Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone; 3-AP): An inhibitor of ribonucleotide reductase with antineoplastic activity

Advances in Enzyme Regulation

Volumn 39, Issue 1, 1999, Pages 3-12

  Finch, Rick A ^a   Liu, Mao Chin ^a   Cory, Ann H ^b   Cory, Joseph G ^b   Sartorelli, Alan C ^a  

^a YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b EAST CAROLINA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-AMINOPYRIDINE-2-CARBOXALDEHYDE THIOSEMICARBAZONE; AMINOPYRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; DNA; ENZYME INHIBITOR; HYDROXYUREA; IRON; PYRIDINE DERIVATIVE; RIBONUCLEOTIDE REDUCTASE; THIOSEMICARBAZONE DERIVATIVE; TRIAPINE; UNCLASSIFIED DRUG;

ANIMAL; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; BIOSYNTHESIS; CELL CULTURE; CELL DIVISION; CONFERENCE PAPER; DOSE RESPONSE; DRUG EFFECT; DRUG RESISTANCE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; IN VITRO STUDY; LEUKEMIA L 1210; METABOLISM; MOUSE; MOUSE STRAIN; NONHUMAN;

EID: 0032832996     PISSN: 00652571     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2571(98)00017-X     Document Type: Conference Paper

References (32)

1. L. THELANDER and P. REICHARD, Reduction of ribonucleotides, Annu. Rev. Biochem. 48, 133-158 (1979).
2. J. G. CORY and A. SATO, Regulation of ribonucleotide reductase activity in mammalian cells, Mol. Cell Biochem. 53, 257-266 (1983).
3. H. L. ELFORD, M. FREESE, E. PASSAMANI and H. P. MORRIS, Ribonucleotide reductase and cell proliferation 1. Variations of ribonucleotide reductase activity with tumor growth in a series of rat hepatomas, J. Biol. Chem. 245, 5228-5233 (1970).
4. G. WEBER, Biochemical strategy of cancer cells and the design of chemotherapy, Cancer Res. 43, 3466-3492 (1983).
5. M. THELANDER, A. GRASLUND and L. THELANDER, Subunit M2 of mammalian ribonucleotide reductase, J. Biol. Chem. 260, 2737-2741 (1985).
6. I. H. KRAKOFF, Clinical and pharmacologic effects of hydroxyurea, pp. 789-792 in Antineoplastic and Immunosuppressive Agents, Part 2 (A. C. SARTORELLI and D. G. JOHNS, eds.). Springer-Verlag, New York (1975).
7. G. L. BECKLOFF, H. J. LERNER, D. FROST, F. M. RUSSO-ALESI and S. GITOMER, Hydroxyurea (NSC-32065) in biologic fluids: Dose-concentration relationship, Cancer Chemother. Rep. 48, 57-58 (1965).
8. E. C. MOORE and R. B. HURLBERT. The inhibition of ribonucleoside diphosphate reductase by hydroxyurea, guanazole and pyrazoloimidazole (IMPY), pp. 165-201 in Inhibitors of Ribonucleoside Diphosphate Reductase Activity (J. G. CORY and A. H. CORY, eds.). Pergamon Press, Oxford (1989).
9. R. C. DONEHOWER, Hydroxyurea. pp. 253-260 in Cancer Chemotherapy and Biotherapy (B. A. CHABNER and C. L. LONGO, eds.). Lippincott-Raven, Philadelphia (1996).
10. E. C. MOORE and A. C. SARTORELLI, The inhibition of ribonucleotide reductase by α-(N)-heterocyclic carboxaldehyde thiosemicarbazones, pp. 203-215 in Inhibitors of Ribonucleoside Diphosphate Reductase Activity (J. G. CORY and A. H. CORY, eds.). Pergamon Press, Oxford (1989).
11. R. W. BROCKMAN, J. R. THOMSON, M. J. BELL and H. SKIPPER, Observations on the antileukemic activity of pyridine-2-carboxaldehyde thiosemicarbazone and thiocarbohydrazone, Cancer Res. 16, 167-170 (1956).
12. F. A. FRENCH and E. J. J. BLANZ JR., The carcinostatic activity of thiosemicarbazones of formyl heteroaromatic compounds. III. Primary correlations, J. Med. Chem. 9, 585-589 (1966).
13. K. C. AGRAWAL and A. C. SARTORELLI, Potential antitumor agents. II. Effects of modification in the side chain of 1-formylisoquinoline thiosemicarbazone, J. Med. Chem. 12, 771-774 (1969).
14. F. A. FRENCH and E. J. BLANZ, JR., Chemotherapy studies on experimental mouse tumors, X. Cancer Chemother. Rep., Pt. 2, 2, 199-235 (1971).
15. K. C. AGRAWAL and A. C. SARTORELLI, α-(N)-Heterocyclic carboxaldehyde thiosemicarbazones, pp. 793-807 in Antineoplastic and Immunosuppressive Agents, Part 2 (A. C. SARTORELLI and D. G. JOHNS, eds.). Springer-Verlag, New York (1975).
16. W. ANTHOLINE, J. KNIGHT, H. WHELAN and D. H. PETERING, Studies of the reaction of 2-formylpyridine thiosemicarbazone and its iron and copper complexes with biological systems, Mol. Pharmacol. 13, 89-98 (1977).
17. A. C. SARTORELLI, K. C. AGRAWAL, A. S. TSIFTSOGLOU and E. C. MOORE, Characterization of the biochemical mechanism of action of α-(N)-heterocyclic carboxaldehyde thiosemicarbazones, Advan. Enzyme Regul. 15, 117-139 (1977).
18. R. C. DECONTI, B. R. TOFTNESS, K. C. AGRAWAL, R. TOMCHIK, J. A. R. MEAD, J. R. BERTINO, A. C. SARTORELLI and W. A. CREASEY, Clinical and pharmacological studies with 5-hydroxy-2-formylpyridine thiosemicarbazone, Cancer Res. 32, 1455-1462 (1972).
19. I. H. KRAKOFF, E. ETCUBANAS, C. TAN, K. MAYER, V. BETHUNE and J. H. BURCHENAL, Clinical trial of 5-hydroxypicolinaldehyde thiosemicarbazone (5-HP; NSC 107392), with special reference to its iron chelating properties, Cancer Chemother. Rep. Part I 58, 207-212 (1974).
20. M-C. LIU, T-S. LIN and A. C. SARTORELLI, Synthesis and antitumor evaluation of amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone, J. Med Chem. 35, 3672-3677 (1992).
21. L. ACHREMOWICZ and L. SYPER, Reaction of 3-nitropicoline N-oxides with acetic anhydride, Roczniki Chem. 46, 409-419 (1972).
22. M-C. LIU, T. S. LIN and A. C. SARTORELLI, A one-pot synthesis of 3-nitro- and 3,5-dinitro-2-picolines, Synth. Commun. 20, 2965-2970 (1990).
23. K. C. AGRAWAL, P. D. MOONEY and A. C. SARTORELLI, Antitumor agents. 13. 4-Methyl-5-amino-1-formylisoquinoline thiosemicarbazone, J. Med. Chem. 19, 970-972 (1976).
24. G. L. CARTER and J. G. CORY, Cross-resistance patterns in hydroxyurea-resistant leukemia L1210 cells, Cancer Res. 48, 5796-5799 (1988).
25. A. H. CORY, T. C. OWEN, J. A. BARLTROP and J. G. CORY, Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture, Cancer Commun. 3, 207-212 (1991).
26. J. G. CORY, A. E. FLEISCHER and J. B. MUNRO, Reconstitution of the ribonucleotide reductase from Ehrlich tumor cells, J. Biol. Chem. 253, 2898-2901 (1978).
27. J. G. CORY, A. H. CORY, G. RAPPA, A. LORICO, M-C. LIU, T-S. LIN and A. C. SARTORELLI, Inhibitors of ribonucleotide reductase: Comparative effects of amino- and hydroxy-substituted pyridine-2-carboxaldehyde thiosemicarbazones, Biochem. Pharmacol. 48, 335-344 (1994).
28. J. R. STEEPER and C. D. STEUART, A rapid assay for CDP reductase activity in mammalian cell extracts, Anal. Biochem. 34, 123-130 (1970).
29. E. C. MOORE, The effect of ferrous iron and dithioerythritol on inhibition by hydroxyurea of ribonucleotide reductase, Cancer Res. 29, 291-295 (1969).
30. R. W. BROCKMAN, S. SHADDIX, V. STRINGER and D. ADAMSON, Enhancement by deferoxamine of inhibition of DNA synthesis by ribonucleotide reducase inhibitors, Proc. Am. Assoc. Cancer Res. 13, 88 (1972).
31. J. G. CORY, A. H. CORY, G. RAPPA, A. LORICO, M-C. LIU, T-S. LIN and A. C. SARTORELLI, Structure-function relationships for a new series of pyridine-2-carboxaldehyde thiosemicarbazones on ribonucleotide reductase activity and tumor cell growth in culture and in vivo, Advan. Enzyme Regul. 35, 55-68 (1995).
32. K. SHYAM, P. G. PENKETH, A. A. DIVO, R. H. LOOMIS, C. L. PATTON and A. C. SARTORELLI, Synthesis and evaluation of 1,2,2-tris(sulfonyl)hydrazines as antineoplastic and trypanocidal agents, J. Med. Chem. 33, 2259-2264 (1990).