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Soft‐ionization mass spectrometry study of deoxynucleoside bioclusters and deoxynucleoside‐antitumor medicinal preparation clusters
Author(s) -
Sukhodub Leonid F.
Publication year - 1995
Publication title -
mass spectrometry reviews
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.035
H-Index - 126
eISSN - 1098-2787
pISSN - 0277-7037
DOI - 10.1002/mas.1280140402
Subject(s) - chemistry , nucleobase , fast atom bombardment , mass spectrometry , tautomer , mass spectrum , field desorption , base pair , nucleotide , dna , stereochemistry , ionization , chromatography , organic chemistry , biochemistry , ion , gene
This article reviews the results of mass spectrometric investigations of the formation mechanism and the energy stabilty of the bioclusters DNA and RNA nucleotide pairs, and nucleoitde base clusters containing certain antitumor medicinal preparations. All of the results discussed were obtained using temperature‐dependent field ionization mass spectrometry (TD‐FIMS) and well‐known and approved desorption mass spectrometry techniques; e.g., fast atom bombardment (FAB) and plasma‐desorption mass spectrometry (PDMS). A variety of data are presented on the formation enthalpies of Watson–Crick (Hoogsteen) and other H‐bonded base‐pairs, nucleobase stacking dimers, base hydrates, and their complementary pairs in vacuum. Analysis of the data permitted a thermodynamic stability sequence of bioclusters under study to be constructed. The nucleobases in rare (enol and imine) tautomer forms are shown to produce H‐bonded pairs comparable in energy with the canonical A · T pair. This review summarizes the results of recent investigations into the interactions of DNA, nucleosides, bases, and some amino acids with antitumor preparations such as triethylene thiophosphate amide (thio TEPA), prospydine (Psp), farmorubicin (Far), and doxorubicin (Dox). The specific features of the Dox and Far clusters formation observed in the mass spectra are found to correlate with the antitumor chemotherapeutic activity of these antibiotics. © 1996 John Wiley & Sons, Inc.