Fluorescent 7-diethylaminocoumarin pyrrolobenzodiazepine conjugates: Synthesis, DNA interaction, cytotoxicity and differential cellular localization

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 6, 2008, Pages 2147-2151

  Wells, Geoffrey ^a   Suggitt, Marie ^b   Coffils, Marissa ^b   Baig, Mirza A H ^a   Howard, Philip W ^a,b   Loadman, Paul M ^b   Hartley, John A ^b,c   Jenkins, Terence C ^d   Thurston, David E ^a,b  

^a IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

^d Morvus Technology Limited   (United Kingdom)

Author keywords

Anticancer agents; Antitumour agents; DNA sequence selective; DNA binding; Fluorescence conjugates; Nuclear penetration; PBDs; Pyrrolobenzodiazepines

Indexed keywords

AMINOCOUMARIN DERIVATIVE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CELLULAR DISTRIBUTION; CHEMICAL REACTION; CONTROLLED STUDY; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DISTRIBUTION; DRUG DNA INTERACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

BENZODIAZEPINES; CELL NUCLEUS; CELL SURVIVAL; CYTOPLASM; DNA; FEMALE; HUMANS; MELANOMA; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; OVARIAN NEOPLASMS; PYRROLES; TUMOR CELLS, CULTURED;

EID: 40849096399     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.083     Document Type: Article

References (18)

1. Thurston D.E. Chemistry and Pharmacology of Anticancer Drugs (2006), CRC Press (Taylor & Francis), Boca Raton, FL, USA pp 281
2. Dervan P.B., and Edelson B.S. Curr. Opin. Struct. Biol. 13 (2003) 284
3. Belitsky J.M., Leslie S.J., Arora P.S., Beerman T.A., and Dervan P.B. Bioorgan. Med. Chem. 10 (2002) 3313
4. Dudouet B., Burnett R., Dickinson L.A., Wood M.R., Melander C., Belitsky J.M., Edelson B., Wurtz N., Briehn C., Dervan P.B., and Gottesfeld J.M. Chem. Biol. 10 (2003) 859
5. Crowley K.S., Phillion D.P., Woodard S.S., Schweitzer B.A., Singh M., Shabany H., Burnette B., Hippenmeyer P., Heitmeier M., and Bashkin J.K. Bioorg. Med. Chem. Lett. 13 (2003) 1565
6. Best T.P., Edelson B.S., Nickols N.G., and Dervan P.B. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 12063
7. Kumar R., Rai D., Marcus S.L., Ko S.C.C., and Lown J.W. Lett. Org. Chem. 1 (2004) 154
8. Sharma S.K., Morrissey A.T., Miller G.G., Gmeiner W.H., and Lown J.W. Bioorg. Med. Chem. Lett. 11 (2001) 769
9. 6 calc. 547.2551 found 547.2539.
10. Calderon, L. G. PhD Thesis, University of Portsmouth, 1999.
11. Howard, P. W.; Kang, G.-D. Intl. Patent Appl. WO2005085259, 2005.
12. 6 calc. 617.3334 found 617.3317.
13. 7 calc. 632.3079 found 632.3055.
14. O'Brien J., Wilson I., Orton T., and Pognan F. Eur. J. Biochem. 267 (2000) 5421
15. Mcconnaughie A.W., and Jenkins T.C. J. Med. Chem. 38 (1995) 3488
16. Antonow D., Jenkins T.C., Howard P.W., and Thurston D.E. Bioorgan. Med. Chem. 15 (2007) 3041
17. Thurston D.E., Bose D.S., Howard P.W., Jenkins T.C., Leoni A., Baraldi P.G., Guiotto A., Cacciari B., Kelland L.R., Foloppe M.P., and Rault S. J. Med. Chem. 42 (1999) 1951
18. Hartley J.A., Spanswick V.J., Brooks N., Clingen P.H., McHugh P.J., Hochhauser D., Pedley R.B., Kelland L.R., Alley M.C., Schultz R., Hollingshead M.G., Schweikart K.M., Tomaszewski J.E., Sausville E.A., Gregson S.J., Howard P.W., and Thurston D.E. Cancer Res. 64 (2004) 6693