Selective inhibition of bacterial and human topoisomerases by N-arylacyl O-sulfonated aminoglycoside derivatives

ACS Medicinal Chemistry Letters

Volumn 4, Issue 5, 2013, Pages 470-474

  Fenner, Amanda M ^a   Oppegard, Lisa M ^b   Hiasa, Hiroshi ^b   Kerns, Robert J ^a  

^a UNIVERSITY OF IOWA   (United States)

^b UNIVERSITY OF MINNESOTA MEDICAL SCHOOL   (United States)

Author keywords

aminoglycoside derivatives; ciprofloxacin induced DNA cleavage; glycosaminoglycan mimic; sulfated oligosaccharide; Topoisomerase inhibitor

Indexed keywords

AMINOGLYCOSIDE DERIVATIVE; CIPROFLOXACIN; DNA TOPOISOMERASE; HEPARIN BINDING PROTEIN;

ARTICLE; CYTOTOXICITY; DNA CLEAVAGE; DRUG DNA BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SULFONATION;

EID: 84877686986     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3004507     Document Type: Article

References (25)

1. Levine, C.; Hiasa, H.; Marians, K. J. DNA gyrase and topoisomerase IV: biochemical activities, physiological roles during chromosome replication, and drug sensitivities Biochim. Biophys. Acta 1998, 1400, 29-43
2. Schvartzman, J. B.; Stasiak, A. A topological view of the replicon EMBO Rep. 2004, 5, 256-261
3. Wang, J. C. DNA topoisomerases Annu. Rev. Biochem. 1985, 54, 665-697
4. Gellert, M.; O'Dea, M. H.; Itoh, T.; Tomizawa, J. Novobiocin and coumermycin inhibit DNA supercoiling catalyzed by DNA gyrase Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 4474-4478
5. Sugino, A.; Peebles, C. L.; Kreuzer, K. N.; Cozzarelli, N. R. Mechanism of action of nalidixic acid: purification of Escherichia coli nalA gene product and its relationship to DNA gyrase and a novel nicking-closing enzyme Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 4767-4771
6. Ishii, K.; Katase, A.; Andoh, T.; Seno, N. Inhibition of topoisomerase I by heparin Biochem. Biophys. Res. Commun. 1982, 104, 541-547
7. Harisi, R.; Dudas, J.; Timar, F.; Pogany, G.; Timar, J.; Kovalszky, I.; Szendroi, M.; Jeney, A. Invasive growth and topoisomerase-switch induced by tumorous extracellular matrix in osteosarcoma cell culture Cell. Biol. Int. 2005, 29, 959-967
8. Ishii, K.; Futaki, S.; Uchiyama, H.; Nagasawa, K.; Andoh, T. Mechanism of inhibition of mammalian DNA topoisomerase I by heparin Biochem. J. 1987, 241, 111-119
9. Kovalszky, I.; Dudas, J.; Olah-Nagy, J.; Pogany, G.; Tovary, J.; Timar, J.; Kopper, L.; Jeney, A.; Iozzo, R. V. Inhibition of DNA topoisomerase I activity by heparan sulfate and modulation by basic fibroblast growth factor Mol. Cell. Biochem. 1998, 183, 11-23
10. Bojanowski, K.; Lelievre, S.; Markovits, J.; Couprie, J.; Jacquemin-Sablon, A.; Larsen, A. K. Suramin is an inhibitor of DNA topoisomerase II in vitro and in Chinese hamster fibrosarcoma cells Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3025-3029
11. Onda, T.; Toyoda, E.; Miyazaki, O.; Seno, C.; Kagaya, S.; Okamoto, K.; Nishikawa, K. NK314, a novel topoisomerase II inhibitor, induces rapid DNA double-strand breaks and exhibits superior antitumor effects against tumors resistant to other topoisomerase II inhibitors Cancer Lett. 2008, 259, 99-110
12. Umemura, K.; Yanase, K.; Suzuki, M.; Okutani, K.; Yamori, T.; Andoh, T. Inhibition of DNA topoisomerases I and II, and growth inhibition of human cancer cell lines by a marine microalgal polysaccharide Biochem. Pharmacol. 2003, 66, 481-487
13. Bittoun, P.; Avramoglou, T.; Vassy, J.; Crepin, M.; Chaubet, F.; Fermandjian, S. Low-molecular-weight dextran derivatives (f-CMDB) enter the nucleus and are better cell-growth inhibitors compared with parent CMDB polymers Carbohydr. Res. 1999, 322, 247-255
14. Huang, L.; Kerns, R. J. Diversity-oriented chemical modification of heparin: Identification of charge-reduced N -acyl heparin derivatives having increased selectivity for heparin-binding proteins Bioorg. Med. Chem. 2006, 14, 2300-2313
15. Huang, L.; Fernandez, C.; Kerns, R. J. Different protein-binding selectivities for N -acyl heparin derivatives having N -phenylacetyl and heterocycle analogs of N -phenylacetyl substituted in place of N -sulfo groups Bioorg. Med. Chem. Lett. 2007, 17, 419-423
16. Fernandez, C.; Hattan, C. M.; Kerns, R. J. Semi-synthetic heparin derivatives: chemical modifications of heparin beyond chain length, sulfate substitution pattern and N -sulfo/ N -acetyl groups Carbohydr. Res. 2006, 341, 1253-1265
17. Champoux, J. J. DNA topoisomerases: structure, function, and mechanism Annu. Rev. Biochem. 2001, 70, 369-413
18. Kumar, V.; Remers, W. A. Aminoglycoside antibiotics. 4. Regiospecific partial synthesis of ribostamycin and 4″-thioribostamycin J. Org. Chem. 1981, 46, 4298-4300
19. Chen, G.; Pan, P.; Yao, Y.; Chen, Y.; Meng, X.; Li, Z. Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation Tetrahedron 2008, 64, 9078-9087
20. Igarashi, K.; Honma, T. Aprosamine derivatives. Belgian Patent 890.873, Feb 15, 1982.
21. Fenner, A. M.; Kerns, R. J. Synthesis, separation, and characterization of amphiphilic sulfated oligosaccharides enabled by reversed-phase ion pairing LC and LC-MS methods Carbohydr. Res. 2011, 346, 2792-2800
22. Ishii, K.; Futaki, S.; Uchiyama, H.; Nagasawa, K.; Andoh, T. Mechanism of inhibition of mammalian DNA topoisomerase I by heparin Biochem. J. 1987, 241, 111-119
23. Reece, R. J.; Maxwell, A. DNA gyrase: structure and function Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375
24. Froelich-Ammon, S. J.; Osheroff, N. Topoisomerase poisons: harnessing the dark side of enzyme mechanism J. Biol. Chem. 1995, 270, 21429-21432
25. Hiasa, H. The Glu-84 of the ParC subunit plays critical roles in both topoisomerase IV-quinolone and topoisomerase IV-DNA interactions Biochemistry 2002, 41, 11779-11785