Thymidylate Synthase Activity and the Cell Growth Are Inhibited by the β-Carboline-Benzoquinolizidine Alkaloid Deoxytubulosine

Journal of Biochemical and Molecular Toxicology

Volumn 12, Issue 3, 1998, Pages 167-173

  Narasimha Rao, K ^a   Bhattacharya, R K ^a   Venkatachalam, S R ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Alangium lamarckii; Cytotoxicity; Deoxytubulosine; Inhibition; Lactobacillus leichmannii; Thymidylate Synthase

Indexed keywords

ALANGIUM; ALANGIUM LAMARCKII; LACTOBACILLUS LEICHMANNII;

CARBOLINE BENZOQUINOLIZIDINE ALKOLID DEOXYTUBULOSINE; CARBOLINE-BENZOQUINOLIZIDINE ALKOLID DEOXYTUBULOSINE; DRUG DERIVATIVE; EMETINE; GROWTH INHIBITOR; QUINOLIZINE DERIVATIVE; THYMIDYLATE SYNTHASE; TUBERCIDIN;

ARTICLE; CELL DIVISION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; GROWTH, DEVELOPMENT AND AGING; KINETICS; LACTOBACILLUS; MEDICINAL PLANT; METABOLISM; PROTEIN BINDING;

CELL DIVISION; EMETINE; GROWTH INHIBITORS; KINETICS; LACTOBACILLUS; MODELS, MOLECULAR; PLANTS, MEDICINAL; PROTEIN BINDING; QUINOLIZINES; THYMIDYLATE SYNTHASE; TUBERCIDIN;

EID: 0031607453     PISSN: 10956670     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0461(1998)12:3<167::aid-jbt5>3.0.co;2-j     Document Type: Article

References (42)

1. R. L. Blakley (1969). Pteridines in the metabolism of purines, pyrimidines and their derivatives. In The Biochemistry of Folic Acid and Related Ptridines, A. Neuberger and E. L. Tatum, eds., pp. 219-266, North-Holland, Amsterdam.
2. M. Friedkin (1973). Thymidylate synthetase. In Advances in Enzymology and Related Areas of Molecular Biology, A. Meister, ed., vol. 38, pp. 235-292, Wiley, New York.
3. A. Kornberg and T. A. Baker (1992). Biosynthesis of DNA precursors. In DNA Replication, 2nd ed., pp. 53-100, W. H. Freeman and Company, New York.
4. R. Langenbach (1976). Thymidylate synthetase of in vitro chemically and virally transformed rat cells. Biochim. Biophys. Acta, 422, 295-301.
5. A. Herzfeld and S. M. Raper (1980). Relative activities of thymidylate synthetase and thymidine kinase in rat tissues. Cancer Res., 40, 744-750.
6. L. G. Navalgund, C. Rossana, A. J. Muench, and L. E. Johnson (1980). Cell cycle regulation of thymidylate synthetase gene expression in cultured mouse fibroblasts. J. Biol. Chem., 255, 7386-7390.
7. P. V. Danenberg (1977). Thymidylate synthetase - a target enzyme in cancer chemotherapy. Biochim. Biophys. Acta, 473, 73-92.
8. N. Tourotoglou and R. Pazdur (1996). Thymidylate synthase inhibitors. Clin. Cancer Res. 2, 227-243.
9. R. B. Dunlap, R. G. L. Harding, and F. M. Huennekens (1971). Thymidylate synthetase from amethopterin-resistant Lactobacillus casei. Biochemistry, 10, 88-97.
10. K. Narasimha Rao and R. L. Kisliuk (1983). Association of RNA with thymidylate synthase from methotrexate-resistant Streptococcus faecium. Proc. Natl. Acad. Sci. USA, 80, 916-920.
11. K. Narasimha Rao, R. L. Kisliuk, Y. Gaumont, R. Deschenes, K. Vestal, M. Karasik, G. F. Maley, M. G. Nair, and C. M. Baugh (1983). Properties of thymidylate synthase from Strotococcus faecium. In Chemistry and Biology of Pteridines, J. A. Blair, ed., pp. 375-379, Walter de Gruyter & Co., Berlin.
12. K. Narasimha Rao and R. L. Kisliuk (1986). RNA association with thymidylate synthase, thymidine kinase and dihydrofolate reductase. Indian J. Microbiol., 26, 105-110.
13. K. Narasimha Rao (1993). Purification, relative molecular mass and subunits of thyidylate synthae from Lactobacillus leichmannii. Indian J. Biochem. Biophys., 30, 26-35.
14. S. R. Venkatachalam, J. T. Kunjappu, and C. K. K. Nair (1994). DNA binding studies on deoxytubulosine, an alkaloid from Alangium lamarckii. Indian J. Chem., 33B, 809-811.
15. K. Narasimha Rao (1993). Ternary complex formation with 5-fluoro-2′-deoxyuridylate and the kinetic properties of thymidylate synthase from Lactobacillus leichmannii. Indian J. Biochem. Biophys., 30, 103-110.
16. K. Narasimha Rao (1994). Physico-chemical properties of thymidylate synthase from Lactobacillus leichmannii: thiol groups, amino acid composition and the terminal end-groups. Indian J. Biochem. Biophys., 31, 138-142.
17. K. Narasimha Rao (1994). Pteroyl- and tetrahydropteroylpolyglutamate effects on the catalytic activity of thymidylate synthase from Lactobacillus leichmannii: a novel method for determining γ-glutamyl chain lengths of the folylpolyglutamates. Indian J. Biochem. Biophys., 31, 184-190.
18. 3H. J. Biol. Chem., 242, 109-113.
19. A. J. Wahba and M. Friedkin (1962). The enzymatic synthesis of thymidylate: 1. Early steps in the purification of thymidylate synthetase of Escherechia coli. J. Biol. Chem., 237, 3794-3801.
20. O. H. Lowry, N. J. Rosebrough, A. L. Farr, and R. J. Randall (1951). Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193, 265-275.
21. W. Wiegrebe, W. J. Kramer, and M. Shamma (1984). The emetine alkaloids. J. Natl. Prod., 47, 397-408, and references therein.
22. H. J. Fromm (1979). Use of competitive inhibitors to study substrate binding order. Meth. Entymol., 63, 467-486.
23. K. Narasimha Rao, R. K. Bhattacharya, and S. R. Venkatachalam (1996). Inhibition of thymidylate synthase by the phenanthroindolizidine alkaloids pergularinine and tylophorinidine. Presented in part at the Indian Society of Cell Biology: XIX All India Cell Biology, Conference and Cell Biology Symposia Proceedings, Calcutta, PNA-20, pp. 68-69.
24. D. V. Santi, C. S. McHenry, and H. Sommer (1974). Mechanism of interaction of thymidylate synthase with 5-fluorodeoxyuridylate, Biochemistry, 13, 471-481.
25. C. W. Carreras and D. V. Santi (1995). The catalytic mechanism and structure of thymidylate synthase. Annu. Rev. Biochem., 64, 721-762.
26. C. -H. Chen, R. A. Davis, and F. Maley (1996). Thermodynamic stabilization of nucleotide binding to thymidylate synthase by a potent benzoquinazoline folate analogue inhibitor. Biochemistry, 35, 8786-8793.
27. M. H. Hanlon and R. Ferone (1996). In vitro uptake, anabolism and cellular retention of 1843U89 and other benzoquinazoline inhibitors of thymidylate synthase. Cancer Res., 56, 3301-3306.
28. R. L. Hagan, J. B. Hynes, M. Pimsler, and R. L. Kisluik (1995). Studies on the antitumor effects of analogues of 5,8-dideazaisofolic acid and 5,8-dideazaisoaminopterin. Biochem. Pharmacol., 50, 803-809.
29. B. K. Shoichet, R. M. Stroud, D. V. Santi, I. D. Kuntz, and K. M. Perry (1993). Structure-based discovery of inhibitors of thymidylate synthase. Science, 259, 1445-1450.
30. M. D. Varney, C. L. Palmer, J. G. Deal, S. Webber, K. M. Welsh, C. A. Bartlet, C. A. Morse, W. W. Smith, and C. A. Janson (1995). Synthesis and biological evaluation of novel 2,6-diaminobenz[cd]indole inhibitors of thymidylate synthase using the protein structure as a guide. J. Med. Chem., 38, 1892-1903.
31. D. V. Santi, C. S. McHenry, and E. R. Perriard (1974). A filter assay for thymidylate synthetase using 5-fluoro-2′-deoxyuridylate as an active site titrant. Biochemistry, 13, 467-470.
32. E. Chu and J. Allegra (1996). The role of thymidylate synthase as an RNA binding protein. BioEssays, 18, 191-198.
33. C. K. Mathews and N. K. Sinha (1982). Are DNA precursors concentrated at replicating sites? Proc. Natl. Acad. Sci. USA, 79, 302-306.
34. S. C. Pakrashi and B. Achari (1970). Demethylcephaeline, a new alkaloid from Alangium lamarckii. Characterization of AL 60, the hypotensive principle from the stem-bark. Experientia, 26, 933-934.
35. S. R. Venkatachalam, S. A. Hassarajani, A. Banerji, and G. Viswanathan (1992). Deoxytubulosine, a potent platelet aggregation inhibitor from Alangium lamarckii. Presented in part at the Indian Society of Bio-Organic Chemists: Fourth National Symposium on Bio-Organic Chemistry, Bombay, P26, p. 46.
36. M. T. Hsieh, F. U. Chueh, H. Y. Tsai, W. H. Peng, and C. C. Hsieh (1993). Effects of Alangium chinense on motor activity and the concentrations of monoamines in rats. Zhonghuia Yaoxue Zazhi, 45, 447-456.
37. G. Mathe', M. Hayat, E. Chenu, H. P. Husson, T. Thevenet, C. Kan, and P. Potier (1978). Oncostatic effects of Alangium vitiense extracts (ICIG-EORTC 1131, 1186 and 1207) on lymphoid murine tumors. Cancer Res., 38, 1465-1467.
38. A. P. Grollman (1967). Structural basis for the inhibition of protein biosynthesis: mode of action of tubulosine. Science, 157, 84-85.
39. A. P. Grollman (1966). Structural basis for inhibition of protein synthesis by emetine and cycloheximide based on an analogy between ipecac alkaloids and glutarimide antibiotics. Proc. Natl. Acad. Sci. USA, 56, 1867-1874.
40. M. R. Siegel and H. D. Sisler (1964). Site of action of cycloheximide in cells of Saccharomyces pastorianus-II. The nature of inhibition of protein synthesis in a cell-free system. Biochim. Biophys. Acta, 87, 83-89.
41. H. L. Hennis and M. Lubin (1964). Cycloheximide: aspects of inhibition of protein synthesis in mammalian cells. Science, 146, 1474-1476.
42. 1. Chem. Biol. Interact., 100, 41-51.