Tuning G-quadruplex vs double-stranded DNA recognition in regioisomeric lysyl-peptidyl-anthraquinone conjugates

Bioconjugate Chemistry

Volumn 22, Issue 10, 2011, Pages 2126-2135

  Zagotto, Giuseppe ^a   Ricci, Antonio ^a   Vasquez, Elena ^a   Sandoli, Andrea ^a   Benedetti, Silvia ^a   Palumbo, Manlio ^a   Sissi, Claudia ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CHAINS; DNA; INDIUM COMPOUNDS; KETONES;

BINDING AFFINITIES; BINDING MODES; DNA RECOGNITION; FUNCTIONALIZED; G-QUADRUPLEXES; LIPOPHILICITY; N-TERMINALS; PLANAR SYSTEMS; RECOGNITION PROCESS; SIDE-CHAINS;

AROMATIC COMPOUNDS;

ANTHRAQUINONE DERIVATIVE; DOUBLE STRANDED DNA; GUANINE QUADRUPLEX; PEPTIDE DERIVATIVE; TELOMERASE;

AMINO TERMINAL SEQUENCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL AGING; CYTOTOXICITY; DNA STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR MECHANICS; MOLECULAR RECOGNITION; SOMATIC CELL; TELOMERE;

EID: 80054827505     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200389w     Document Type: Article

References (26)

1. O'Sullivan, R. J. and Karlseder, J. (2010) Telomeres: protecting chromosomes against genome instability Nat. Rev. Mol. Cell Biol. 11, 171-81
2. Watson, J. D. (1972) Origin of concatemeric T7 DNA Nat. New Biol. 239, 197-201
3. Shay, J. W., Wright, W. E., and Werbin, H. (1991) Defining the molecular mechanisms of human cell immortalization Biochim. Biophys. Acta 1072, 1-7 (Pubitemid 121007526)
4. Shay, J. W. and Bacchetti, S. (1997) A survey of telomerase activity in human cancer Eur. J. Cancer 33, 787-91
5. Greider, C. W. and Blackburn, E. H. (1985) Identification of a specific telomere terminal transferase activity in Tetrahymena extracts Cell 43, 405-13 (Pubitemid 16213265)
6. Folini, M., Gandellini, P., and Zaffaroni, N. (2009) Targeting the telosome: therapeutic implications Biochim. Biophys. Acta 1792, 309-16
7. Neidle, S. (2010) Human telomeric G-quadruplex: the current status of telomeric G-quadruplexes as therapeutic targets in human cancer Febs J. 277, 1118-25
8. Davis, J. (2004) G-quartets 40 years later: from 5?-GMP to molecular biology and supramolecular chemistry Angew. Chem. 43, 668-698 (Pubitemid 38197045)
9. De Cian, A., Lacroix, L., Douarre, C., Temime-Smaali, N., Trentesaux, C., Riou, J. F., and Mergny, J. L. (2008) Targeting telomeres and telomerase Biochimie 90, 131-155 (Pubitemid 350245369)
10. Neidle, S. (2009) The structures of quadruplex nucleic acids and their drug complexes Curr. Opin. Struct. Biol. 19, 239-50
11. Monchaud, D. and Teulade-Fichou, M. P. (2008) A hitchhiker's guide to G-quadruplex ligands Org. Biomol. Chem. 6, 627-36 (Pubitemid 351972601)
12. Perry, P. J., Gowan, S. M., Reszka, A. P., Polucci, P., Jenkins, T. C., Kelland, L. R., and Neidle, S. (1998) 1,4- and 2,6-disubstituted amidoanthracene-9,10-dione derivatives as inhibitors of human telomerase J. Med. Chem. 41, 3253-60 (Pubitemid 28376531)
13. Perry, P. J., Read, M. A., Davies, R. T., Gowan, S. M., Reszka, A. P., Wood, A. A., Kelland, L. R., and Neidle, S. (1999) 2,7-Disubstituted amidofluorenone derivatives as inhibitors of human telomerase J. Med. Chem. 42, 2679-84 (Pubitemid 29344308)
14. Perry, P. J., Reszka, A. P., Wood, A. A., Read, M. A., Gowan, S. M., Dosanjh, H. S., Trent, J. O., Jenkins, T. C., Kelland, L. R., and Neidle, S. (1998) Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones J. Med. Chem. 41, 4873-84 (Pubitemid 28530462)
15. Zagotto, G., Sissi, C., Lucatello, L., Pivetta, C., Cadamuro, S. A., Fox, K. R., Neidle, S., and Palumbo, M. (2008) Aminoacyl-anthraquinone conjugates as telomerase inhibitors: synthesis, biophysical and biological evaluation J. Med. Chem. 51, 5566-74
16. Zagotto, G., Sissi, C., Moro, S., Dal Ben, D., Parkinson, G. N., Fox, K. R., Neidle, S., and Palumbo, M. (2008) Amide bond direction modulates G-quadruplex recognition and telomerase inhibition by 2,6 and 2,7 bis-substituted anthracenedione derivatives Bioorg. Med. Chem. 16, 354-61
17. Dahan, A., Ashkenazi, T., Kuznetsov, V., Makievski, S., Drug, E., Fadeev, L., Bramson, M., Schokoroy, S., Rozenshine-Kemelmakher, E., and Gozin, M. (2007) Synthesis and evaluation of a pseudocyclic tristhiourea-based anion host J. Org. Chem. 72, 2289-96 (Pubitemid 46536155)
18. De Cian, A., Guittat, L., Kaiser, M., Sacca, B., Amrane, S., Bourdoncle, A., Alberti, P., Teulade-Fichou, M. P., Lacroix, L., and Mergny, J. L. (2007) Fluorescence-based melting assays for studying quadruplex ligands Methods 42, 183-95 (Pubitemid 46667236)
19. Risitano, A. and Fox, K. R. (2003) Stability of intramolecular DNA quadruplexes: comparison with DNA duplexes Biochemistry 42, 6507-13 (Pubitemid 36665826)
20. Crothers, D. M. (1971) Statistical thermodynamics of nucleic acid melting transitions with coupled binding equilibria Biopolymers 10, 2147-60
21. Darby, R. A., Sollogoub, M., McKeen, C., Brown, L., Risitano, A., Brown, N., Barton, C., Brown, T., and Fox, K. R. (2002) High throughput measurement of duplex, triplex and quadruplex melting curves using molecular beacons and a LightCycler Nucleic Acids Res. 30, e39
22. Ambrus, A., Chen, D., Dai, J., Bialis, T., Jones, R. A., and Yang, D. (2006) Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution Nucleic Acids Res. 34, 2723-35 (Pubitemid 43985634)
23. Tanious, F. A., Jenkins, T. C., Neidle, S., and Wilson, W. D. (1992) Substituent position dictates the intercalative DNA-binding mode for anthracene-9,10-dione antitumor drugs Biochemistry 31, 11632-40
24. De Cian, A., Cristofari, G., Reichenbach, P., De Lemos, E., Monchaud, D., Teulade-Fichou, M. P., Shin-Ya, K., Lacroix, L., Lingner, J., and Mergny, J. L. (2007) Reevaluation of telomerase inhibition by quadruplex ligands and their mechanisms of action Proc. Natl. Acad. Sci. U. S. A. 104, 17347-52 (Pubitemid 350219845)
25. Lown, J. W. (1993) Anthracycline and anthraquinone anticancer agents: current status and recent developments Pharmacol. Ther. 60, 185-214 (Pubitemid 24117375)
26. Folini, M., Pivetta, C., Zagotto, G., De Marco, C., Palumbo, M., Zaffaroni, N., and Sissi, C. (2010) Remarkable interference with telomeric function by a G-quadruplex selective bisantrene regioisomer Biochem. Pharmacol. 79, 1781-90