UV-Induced DNA Interstrand Cross-Linking and Direct Strand Breaks from a New Type of Binitroimidazole Analogue

Chemical Research in Toxicology

Volumn 28, Issue 5, 2015, Pages 919-926

  Han, Yanyan ^a   Chen, Wenbing ^a   Kuang, Yunyan ^a   Sun, Huabing ^a   Wang, Zhiqiang ^a   Peng, Xiaohua ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; AMINE; CHLORMETHINE; DNA; FREE RADICAL; FUNCTIONAL GROUP; NITROIMIDAZOLE DERIVATIVE; PIPERIDINE; PRODRUG; CHLORMETHINE DERIVATIVE; CROSS LINKING REAGENT; INTERCALATING AGENT;

ARTICLE; CONTROLLED STUDY; DNA ALKYLATION; DNA CLEAVAGE; DNA CROSS LINKING; DNA DAMAGE; DNA STRAND BREAKAGE; GENE REPRESSION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOACTIVATION; PHOTOREACTIVITY; ULTRAVIOLET IRRADIATION; CHEMISTRY; CONFORMATION; DRUG EFFECTS; GENETICS; RADIATION RESPONSE; ULTRAVIOLET RADIATION;

BRASSICACEAE;

ALKYLATING AGENTS; CROSS-LINKING REAGENTS; DNA; DNA BREAKS; INTERCALATING AGENTS; NITROGEN MUSTARD COMPOUNDS; NITROIMIDAZOLES; NUCLEIC ACID CONFORMATION; ULTRAVIOLET RAYS;

EID: 84929577549     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500522r     Document Type: Article

References (49)

1. Noll, D. M., Mason, T. M., and Miller, P. S. (2006) Formation and repair of interstrand cross-links in DNA Chem. Rev. 106, 277 - 301
2. Peng, X. and Greenberg, M. M. (2008) Facile SNP detection using bifunctional, cross-linking oligonucleotide probes Nucleic Acids Res. 36, e31
3. Peng, X., Ghosh, A. K., Van Houten, B., and Greenberg, M. M. (2010) Nucleotide excision repair of a DNA interstrand cross-link produces single- and double-strand breaks Biochemistry 49, 11 - 19
4. Weng, M. W., Zheng, Y., Jasti, V. P., Champeil, E., Tomasz, M., Wang, Y., Basu, A. K., and Tang, M. S. (2010) Repair of mitomycin C mono- and interstrand cross-linked DNA adducts by UvrABC: a new model Nucleic Acids Res. 38, 6976 - 6984
5. Cao, S. P. and X (2014) Exploiting endogenous cellular process to generate quinone methides in vivo Curr. Org. Chem. 18, 70 - 85
6. Zhang, Q. and Wang, Y. (2003) Independent generation of 5-(2′-deoxycytidinyl)methyl radical and the formation of a novel cross-link lesion between 5-methylcytosine and guanine J. Am. Chem. Soc. 125, 12795 - 12802
7. Peng, X. and Gandhi, V. (2012) ROS-activated anticancer prodrugs: a new strategy for tumor-specific damage Ther. Delivery 3, 823 - 833
8. Johnson, K. M., Parsons, Z. D., Barnes, C. L., and Gates, K. S. (2014) Toward hypoxia-selective DNA-alkylating agents built by grafting nitrogen mustards onto the bioreductively activated, hypoxia-selective DNA-oxidizing agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine) J. Org. Chem. 79, 7520 - 7531
9. Peng, X., Hong, I. S., Li, H., Seidman, M. M., and Greenberg, M. M. (2008) Interstrand cross-link formation in duplex and triplex DNA by modified pyrimidines J. Am. Chem. Soc. 130, 10299 - 10306
10. Hong, I. S. and Greenberg, M. M. (2005) DNA interstrand cross-link formation initiated by reaction between singlet oxygen and a modified nucleotide J. Am. Chem. Soc. 127, 10510 - 10511
11. Hong, I. S. and Greenberg, M. M. (2005) Efficient DNA interstrand cross-link formation from a nucleotide radical J. Am. Chem. Soc. 127, 3692 - 3693
12. Weng, X., Ren, L., Weng, L., Huang, J., Zhu, S., Zhou, X., and Weng, L. (2007) Synthesis and biological studies of inducible DNA cross-linking agents Angew. Chem., Int. Ed. 46, 8020 - 8023
13. Veldhuyzen, W. F., Pande, P., and Rokita, S. E. (2003) A transient product of DNA alkylation can be stabilized by binding localization J. Am. Chem. Soc. 125, 14005 - 14013
14. McCrane, M. P., Hutchinson, M. A., Ad, O., and Rokita, S. E. (2014) Oxidative quenching of quinone methide adducts reveals transient products of reversible alkylation in duplex DNA Chem. Res. Toxicol. 27, 1282 - 1293
15. Di Antonio, M., Doria, F., Mella, M., Merli, D., Profumo, A., and Freccero, M. (2007) Novel naphthalene diimides as activatable precursors of bisalkylating agents, by reduction and base catalysis J. Org. Chem. 72, 8354 - 8360
16. Verga, D., Nadai, M., Doria, F., Percivalle, C., Di Antonio, M., Palumbo, M., Richter, S. N., and Freccero, M. (2010) Photogeneration and reactivity of naphthoquinone methides as purine selective DNA alkylating agents J. Am. Chem. Soc. 132, 14625 - 14637
17. Percivalle, C., La Rosa, A., Verga, D., Doria, F., Mella, M., Palumbo, M., Di Antonio, M., and Freccero, M. (2011) Quinone methide generation via photoinduced electron transfer J. Org. Chem. 76, 3096 - 3106
18. Cao, S., Christiansen, R., and Peng, X. (2013) Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors Chemistry 19, 9050 - 9058
19. Cao, S., Wang, Y., and Peng, X. (2012) ROS-inducible DNA cross-linking agent as a new anticancer prodrug building block Chemistry 18, 3850 - 3854
20. Chen, W., Balakrishnan, K., Kuang, Y., Han, Y., Fu, M., Gandhi, V., and Peng, X. (2014) Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes J. Med. Chem. 57, 4498 - 4510
21. Chen, W., Han, Y., and Peng, X. (2014) Aromatic nitrogen mustard-based prodrugs: activity, selectivity, and the mechanism of DNA cross-linking Chemistry 20, 7410 - 7418
22. Kuang, Y., Balakrishnan, K., Gandhi, V., and Peng, X. (2011) Hydrogen peroxide inducible DNA cross-linking agents: targeted anticancer prodrugs J. Am. Chem. Soc. 133, 19278 - 19281
23. 2-induced DNA cross-linking by arylboronates J. Org. Chem. 79, 501 - 508
24. Asquith, J. C., Watts, M. E., Patel, K., Smithen, C. E., and Adams, G. E. (1974) Electron affinic sensitization. V. Radiosensitization of hypoxic bacteria and mammalian cells in vitro by some nitroimidazoles and nitropyrazoles Radiat. Res. 60, 108 - 118
25. Thomson, J. E. and Rauth, A. M. (1974) A comparison of the effectiveness of NF-167 and metronidazole as hypoxic cell sensitizers of KHT tumor cells in vitro Radiat. Res. 60, 489 - 500
26. Foster, J. L. and Wilson, R. L. (1973) Radiosensitization of anoxic cells by metronidazole Br. J. Radiol. 46, 234 - 235
27. Adams, G. E., Ahmed, I., Sheldon, P. W., and Stratford, I. J. (1984) Radiation sensitization and chemopotentiation: RSU 1069, a compound more efficient than misonidazole in vitro and in vivo Br. J. Cancer 49, 571 - 577
28. Stratford, I. J., O'Neill, P., Sheldon, P. W., Silver, A. R., Walling, J. M., and Adams, G. E. (1986) RSU 1069, a nitroimidazole containing an aziridine group. Bioreduction greatly increases cytotoxicity under hypoxic conditions Biochem. Pharmacol. 35, 105 - 109
29. Adams, G. E. and Stratford, I. J. (1986) Hypoxia-mediated nitro-heterocyclic drugs in the radio- and chemotherapy of cancer. An overview Biochem. Pharmacol. 35, 71 - 76
30. Moselen, J. W., Hay, M. P., Denny, W. A., and Wilson, W. R. (1995) N -[2-(2-Methyl-5-nitroimidazolyl)ethyl]-4-(2-nitroimidazolyl)butanamide (NSC 639862), a bisnitroimidazole with enhanced selectivity as a bioreductive drug Cancer Res. 55, 574 - 580
31. Duan, J. X., Jiao, H., Kaizerman, J., Stanton, T., Evans, J. W., Lan, L., Lorente, G., Banica, M., Jung, D., Wang, J., Ma, H., Li, X., Yang, Z., Hoffman, R. M., Ammons, W. S., Hart, C. P., and Matteucci, M. (2008) Potent and highly selective hypoxia-activated achiral phosphoramidate mustards as anticancer drugs J. Med. Chem. 51, 2412 - 2420
32. Chen, Y. and Hu, L. (2009) Design of anticancer prodrugs for reductive activation Med. Res. Rev. 29, 29 - 64
33. Tercel, M., Lee, A. E., Hogg, A., Anderson, R. F., Lee, H. H., Siim, B. G., Denny, W. A., and Wilson, W. R. (2001) Hypoxia-selective antitumor agents. 16. Nitroarylmethyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine J. Med. Chem. 44, 3511 - 3522
34. Mauger, A. B., Burke, P. J., Somani, H. H., Friedlos, F., and Knox, R. J. (1994) Self-immolative prodrugs: candidates for antibody-directed enzyme prodrug therapy in conjunction with a nitroreductase enzyme J. Med. Chem. 37, 3452 - 3458
35. Kuang, Y., Sun, H., Blain, J. C., and Peng, X. (2012) Hypoxia-selective DNA interstrand cross-link formation by two modified nucleosides Chemistry 18, 12609 - 12613
36. Nejedly, K., Kittner, R., Pospisilova, S., and Kypr, J. (2001) Crosslinking of the complementary strands of DNA by UV light: dependence on the oligonucleotide composition of the UV irradiated DNA Biochim. Biophys. Acta 1517, 365 - 375
37. Pospisilova, S. and Kypr, J. (1997) UV light-induced crosslinking of the complementary strands of plasmid pUC19 DNA restriction fragments Photochem. Photobiol. 65, 945 - 948
38. Nejedly, K., Kittner, R., and Kypr, J. (2001) Genomic DNA regions whose complementary strands are prone to UV light-induced crosslinking Arch. Biochem. Biophys. 388, 216 - 224
39. Purkayastha, S., Milligan, J. R., and Bernhard, W. A. (2005) Correlation of free radical yields with strand break yields produced in plasmid DNA by the direct effect of ionizing radiation J. Phys. Chem. B 109, 16967 - 16973
40. Gates, K. S. (2009) An overview of chemical processes that damage cellular DNA: spontaneous hydrolysis, alkylation, and reactions with radicals Chem. Res. Toxicol. 22, 1747 - 1760
41. Roy, M. B., Mandal, P. C., Basu, S., and Bhattacharyya, S. N. (1995) Photosensitization of DNA bases by 4(5)-nitroimidazole: a steady state and flash photolysis study J. Chem. Soc., Faraday Trans. 91, 1191 - 1196
42. Maxam, A. M. and Gilbert, W. (1977) A new method for sequencing DNA Proc. Natl. Acad. Sci. U.S.A. 74, 560 - 564
43. Haraguchi, K., Delaney, M. O., Wiederholt, C. J., Sambandam, A., Hantosi, Z., and Greenberg, M. M. (2002) Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues J. Am. Chem. Soc. 124, 3263 - 3269
44. Su, D. G., Kao, J. L., Gross, M. L., and Taylor, J. S. (2008) Structure determination of an interstrand-type cis-anti cyclobutane thymine dimer produced in high yield by UVB light in an oligodeoxynucleotide at acidic pH J. Am. Chem. Soc. 130, 11328 - 11337
45. Givens, R. S. and Kueper, L. W. (1993) Photochemistry of phosphate esters Chem. Rev. 93, 55 - 56
46. Klán, P., Šolomek, T., Bochet, C. G., Blanc, A., Givens, R., Rubina, M., Popik, V., Kostikov, A., and Wirz, J. (2013) Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy Chem. Rev. 113, 119 - 191
47. Arnold, B., Donald, L., Jurgens, A., and Pincock, J. A. (1985) Homolytic versus heterolytic cleavage for the photochemistry of 1-naphthylmethyl derivatives Can. J. Chem. 63, 3140 - 3146
48. Lin, G. and Li, L. (2013) Oxidation and reduction of the 5-(2′-deoxyuridinyl)methyl radical Angew. Chem., Int. Ed. 52, 5594 - 5598
49. Weng, L., Horvat, S. M., Schiesser, C. H., and Greenberg, M. M. (2013) Deconvoluting the reactivity of two intermediates formed from modified pyrimidines Org. Lett. 15, 3618 - 3621