Evaluation of complexes of DNA duplexes and novel benzoxazoles or benzimidazoles by electrospray ionization mass spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 11, 2004, Pages 1593-1603

  Oehlers, Leon ^a   Mazzitelli, Carolyn L ^a   Brodbelt, Jennifer S ^a   Rodriguez, Mireya ^a   Kerwin, Sean ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICANCER ANALOGS; ELECTROSPRAY IONIZATION;

AROMATIC COMPOUNDS; IONIZATION; MASS SPECTROMETERS; POSITIVE IONS; STOICHIOMETRY; TUMORS;

DNA;

ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CATION; DOUBLE STRANDED DNA; DRUG METABOLITE; LIGAND; MAGNESIUM ION; METAL ION; METHYL 2 (2' HYDROXYPHENYL)BENZOXAZOLE 7 CARBOXYLATE; NICKEL; UK 1; UNCLASSIFIED DRUG; ZINC ION;

ARTICLE; CANCER CELL CULTURE; CORRELATION ANALYSIS; DNA BINDING; ELECTROSPRAY MASS SPECTROMETRY; GENE INTERACTION; HUMAN; HUMAN CELL; METAL BINDING; PROSTATE CANCER; STOICHIOMETRY;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; BENZOXAZOLES; BINDING SITES; CATIONS; DNA ADDUCTS; METALS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 7244250150     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2004.07.015     Document Type: Article

References (50)

1. M.J. Clarke P.J. Sadler Metallopharmaceuticals I DNA Interactions, Topics in Biological Inorganic Chemistry Vol. I 1999 Springer-Verlag Berlin
2. C.L. Propst, T.J. Perun Nucleic Acid Targeted Drug Design 1992 Marcel Dekker, Inc New York
3. S.P. Fricker Metal Compounds in Cancer Therapy 1994 Chapman and Hall Suffolk
4. K.E. Erkkila, D.T. Odom, J.K. Barton Recognition and Reaction of Metallointercalators with DNA Chem. Rev. 99 1999 2888-2795
5. J. Reedijk DNA-Binding Properties of Heavy-Metal Complexes and Consequences of Structural Changes Macromol. Symp. 156 2000 277 284
6. B.S.P. Reddy, S.M. Sondhi, J.W. Lown Synthetic DNA Minor Groove-Binding Drugs Pharmacol. Therapeut. 84 1999 1 111
7. R. Gambari, G. Beriotto, C. Rutidliano, N. Bianchi, C. Mischiati Biospecific Interaction Analysis of Low-Molecular Weight Binding Drugs J. Pharmacol. Exper. Therap. 294 2000 370 377
8. P.A. Permana, R.M. Snapka, L.L. Shen, D.T. W. Chu, J.J. Clement, J.J. Planttner Quinobenzoxazines--A Class of Novel Antitumor Quinolones and Potent Mammalian DNA Topoisomerase-II Catalytic Inhibitors Biochemistry 33 1994 11333 11339
9. J.B. Chaires Energetics of Drug-DNA Interactions Biopolymers 44 3 1998 201 215
10. W Priebe Anthracycline Antibiotics New Analogs, Methods of Delivery, and Mechanisms of Action 1995 American Chemical Society Symposium Series Washington, DC Vol. DLXXIV
11. D.C. Gale, D.R. Goodlett, K.J. Light-Wahl, R.D. Smith Observation of Duplex DNA-Drug Noncovalent Complexes by Electrospray Ionization Mass Spectrometry J. Am. Chem. Soc. 116 1994 6027 6028
12. Y.L. Hsieh, Y.-T. Li, J.D. Henion, B Ganem Studies of Noncovalent Interactions of Actinomycin D with Single-Stranded Oligodeoxynucleotides by Ion Spray Mass Spectrometry and Tandem Mass Spectrometr Biol. Mass Spectrom. 23 1994 272 277
13. D.C. Gale, R.D. Smith Characterization of Noncovalent Complexes Formed Between Minor Groove Binding Molecules and Duplex DNA by Electrospray Ionization Mass Spectrometry J. Am. Soc. Mass Spectrom. 6 1995 1154 1160
14. A. Triolo, F.M. Arcamone, A. Raffaelli, P. Salvadori Noncovalent Complexes Between DNA-Binding Drugs and Doubly-stranded DeoxyoligonucleotidesA Study by Ionspray Mass Spectrometry J. Mass Spectrom. 32 1997 1186 1193
15. A. Kapur, J.L. Beck, M.M. Sheil Observation of Daunomycin and Nogalamycin Complexes with Duplex DNA Using Electrospray Ionization Mass Spectrometry Rapid Commun. Mass Spectrom. 13 1999 2489 2492
16. V. Gabelica, E. De Pauw, F. Rosu Interaction Between Antitumor Drugs and a Double-Stranded Oligonucleotide Studied by Electrospray Ionization Mass Spectrometry J. Mass Spectrom. 34 1999 1328
17. K.X. Wan, T. Shibue, M.L. Gross Noncovalent Complexes Between DNA-Binding Drugs and Double-Stranded OligodeoxynucelotidesA Study by ESI Ion Trap Mass Spectrometry J. Am. Chem. Soc. 122 2000 300 306
18. K.X. Wan, M.L. Gross, T. Shibue Gas-Phase Stability of Double-Stranded Oligodeoxynucleotides and Their Noncovalent Complexes with DNA-Binding Drugs as Revealed by Collisional Activation in an Ion Trap J. Am. Soc. Mass Spectrom. 11 2000 450 459
19. V. Gabelica, F. Rosu, C. Houssier, E. De Pauw Gas Phase Thermal Denaturation of an Oligonucleotide Duplex and Its Complexes with Minor Groove Binders Rapid Commun. Mass Spectrom. 14 2000 464 468
20. P. Iannitti-Tito, A. Weimann, G. Wickham, M.M. Sheil Structural Analysis of Drug-DNA Adducts by Tandem Mass Spectrometry Analyst 125 2000 627 633
21. - Anal. Biochem. 284 2000 77 86
22. A. Harsch, L.A. Marzilli, R.C. Bunt, J. Stubbe, P. Vouros Accurate and Rapid Modeling of Iron-Bleomycin-Induced DNA Damage using Tethered Duplex Oligonucleotides and Electropsray Ionization Ion Trap Mass Spectrometric Analysis Nucleic Acids Res. 28 9 2000 1978 1985
23. R.H. Griffey, M.J. Greig, H. An, H. Sasmor, S. Manalili Targeted Site-Specific Gas-Phase Cleavage of Oligoribonucleotides. Application in Mass Spectrometry-Based Identification of Ligand Binding Sites J. Am. Chem. Soc. 121 1999 474 475
24. R.H. Griffey, S.A. Hofstadler, K.A. Sannes-Lowery, D.J. Ecker, S.T. Crooke Determinants of Aminoglycoside Binding Specificity for rRNA by Using Mass Spectrometry Proc. Natl. Acad. Sci. U.S.A. 96 1999 10129 10133
25. K.A. Sannes-Lowery, H.-Y. Mei, J.A. Loo Studying Aminoglycoside Binding to HIV-1 TAR RNA by Electrospray Ionization Mass Spectrometry Int. J. Mass Spectrom. 193 1999 115 121
26. K.A. Sannes-Lowery, J.J. Drader, R.H. Griffey, S.A. Hofstadler Fourier-Transform Ion Cyclotron Resonance Mass Spectrometry as a High Throughput Affinity Screen to Identify RNA Binding Ligands Trends Anal. Chem. 19 8 2000 481 491
27. R.H. Griffey, K.A. Sannes-Lowery, J.J. Drader, M. Venkratraman, E.E. Swayze, S.A. Hofstadler Characterization of Low-Affinity Complexes Between RNA and Small Molecules Using Electrospray Ionization Mass Spectormetry J. Am. Chem. Soc. 122 2000 9933 9938
28. K.A. Sannes-Lowery, R.H. Griffey, S.A. Hofstadler Measuring Dissociation Constants of RNA and Aminoglycosides Antibiotics by Electrospray Ionization Mass Spectrometry Anal. Biochem. 280 2000 264 271
29. P. Iannitte, M.M. Sheil, G. Wickham High Sensitivity and Fragmentation Specificity in the Analysis of Drug-DNA Adducts by Electrospray Tandem Mass Spectrometry J. Am. Chem. Soc. 119 1997 1490 1491
30. J.L. Beck, M.L. Colgrave, S.F. Ralph, M.M. Sheil Electrospray Ionization Mass Spectrometry of Oligonucleotide Complexes with Drugs, Metals, and Proteins Mass Spectrom. Rev. 20 2001 61 87
31. S.A. Hofstadler, R.H. Griffey Analysis of Noncovalent Complexes of DNA and RNA by Mass Spectrometry Chem. Rev. 101 2001 377 390
32. M.L. Reyzer, J.S. Brodbelt, S.M. Kerwin, D. Kumar Evaluation of Complexation of Metal Mediated DNA Binding Drugs to Oligonucleotides via Electrospray Ionization Mass Spectrometry Nucleic Acids Res. 29 2001 e103
33. M.L. Colgrave, J.L. Beck, M.M. Sheil, M.S. Searle Electrospray Ionization Mass Spectrometric Detection of Weak Noncovalent Interactions in Nogalamycin-DNA Complexes Chem. Commun. 6 2002 556 557
34. R. Gupta, A. Kapur, J.L. Beck, M.M. Sheil Positive Ion Electrospray Ionization Mass Spectrometry of Double-Stranded DNA/Drug Complexes Rapid Commun. Mass Spectrom 15 2001 2472 2480
35. W. David, S.M. Kerwin, J.S. Brodbelt Investigation of Quadruplex DNA-Drug Interations by Electrospray Ionization-Mass Spectrometry Anal. Chem. 74 2002 2029 2033
36. A. Kapur, J.L. Beck, M.M. Sheil Observation of Daunomycin and Nogalamycin Complexes with Duplex DNA Using Electrospray Ionization Mass Spectrometry Rapid Commun. Mass Spectrom. 13 1999 2489 2497
37. L. Guittat, P. Alberti, F. Rosu, S. Van Miert, E. Thetiot, L. Pieters, V. Gabelica, E. De Pauw, A. Ottaviani, J.-F. Riou, J.-L. Mergney Interactions of Cryptolepine and Neocyrptolepine with Unusual DNA Structures Biochimie 85 2003 535 547
38. V. Gabelica, N. Galic, F. Rosu, C. Houssier, E. De Pauw Influence of Response Factors on Determining equilibrium Association Constants of Noncovalent Complexes by Electrospray Ionization Mass Spectrometry J. Mass Spectrom. 38 2003 491 501
39. J.L. Beck, R. Gupta, T. Urathamakul, N.L. Williamson, M.M. Sheil, J.R. Aldrich-Wright, S.F. Ralph Probbing DNA Selectivity of Ruthenium Metallointercalators Using ESI Mass Spectrometry Chem. Commun. (Camb) 5 2003 626 627
40. M.L. Colgrave, J.L. Beck, M.M. Sheil, M.S. Searle Electrospray Ionization Mass Spectrometric Detection of Weak Noncovalent Interactions in Nogalamycin-DNA Complexes Chem. Commun. (Camb) 6 2002 556 557
41. B. Reynolds, Michael, R. DeLuca, Mark, M. Kerwin, Sean The Novel Bis(benzoxazole) Cytotoxic Natural Product UK-1 is a Magnesium Ion-Dependent DNA Binding Agent and Inhibitor of Human Topoisomerase II Bioorg. Chem. 27 4 1999 326 337
42. D. Kumar, M.R. Jacob, M.B. Reynolds, S.M. Kerwin Synthesis and Evaluation of Anticancer Benzoxazoles and Benzimidazoles Related to UK-1 Bioorg. Med. Chem. 10 2002 3997 4004
43. B.B. Wang, N. Maghami, V.L. Goodlin, P.J. Smith Critical Structural Motif for the Catalytic Inhibition of Human Topoisomerase II by UK-1 and Analogs Bioorg. Med. Chem. Lett. 14 2004 3221 3226
44. 3H]Thymidine Incorporation Assay J. Immun. Methods 170 1994 211 224
45. L.L. Shen, L.A. Mitscher, P.N. Sharma, T.J. O'Donnell, D.W. Chu, C.S. Cooper, T. Rosen, A.G. Pernet Mechanism of Inhibition of DNA Gyrase by Quinolone Antibacterials A Cooperative Drug-DNA Binding Model Biochemistry 28 1989 3886 3894
46. K.J. Marians, H. Hiasa Mechanism of Quinolone Action. A Drug-Induced Structural Perturbation of the DNA Precedes Strand Cleavage by Topoisomerase IV J. Biol. Chem. 272 1997 9401 9409
47. S.C. Kampranis, A. Maxwell The DNA Gyrase-Quinolone Complex. ATP Hydrolysis and the Mechanism of DNA Cleavage J. Biol. Chem. 273 1998 22615 22626
48. A.B. Khodursky, N.R. Cozzarelli The Mechanism of Inhibition of Topoisomerase IV by Quinolone Antibacterials J. Biol. Chem. 273 1998 27668 27677
49. E.-J. Lee, J.-A. Yeo, C.-B. Cho, G.-J. Lee, S.-W. Han, S.-K. Kim Amine Group of Guanine Enhances the Binding of Norfloxacin Antibiotics to DNA Eur. J. Biochem. 267 2000 6018 6024
50. H.-M. Lee, J.-K. Kim, S.-K. Kim Molecular Modeling Study of the Norfloxacin-DNA Complex J. Biomol. Struct. Dynamics 19 2002 1083 1091