The different biological effects of Telomestatin and TMPyP4 can be attributed to their selectivity for interaction with intramolecular or intermolecular G-quadruplex structures

Cancer Research

Volumn 63, Issue 12, 2003, Pages 3247-3256

  Kim, Mu Yong ^a,c   Gleason Guzman, Mary ^a,c   Izbicka, Elzbieta ^d   Nishioka, David ^e   Hurley, Laurence H ^b,c  

^a UNIVERSITY OF ARIZONA   (United States)

^b The University of Arizona   (United States)

^c UNIVERSITY OF ARIZONA   (United States)

^d CTRC Institute for Drug Development   (United States)

^e GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,10,15,10 TETRAKIS(N METHYL 4 PYRIDYL)PORPHYRIN; MONOVALENT CATION; PORPHYRIN DERIVATIVE; SINGLE STRANDED DNA; TELOMERASE; TELOMERASE INHIBITOR; TELOMESTATIN; UNCLASSIFIED DRUG;

ANAPHASE; ANIMAL TISSUE; ARTICLE; CELL PROLIFERATION; CHROMOSOME STRUCTURE; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA STRUCTURE; DRUG BINDING; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG EFFECT; DRUG ISOLATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; FACILITATION; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; MOLECULAR INTERACTION; MOLECULAR STABILITY; NONHUMAN; ONCOGENE C MYC; PRIORITY JOURNAL; PROMOTER REGION; SEA URCHIN; STREPTOMYCES; STREPTOMYCES ANULATUS; TELOMERE;

ANAPHASE; ANIMALS; ASPERGILLUS NUCLEASE S1; CELL LINE, TRANSFORMED; DNA; ENZYME INHIBITORS; HUMANS; MACROMOLECULAR SUBSTANCES; NUCLEIC ACID CONFORMATION; OXAZOLES; PORPHYRINS; POTASSIUM; SEA URCHINS; SODIUM; SUBSTRATE SPECIFICITY; TELOMERASE; TELOMERE;

EID: 0037731436     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. Makarov, V. L., Hirose, Y., and Langmore, J. P. Long G tails at both ends of human chromosomes suggest a C strand degradation mechanism for telomere shortening. Cell, 88: 657-666, 1997.
2. McElligott, R., and Wellinger, R. J. The terminal DNA structure of mammalian chromosomes, EMBO J., 16: 3705-3714, 1997.
3. Griffith, J. D., Comeau, L., Rosenfield, S., Stansel, R. M., Bianchi, A., Moss, H., and de Lange, T. Mammalian telomeres end in a large duplex loop. Cell, 97: 503-514, 1999.
4. Stansel, R. M., de Lange, T., and Griffith, J. D. T-loop assembly in vitro involves binding of TRF2 new the 3′ telomeric overhang. EMBO J., 20: 5532-5540, 2001.
5. Kalseder, J., Smogorzewska, A., and de Lange, T. Senescence induced by altered telomere state, not telomere loss. Science (Wash. DC), 295: 2446-2449, 2002.
6. Olovnikov, A. M. A theory of marginotomy. The incomplete copying of template margin in enzymic synthesis of polynucleotides and biological significance of the phenomenon. J. Theor. Biol., 41: 181-190, 1973.
7. Harley, C. B., Futcher, A. B., and Greider, C. W. Telomeres shorten during ageing of human fibroblasts. Nature (Lond.). 345: 458-460, 1990.
8. Smogorzewska, A., and de Lange, T. Different telomere damage signaling pathways in human and mouse cells. EMBO J., 21: 4338-4348, 2002.
9. Shay, J. W., Pereira-Smith, O. M., and Wright, W. E. A role for both RB and p53 in the regulation of human cellular senescence. Exp. Cell Res., 196: 33-39, 1991.
10. Shay, J. W., and Bacchetti, S. A survey of telomerase activity in human cancer. Eur. J. Cancer, 33: 787-791, 1997.
11. Mergny, J. L., Riou, J. F., Mailliet, P., Teulade-Fichou, M. P., and Gilson, E. Natural and pharmacological regulation of telomerase. Nucleic Acids Res., 30: 839-865, 2002.
12. Rezler, E. M., Bearss, D. J., and Hurley, L. H. Telomeres and telomerases as drug targets. Curr. Opin. Pharmacol., 4: 415-423, 2002.
13. Neidle, S. and Parkinson, G. Telomere maintenance as a target for anticancer drug discovery. Nat. Rev. Drug Discov., 1: 383-393, 1991.
14. Rezler, E. M., Bearss, D. J., and Harley, L. H. Telomerase inhibition and telomere disruption as processes for drug targeting. Annu. Rev. Pharmacol. Toxicol., 43: 359-379, 2002.
15. 3] G-tetraplex. Structure., 15: 263-282, 1993.
16. Parkinson, G. N., Lee, M. P., and Neidle, S. Crystal structure of parallel quadruplexes from human telomeric DNA. Nature (Lond.), 417: 876-880, 2002.
17. Keniry, M. A. Quadruplex structures in nucleic acids. Biopolymers, 56: 123-146, 2001.
18. Kerwin, S. M. G-Quadruplex DNA as a target for drug design. Curr. Pharm. Des., 6: 441-478, 2000.
19. Giraldo, R., Suzuki, M., Chapman, L., and Rhodes, D. Promotion of parallel DNA quadruplexes by a yeast telomere binding protein: a circular dichroism study. Proc. Natl. Acad. Sci. USA, 91: 7658-7662, 1994.
20. Fang, G., and Cech, T. R. The β subunit of Oxytricha telomere-binding protein promotes G-quartet formation by telomeric DNA. Cell, 74: 875-885, 1993.
21. Fang, G., and Cech, T. R. Characterization of a G-quartet formation reaction promoted by the β-subunit of the Oxytricha telomere-binding protein. Biochemistry, 32: 11646-11657, 1993.
22. Sun, H., Bennett, R. J., and Maizels, N. The Saccharomyces cerevisiae Sgs1 helicase efficiently unwinds G-G paired DNAs. Nucleic Acids Res., 27: 1978-1984, 1999.
23. Schaffitzel, C., Berger, I., Postberg, J., Hanes, J., Lipps, H. J., and Pluckthun, A. In vitro generated antibodies specific for telomeric guanine-quadruplex DNA react with Stylonychia lemnae macronuclei. Proc. Natl. Acad. Sci. USA, 98: 8572-8577, 2001.
24. Izbicka, E., Nishioka, D., Marcell, V., Raymond, E., Davidson, K. K., Lawrence, R. A., Wheelhouse, R. T., Hurley, L. H., Wu, R. S., and Von Hoff, D. D. Telomere-interactive agents affect proliferation rates and induce chromosomal destabilization in sea urchin embryos. Anticancer Drug Des., 14: 355-365, 1999.
25. Grad, C. L., Han. H., Muñoz, R. M., Waitman, S., Von Hoff, D. D., Hurley, L. H., and Bearss, D. J. The cationic porphyrin TMPyP4 downregulates c-MYC and hTERT expression and inhibits tumor growth in vivo. Mol. Cancer Ther., 1: 565-573, 2002.
26. Gowan, S. M., Harrison, J. R., Patterson, L., Valenti, M., Read, M. A. Neidle, S., and Kelland, L. R. A G-quadruplex-interactive potent small-molecule inhibitor of telomerase exhibiting in vitro and in vivo antitumor activity. Mol. Pharmacol., 61: 1154-1162, 2002.
27. Izbicka, E, Wheelhouse, R. T., Raymond, E., Davidson, K. K., Lawrence, R. A., Sun, D., Windle, B. E., Hurley, L. H., and Von Hoff, D. D. Effects of cationic porphyrins as G-quadruplex interactive agents in human tumor cells. Cancer Res., 59: 639-644, 1999.
28. Read, M., Harrison, R. J., Romagnoli, B., Tanious, F. A., Gowan, S. H., Reszka, A. P., Wilson, W. D., Kelland, L. R., and Neidle, S. Structure-based design of selective and potent G-quadruplex-mediated telomerase inhibitors. Proc. Natl. Acad. Sci. USA, 98: 4844-4849, 2001.
29. Riou, J. F., Guittat, L., Mailliet, P., Laoui, A., Renou, E., Petitgenet, O., Mégnin-Chanet, F., Hélène, C., and Mergny, J. L. Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands. Proc. Natl. Acad. Sci. USA, 99: 2672-2677, 2002.
30. Gowan, S. M., Heald, R., Stevens, M. F., and Kelland, L. R. Potent inhibition of telomerase by small-molecule pentacyclic acridines capable of interacting with G-quadruplexes. Mol. Pharmacol., 60: 981-988, 2001.
31. Duan, W., Rangan, A., Vankayalapati, H., Kim, M-Y., Zeng, Q., Sun, D., Han, H., Fedoroff, O. Yu., Nishioka, D., Rha, S. Y., Izbicka, E., Von Hoff, D. D., and Hurley, L. H. Design and synthesis of fluoroquinophenoxazines that interact with human telomeric G-quadruplexes and their biological effects. Mol. Cancer Ther., 1: 103-120, 2001.
32. Kim, M-Y., Duan, W., Gleason-Guzman, M., and Hurley, L. H. Design, synthesis, and biological evaluation of a series of fluoroquinoanthroxazines with contrasting dual mechanisms of action against topoisomerase II and G-quadruplexes. J. Med. Chem., 46: 571-583, 2003.
33. Shin-ya, K., Wierzba, K., Matsuo, K., Ohtani, T., Yamada, Y., Furihata, K., Hayakawa, Y., and Seto, H. Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus. J. Am. Chem. Soc., 123: 1262-1263, 2001.
34. Kim, M-Y., Vankayalapati, H., Shin-Ya, K., Wierzba, K., and Hurley, L. H. Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular G-quadruplex. J. Am. Chem. Soc., 124: 2098-2099, 2002.
35. Han, H., Hurley, L. H., and Salazar, M. A DNA polymerase stop assay for G-quadruplex-interactive compounds. Nucleic Acids Res., 27: 537-542, 1999.
36. Henderson, E., Hardin, C. C., Walk, S. K., Tinoco, I., Jr., and Blackburn, E. H. Telomeric DNA oligonucleotides form novel intramolecular structures containing guanine-guanine base pairs. Cell, 51: 899-908, 1987.
37. Williamson, J. R., Raghuraman, M. K., and Cech, T. R. Monovalent cation-induced structure of telomeric DNA: the G-quartet model. Cell, 59: 871-880, 1989.
38. Arimondo, P. B., Riou, J. F., Mergny, J. L., Tazi, J., Sun, J. S., Garestier, T., and Hélène, C. Interaction of human DNA topoisomerase I with G-quartet structures. Nucleic Acids Res., 28, 4832-4838, 2000.
39. Han, H., Cliff, C. L., and Hurley, L. H. Accelerated assembly of G-quadruplex structures by a small molecule. Biochemistry, 38: 6981-6986, 1999.
40. Holt, S. E., Glinsky, V. V., Ivanova, A. B., and Glinsky, G. V. Resistance to apoptosis in human cells conferred by telomerase function and telomere stability. Mol. Carcinog. 25: 241-248, 1999.
41. Dunham, M. A., Neumann, A. A. Fasching, C. L., and Reddel, R. R. Telomere maintenance by recombination in human cells. Nat. Genet., 26: 447-450, 2000.
42. Acevedo, O. L., Dickinson, L. A., Macke, T. J., and Thomas, C. A., Jr. The coherence of synthetic telomeres. Nucleic Acids Res. 19: 3409-3419, 1991.
43. Sambrook, J., Fritsch, E. F., and Maniatis, T. Molecular Cloning: A Laboratory Manual, Ed. 2, pp. 5.78-5.79. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press, 1989.
44. Siddiqai-Jain, A., Grand, C. L., Bearss, D. J., and Hurley, L. H. Direct evidence for a G-quadruplex in a promoter region and its targeting with a small molecule to repress c-MYC transcription. Proc. Natl. Acad. Sci. USA, 99: 11593-11598, 2002.
45. Hurley, L. H. DNA and its associated processes as targets for cancer therapy. Nat. Rev. Cancer. 2: 188-200, 2002.
46. Simonsson, T. Pecinka, P., and Kubista, M. DNA tetraplex formation in the control region of c-myc. Nucleic Acids Res., 26: 1167-1172, 1998.
47. Shin-ya, K., Park, H. R., Wierzba, K., Matsuo, K. I., Ohtani, T., Ito, R., Hayakawa, Y., and Seto, H. Telomestatin, a novel telomerase inhibitor of microbial origin, 93rd Annual Meeting of American Association for Cancer Researh. Prog. Am. Assoc. Cancer Res., 251, 2002.
48. Zahler, A. M., Williamson, J. R. Cech, T. R. and Prescott, D. M, Inhibition of telomerase by G-quartet DNA structures. Nature (Lond.), 350: 718-720, 1991.
49. Hurley, L. H. DNA and associated targets for drug design. J. Med. Chem., 32: 2027-2033, 1989,