Fast atom bombardment and high performance tandem mass spectrometry of platinum(II) oligodeoxyribonucleotide fragments

Costello, Catherine E.; Comess, Kenneth M.; Plaziak, Adam S.; Bancroft, Daniel P.; Lippard, Stephen J.

doi:10.1016/0168-1176(92)87020-f

Cited by 24 publications

(22 citation statements)

References 58 publications

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“…The major product ions observed from positively charged precursors were platinated w n -type sequence ions, often accompanied by ions resulting from loss of one or both NH 3 groups. These observations were consistent with earlier FAB-MS/MS studies of cisplatin adducts (Martin, Schreiner, & Van Breemen, 1991;Costello et al, 1992). In our study, the major and minor adducts were shown to be 1,3-GG and 1,3-AG crosslinks, respectively.…”

Section: A Platinum Complexessupporting

confidence: 95%

“…Hence, a number of the studies discussed below combine MS methods with enzymatic digestion to identify binding sites. Prior to the advent of ESI-MS, a number of groups also analyzed metal±oligonucleotide (Martin, Schreiner, & Van Breemen, 1991;Costello et al, 1992). More recently MALDI has been used effectively to detect metal±oligonucleotide adducts (Costello, Nordhoff, & Hillen Kamp, 1994;Gonnet et al, 1996b;Hettich, 1999).…”

Section: Dna±metal Ion Complexesmentioning

confidence: 97%

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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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Section: A Platinum Complexessupporting

confidence: 95%

Section: Dna±metal Ion Complexesmentioning

confidence: 97%

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

Beck

Colgrave

Ralph

et al. 2001

Mass Spectrometry Reviews

227

204

View full text Add to dashboard Cite

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“…Thus, with FAB-MS, a method for the generation of cisplatin complexes with oligonucleotides was found and used to study cisplatin and its trans-analog (Costello et al, 1992). For a series of hexanucleotides, singly-charged intact complexes of the oligonucleotide and cisplatin were observed, acompanied by ions that correspond to the loss of one or two ammine groups.…”

Section: Molecular Recognition and Supramolecular Chemistrymentioning

confidence: 99%

Molecular recognition and supramolecular chemistry in the gas phase

Schalley

2001

Mass Spectrometry Reviews

289

178

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Supramolecular chemistry, in particular, the fields of molecular recognition and self-assembly, profit much from the development of soft ionization techniques and advanced methods for mass analysis and gas-phase chemistry. Vice versa, weakly bonded architectures and host-guest complexes represent a veritable challenge for the mass spectrometrist, leading to further development of methods and techniques. This review describes the state-of-the-art in this field, and includes topics such as the effects of solvation on meta binding to crown ethers, chiral discrimination of guests by chiral hosts, the elucidation of the secondary structure of self assembled complexes, and the mechanistic pathways of self assembly or the fragmentations of supramolecular complexes in the gas phase.

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“…The first reports on platinated oligonucleotides in connection with FAB tandem mass spectrometry were published in 1991 by Martin et al [61] and in 1992 by Costello et al [62]. They found consistently that loss of NH 3 groups from the ligand sphere of platinum is one of the dominant reaction pathways together with Nglycosidic bond cleavage.…”

mentioning

confidence: 97%

The influence of cisplatin on the gas-phase dissociation of oligonucleotides studied by electrospray ionization tandem mass spectrometry

Nyakas

Eymann

Schürch

2009

J. Am. Soc. Mass Spectrom.

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cis-Diamminedichloroplatinum(II) (cisplatin, DDP) is a cornerstone of anticancer therapy and has become one of the most widely used drugs for the treatment of various epithelial malignancies. The cytotoxicity of cisplatin is mainly based upon its affinity to adjacent guanines in nucleic acids, resulting in the formation of 1,2-intrastrand adducts. In this study the gas-phase dissociation of DNA- and RNA-cisplatin adducts is investigated by electrospray ionization (ESI) tandem mass spectrometry (MS/MS). The fundamental mechanistic aspects of fragmentation are elucidated to provide the basis for the tandem mass spectrometric determination of binding motifs and binding sites of this important anticancer drug. It is shown that the binding of cisplatin to vicinal guanines drastically alters the gas-phase fragmentation behavior of oligonucleotides. The 3'-C-O bond adjacent to the GG base pair is preferentially cleaved, leading to extensive formation of the corresponding w-ion. This observation was even made for oligoribonucleotides, which usually tend to form c- and y-ions under CID conditions. The absence of complementary ions of equal abundance indicates that oligonucleotide-cisplatin adducts are following more than one dissociation pathway in the gas-phase. Several mechanisms that explain the increased cleavage of the 3'-C-O bond and the lack of the complementary a-ion are proposed. Results of additional MS/MS experiments on methylphosphonate-oligodeoxynucleotides confirm the proposed mechanisms.

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Fast atom bombardment and high performance tandem mass spectrometry of platinum(II) oligodeoxyribonucleotide fragments

Cited by 24 publications

References 58 publications

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

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

Molecular recognition and supramolecular chemistry in the gas phase

The influence of cisplatin on the gas-phase dissociation of oligonucleotides studied by electrospray ionization tandem mass spectrometry

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