Synthesis of macrocyclic hexaoxazole (6OTD) dimers, containing guanidine and amine functionalized side chains, and an evaluation of their telomeric G4 stabilizing properties

Journal of Nucleic Acids

Volumn 2010, Issue , 2010, Pages

  Iida, Keisuke ^a   Tera, Masayuki ^a   Hirokawa, Takatsugu ^b   Shin Ya, Kazuo ^b   Nagasawa, Kazuo ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DIMER; FUNCTIONAL GROUP; GUANIDINE DERIVATIVE; GUANINE QUADRUPLEX; MACROCYCLIC COMPOUND; OXAZOLE DERIVATIVE; POTASSIUM; TELOMESTATIN;

ARTICLE; DNA SEQUENCE; DNA STRUCTURE; DRUG DNA INTERACTION; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE RESONANCE ENERGY TRANSFER; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 77957942511     PISSN: 20900201     EISSN: 2090021X     Source Type: Journal    
DOI: 10.4061/2010/217627     Document Type: Article

References (42)

1. Patel D. J., Phan A. T., Kuryavyi V., Human telomere, oncogenic promoter and 5′ -UTR G-quadruplexes: diverse higher order DNA and RNA targets for cancer therapeutics. Nucleic Acids Research 2007 35 22 7429 7455 10.1093/nar/gkm711 2-s2.0-38049030699
2. Neidle S., Parkinson G. N., Quadruplex DNA crystal structures and drug design. Biochimie 2008 90 8 1184 1196 10.1016/j.biochi.2008.03.003 2-s2.0-47649109401
3. Phan A. T., Human telomeric G-quadruplex: structures of DNA and RNA sequences. FEBS Journal 2010 277 5 1107 1117 10.1111/j.1742-4658.2009.07464.x 2-s2.0-76349097100
4. Wang Y., Patel D. J., Solution structure of the human telomeric repeat d[AG3(T2AG3)3] G-tetraplex. Structure 1993 1 4 263 282 2-s2.0-0027918585 (Pubitemid 2031126)
5. Xu Y., Noguchi Y., Sugiyama H., The new models of the human telomere d[AGGG(TTAGGG)3] in K+ solution. Bioorganic and Medicinal Chemistry 2006 14 16 5584 5591 10.1016/j.bmc.2006.04.033 2-s2.0-33745612968 (Pubitemid 43994462)
6. Dai J., Punchihewa C., Ambrus A., Chen D., Jones R. A., Yang D., Structure of the intramolecular human telomeric G-quadruplex in potassium solution: a novel adenine triple formation. Nucleic Acids Research 2007 35 7 2440 2450 10.1093/nar/gkm009 2-s2.0-34249846802 (Pubitemid 47073725)
7. Phan A. T., phantuan@ntu.edu.sg Kuryavyi V., Luu K. N., Patel D. J., Structure of two intramolecular G-quadruplexes formed by natural human telomere sequences in K+ solution. Nucleic Acids Research 2007 35 19 6517 6525 2-s2.0-33847675742 10.1093/nar/gkm706 (Pubitemid 350111619)
8. Parkinson G. N., Lee M. P. H., Neidle S., Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 2002 417 6891 876 880 10.1038/nature755 2-s2.0-0037142071 (Pubitemid 34670337)
9. Simonsson T., Pecinka P., Kubista M., DNA tetraplex formation in the control region of c-myc. Nucleic Acids Research 1998 26 5 1167 1172 10.1093/nar/26.5.1167 2-s2.0-0032030327 (Pubitemid 28291685)
10. Rankin S., Reszka A. P., Huppert J., Putative DNA quadruplex formation within the human c-kit oncogene. Journal of the American Chemical Society 2005 127 30 10584 10589 10.1021/ja050823u 2-s2.0-23044485047 (Pubitemid 41061432)
11. Dai J., Dexheimer T. S., Chen D., An intramolecular G-quadruplex structure with mixed parallel/antiparallel G-strands formed in the human BCL-2 promoter region in solution. Journal of the American Chemical Society 2006 128 4 1096 1098 10.1021/ja055636a 2-s2.0-31944444804 (Pubitemid 43190620)
12. Cogoi S., Xodo L. E., G-quadruplex formation within the promoter of the KRAS proto-oncogene and its effect on transcription. Nucleic Acids Research 2006 34 9 2536 2549 10.1093/nar/gkl286 2-s2.0-33744472232 (Pubitemid 43985618)
13. Neidle S., Human telomeric G-quadruplex: the current status of telomeric G-quadruplexes as therapeutic targets in human cancer. FEBS Journal 2010 277 5 1118 1125 10.1111/j.1742-4658.2009.07463.x 2-s2.0-76349122184
14. Ou T.-M., Lu Y.-J., Tan J.-H., Huang Z.-S., Wong K.-Y., Gu L.-Q., G-quadruplexes: targets in anticancer drug design. ChemMedChem 2008 3 5 690 713 10.1002/cmdc.200700300 2-s2.0-47649124369
15. Riou J. F., Guittat L., Mailliet P., Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands. Proceedings of the National Academy of Sciences of the United States of America 2002 99 5 2672 2677 10.1073/pnas.052698099 2-s2.0-0037022658 (Pubitemid 34240519)
16. Bejugam M., Sewitz S., Shirude P. S., Rodriguez R., Shahid R., Balasubramanian S., Trisubstituted isoalloxazines as a new class of G-quadruplex binding ligands: small molecule regulation of c-kit oncogene expression. Journal of the American Chemical Society 2007 129 43 12926 12927 10.1021/ja075881p 2-s2.0-35848942604 (Pubitemid 350058320)
17. 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. Proceedings of the National Academy of Sciences of the United States of America 2002 99 18 11593 11598 10.1073/pnas.182256799 2-s2.0-0037015078 (Pubitemid 34994444)
18. Palumbo S. L., Memmott R. M., Uribe D. J., Krotova-Khan Y., Hurley L. H., Ebbinghaus S. W., A novel G-quadruplex-forming GGA repeat region in the c-myb promoter is a critical regulator of promoter activity. Nucleic Acids Research 2008 36 6 1755 1769 10.1093/nar/gkm1069 2-s2.0-41849123908 (Pubitemid 351494223)
19. Cogoi S., Xodo L. E., G-quadruplex formation within the promoter of the KRAS proto-oncogene and its effect on transcription. Nucleic Acids Research 2006 34 9 2536 2549 10.1093/nar/gkl286 2-s2.0-33744472232 (Pubitemid 43985618)
20. Hayflick L., Moorhead P. S., The serial cultivation of human diploid cell strains. Experimental Cell Research 1961 25 3 585 621 2-s2.0-0344622606
21. Blasco M. A., mblasco@cnio.es Telomere length, stem cells and aging. Nature Chemical Biology 2007 3 10 640 649 2-s2.0-33748871127 10.1038/nchembio.2007.38 (Pubitemid 47417712)
22. Arora A., Kumar N., Agarwal T., Maiti S., Retraction: human telomeric G-quadruplex: targeting with small molecules. FEBS Journal 2010 277 5 1345 10.1111/j.1742-4658.2009.07461.x 2-s2.0-76349125960
23. Shin-ya K., Wierzba K., Matsuo K., Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus. Journal of the American Chemical Society 2001 123 6 1262 1263 10.1021/ja005780q 2-s2.0-0035857396 (Pubitemid 32148203)
24. Doi T., Yoshida M., Shin-ya K., Takahashi T., Total synthesis of (R)-telomestatin. Organic Letters 2006 8 18 4165 4167 10.1021/ol061793i 2-s2.0-33748948394 (Pubitemid 44432878)
25. Shirude P. S., Gillies E. R., Ladame S., Macrocyclic and helical oligoamides as a new class of G-quadruplex ligands. Journal of the American Chemical Society 2007 129 39 11890 11891 10.1021/ja073775h 2-s2.0-34848865663 (Pubitemid 47512006)
26. Kim M.-Y., Vankayalapati H., Shin-ya K., Wierzba K., Hurley L. H., Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular G-quadruplex. Journal of the American Chemical Society 2002 124 10 2098 2099 10.1021/ja017308q 2-s2.0-0037070575 (Pubitemid 34267081)
27. Rosu F., Gabelica V., v.gabelica@ulg.ac.be Shin-ya K., Pauw E. D., Telomestatin-induced stabilization of the human telomeric DNA quadruplex monitored by electrospray mass spectrometry. Chemical Communications 2003 9 21 2702 2703 2-s2.0-0036849582 (Pubitemid 37392841)
28. Rezler E. M., Seenisamy J., Bashyam S., Telomestatin and diseleno sapphyrin bind selectively to two different forms of the human telomeric G-quadruplex structure. Journal of the American Chemical Society 2005 127 26 9439 9447 10.1021/ja0505088 2-s2.0-21644460419 (Pubitemid 40934756)
29. Tera M., Sohtome Y., Ishizuka H., Design and synthesis of telomestatin derivatives and their inhibitory activity of telomerase. Heterocycles 2006 69 1 505 514 2-s2.0-33947354215
30. Tera M., Ishizuka H., Takagi M., Suganuma M., Shin-ya K., Nagasawa K., Macrocyclic hexaoxazoles as sequence- and mode-selective G-quadruplex binders. Angewandte Chemie: International Edition 2008 47 30 5557 5560 10.1002/anie.200801235 2-s2.0-49649096112
31. Tera M., Iida K., Ishizuka H., Synthesis of a potent G-quadruplex-binding macrocyclic heptaoxazole. ChemBioChem 2009 10 3 431 435 10.1002/cbic.200800563 2-s2.0-60349105930
32. Minhas G. S., Pilch D. S., Kerrigan J. E., LaVoie E. J., Rice J. E., Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles. Bioorganic and Medicinal Chemistry Letters 2006 16 15 3891 3895 10.1016/j.bmcl.2006.05.038 2-s2.0-33745132752 (Pubitemid 43903232)
33. Iida K., Tera M., Hirokawa T., Shin-ya K., Nagasawa K., knaga@cc.tuat.ac.jp G-quadruplex recognition by macrocyclic hexaoxazole (6OTD) dimer: greater selectivity than monomer. Chemical Communications 2009 42 6481 6483 2-s2.0-62349129278 10.1039/b910242f
34. De Cian A., Guittat L., Kaiser M., Fluorescence-based melting assays for studying quadruplex ligands. Methods 2007 42 2 183 195 2-s2.0-0033812999 10.1016/j.ymeth.2006.10.004 (Pubitemid 46667236)
35. Mergny J.-L., Maurizot J.-C., Fluorescence resonance energy transfer as a probe for G-quartet formation by a telomeric repeat. ChemBioChem 2001 2 2 124 132 2-s2.0-0035793647 (Pubitemid 33722537)
36. Deeley J., Bertram A., Pattenden G., Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin. Organic and Biomolecular Chemistry 2008 6 11 1994 2010 10.1039/b802477d 2-s2.0-43749097876 (Pubitemid 351693246)
37. Hernandez D., Vilar G., Riego E., Synthesis of IB-01211, a cyclic peptide containing 2,4-concatenated thia- and oxazoles, via Hantzsch macrocyclization. Organic Letters 2007 9 5 809 811 10.1021/ol063023c 2-s2.0-33947132690
38. Hernandez D., Altuna M., Cuevas C., Aligu R., Albericio F., Alvarez M., Synthesis and antitumor activity of mechercharmycin A analogues. Journal of Medicinal Chemistry 2008 51 18 5722 5730 10.1021/jm800513w 2-s2.0-52449105717
39. Kunishima M., Kawachi C., Iwasaki F., Terao K., Tani S., Synthesis and characterization of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)- 4-methylmorpholinium chloride. Tetrahedron Letters 1999 40 29 5327 5330 10.1016/S0040-4039(99)00968-5 2-s2.0-0033575461 (Pubitemid 29317678)
40. Balagurumoorthy P., Brahmachari S. K., Structure and stability of human telomeric sequence. Journal of Biological Chemistry 1994 269 34 21858 21869 2-s2.0-0027990373
41. Rosu F., Gabelica V., Houssier C., Colson P., Pauw E. D., Triplex and quadruplex DNA structures studied by electrospray mass spectrometry. Rapid Communications in Mass Spectrometry 2002 16 18 1729 1736 10.1002/rcm.778 2-s2.0-0036376018 (Pubitemid 35033730)
42. Li H., Liu Y., Lin S., Yuan G., Spectroscopy probing of the formation, recognition, and conversion of a G-quadruplex in the promoter region of the bcl-2 oncogene. Chemistry European Journal 2009 15 10 2445 2452 10.1002/chem.200801922 2-s2.0-62349129278