Synthesis and G-quadruplex-binding properties of defined acridine oligomers

Journal of Nucleic Acids

Volumn 2010, Issue , 2010, Pages

  Ferreira, Rubén ^a   Aviñó, Anna ^a   Pérez Tomás, Ricardo ^b   Gargallo, Raimundo ^c   Eritja, Ramon ^a  

^a BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^b L'Hospitalet de Llobregat ^*  (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOETHYLGLYCINE; ACRIDINE DERIVATIVE; ACRIDINE OLIGOMER DERIVATIVE; GLYCINE DERIVATIVE; GUANINE QUADRUPLEX; OLIGOMER; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; BINDING KINETICS; CELL VIABILITY; COMPLEX FORMATION; CONTROLLED STUDY; DNA BINDING; DNA SEQUENCE; DNA STRUCTURE; FLUORESCENCE SPECTROSCOPY; HUMAN; HUMAN CELL; ONCOGENE C MYC; PRIORITY JOURNAL; PROTO ONCOGENE; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS;

EID: 79959880898     PISSN: 20900201     EISSN: 2090021X     Source Type: Journal    
DOI: 10.4061/2010/489060     Document Type: Article

References (30)

1. Palchaudhuri R., Hergenrother P. J., DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action. Current Opinion in Biotechnology 2007 18 6 497 503 2-s2.0-37549056566 10.1016/j.copbio.2007.09.006
2. Neto B. A. D., brenno.ipi@gmail.com Lapis A. A. M., Recent developments in the chemistry of deoxyribonucleic acid (DNA) intercalators: principles, design, synthesis, applications and trends. Molecules 2009 14 5 1725 1746 2-s2.0-0019387686 10.3390/molecules14051725
3. 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 2-s2.0-38049030699 10.1093/nar/gkm711
4. Parkinson G. N., Lee M. P. H., Neidle S., Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 2002 417 6891 876 880 2-s2.0-0037142071 10.1038/nature755 (Pubitemid 34670337)
5. Huppert J. L., Hunting G-quadruplexes. Biochimie 2008 90 8 1140 1148 2-s2.0-47649101029 10.1016/j.biochi.2008.01.014
6. Hurley L. H., Secondary DNA structures as molecular targets for cancer therapeutics. Biochemical Society Transactions 2001 29 6 692 696 2-s2.0-0035206465 10.1042/0300-5127:0290692 (Pubitemid 33131762)
7. Han H., Hurley L. H., G-quadruplex DNA: a potential target for anti-cancer drug design. Trends in Pharmacological Sciences 2000 21 4 136 142 2-s2.0-0034176194 10.1016/S0165-6147(00)01457-7 (Pubitemid 30190138)
8. Campbell N. H., Parkinson G. N., Reszka A. P., Neidle S., Structural basis of DNA quadruplex recognition by an acridine drug. Journal of the American Chemical Society 2008 130 21 6722 6724 2-s2.0-44349142304 10.1021/ja8016973 (Pubitemid 351748405)
9. Monchaud D., Teulade-Fichou M.-P., A hitchhiker's guide to G-quadruplex ligands. Organic and Biomolecular Chemistry 2008 6 4 627 636 2-s2.0-39049147645 10.1039/b714772b (Pubitemid 351972601)
10. Haider S. M., Parkinson G. N., Neidle S., Structure of a G-quadruplex-ligand complex. Journal of Molecular Biology 2003 326 1 117 125 2-s2.0-0037423728 10.1016/S0022-2836(02)01354-2 (Pubitemid 36279362)
11. Moore M. J. B., Schultes C. M., Cuesta J., Cuenca F., Gunaratnam M., Tanious F. A., Wilson W. D., Neidle S., Trisubstituted acridines as G-quadruplex telomere targeting agents. Effects of extensions of the 3,6- and 9-side chains on quadruplex binding, telomerase activity, and cell proliferation. Journal of Medicinal Chemistry 2006 49 2 582 599 2-s2.0-31544446381 10.1021/jm050555a (Pubitemid 43157489)
12. Avió A., Navarro I., Farrera-Sinfreu J., Royo M., Aymamí J., Delgado A., Llebaria A., Albericio F., Eritja R., Solid-phase synthesis of oligomers carrying several chromophore units linked by phosphodiester backbones. Bioorganic and Medicinal Chemistry Letters 2008 18 7 2306 2310 2-s2.0-41149131423 10.1016/j.bmcl.2008.02.074 (Pubitemid 351442902)
13. Farrera-Sinfreu J., Avió A., Navarro I., Aymamí J., Beteta N. G., Varón S., Pérez-Tomás R., Castillo-Avila W., Eritja R., Albericio F., Royo M., Design, synthesis and antiproliferative properties of oligomers with chromophore units linked by amide backbones. Bioorganic and Medicinal Chemistry Letters 2008 18 7 2440 2444 2-s2.0-41349088667 10.1016/j.bmcl.2008.02.045 (Pubitemid 351447285)
14. Arya D. P., Willis B., Reaching into the major groove of B-DNA: synthesis and nucleic acid binding of a neomycin-Hoechst 33258 conjugate. Journal of the American Chemical Society 2003 125 41 12398 12399 2-s2.0-0141919831 10.1021/ja036742k (Pubitemid 37254744)
15. Fechter E. J., Olenyuk B., Dervan P. B., Design of a sequence-specific DNA bisintercalator. Angewandte Chemie - International Edition 2004 43 27 3591 3594 2-s2.0-4544231489 10.1002/anie.200454231 (Pubitemid 39257546)
16. 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 2-s2.0-0037015078 10.1073/pnas.182256799 (Pubitemid 34994444)
17. Dai J., Dexheimer T. S., Chen D., Carver M., Ambrus A., Jones R. A., Yang 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 2-s2.0-31944444804 10.1021/ja055636a (Pubitemid 43190620)
18. del Toro M., Bucek P., Avió A., Jaumot J., González C., Eritja R., Gargallo R., raimongargallo@ub.edu Targeting the G-quadruplex-forming region near the P1 promoter in the human BCL-2 gene with the cationic porphyrin TMPyP4 and with the complementary C-rich strand. Biochimie 2009 91 7 894 902 2-s2.0-0034937979 10.1016/j.biochi.2009.04.012
19. Dyson R. M., Kaderli S., Lawrance G. A., Maeder M., Second order global analysis: the evaluation of series of spectrophotometric titrations for improved determination of equilibrium constants. Analytica Chimica Acta 1997 353 2-3 381 393 2-s2.0-0030728038 10.1016/S0003-2670(97)87800-2 (Pubitemid 27511750)
20. Stengele K.-P., Pfleiderer W., Improved synthesis of oligodeoxyribonucleotides. Tetrahedron Letters 1990 31 18 2549 2552 2-s2.0-0025310687 10.1016/0040-4039(90)80122-3 (Pubitemid 20188057)
21. Will D. W., Breipohl G., Langner D., Knolle J., Uhlmann E., The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy. Tetrahedron 1995 51 44 12069 12082 2-s2.0-0028866843 10.1016/0040-4020(95)00766-2
22. Granotier C., Pennarun G., Riou L., Hoffschir F., Gauthier L. R., De Cian A., Gomez D., Mandine E., Riou J.-F., Mergny J.-L., Mailliet P., Dutrillaux B., Boussin F. D., Preferential binding of a G-quadruplex ligand to human chromosome ends. Nucleic Acids Research 2005 33 13 4182 4190 2-s2.0-23044460408 10.1093/nar/gki722 (Pubitemid 41487277)
23. Gros J., Rosu F., Amrane S., De Cian A., Gabelica V., Lacroix L., Mergny J.-L., Guanines are a quartet's best friend: iImpact of base substitutions on the kinetics and stability of tetramolecular quadruplexes. Nucleic Acids Research 2007 35 9 3064 3075 2-s2.0-34250682662 10.1093/nar/gkm111 (Pubitemid 47073644)
24. Bock L. C., Griffin L. C., Latham J. A., Vermaas E. H., Toole J. J., Selection of single-stranded DNA molecules that bind and inhibit human thrombin. Nature 1992 355 6360 564 566 2-s2.0-0026575221 10.1038/355564a0
25. 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)
26. Ren J., Chaires J. B., Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry 1999 38 49 16067 16075 2-s2.0-0033534146 10.1021/bi992070s (Pubitemid 129520527)
27. Ragazzon P., Chaires J. B., Use of competition dialysis in the discovery of G-quadruplex selective ligands. Methods 2007 43 4 313 323 2-s2.0-35448975647 10.1016/j.ymeth.2007.08.003 (Pubitemid 47633211)
28. White E. W., Tanious F., Ismail M. A., Reszka A. P., Neidle S., Boykin D. W., Wilson W. D., Structure-specific recognition of quadruplex DNA by organic cations: influence of shape, substituents and charge. Biophysical Chemistry 2007 126 1-3 140 153 2-s2.0-33846569026 10.1016/j.bpc.2006.06.006 (Pubitemid 46186645)
29. Green J. J., Ladame S., Ying L., Klenerman D., Balasubramanian S., Investigating a quadruplex - ligand interaction by unfolding kinetics. Journal of the American Chemical Society 2006 128 30 9809 9812 2-s2.0-33746611174 10.1021/ja0615425 (Pubitemid 44147965)
30. Burger A. M., Dai F., Schultes C. M., Reszka A. P., Moore M. J., Double J. A., Neidle S., The G-quadruplex-interactive molecule BRACO-19 inhibits tumor growth, consistent with telomere targeting and interference with telomerase function. Cancer Research 2005 65 4 1489 1496 2-s2.0-13944272246 10.1158/0008-5472.CAN-04-2910 (Pubitemid 40270178)