Identification of the Adduct Between a 4-Aza-3-ene-1,6-diyne and DNA Using Electrospray Ionization Mass Spectrometry

Journal of the American Society for Mass Spectrometry

Volumn 17, Issue 10, 2006, Pages 1342-1352

  Sherman, Courtney L ^a   Pierce, Sarah E ^a   Brodbelt, Jennifer S ^a   Tuesuwan, Bodin ^a   Kerwin, Sean M ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; DISEASE CONTROL; DISSOCIATION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; TUMORS;

CYTOSINE AMINE; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; ENEDIYNE LIGAND;

DNA;

1 METHYL 2 (PHENYLETHYNYL) 3 (3 PHENYLPROP 2 YNYL) 3H BENZIMIDAZOLIUM; CYTOSINE; DEOXYCYTIDINE; DNA; IMIDAZOLE DERIVATIVE; NUCLEIC ACID BASE; OLIGONUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; DNA CLEAVAGE; ELECTROSPRAY MASS SPECTROMETRY; FLOW INJECTION ANALYSIS;

ALKYNES; BENZIMIDAZOLES; DNA ADDUCTS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; INDICATORS AND REAGENTS; OLIGONUCLEOTIDES; PIPERIDINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 33748975581     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2006.05.015     Document Type: Article

References (59)

1. Edo K., Mizugaki M., Koide Y., Seto H., Furihata K., Otake N., and Ishida N. The Structure of Neocarzinostatin Chromophore Possessing a Novel Bicyclo[7,3,0]dodecadiyne System. Tetrahedron Lett 26 (1985) 331-334
2. Nicolaou K.C., and Dai W.-M. Chemistry and Biology of the Enediyne Anticancer Antibiotics. Angew. Chem. Int. Ed. Eng 30 (1991) 1387-1416
3. Nicolaou K.C., Smith A.L., and Yue E.W. Chemistry and Biology of Natural and Designed Enediynes. Proc. Natl. Acad. Sci. U.S.A 90 (1993) 5881-5888
4. Smith A.L., and Nicolaou K.C. The Enediyne Antibiotics. J. Med. Chem 39 (1996) 2103-2117
5. Galm U., Hager M.H., Van Lanen S.G., Ju J., Thorson J.S., and Shen B. Antitumor Antibiotics: Bleomycin, Enediynes, and Mitomycin. Chem. Rev 105 (2005) 739-758
6. I. J. Am. Chem. Soc 109 (1987) 3464-3466
7. I. J. Am. Chem. Soc 109 (1987) 3466-3468
8. Konishi M., Ohkuma H., Matsumoto K., Tsuno T., Kamei H., Miyaki T., Oki T., Kawaguchi H., VanDuyne G.D., and Clardy J. Dynemicin A, a Novel Antibiotic with the Anthraquinone and 1,5-Diyn-3-ene Subunit. J. Antibiot 42 (1989) 1449-1452
9. Golik J., Clardy J., Dubay G., Groenewold G., Kawaguchi H., Konishi M., Krishnan B., Ohkuma H., Saitoh K., and Doyle T.W. Esperamicins, a Novel Class of Potent Antitumor Antibiotics. II. Structure of Esperamicin X. J. Am. Chem. Soc 109 (1987) 3461-3462
10. 1b. J. Am. Chem. Soc 109 (1987) 3462-3464
11. Jones G.B., and Fouad F.S. Designed Enediyne Antitumor Agents. Curr. Pharm. Des 8 (2002) 2415-2440
12. Klein M., Walenzyk T., and König B. Electronic Effects on the Bergman Cyclization of Enediynes. A Review. Collect. Czech. Chem. Commun 69 (2004) 945-965
13. McPhee M.M., and Kerwin S.M. Synthesis and Metal Ion Binding Studies of Enediyne-Containing Crown Ethers. J. Org. Chem 61 (1996) 9385-9393
14. Jones G.B., Wright J.M., Rush T.M., Plourde II G.W., Kelton T.F., Mathews J.E., Huber R.S., and Davidson J.P. Facile Unmasking of Dicobalt Hexacarbonyl Complexes of 1-Cyclodecene-3,9-Diynes (Enediynes). J. Org. Chem 62 (1997) 9379-9381
15. Dai W.-M., Lai K.W., Wu A., Hamaguchi W., Lee M.Y.H., Zhou L., Ishii A., and Nishimoto S. DNA. Cleavage Potency, Cytotoxicity, and Mechanism of Action of a Novel Class of Enediyne Prodrugs. J. Med. Chem 45 (2002) 758-761
16. Banfi L., and Guanti G. Synthesis of Intramolecularly Activated Lactenediynes and the Evaluation of Their Activity Against Plasmid DNA. Eur. J. Org. Chem 22 (2002) 3745-3755
17. Schmittel M., Viola G., Dall'Acqua F., and Morbach G. A Novel Concept to Activate Enediynes for DNA Cleavage. Chem. Commun 5 (2003) 646-647
18. Guanti G., and Riva R. Simplified Dynemicin Analogs: Diastereoselective Synthesis and Evaluation of Their Activity Against Plasmid DNA. Org. Biomol. Chem 1 (2003) 3967-3976
19. Suzuki I., Shigenaga A., Nemoto H., and Shibuya M. Synthesis and DNA Damaging Ability of Enediyne-Polyamine Conjugates. Tetrahedron Lett 45 (2004) 1955-1959
20. Usuki T., Inoue M., Hirama M., and Tanaka T. Rational Design of a Supra C-1027: Kinetically Stabilized Analog of the Antitumor Enediyne Chromoprotein. J. Am. Chem. Soc 126 (2004) 3022-3023
21. Suzuki I., Uno S., Tsuchiya Y., Shigenaga A., Hisao N., and Shibuya M. Synthesis and DNA Damaging Ability of Enediyne Model Compounds Possessing Photo-Triggering Devices. Bioorg. Med. Chem. Lett 14 (2004) 2959-2962
22. Fouad F.S., Crasto C.F., Lin Y., and Jones G.B. Photoactivated Enediynes: Targeted Chimeras which Undergo Photo-Bergman Cyclization. Tetrahedron. Lett 45 (2004) 7753-7756
23. Basak A., Roy S.K., and Mandal S. Activation of Macrocyclic Enediynes by Transannular Cyclization. Angew. Chem. Int. Ed 44 (2005) 132-135
24. Boger D.L., and Zhou J.C.D.P.I. 3-Enediyne and CDPI3-EDTA Conjugates: A New Class of DNA Cleaving Agents. J. Org. Chem 58 (1993) 3018-3024
25. Toshima K., Ohta K., Ohashi A., Nakamura T., Nakata M., and Matsumura S. Design, Synthesis, and DNA Cleaving Profiles of Hybrids Containing the Novel Enediyne and Naturally Occurring DNA Intercalators. J. Chem. Soc. Chem. Commun (1993) 1525-1527
26. Tokuda M., Fujiwara K., Gomibuchi T., Hirama M., Uesugi M., and Sugiura Y. Synthesis of a Hybrid Molecule Containing Neocarzinostatin Chromophore Analog and Minor Groove Binder. Tetrahedron. Lett 34 (1993) 669-672
27. David W.M., Kumar D., and Kerwin S.M. Synthesis of a Heterocyclic Aza-Enediyne and Its DNA-Cleavage Properties. Bioorg. Med. Chem. Lett 10 (2000) 2509-2512
28. Kumar D., David W.M., and Kerwin S.M. N-Propargyl-2-alkynylbenzothiazolium Aza-Enediynes: Role of the 2-Alkynylbenzothiazolium Functionality in DNA Cleavage. Bioorg. Med. Chem. Lett 11 (2001) 2971-2974
29. Tuntiwechapikul W., David W.M., Kumar D., Salazar M., and Kerwin S.M.D.N.A. Modification by 4-aza-3-ene-1,6-diynes: DNA Cleavage, pH-Dependent Cytosine-Specific Interactions, and Cancer Cell Cytotoxicity. Biochemistry 41 (2002) 5283-5290
30. Sinha S.C., Li L.-S., Miller G.P., Dutta S., Rader C., and Lerner R.A. Prodrugs of Dynemicin Analogs for Selective Chemotherapy Mediated by an Aldolase Catalytic Ab. Proc. Natl. Acad. Sci. U.S.A 101 (2004) 3095-3099
31. Liebisch G., Drobnik W., Lieser B., and Schmitz G. High-Throughput Quantification of Lysophosphatidylcholine by Electrospray Ionization Tandem Mass Spectrometry. Clin. Chem 48 (2002) 2217-2224
32. Gooding K.B., Higgs R., Hodge B., Stauffer E., Heinz B., McKnight K., Philpps K., Shapiro M., Winkler M., Ng W.-L., and Julian R.K. High Throughput Screening of Library Compounds Against an Oligonucleotide Substructure of an RNA Target. J. Am. Soc. Mass Spectrom 15 (2004) 884-892
33. Qian J., Voorbach M.J., Huth J.R., Coen M.L., Zhang H., Ng S.-C., Comess K.M., Petros A.M., Rosenberg S.H., Warrior U., and Burns D.J. Discovery of Novel Inhibitors of Bcl-xL Using Multiple High-Throughput Screening Platforms. Anal. Biochem 328 (2004) 131-138
34. Limbach P.A. Indirect Mass Spectrometric Methods for Characterizing and Sequencing Oligonucleotides. Mass Spectrom. Rev 15 (1996) 297-336
35. Nordhoff E., Kirpekar F., and Roepstorff P. Mass Spectrometry of Nucleic Acids. Mass Spectrom. Rev 15 (1996) 67-138
36. McLuckey S.A., Van Berkel G.J., and Glish G.L. Tandem Mass Spectrometry of Small Multiply Charged Oligonucleotides. J. Am. Soc. Mass Spectrom 3 (1992) 60-70
37. Beck J.L., Colgrave M.L., Ralph S.F., and Sheil M.M. Electrospray Ionization Mass Spectrometry of Oligonucleotide Complexes with Drugs, Metals, and Proteins. Mass Spectrom. Rev 20 (2001) 61-87
38. Hofstadler S.A., and Griffey R.H. Analysis of Noncovalent Complexes of DNA and RNA by Mass Spectrometry. Chem. Rev 101 (2001) 377-390
39. Van den Driessche B., Lemiere F., Van Dongen W., and Esmans E.L. Structural Characterization of Melphalan Modified 2′-Oligodeoxynucleotides by Miniaturized LC-ES MS/MS. J. Am. Soc. Mass Spectrom 15 (2004) 568-579
40. Iannitti P., Sheil M.M., and Wickham G. 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
41. Richter S.N., Menegazzo I., Fabris D., and Palumbo M. Concerted bis-Alkylating Reactivity of Clerocidin Towards Unpaired Cytosine Residues in DNA. Nucleic Acids Res 32 (2004) 5658-5667
42. Harsch A., Marzilli L.A., Bunt R.C., Stubbe J., and Vouros P. Accurate and Rapid Modeling of Iron-Bleomycin-Induced DNA Damage Using Tethered Duplex Oligonucleotides and Electrospray Ionization Ion Trap Mass Spectrometric Analysis. Nucleic Acids Res 28 (2000) 1978-1985
43. Hoes I., Van Dongen W., Lemiere F., Esmans E.L., Van Bockstaele D., and Berneman Z.N. Comparison Between Capillary and Nano Liquid Chromatography-Electrospray Mass Spectrometry for the Analysis of Minor DNA-Melphalan Adducts. J. Chromatogr. B Anal. Technol. Biomed. Life Sci 748 (2000) 197-212
44. Balcome S., Park S., Quirk Dorr D.R., Hafner L., Phillips L., and Tretyakova N. Adenine-Containing. DNA-DNA Cross-Links of Antitumor Nitrogen Mustards. Chem. Res. Toxicol 17 (2004) 950-962
45. Wang Y., Zhang Q., and Wang Y. Tandem Mass Spectrometry for the Determination of the Sites of DNA Interstrand Cross-Link. J. Am. Soc. Mass Spectrom 15 (2004) 1565-1571
46. Wang Y., and Wang Y. Structure Elucidation of DNA Interstrand Cross-Link by a Combination of Nuclease p1 Digestion with Mass Spectrometry. Anal. Chem 75 (2003) 6306-6313
47. Franska M., Franski R., Schroeder G., Springer A., Beck S., and Linscheid M. Electrospray Ionization Mass Spectrometric Study of Purine Base-Cisplatin Complexes. Rapid Commun. Mass Spectrom 19 (2005) 970-974
48. Gupta R., Beck J.L., Sheil M.M., and Ralph S.F. Identification of Bifunctional GA and AG Intrastrand Cross-Links Formed Between Cisplatin and DNA. J. Inorg. Biochem 9 (2005) 552-559
49. Warnke U., Rappel C., Meier H., Kloft C., Galanski M., Hartinger C.G., Keppler B.K., and Jaehde U. Analysis of Platinum Adducts with DNA Nucleotides and Nucleosides by Capillary Electrophoresis Coupled to ESI-MS: Indications of Guanosine 5′-Monophosphate O6-N7 Chelation. Chem. Biochem 5 (2004) 1543-1549
50. Gupta R., Kapur A., Beck J.L., and Sheil M.M. Positive Ion Electrospray Ionization Mass Spectrometry of Double-Stranded DNA/Drug Complexes. Rapid Commun. Mass Spectrom 15 (2001) 2472-2480
51. Kung A., Strickmann D.B., Galanski M., and Keppler B.K. Comparison of the Binding Behavior of Oxaliplatin, Cisplatin, and Analogs to 5′-GMP in the Presence of Sulfur-Containing Molecules by Means of Capillary Electrophoresis and Electrospray Mass Spectrometry. J. Inorg. Biochem 86 (2001) 691-698
52. Sturla S.J., Scott J., Lao Y., Hecht S.S., and Villalta P.W. Mass Spectrometric Analysis of Relative Levels of Pyridyloxobutylation Adducts Formed in the Reaction of DNA with a Chemically Activated Form of the Tobacco-Specific Carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-Butanone. Chem. Res. Toxicol 18 (2005) 1048-1055
53. Borges C., Lemiere F., Embrechts J., van Dongen W., and Esmans E.L. Characterization of Estrone-Nucleic Acid Adducts Formed by Reaction of 3,4-Estrone-o-Quinone with 2′-Deoxynucleosides/Deoxynucleotides Using Capillary Liquid Chromatography/Electrospray Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom 18 (2004) 2191-2200
54. Colgrave M.L., Iannitti-Tito P., Wickham G., and Sheil M.M. Rapid Determination of Sequence Selectivity and Stability of Alkylated Oligonucleotide Adducts by Electrospray Tandem Mass Spectrometry. Aust. J. Chem 56 (2003) 401-413
55. Inagaki S., Esaka Y., Deyashiki Y., Sako M., and Goto M. Analysis of DNA Adducts of Acetaldehyde by Liquid Chromatography-Mass Spectrometry. J. Chromatogr. A 987 (2003) 341-347
56. Little D.P., Chorush R.A., Speir J.P., Senko M.W., Kelleher N.L., and McLafferty F.W. Rapid Sequencing of Oligonucleotides by High-Resolution Mass Spectrometry. J. Am. Chem. Soc 116 (1994) 4893-4897
57. Little D.P., Speir J.P., Senko M.W., O'Connor P.B., and McLafferty F.W. Infrared Multiphoton Dissociation of Large Multiply Charged Ions for Biomolecule Sequencing. Anal. Chem 66 (1994) 2809-2815
58. Keller K.M., and Brodbelt J.S. Collisionally Activated Dissociation and Infrared Multiphoton Dissociation of Oligonucleotides in a Quadrupole Ion Trap. Anal. Biochem 326 (2004) 200-210
59. Schultz K.N., and Håkansson K. Rapid Electron Capture Dissociation of Mass-Selectively Accumulated Oligodeoxynucleotide Dications. Int. J. Mass Spectrom 234 (2004) 123-130