Structure-activity relationships among guanine-quadruplex telomerase inhibitors

Pharmacology and Therapeutics

Volumn 85, Issue 3, 2000, Pages 133-139

  Neidle, Stephen ^a   Harrison, R John ^a   Reszka, Anthony P ^a   Read, Martin A ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

Inhibitors; Molecular modelling; Quadruplex; Telomerase

Indexed keywords

ANTHRAQUINONE DERIVATIVE; ENZYME INHIBITOR; POLYCYCLIC HYDROCARBON; TELOMERASE; TRICYCLIC AROMATIC COMPOUND;

CANCER; CELL GROWTH; CONFERENCE PAPER; DRUG DEVELOPMENT; HYPOTHESIS; LIGAND BINDING; MOLECULAR MODEL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CELL TRANSFORMATION, NEOPLASTIC; DNA; GUANINE; HUMANS; LIGANDS; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; TELOMERASE; TELOMERE;

EID: 0034018083     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(99)00065-0     Document Type: Review

References (45)

1. Agbandje M., Jenkins T.C., McKenna R., Reszka A.P., Neidle S. Anthracene-9,10-diones as potential anticancer agents. Synthesis, DNA binding and biological studies on a series of 2,6-disubstituted derivatives. J Med Chem. 35:1992;1418-1429.
2. Allsopp R.C., Harley C.B. Evidence for a critical telomere length in senescent human fibroblasts. Exp Cell Res. 219:1995;130-136.
3. Blackburn E.H. Structure & function of telomeres. Nature. 350:1991;569-573.
4. Blasko M.A., Lee H.-W., Hande M.P., Samper E., Lansdorp P.M., DePinho R.A., Greider C.W. Telomere shortening and tumor formation by mouse cells lacking telomerase RNA. Cell. 91:1997;25-34.
5. Bodnar A.G., Ouellette M., Frolkis M., Holt S.E., Chiu C.P., Morin G.B., Harley C.B., Shay J.W., Lichtsteiner S., Wright W.E. Extension of life-span by introduction of telomerase into normal human cells. Science. 279:1998;349-352.
6. Collier D.A., Neidle S. Molecular modeling, DNA binding and antitumour properties of some substituted amidoanthraquinones. J Med Chem. 31:1988;847-857.
7. Counter C.M., Hirte H.W., Bacchetti S., Harley C.B. Telomerase activity in human ovarian carcinoma. Proc Natl Acad Sci USA. 91:1994;2900-2904.
8. Counter C.M., Hahn W.C., Wei W., Caddle S.D., Beijersbergen R.L., Lansdorp P.M., Sedivy J.M., Weinberg R.A. Dissociation among in vitro telomerase activity, telomere maintenance and cellular immortalization. Proc Natl Acad Sci USA. 95:1998;14723-14728.
9. de Lange T., Jacks T. For better or worse? Telomerase inhibition & cancer. Cell. 98:1999;273-275.
10. Fedoroff O.Y., Salazar M., Han H., Chemeris V.V., Kerwin S.M., Hurley L.H. NMR-based model of a telomerase-inhibiting compound bound to G-quadruplex DNA. Biochemistry. 37:1998;12367-12374.
11. Fletcher T.M., Sun D., Salazar M., Hurley L.H. Effect of DNA secondary structure on human telomerase activity. Biochemistry. 37:1998;5536-5541.
12. Guo Q., Lu M., Marky L.A., Kallenbach N.R. Interaction of the dye ethidium bromide with DNA containing guanine repeats. Biochemistry. 31:1992;2451-2455.
13. Hahn W.C., Counter C.M., Lundberg A.S., Beijersbergen R.L., Brooks M.W., Weinberg R.A. Creation of human tumour cells with defined genetic elements. Nature. 400:1999;464-468. a.
14. Hahn W.C., Stewart S.A., Brooks M.W., York S.G., Eaton E., Kurachi A., Beijersbergen R.L., Knoll J.H.M., Meyerson M., Weinberg R.A. Inhibition of telomerase limits the growth of human cancer cells. Nat Med. 5:1999;1164-1170. b.
15. Hamilton S.E., Corey D.R. Telomerase. anti-cancer target or just a fascinating enzyme? Chem Biol. 3:1996;863-867.
16. Han H., Cliff C.L., Hurley L.H. Accelerated assembly of G-quadruplex structures by a small molecule. Biochemistry. 38:1999;6981-6986.
17. Harley C.B., Futcher A.B., Greider C.W. Telomeres shorten during ageing of human fibroblasts. Nature. 345:1990;458-460.
18. Harrison R.J., Gowan S.M., Kelland L.R., Neidle S. Human telomerase inhibition by substituted acridine derivatives. Bioorg Med Chem Lett. 9:1999;2463-2468.
19. Hoos A., Hepp H.H., Kaul S., Ahlert T., Bastert G., Wallwiener D. Telomerase activity correlates with tumor aggressiveness and reflects therapy effect in breast cancer. Int J Cancer. 79:1998;8-12.
20. Izbicka E., Wheelhouse R.T., Raymond E., Davidson K.K., Lawrence R.A., Sun D., Windle B.E., Hurley L.H., Von Hoff D.D. Effects of cationic porphyrins as G-quadruplex interactive agents in human tumor cells. Cancer Res. 59:1999;639-644.
21. Kim N.W., Piatyszek M.A., Prowse K.R., Harley C.B., West M.D., Ho P.L.C., Coviello G.M., Wright W.E., Weinrich R.L., Shay J.W. Specific association of human telomerase activity with immortal cells and cancer. Science. 266:1994;2011-2015.
22. Lee H.-W., Blasco M.A., Gottlieb G.J., Horner J.W., Greider C.W., DePinho R.A. Essential role of mouse telomerase in highly proliferative organs. Nature. 392:1998;569-574.
23. Lingner J., Hughes T.R., Shevchenko A., Mann M., Lundblad V., Cech T.R. Reverse transcriptase motifs in the catalytic subunit of telomerase. Science. 276:1997;561-565.
24. Mergny J.-L., Hélène C. G-quadruplex DNA. a target for drug design Nat Genet. 4:1998;1366-1367.
25. n among vertebrates. Proc Natl Acad Sci USA. 86:1989;7049-7053.
26. Morin G.B. The human telomere terminal transferase activity is a ribonucleoprotein that synthesises ttaggg repeats. Cell. 59:1989;521-529.
27. Neidle S., Kelland L.R. Telomerase as an anti-cancer target. current status and future prospects Anticancer Drug Des. 14:1999;341-347.
28. Niida H., Matsumoto T., Satoh H., Shiwa M., Tokutake Y., Furuichi Y., Shinkai Y. Severe growth defect in mouse cells lacking the telomerase RNA component. Nat Genet. 19:1998;203-206.
29. O'Reilly M., Teichmann S.A., Rhodes D. Telomerases. Curr Opin Struct Biol. 9:1999;58-65.
30. Patel D.J., Bouaziz S., Kattani A., Wang I. Structures of guanine-rich and cytosine-rich quadruplexes formed in vitro by telomeric, centromeric and triplet repeat disease DNA sequences. Neidle S. Oxford Handbook of Nucleic Acid Structure. 1999;389-453 Oxford University Press, Oxford.
31. Perry P.J., Gowan S.M., Reszka A.P., Polucci P., Jenkins T.C., Kelland L.R., Neidle S. 1,4- and 2,6-Disubstituted amidoanthracene-9,10-dione derivatives as inhibitors of human telomerase. J Med Chem. 41:1998;3253-3260. a.
32. Perry P.J., Reszka A.P., Wood A.A., Read M.A., Gowan S.M., Dosanjh H.S., Trent J.O., Jenkins T.C., Kelland L.R., Neidle S. Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones. J Med Chem. 41:1998;4873-4884. b.
33. Perry P.J., Gowan S.M., Read M.A., Kelland L.R., Neidle S. Design, synthesis and evaluation of human telomerase inhibitors based on a tetracyclic structural motif. Anticancer Drug Des. 14:1999;373-382. a.
34. Perry P.J., Read M.A., Davies R.T., Gowan S.M., Reszka A.P., Wood A.A., Kelland L.R., Neidle S. 2,7-Disubstituted amidofluorenone derivatives as inhibitors of human telomerase. J Med Chem. 42:1999;2679-2684. b.
35. Pitts A.E., Corey D.R. The telomerase challenge - an unusual problem in drug discovery. Drug Discov Today. 4:1999;155-161.
36. Raymond E., Sun D., Chen S.-F., Windle B., Von Hoff D.D. Agents that target telomerase and telomeres. Curr Opin Biotechnol. 7:1996;583-591.
37. Read M.A., Wood A.A., Harrison R.J., Gowan S.M., Kelland L.R., Dosanjh H.S., Neidle S. Molecular modelling studies on G-quadruplex complexes of telomerase inhibitors. structure-activity relationships J Med Chem. 42:1999;4538-4546.
38. Sano T., Asai A., Fujimaki T., Kirino T. Telomerase activity in 144 brain tumours. Br J. Cancer. 77:1998;1633-1637.
39. Sharma S., Raymond E., Soda H., Sun D., Ilsenbeck S.G., Sharma A., Izbicka E., Windle B., Von Hoff D.D. Preclinical & clinical strategies for development of telomerase and telomere inhibitors. Ann Oncol. 8:1997;1063-1074.
40. Sun D., Thompson B., Cathers B.E., Salazar M., Kerwin S.M., Trent J.O., Jenkins T.C., Neidle S., Hurley L.H. Inhibition of human telomerase by a G-quadruplex-interactive compound. J Med Chem. 40:1997;2113-2116.
41. Sun D., Lopez-Guajardo C.C., Quada J., Hurley L.H., Von Hoff D.D. Regulation of catalytic activity and processivity of human telomerase. Biochemistry. 38:1999;4037-4044.
42. 3] G-tetraplex. Structure. 1:1993;263-282.
43. Wheelhouse R., Sun D., Han H., Han F.X., Hurley L.H. Cationic porphyrins as telomerase inhibitors. the interaction of tetra-(N-methyl-4-pyridyl)porphine with quadruplex DNA J Am Chem Soc. 120:1998;3261-3262.
44. Zahler A.M., Williamson J.R., Cech T.R., Prescott D.M. Inhibition of telomerase by G-quartet DNA structures. Nature. 350:1991;718-720.
45. Zhu J., Wang H., Bishop J.M., Blackburn E.H. Telomerase extends the lifespan of virus-transformed human cells without net telomere lengthening. Proc Natl Acad Sci USA. 96:1999;3723-3728.