Effect of base sequence on the DNA cross-linking properties of pyrrolobenzodiazepine (PBD) dimers

Nucleic Acids Research

Volumn 39, Issue 13, 2011, Pages 5800-5812

  Rahman, Khondaker M ^a   James, Colin H ^a   Thurston, David E ^a,b  

^a Gene Targeting Drug Design Research Group   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; DIMER; DNA; DRG 16; ELB 21; GUANINE; OLIGONUCLEOTIDE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; SJG 136; THYMINE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CONTROLLED STUDY; DNA CROSS LINKING; DNA SEQUENCE; DRUG DESIGN; DRUG DNA INTERACTION; DRUG RESEARCH; DRUG STRUCTURE; MASS SPECTROMETRY; MOLECULAR MODEL; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

BASE SEQUENCE; BENZODIAZEPINES; BENZODIAZEPINONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CROSS-LINKING REAGENTS; DIMERIZATION; DNA; MASS SPECTROMETRY; MODELS, MOLECULAR; OLIGONUCLEOTIDES; PYRROLES;

EID: 80052225565     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkr122     Document Type: Article

References (23)

1. Cipolla, L., Araujo, A.C., Airoldi, C. and Bini, D. (2009) Pyrrolo[2, 1-c][1, 4]benzodiazepines as a scaffold for the design and synthesis of anti-tumour drugs. Anticancer Agents Med. Chem., 9, 1-31.
2. Kamal, A., Rao, M.V., Laxman, N., Ramesh, G. and Reddy, G.S.K. (2002) Recent developments in the design, synthesis and structure-activity relationship studies of Pyrrolo[2, 1-c][1, 4]benzodiazepines as DNA-interactive antitumour antibiotics. Curr. Med. Chem. Anticancer Agents, 2, 215-254. (Pubitemid 34649874)
3. Thurston, D.E. (1993) In Neidle, S. and Waring, M.J. (eds), Molecular Aspects of Anticancer Drug-DNA Interactions, Vol. 1. The Macmillan Press Ltd., London, UK, pp. 54-88.
4. Bose, D.S., Thompson, A.S., Smellie, M., Berardini, M.D., Hartley, J.A., Jenkins, T.C., Neidle, S. and Thurston, D.E. (1992) Effect of linker length on DNA-binding affinity, cross-linking efficiency and cytotoxicity of C8-linked pyrrolobenzodiazepine dimers. Chem. Commun., 20, 1518-1520.
5. Gregson, S.J., Howard, P.W., Gullick, D.R., Hamaguchi, A., Corcoran, K.E., Brooks, N.A., Hartley, J.A., Jenkins, T.C., Patel, S., Guille, M.J. et al. (2004) Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2, 1-c][1, 4]benzodiazepine (PBD) dimers. J. Med. Chem., 47, 1161-1174. (Pubitemid 38229118)
6. Hochhauser, D., Meyer, T., Spanswick, V.J., Wu, J., Clingen, P.H., Loadman, P., Cobb, M., Gumbrell, L., Begent, R.H., Hartley, J.A. et al. (2009) Phase I study of sequence-selective minor groove DNA binding agent SJG-136 in patients with advanced solid tumors. Clin. Cancer Res., 15, 2140-2147.
7. Janjigian, Y.Y., Lee, W., Kris, M.G., Miller, V.A., Krug, L.M., Azzoli, C.G., Senturk, E., Calcutt, M.W. and Rizvi, N.A. (2010) A phase I trial of SJG-136 (NSC#694501) in advanced solid tumors. Cancer Chemother. Pharmacol., 65, 833-838.
8. Puzanov, I., Lee, W., Chen, A., Calcutt, M.D., Hachey, D.L., Vermeulen, W.L., Spanswick, V.J., Hartley, J.A. and Rothenberg, M.L. (2011) Phase I, pharmacokinetic and pharmacodynamic study of SJG-136, a novel DNA sequence selective minor groove cross-linking agent, in advanced solid tumors. Clin. Cancer Res, [Epub ahead of print 23 February 2011, DOI: 10.1158/1078-0432.CCR- 10-2056].
9. Narayanaswamy, M., Griffiths, W.J., Howard, P.W. and Thurston, D.E. (2008) An assay combining high-performance liquid chromatography and mass spectrometry to measure DNA interstrand cross-linking efficiency in oligonucleotides of varying sequences. Anal. Biochem., 374, 173-181.
10. Rahman, K.M., Mussa, V., Narayanaswamy, M., James, C.H., Howard, P.W. and Thurston, D.E. (2009) Observation of a dynamic equilibrium between DNA hairpin and duplex forms of covalent adducts of a minor groove binding agent. Chem. Commun., 2, 227-229.
11. Rahman, K.M., Vassoler, H., James, C.H. and Thurston, D.E. (2010) DNA sequence preference and adduct orientation of pyrrolo[2, 1-c][1, 4]benzodiazepine antitumor agents. ACS Med. Chem. Lett., 1, 427-432.
12. Rahman, K.M., Thompson, A.S., James, C.H., Narayanaswamy, M. and Thurston, D.E. (2009) The pyrrolobenzodiazepine dimer SJG-136 forms sequence-dependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrand cross-links. J. Am. Chem. Soc., 131, 13756-13766.
13. Gregson, S.J., Howard, P.W., Hartley, J.A., Brooks, N.A., Adams, L.J., Jenkins, T.C., Kelland, L.R. and Thurston, D.E. (2001) Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity. J. Med. Chem., 44, 737-748. (Pubitemid 32171670)
14. Gregson, S.J., Howard, P.W., Jenkins, T.C., Kelland, L.R. and Thurston, D.E. (1999) Synthesis of a novel C2/C20-exo unsaturated pyrrolobenzodiazepine cross-linking agent with remarkable DNA binding affinity and cytotoxicity. Chem. Commun., 9, 797-798. (Pubitemid 29216725)
15. Wells, G., Martin, C.R.H., Howard, P.W., Sands, Z.A., Laughton, C.A., Tiberghien, A., Woo, C.K., Masterson, L.A., Stephenson, M.J., Hartley, J.A. et al. (2006) Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates. J. Med. Chem., 49, 5442-5461. (Pubitemid 44373177)
16. Hadjivassileva, T., Thurston, D.E. and Taylor, P.W. (2005) Pyrrolobenzodiazepine dimers: novel sequence-selective, DNA-interactive, cross-linking agents with activity against Gram-positive bacteria. J. Antimicrob. Chemother., 56, 513-518. (Pubitemid 41264129)
17. Hadjivassileva, T., Stapleton, P.D., Thurston, D.E. and Taylor, P.W. (2007) Interactions of pyrrolobenzodiazepine dimers and duplex DNA from methicillin-resistant Staphylococcus aureus. Int. J. Antimicrob. Agents, 29, 672-678. (Pubitemid 46710358)
18. Case, D.A., Darden, T.A., Cheatham, T.E. III, Simmerling, C.L., Wang, J., Duke, R.E., Luo, R., Merz, K.M., Pearlman, D.A., Crowley, M. et al. (2006) AMBER 9. Amber 9. University of California, San Francisco.
19. Smellie, M., Bose, D.S., Thompson, A.S., Jenkins, T.C., Hartley, J.A. and Thurston, D.E. (2003) Sequence-selective recognition of duplex DNA through covalent interstrand cross-linking: kinetic and molecular modeling studies with pyrrolobenzodiazepine dimers. Biochemistry, 42, 8232-8239. (Pubitemid 36858984)
20. Alley, M.C., Hollingshead, M.G., Pacula-Cox, C.M., Waud, W.R., Hartley, J.A., Howard, P.W., Gregson, S.J., Thurston, D.E. and Sausville, E.A. (2004) SJG-136 (NSC 694501), A novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: part 2: efficacy evaluations. Cancer Res., 64, 6700-6706. (Pubitemid 39297933)
21. 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. et al. (2004) SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: part 1: cellular pharmacology, in vitro and initial in vivo antitumor activity. Cancer Res., 64, 6693-6699. (Pubitemid 39297932)
22. Hartley, J.M., Spanswick, V.J., Gander, M., Giacomini, G., Whelan, J., Souhami, R.L. and Hartley, J.A. (1998) Detection of DNA interstrand crosslinking in clinical samples using the single cell COMET assay. Ann. Oncol., 9, 645.
23. Redon, C.E., Nakamura, A.J., Zhang, Y.W., Ji, J.P., Bonner, W.M., Kinders, R.J., Parchment, R.E., Doroshow, J.H. and Pommier, Y. (2010) Histone yH2AX and poly(ADP-ribose) as clinical pharmacodynamic biomarkers. Clin. Cancer Res., 16, 4532-4542.