Modifications at the C-terminus to improve pyrrole-imidazole polyamide activity in cell culture

Journal of Medicinal Chemistry

Volumn 52, Issue 23, 2009, Pages 7380-7388

  Jacobs, Claire S ^a   Dervan, Peter B ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYLIMIDAZOLE; 1 METHYLPYRROLE; ANDROGEN RECEPTOR; POLYAMIDE; PROSTATE SPECIFIC ANTIGEN;

ARTICLE; BIOLOGICAL ACTIVITY; CELL CULTURE; CELL STRAIN LNCAP; CONTROLLED STUDY; DNA BINDING; DNA RESPONSIVE ELEMENT; DRUG ACTIVITY; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; GENE CONTROL; GENE EXPRESSION; HUMAN; HUMAN CELL;

ANDROGENS; BASE SEQUENCE; CELL LINE; CELL PROLIFERATION; CELL SURVIVAL; DNA; GENE EXPRESSION REGULATION; IMIDAZOLES; INHIBITORY CONCENTRATION 50; NUCLEIC ACID DENATURATION; NYLONS; OXIMES; PYRROLES; RESPONSE ELEMENTS; TRANSITION TEMPERATURE;

EID: 72249122756     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900256f     Document Type: Article

References (25)

1. Brennan, P.; Donev, R.; Hewamana, S. Targeting transcription factors for therapeutic benefit. Mol. BioSyst. 2008, 4, 909-919.
2. Berg, T. Inhibition of transcription factors with small organic molecules. Curr. Opin. Chem. Biol. 2008, 12, 464-471.
3. Dervan, P. B.; Edelson, B. S. Recognition of the DNA minor groove by pyrrole-imidazole polyamides. Curr. Opin. Struct. Biol. 2003, 13, 284-299.
4. White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Recognition of the four Watson-Crick base pairs in theDNA minor groove by synthetic ligands. Nature 1998, 391, 468-471.
5. Kielkopf, C. L.; Baird, E. E.; Dervan, P. B.; Rees, D. C. Structural basis for G.C recognition in the DNA minor groove. Nat. Struct. Biol. 1998, 5, 104-109.
6. Foister, S.; Marques, M. A.; Doss, R. M.; Dervan, P. B. Shape selective recognition of T/A base pairs by hairpin polyamides containing N-terminal 3-methoxy (and 3-chloro) thiophene residues. Bioorg. Med. Chem. 2003, 11, 4333-4340.
7. Hsu, C. F.; Phillips, J. W.; Trauger, J. W.; Farkas, M. E.; Belitsky, J. M.; Heckel, A.; Olenyuk, B. Z.; Puckett, J. W.; Wang, C. C.; Dervan, P. B. Completion of a programmable DNA-binding small molecule library. Tetrahedron 2007, 63, 6146-6151.
8. Nickols, N. G.; Jacobs, C. S.; Farkas, M. E.; Dervan, P. B. Improved nuclear localization of DNA-binding polyamides. Nucleic Acids Res. 2007, 35, 363-370.
9. Belitsky, J. M.; Leslie, S. J.; Arora, P. S.; Beerman, T. A.; Dervan, P. B. Cellular uptake of N-methylpyrrole/N-methylimidazole polyamide-dye conjugates. Bioorg. Med. Chem. 2002, 10, 3313-3318.
10. Crowley, K. S.; Phillion, D. P.; Woodard, S. S.; Schweitzer, B. A.; Singh, M.; Shabany, H.; Burnette, B.; Hippenmeyer, P.; Heitmeier, M.; Bashkin, J. K. Controlling the intracellular localization of fluorescent polyamide analogues in cultured cells. Bioorg. Med. Chem. Lett. 2003, 13, 1565-1570.
11. Best, T. P.; Edelson, B. S.; Nickols, N. G.; Dervan, P. B. Nuclear localization of pyrrole-imidazole polyamide-fluorescein conjugates in cell culture. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 12063-12068.
12. Edelson, B. S.; Best, T. P.; Olenyuk, B.; Nickols, N. G.; Doss, R. M.; Foister, S.; Heckel, A.; Dervan, P. B. Influence of structural variation on nuclear localization of DNA-binding polyamidefluorophore conjugates. Nucleic Acids Res. 2004, 32, 2802-2818.
13. Olenyuk, B. Z.; Zhang, G. J.; Klco, J. M.; Nickols, N. G.; Kaelin, W. G.Jr.; Dervan, P. B. Inhibition of vascular endothelial growth factor with a sequence-specific hypoxia response element antagonist. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 16768-16773.
14. Nickols, N. G.; Dervan, P. B. Suppression of androgen receptormediated gene expression by a sequence-specific DNA-binding polyamide. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 10418-10423.
15. Nickols, N. G.; Jacobs, C. S.; Farkas, M. E.; Dervan, P. B. Modulating hypoxia-inducible transcription by disrupting the HIF-1-DNA interface. ACS Chem. Biol. 2007, 2, 561-571.
16. Harki, D. A.; Satyamurthy, N.; Stout, D. B.; Phelps, M. E.; Dervan, P. B. In vivo imaging of pyrrole-imidazole polyamides with positron emission tomography. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 13039-13044.
17. Tjernberg, A.; Markova, N.; Griffiths, W. J.; Hallen, D. DMSOrelated effects in protein characterization. J. Biomol. Screening 2006, 11, 131-137.
18. Dose, C.; Farkas, M. E.; Chenoweth, D. M.; Dervan, P. B. Next generation hairpin polyamides with (R)-3,4-diaminobutyric acid turn unit. J. Am. Chem. Soc. 2008, 130, 6859-6866.
19. Kalia, J.; Raines, R. T. Hydrolytic stability of hydrazones and oximes. Angew. Chem., Int. Ed. 2008, 47, 7523-7526.
20. Juliano, R. L.; Ling, V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Biophys. Acta 1976, 455, 152-162.
21. Ueda, K.; Cardarelli, C.; Gottesman,M. M.; Pastan, I. Expression of a full-length cDNA for the human "MDR1" gene confers resistance to colchicine, doxorubicin, and vinblastine. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 3004-3008.
22. Belitsky, J. M.; Nguyen, D. H.; Wurtz, N. R.; Dervan, P. B. Solidphase synthesis of DNA binding polyamides on oxime resin. Bioorg. Med. Chem. 2002, 10, 2767-2774.
23. Baird, E. E.; Dervan, P. B. Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids. J. Am. Chem. Soc. 1996, 118, 6141-6146.
24. Salisbury, C. M.; Maly, D. J.; Ellman, J. A. Peptide microarrays for the determination of protease substrate specificity. J. Am. Chem. Soc. 2002, 124, 14868-14870.
25. Wallace, E.; Hurley, B.; Yang, H.; Lyssikatos, J.; Blake, J.; Marlow, A. Heterocyclic Inhibitors of MEK and Methods of Use Thereof. U.S. Patent Application 20050054701 A1, 2005.