Strategy for imidazotetrazine prodrugs with anticancer activity independent of MGMT and MMR

ACS Medicinal Chemistry Letters

Volumn 3, Issue 12, 2012, Pages 965-968

  Garelnabi, Elrashied A E ^a,c   Pletsas, Dimitrios ^a   Li, Li ^a   Kiakos, Konstantinos ^b   Karodia, Nazira ^a   Hartley, John A ^b   Phillips, Roger M ^a   Wheelhouse, Richard T ^a  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF KHARTOUM   (Sudan)

Author keywords

13C NMR; aziridinium; cancer; DNA; Imidazotetrazine; Temozolomide

Indexed keywords

IMIDAZOLE DERIVATIVE; IMIDAZOTETRAZINE; PRODRUG; TETRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DNA ALKYLATION; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 84871241597     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml300132t     Document Type: Article

References (20)

1. Newlands, E. S.; Stevens, M. F. G.; Wedge, S. R.; Wheelhouse, R. T.; Brock, C. Temozolomide: A Review of its Discovery, Chemical Properties, Pre-clinical Development and Clinical Trials Cancer Treatment Rev. 1997, 23, 35-61
2. Datamonitor. Commercial Insight: Cytotoxic Therapies; 2009.
3. Wheelhouse, R. T.; Stevens, M. F. G. Decomposition of the Antitumour Drug Temozolomide in Deuteriated Phosphate Buffer: Methyl Group Transfer is Accompanied by Deuterium Exchange J. Chem. Soc., Chem. Commun. 1993, 1177-1178
4. Denny, B. J.; Wheelhouse, R. T.; Stevens, M. F. G.; Tsang, L. L. H. NMR and Molecular Modeling Investigation of the Mechanism of Activation of the Antitumor Drug Temozolomide and its Interaction with DNA Biochemistry 1994, 33, 9045-9051
5. Stevens, M. F. G.; Hickman, J. A.; Langdon, S. P.; Chubb, D.; Vickers, L.; Stone, R.; Baig, G.; Goddard, C.; Gibson, N. W.; Slack, J. A.; Newton, C.; Lunt, E.; Fizames, C.; Lavelle, F. Antitumor Imidazotetrazines 13. Antitumor Activity and Pharmacokinetics in Mice of 8-Carbamoyl-3-Methyl-Imidazo-[5,1-d]-1, 2,3,5-tetrazin-4(3H)-one (CCRG 81045-M&B-39831), a Novel Drug with Potential as an Alternative to Dacarbazine Cancer Res. 1987, 47, 5846-5852
6. McGarrity, J. F.; Smyth, T. Hydrolysis of Diazomethane-Kinetics and Mechanism J. Am. Chem. Soc. 1980, 102, 7303-7308
7. Wang, Y.; Wheelhouse, R. T.; Zhao, L.; Langnel, D. A. F.; Stevens, M. F. G. Antitumour Imidazotetrazines. Part 36. Conversion of 5-Aminoimidazole-4- carboxamide to Imidazo-[5,1-d]-1,2,3,5-tetrazin4(3H)-ones and Imidazo-[1,5-A]-1,3,5-triazin4(3H)-ones Related in Structure to the Antitumour Agents Temozolomide and Mitozolomide J. Chem. Soc., Perkin Trans. 1 1998, 1669-1676
8. Newlands, E. S.; Blackledge, G.; Slack, J. A.; Goddard, C.; Brindley, C. J.; Holden, L.; Stevens, M. F. G. Phase-I Clinical Trial of Mitozolomide Cancer Treatment Rep. 1985, 69, 801-805
9. Darkes, M. J. M.; Plosker, G. L.; Jarvis, B. Temozolomide a Review of its Use in the Treatment of Malignant Gliomas, Malignant Melanoma and Other Advanced Cancers Am. J. Cancer 2002, 1, 55-80
10. Pletsas, D.; Wheelhouse, R. T.; Pletsa, V.; Nicolaou, A.; Jenkins, T. C.; Bibby, M. C.; Kyrtopoulos, S. A. Polar, Functionalized Guanine- O6 Derivatives Resistant to Repair by O6 -Alkylguanine-DNA Alkyltransferase: Implications for the Design of DNA-modifying Drugs Eur. J. Med. Chem. 2006, 41, 330-339
11. Stevens, M. F. G.; Hickman, J. A.; Stone, R.; Gibson, N. W.; Baig, G. U.; Lunt, E.; Newton, C. G. Antitumor Imidazotetrazines 1. Synthesis and Chemistry of 8-Carbamoyl-3-(2-chloroethyl)imidazo-[5,1-d]-1,2,3,5-tetrazin-4(3H)-one, a Novel Broad-spectrum Antitumor Agent J. Med. Chem. 1984, 27, 196-201
12. 15N) Magnetic Resonance Investigation of Temozolomide and Mitozolomide J. Chem. Soc., Perkin Trans. 1 1995, 249-252
13. Pretsch, E.; Clerc, T.; Seibl, J.; Simone, G. Tables of Spectral Data for Structure Determination of Organic Compounds, 2 nd ed.; Springer-Verlag: Berlin, 1989.
14. Gim, H. J.; Kang, B.; Jeon, R. Synthesis and Biological Activity of 5-{4-[2-(Methyl- p -substituted phenylamino)ethoxy]benzyl}thiazolidine-2,4- diones Arch. Pharm. Res. 2007, 30, 1055-1061
15. Schmidt, B. F.; Snyder, E. J.; Carroll, R. M.; Farnsworth, D. W.; Michejda, C. J.; Smith, R. H. Triazinines: Synthesis and Proteolytic Decomposition of a New Class of Cyclic Triazenes J. Org. Chem. 1997, 62, 8660-8665
16. Schmiedekamp, A.; Smith, R. H.; Michejda, C. J. Ab Initio Studies of Triazenes in Relation to Experimental Findings J. Org. Chem. 1988, 53, 3433-3436
17. Smith, R. H.; Wladkowski, B. D.; Taylor, J. E.; Thompson, E. J.; Pruski, B.; Klose, J. R.; Andrews, A. W.; Michejda, C. J. Acid-Catalyzed Decomposition of 1-Alkyltriazolines-A Mechanistic Study J. Org. Chem. 1993, 58, 2097-2103
18. Barvaux, V. A.; Ranson, M.; Brown, R.; McElhinney, R. S.; McMurry, T. B. H.; Margison, G. P. Dual Repair Modulation Reverses Temozolomide Resistance In Vitro Mol. Cancer Ther. 2004, 3, 123-127
19. Clark, A. S.; Deans, B.; Stevens, M. F. G.; Tisdale, M. J.; Wheelhouse, R. T.; Denny, B. J.; Hartley, J. A. Antitumor Imidazotetrazines 32. Synthesis of Novel Imidazotetrazinones and Related Bicyclic Heterocycles to Probe the Mode of Action of the Antitumor Drug Temozolomide J. Med. Chem. 1995, 38, 1493-1504
20. Arrowsmith, J.; Jennings, S. A.; Langnel, D. A. F.; Wheelhouse, R. T.; Stevens, M. F. G. Antitumour Imidazotetrazines. Part 39. Synthesis of Bis(imidazotetrazine)s with Saturated Spacer Groups J. Chem. Soc., Perkin Trans. 1 2000, 4432-4438