different adducts with IQ and one adduct with PhIP. An unusual non-depurinating dG-N7-IQ adduct has been characterized and a mechanism is proposed for its formation on the basis of the reactivity of arylamines. A dA-N 6 -IQ adduct has been identified for the first time in this work, showing that HAAs can generate DNA adducts with bases other than dG. (J Am Soc

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Section: Iq-deoxynucleoside Adductssupporting

confidence: 75%

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSⁿ and accurate mass measurement of fragment ions

Jamin

Arquier

Canlet

et al. 2007

J. Am. Soc. Mass Spectrom.

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“…The sensitivity CNL of analysis is much lower than SRM, which was highlighted by Gangl et al when R.Singh and P.B.Farmer they studied the formation of DNA adducts by the heterocyclic aromatic amine 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ) in vitro and in Cynomologus monkeys. The authors found that CNL gave a limit of detection of 1 adduct per 10 4 unmodified DNA bases compared with SRM where the limit of detection was 1 adduct per 10 7 unmodified DNA bases (100).…”

Section: Mass Spectrometry In the Analysis Of Dna Adductsmentioning

confidence: 99%

Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection

2005

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“…More recently, ESI coupled either with CE or with capillary liquid chromatography (Gangl, Turesky, & Vouros, 1999) has been shown to be useful for the screening of in vivo DNA adducts. A recent review by Apruzzese and Vouros (Apruzzese & Vouros, 1998) provides an overview of the analysis of DNA adducts by capillary methods coupled to MS.…”

Section: A Covalent Bindingmentioning

confidence: 99%

Electrospray ionization mass spectrometry of oligonucleotide complexes with drugs, metals, and proteins

Beck

Colgrave

Ralph

et al. 2001

Mass Spectrometry Reviews

227

204

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I. Introduction 61 II. Binding of Small Molecules to DNA 62 A. Covalent Binding 62 B. Reversible (Noncovalent) DNA-Binding Agents 65 III. DNA-Metal Ion Complexes 67 A. Platinum Complexes 70 B. Other Metal Ions 73 IV. DNA-Protein Complexes 74 A. Introduction 74 B. ESI-MS of DNA-Protein Complexes 76 C. ESI-MS Analysis of Proteolytic Products of DNA-Protein Complexes 79 D. ESI-MS of Ternary DNA-Protein-Ligand Complexes 80 V. Conclusions 80 Abbreviations 81 References 81 --Interactions of DNA with drugs, metal ions, and proteins are important in a wide variety of biological processes. With the advent of electrospray ionization (ESI) and matrix-assisted laser desorption ionization (MALDI), mass spectrometry (MS) is now a well-established tool for the characterization of the primary structures of biopolymers. The gentle nature of the ESI process, however, means that ESI-MS is also finding application for the study of noncovalent and other fragile biomolecular complexes. We outline here the progress, to date, in the use of ESI-MS for the study of noncovalent drug-DNA and protein-DNA complexes together with strategies that can be employed to examine the binding of small molecules and metal complexes to DNA. In the case of covalent complexes with DNA, sequence information can be derived from ESI-MS used in conjunction with tandem mass spectrometry (MS/MS) and/or enzymatic digestion. MS/MS can also be used to probe the relative binding affinities of drugs that bind to DNA via noncovalent interactions. Overall, the work in this area, to date has demonstrated that ESI-MS and MS/MS will prove to be valuable complements to other structural methods, offering advantages in terms of speed, specificity, and sensitivity. (c) 2001 John Wiley & Sons, Inc.

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Determination of in Vitro- and in Vivo-Formed DNA Adducts of 2-Amino-3-methylimidazo[4,5-f]quinoline by Capillary Liquid Chromatography/Microelectrospray Mass Spectrometry

Cited by 50 publications

References 42 publications

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSⁿ and accurate mass measurement of fragment ions

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSⁿ and accurate mass measurement of fragment ions

Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection

Electrospray ionization mass spectrometry of oligonucleotide complexes with drugs, metals, and proteins

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Determination of in Vitro- and in Vivo-Formed DNA Adducts of 2-Amino-3-methylimidazo[4,5-f]quinoline by Capillary Liquid Chromatography/Microelectrospray Mass Spectrometry

Cited by 50 publications

References 42 publications

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSn and accurate mass measurement of fragment ions

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSn and accurate mass measurement of fragment ions

Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection

Electrospray ionization mass spectrometry of oligonucleotide complexes with drugs, metals, and proteins

Contact Info

Product

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New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSⁿ and accurate mass measurement of fragment ions

New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSⁿ and accurate mass measurement of fragment ions