Design and synthesis of a DNA-crosslinking azinomycin analogue

Organic and Biomolecular Chemistry

Volumn 3, Issue 19, 2005, Pages 3585-3589

  Casely Hayford, Maxwell A ^a,c   Pors, Klaus ^a,d   James, Colin H ^a   Patterson, Laurence H ^a,d   Hartley, John A ^b   Searcey, Mark ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c MEDWAY SCHOOL OF PHARMACY   (United Kingdom)

^d UNIVERSITY OF BRADFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; CONCENTRATION (PROCESS); DNA; DRUG THERAPY; SYNTHESIS (CHEMICAL);

ANTITUMOR ACTIVITY; AZINOMYCINS; DNA-CROSSLINKING; EPOXIDES;

CROSSLINKING;

ANTINEOPLASTIC ANTIBIOTIC; AZINOMYCIN A; AZINOMYCIN B; CHLORMETHINE; CROSS LINKING REAGENT; DNA; EPOXIDE; GLYCOPEPTIDE; NAPHTHALENE DERIVATIVE; PEPTIDE;

ALKYLATION; ARTICLE; CELL CULTURE; CHEMICAL MODEL; CHEMISTRY; DRUG SCREENING; HUMAN; SYNTHESIS;

ALKYLATION; ANTIBIOTICS, ANTINEOPLASTIC; CROSS-LINKING REAGENTS; DNA; DRUG SCREENING ASSAYS, ANTITUMOR; EPOXY COMPOUNDS; GLYCOPEPTIDES; HUMANS; MECHLORETHAMINE; MODELS, CHEMICAL; NAPHTHALENES; PEPTIDES; TUMOR CELLS, CULTURED;

EID: 27144468075     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508908e     Document Type: Article

References (26)

1. K. Nagaoka, M. Matsumoto, J. Oono, K. Yokoi, S. Ishizeki and T. Nakashima, J. Antibiot. (Tokyo), 1986, 39, 1527-1532.
2. R. W. Armstrong, M. E. Salvati and M. Nguyen. J. Am. Chem. Soc., 1992, 114, 3144-3145.
3. T. J. Hodgkinson and M. Shipman, Tetrahedron, 2001, 57, 4467-4488.
4. R. S. Coleman, J. Li and A. Navarro, Angew. Chem., Int. Ed., 2001, 40, 1736-1739.
5. T. Fujiwara, I. Saito and H. Sugiyama, Tetrahedron Lett., 1999, 40, 315-318.
6. R. S. Coleman, R. J. Perez, C. H. Burk and A. Navarro, J. Am. Chem. Soc., 2002, 124, 13008-13017.
7. M. Casely-Hayford and M. Searcey, The Azinomycins. Discovery, Synthesis and DNA-Binding Studies, in DNA and RNA Binders From Small Molecules to Drugs, ed. M. Demeunynck, C. Bailly and W. D. Wilson, Wiley-VCH, Weinheim, 2002, pp. 676-696.
8. S. Alcaro and R. S. Coleman. J. Org. Chem., 1998, 63, 4620-4625.
9. S. Alcaro and R. S. Coleman, J. Med. Chem., 2000, 43, 2783-2788.
10. S. Ishizeki, M. Ohtsuka, M. K. Irinoda, K. I. Kukita, K.-K. Nagaoka and T. Nakashima, J. Antibiot. (Tokyo), 1987, 40, 60-65.
11. H. Zang and K. S. Gates, Biochemistry, 2000, 39, 14968-14975.
12. R. S. Coleman, C. H. Burk, A. Navarro, R. W. Brueggemeier and E. S. Diaz-Cruz, Org. Lett., 2002, 4, 3545-3548.
13. M. A. Casely-Hayford, K. Pors, L. H. Patterson, C. Gerner. S. Neidle and M. Searcey, Bioorg. Med. Chem. Lett., 2005, 15, 653-656.
14. J. A. Hartley, A. Hazrati, L. R. Kelland, R. Khanim, M. Shipman, F. Suzenet and L. F. Walker, Angew. Chem., Int. Ed., 2000, 39, 3467-3470.
15. M. Hashimoto, M. Matsumoto, K. Yamada and S. Terashima, Tetrahedron, 2003, 59, 3089-3097.
16. R. C. LePla, C. A. S. Landreau, M. Shipman and G. D. D. Jones, Org. Biomol. Chem., 2005, 3, 1174-1175.
17. R. S. Coleman, C. H. Burk, A. Navarro. R. W. Brueggemeier and E. S. Diaz-Cruz, Org. Lett., 2002, 4, 3545 3548.
18. K. Shishido, S. Haruna, H. Iitsuka and M. Shibuya, Heterocycles, 1998, 49, 109-112.
19. K. Miyashita, M. Park, S. Adachi, S. Seki, S. Obika and T. Imanishi, Bioorg. Med. Chem. Lett., 2002, 12, 1075-1077.
20. H. J. Bryant, C. Y. Dardonville, T. J. Hodgkinson, M. B. Hursthouse, K. M. A. Malik and M. Shipman, J. Chem. Soc., Perkin Trans. 1, 1998, 1249 1255.
21. K. Pors, J. A. Plumb, R. Brown, P. Teesdale-Spittle, M. Searcey, P. J. Smith and L. H. Patterson. J. Med. Chem., submitted.
22. R. S. Coleman and J. A. Shah, Synthesis. 1999, 1399-1400.
23. J. A. Hartley, A. Hazrati, T. J. Hodgkinson, L. R. Kelland, R. Khanim, M. Shipman and F. Suzenet, Chem. Commun., 2000. 2325-2326.
24. M. Hashimoto, M. Matsumoto, K. Yamada and S. Terashima, Tetrahedron Lett., 1994, 35, 2207-2210.
25. R. C. LePla, C. A. S. Landreau, M. Shipman, J. A. Hartley and G. D. D. Jones, Bioorg. Med. Chem. Lett., 2005, 15, 2861-2864.
26. J. A. Hartley, M. D. Berardini and R. L. Souhami, Anal. Biochem., 1991, 193, 131-134