Anticancer activity and cellular repression of c-MYC by the G-quadruplex-stabilizing 11-piperazinylquindoline is not dependent on direct targeting of the G-quadruplex in the c-MYC promoter

Journal of Medicinal Chemistry

Volumn 55, Issue 13, 2012, Pages 6076-6086

  Boddupally, Peda V L ^a   Hahn, Seongmin ^a   Beman, Cristina ^a   De, Biswanath ^a   Brooks, Tracy A ^a,b   Gokhale, Vijay ^a,b   Hurley, Laurence H ^a,b  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11 (4 METHYLPIPERAZIN 1 YL) 10H INDOLO[3,2 B]QUINOLINE; 11 (PIPERAZIN 1 YL) 10H INDOLO[3,2 B]QUINOLINE; 11 [4 (3 METHOXYPROPYL)PIPERAZIN 1 YL] 10H INDOLO[3,2 B]QUINOLINE; 11 [4 [4 (PIPERAZIN 1 YL)ETHYL]PIPERAZIN 1 YL] 10H INDOLO[3,2 B]QUINOLINE; 2 [4 (10H INDOLO[3,2 B]QUINOLIN 11 YL)ETHYL]MORPHOLINE; 2 [4 (10H INDOLO[3,2 B]QUINOLIN 11 YL)PIPERAZIN 1 YL] N,N DIETHYLETHANAMINE; 2 [4 (10H INDOLO[3,2 B]QUINOLIN 11 YL)PIPERAZIN 1 YL] N,N DIMETHYLETHANAMINE; 2 [4 [2 (3,4 DIFLUOROPHENYL) 10H INDOLO[3,2 B]QUINOLIN 11 YL]PIPERAZIN 1 YL] N,N DIMETHYLETHANAMINE; 3 [11 [4 [2 (DIMETHYLAMINO)ETHYL]PIPERAZIN 1 YL] 10H INDOLO[3,2 B]QUINOLIN 10 YL] N,N DIMETHYLPROPAN 1 AMINE; 3 [4 (10H INDOLO[3,2 B]QUINOLIN 11 YL)PIPERAZIN 1 YL] N,N DIMETHYLPROPAN 1 AMINE; 3 [4 (10H INDOLO[3,2 B]QUINOLIN 11 YL)PIPERAZIN 1 YL] PROPAN 1 OL; 4 [4 (10H INDOLO[3,2 B]QUINOLIN 11 YL)PHENETHYL]MORPHOLINE; GUANINE QUADRUPLEX; INDOLE DERIVATIVE; N,N DIMETHYL 2 [4 [2 (PYRIDIN 4 YL) 10H INDOLO[3,2 B]QUINOLIN 11 YL]PIPERAZIN 1 YL]ETHANAMINE; N,N DIMETHYL 2 [4 [2 [4 (2 MORPHOLINOETHYL)PHENYL] 10H INDOLO[3,2 B]QUINOLIN 11 YL]PIPERAZIN 1 YL]ETHANAMINE; N,N DIMETHYL 3 [11 (4 METHYLPIPERAZIN 1 YL) 10H INDOLO[3,2 B]QUINOLIN 10 YL]PROPAN 1 AMINE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HCT116; CYTOTOXICITY; DOWN REGULATION; DRUG MECHANISM; DRUG SYNTHESIS; GENE EXPRESSION; IC 50; LYMPHOMA CELL LINE; MELTING POINT; ONCOGENE C MYC; PROMOTER REGION; STRUCTURE ACTIVITY RELATION; TRANSCRIPTION REGULATION;

ALKALOIDS; ANTINEOPLASTIC AGENTS; G-QUADRUPLEXES; GENE EXPRESSION REGULATION; HCT116 CELLS; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; NEOPLASMS; PROMOTER REGIONS, GENETIC; PROTO-ONCOGENE PROTEINS C-MYC; QUINOLINES; SILENCER ELEMENTS, TRANSCRIPTIONAL;

EID: 84863814733     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300282c     Document Type: Article

References (20)

1. Eisenman, R. N. Deconstructing myc Genes Dev. 2001, 15, 2023-2030 (Pubitemid 32762045)
2. Pelengaris, S.; Khan, M.; Evan, G. c-MYC: more than just a matter of life and death Nat. Rev. Cancer 2002, 2, 764-776 (Pubitemid 37328911)
3. Schmidt, E. V. The role of c -myc in regulation of translation initiation Oncogene 2004, 23, 3217-3221 (Pubitemid 38638833)
4. Nesbit, C. E.; Tersak, J. M.; Prochownik, E. V. MYC oncogenes and human neoplastic disease Oncogene 1999, 18, 3004-3016 (Pubitemid 29276540)
5. Nilsson, J. A.; Cleveland, J. L. Myc pathways provoking cell suicide and cancer Oncogene 2003, 22, 9007-9021 (Pubitemid 38121701)
6. Slamon, D. J.; deKernion, J. B.; Verma, I. M.; Cline, M. J. Expression of cellular oncogenes in human malignancies Science 1984, 224, 256-262 (Pubitemid 14172510)
7. Seenisamy, J.; Rezler, E. M.; Powell, T. J.; Tye, D.; Gokhale, V.; Joshi, C. S.; Siddiqui-Jain, A.; Hurley, L. H. The dynamic character of the G-quadruplex element in the c-MYC promoter and modification by TMPyP4 J. Am. Chem. Soc. 2004, 126, 8702-8709 (Pubitemid 38955732)
8. Siddiqui-Jain, A.; Grand, C. L.; Bearss, D. J.; 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. U.S.A. 2002, 99, 11593-11598 (Pubitemid 34994444)
9. Chan, D.-S.; Yang, H.; Kwan, M.-H.; Cheng, Z.; Lee, P.; Bai, L.-P.; Jiang, Z.-H.; Wong, C.-Y.; Fong, W.-F.; Leung, C.-H.; Ma, D.-L. Structure-based optimization of FDA-approved drug methylene blue as a c -myc G-quadruplex DNA stabilizer Biochimie 2011, 93, 1055-1064
10. Ma, Y.; Ou, T.-M.; Tan, J.-H.; Hou, J.-Q.; Huang, S.-L.; Gu, L.-Q.; Huang, Z.-S. Quinolino-benzo-[5,6]-dihydroisoquindolium compounds derived from berberine: a new class of highly selective ligands for G-quadruplex DNA in c -myc oncogene Eur. J. Med. Chem. 2011, 46, 1906-1913
11. Ou, T. M.; Lu, Y. J.; Zhang, C.; Huang, Z. S.; Wang, X. D.; Tan, J. H.; Chen, Y.; Ma, D. L.; Wong, K. Y.; Tang, J. C.; Chan, A. S.; Gu, L. Q. Stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc by quindoline derivatives J. Med. Chem. 2007, 50, 1465-1474 (Pubitemid 46566333)
12. Peng, D.; Tan, J. H.; Chen, S. B.; Ou, T. M.; Gu, L. Q.; Huang, Z. S. Bisaryldiketene derivatives: a new class of selective ligands for c -myc G-quadruplex DNA Bioorg. Med. Chem. 2010, 18, 8235-8242
13. Guyen, B.; Schultes, C. M.; Hazel, P.; Mann, J.; Neidle, S. Synthesis and evaluation of analogues of 10 H- indolo[3,2 -b ]quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase Org. Biomol. Chem. 2004, 2, 981-988
14. Brown, R. V.; Danford, F. L.; Gokhale, V.; Hurley, L. H.; Brooks, T. A. Demonstration that drug-targeted down-regulation of MYC in non-Hodgkins lymphoma is directly mediated through the promoter G-quadruplex J. Biol. Chem. 2011, 286, 41018-41027
15. Chaires, J. B. A Competition Dialysis Assay for the Study of Structure-Selective Ligand Binding to Nucleic Acids. In Current Protocols in Nucleic Acid Chemistry; John Wiley and Sons, Inc.: New York, 2003; Vol. 1, pp 8.3.1-8.3.8.
16. Mossman, B. T. In vitro approaches for determining mechanisms of toxicity and carcinogenicity by asbestos in the gastrointestinal and respiratory tracts Environ. Health Perspect. 1983, 53, 155-161 (Pubitemid 14162054)
17. Bierer, D. E.; Dubenko, L. G.; Zhang, P.; Lu, Q.; Imbach, P. A.; Garofalo, A. W.; Phuan, P.-W.; Fort, D. M.; Litvak, J.; Gerber, R. E.; Sloan, B.; Luo, J.; Cooper, R.; Reaven, G. M. Antihyperglycemic activities of cryptolepine analogues: an ethnobotanical lead structure isolated from Cryptolepis sanguinolenta J. Med. Chem. 1998, 41, 2754-2764 (Pubitemid 28350342)
18. Takeuchi, Y.; Kitaomo, M.; Chang, M.-r.; Shirasaka, S.; Shimamura, C.; Okuno, Y.; Yamato, M.; Harayama, T. Synthesis and antitumor activity of fused quinoline derivatives. V. Methylindolo[3,2 -b ]quinolines Chem. Pharm. Bull. (Tokyo) 1997, 45, 2096-2099 (Pubitemid 28047327)
19. Dash, J.; Shirude, P. S.; Balasubramanian, S. G-quadruplex recognition by bis-indole carboxamides Chem. Commun. (Cambridge, U. K.) 2008, 3055-3057 (Pubitemid 351904572)
20. El Bakali, J.; Klupsch, F.; Guédin, A.; Brassart, B.; Fontaine, G.; Farce, A.; Roussel, P.; Houssin, R.; Bernier, J.-L.; Chavatte, P.; Mergny, J.-L.; Riou, J.-F.; Hénichart, J. P. 2,6-Diphenylthiazolo[3,2 -b ][1,2,4]triazoles as telomeric G-quadruplex stabilizers Bioorg. Med. Chem. Lett. 2009, 19, 3434-3438