Synthesis and evaluation of quindoline derivatives as G-quadruplex inducing and stabilizing ligands and potential inhibitors of telomerase

Journal of Medicinal Chemistry

Volumn 48, Issue 23, 2005, Pages 7315-7321

  Zhou, Jin Lin ^a   Lu, Yu Jing ^a   Ou, Tian Miao ^a   Zhou, Jun Min ^a   Huang, Zhi Shu ^a   Zhu, Xiao Feng ^a   Du, Cui Juan ^a   Bu, Xian Zhang ^a   Ma, Lin ^a   Gu, Lian Quan ^a   Li, Yue Ming ^a,b   Chan, Albert Sun Chi ^a,b  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

(10H BENZOFURO[3,2 B]QUINOLIN 11 YL) N,N DIMETHYLMETHANE 1,2 DIAMINE; (10H BENZOFURO[3,2 B]QUINOLIN 11 YL) N,N DIMETHYLPROPANE 1,2 DIAMINE; (10H BENZOFURO[3,2 B]QUINOLIN 11 YLAMINO)ETHANOL; (10H BENZOFURO[3,2 B]QUINOLIN 11 YLAMINO)PROPANOL; (10H INDOLO[3,2 B]QUINOLIN 11 YL)(2 MORPHOLIN 4 YLETHYL)AMINE; CRYPTOLEPINE; DNA; LIGAND; N' (10H BENZOFURO[3,2 B]QUINOLIN 11 YL)(2 MORPHOLIN 4 YLETHYL)AMINE; N' (10H INDOLO[3,2 B]QUINOLIN 11 YL) N,N DIMETHYLETHANE 1,2 DIAMINE; N' (10H INDOLO[3,2 B]QUINOLIN 11 YL) N,N DIMETHYLPROPANE 1,3 DIAMINE; N' (10H INDOLO[3,2 B]QUINOLIN 11 YL)(2 MORPHOLIN 4 YLETHYL)AMINE; N' (10H INDOLO[3,2 B]QUINOLIN 11 YLAMINO)ETHANOL; N' (10H INDOLO[3,2 B]QUINOLIN 11 YLAMINO)PROPANOL; QUINDOLINE; QUINDOLINE DERIVATIVE; TELOMERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING COMPETITION; CIRCULAR DICHROISM; CONTROLLED STUDY; DNA SEQUENCE; DRUG DESIGN; DRUG DNA INTERACTION; DRUG POTENCY; DRUG SYNTHESIS; ELECTRON TRANSPORT; ENZYME ACTIVITY; ENZYME INHIBITION; GEL MOBILITY SHIFT ASSAY; HUMAN; HUMAN CELL; IC 50; LIGAND BINDING; SUBSTITUTION REACTION; TELOMERIC REPEAT AMPLIFICATION PROTOCOL;

ALKALOIDS; ANTINEOPLASTIC AGENTS; CIRCULAR DICHROISM; DIALYSIS; DNA; ELECTROPHORETIC MOBILITY SHIFT ASSAY; HUMANS; INDOLES; LIGANDS; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; TELOMERASE; THERMODYNAMICS;

EID: 28544447925     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050041b     Document Type: Article

References (38)

1. (a) Blackburn, E. H. Structure and function of telomeres. Nature 1991, 350, 569-573.
2. (b) Harley, C. B.; Futcher, A. B.; Greider, C. W. Telomeres shorten during aging of human fibroblasts. Nature 1990, 345, 458-460.
3. Allsopp, R. C.; Harley, C. B. Evidence for a critical telomere length in senescent human fibroblasts. Exp. Cell Res. 1995, 219, 130-136.
4. Simomson, T.; Pecinka, P.; Kubista, M. DNA tetraplex formation in the control region of c-myc. Nucleic Acids Res. 1998, 26, 1167-1172.
5. Greider, C. W.; Blackburn, E. H. Identification of a specific telomere terminal transferase activity in Tetrahymena extracts. Cell 1985, 43, 405-413.
6. (b) Feng, J.; Funk, W.; Wang, S.-S.; Weinrich, S. L.; Avilion, A. A.; Chiu, C.-P.; Adam, R. R.; Chang, E. The RNA component of human telomerase. Science 1995, 269, 1236.
7. Kim, N. W.; Piatyszek, M. A.; Prowse, K. R.; Harley, C. B.; West, M. D.; Ho, P. L.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J. W. Specific association of human telomerase activity with immortal cell and cancer. Science 1994, 266, 2011-2015.
8. Bryan, T. M.; Cech, T. R. Telomerase and maintenance of chromosome ends. Curr. Opin. Cell Biol. 1999, 11, 318-322.
9. (a) Keith, W. N.; Evens, T. R.; Glasspool, R. M. Telomerase and cancer: time to move from a promising target to clinical reality. J. Pathol. 2001, 195, 404-414.
10. (b) Herbert, B. S.; Pitts, A. E.; Baker, S. I.; Hamilton, S. E.; Wright, W. E.; Shay, J. W.; Corey, D. R. Inhibition of human telomerase in immortal human cells leads to progressive telomere shortening and cell death. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 14276-14281.
11. Mergny, J.-L.; Riou, J.-F.; Mailliet, P.; Teulade-Fichou, M.-P.; Gilson, E. Natural and pharmacological regulation of telomerase. Nucleic Acids Res. 2002, 30, 839-865.
12. (a) Holt, S. J.; Petrow, V. Cabarzole, cabolines, and [related compounds part 1]. J. Chem. Soc. 1947, 607-611.
13. (b) Bierer, D. E.; Dubenko, L. G.; Zhang, P. Antihyperglycemic activities of cryptolepine analogues: an ethnobotanical lead structure from Cryptolepis sanguinolenta. J. Med. Chem. 1998, 41, 2754-2764.
14. Radl, S.; Konvicka, P.; Vachal, P. A new approach to the synthesis of benzofuro[3,2-6]quinolines, benzothieno[3,2-6]quinolines and indolo[3,2-6]qumolines. J. Heterocycl. Chem. 2000, 37, 855-862.
15. Yang, S.-W.; Abdel-Kader, M.; Malone, S.; Werkhoven, M. C.; Wisse, J. H.; Bursuker, I.; Neddermann, K.; Fairchild, C.; Raventos-Suarez, C.; Menendez, A. T.; Lane, K.; Kingston, D. G. Synthesis and Biological Evaluation of Analogues of Cryptolepine, an Alkaloid Isolated from Suriname Rainforest. J. Nat. Prod. 1999, 62, 976-983.
16. Lisgarten, J. N.; Coll, M.; Portugal, J.; Wright, C. W.; Aymami, J. The antimalarial and cytotoxic drug cryptolepine intercalates into DNA at cytosine-cytosine sites. Nat. Struct. Biol. 2002, 9, 57-60.
17. Bonjean, K.; De Pauw-Gillet, M. C.; Defresne, M. P.; Colson, P.; Houssier, C.; Dassonneville, L.; Bailly, C.; Grimers, R.; Wright, C.; Quetin-Leclercq, J.; Tits, M.; Angenot, L. The DNA intercalatin alkaloid cryptolepine interferes with topoisomerase II and inhibits primary DNA synthesis in B16 melanoma cells. Biochemistry 1998, 37, 5136-5146.
18. (a) Caprio, V.; Guyen, B.; Opoku-Boahen, Y.; Mann, J.; Gowan, S. M.; Kelland, L. M.; Read, M. A.; Neidle, S. A novel inhibitor of human telomerase derived from 10H-indolo-[3,2-b]quinoline. Bioorg. Med. Chem. Lett. 2000, 10, 2063-2066.
19. (b) Guyen, B.; Schultes, C.; Hazel, C.; Mann, J.; Neidle, S. Synthesis and evaluation of analogues of 10H-indolo-[3,2-b]quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase. Org. Biomol. Chem. 2004, 2, 981-988.
20. (a) Zahler, A. M.; Williamson, J. R.; Cech, T. R.; Prescott, D. M. Inhibition of telomerase by G-quartet DNA structures. Nature (London) 1991, 350, 718-720.
21. (b) Han, H.; Hurley, L. H. Trends Pharmacol. Sci. 2000, 21, 136-142.
22. Hurley, L. H. Nat. Rev. Cancer 2002, 2, 188-200.
23. Neidle, S.; Parkinson, G. Telomere maintenance as a target for anticancer drug discovery. Nat. Rev. Drug Discovery 2002, 1, 383-393.
24. (a) Haider, S. M.; Parkinson, G. N.; Neidle, S. Structure of a G-quadruplex-ligand complex. J. Mol. Biol. 2003, 326, 117-125.
25. (b) Clark, G. R.; Pytel, P. D.; Squire, C. J.; Neidle, S. Structure of the first parallel DNA quadruplex-drug complex. J. Am. Chem. Soc. 2003, 125, 4066-40677.
26. Lisgarten, J. N.; Portugal, J.; Coll, M.; Wright, C. W.; Aymami, J. The antimalarial and cytotoxic drug cryptolepine intercalates into DNA at cytosine-cytosine sites. Nat. Stuct. Biol. 2002, 9, 57-60.
27. (a) Irvin, J. L.; Irvin, E. M. Spectrophotometric and potentiometric evaluation of apparent acid dissociation exponents of various 4-aminoquinolines. J. Am. Chem. Soc. 1947, 69, 1091-1099.
28. (b) Knight, S. B.; Wallick, R. H.; Bowen, J. The ultraviolet absorption spectra and the dissociation constants of the monobromoquinolines. J. Am. Chem. Soc. 1954, 76, 3780-3783.
29. (a) Li, W.; Wu, P.; Ohmichi, T.; Sugimoto, N. Characterization and thermodynamic properties of quadruplex/druplex competition. FEBS Lett. 2002, 526, 77-81.
30. (b) Balagurumoorthy, P.; Brahmachari, S. K.; Mohanty, D.; Bansal, M.; Sasisekharan, V. Hairpin and parallel quartet structures for telomeric sequences. Nucleic Acids Res. 1992, 20, 4061-4067.
31. Balagurumoorthy, P.; Brahmachari, S. K. Structure and Stability of human telomere sequence. J. Biol. Chem. 1994, 269, 21858-21869.
32. Lu, M.; Guo, Q.; Kallenbach, N. R. Structure and stability of sodium and potassium complexes of dT4G4 and dT4G4T. Biochemistry 1992, 31, 2455-2459.
33. Marathias, M. V.; Bolton, H. P. Determinants of DNA quadruplex structural type: sequence and potassium binding. Biochemistry 1999, 38, 4355-4364.
34. (a) Han, H.; Langley, D. R.; Rangan, A.; Hurley, L. H. Selective interactions of cationic porphyrins with G-quadruplex structures. J. Am. Chem. Soc. 2001, 123, 8902-8913.
35. (b) Han, H.; Cliff, C. L.; Hurley, L. H. Accelerated assembly of G-quadruplex structures by a small molecule. Biochemistry 1999, 38, 6981-6986.
36. Ren, J.; Chaires, J. B. Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry 1999, 38, 16067-16075.
37. Krupp, G.; Kuhne, K.; Tamm, S.; Klapper, W.; Heidorm, K.; Rott, A.; Parwaresch, R. Molecular basis of artifacts in the detection of telomerase activity and a modified primer for a more robust "TRAP" assay. Nucleic Acids Res. 1997, 25, 919-921.
38. Stothard, J. R.; Frame, I. A.; Miles, M. A. An evaluation of four staining methods for the detection of DNA in nondenaturing polyacrylamide gels. Anal. Biochem. 1997, 253, 262-264.