Bioreductively activated reactive oxygen species (ROS) generators as MRSA inhibitors

ACS Medicinal Chemistry Letters

Volumn 5, Issue 7, 2014, Pages 777-781

  Khodade, Vinayak S ^a   Sharath Chandra, Mallojjala ^a   Banerjee, Ankita ^b   Lahiri, Surobhi ^b   Pulipeta, Mallikarjuna ^b   Rangarajan, Radha ^b   Chakrapani, Harinath ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

DNA damage; Drug resistance; MRSA; reactive oxygen species; RecA; superoxide radical

Indexed keywords

6 (PROP 2 YNYL)BENZO[B]PHENANTHRIDINE 5,7,12(6H) TRIONE; ANTIBIOTIC AGENT; BENZO[B]PHENANTHRIDINE 5,7,12(6H) TRIONE; POLYDEOXYRIBONUCLEOTIDE SYNTHASE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL CELL; BACTERIAL GROWTH; BACTERIAL STRAIN; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DNA DAMAGE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REAL TIME POLYMERASE CHAIN REACTION; UPREGULATION;

EID: 84904368665     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml5001118     Document Type: Article

References (30)

1. Klevens, R. M.; Morrison, M. A.; Nadle, J.; Petit, S.; Gershman, K.; Ray, S.; Harrison, L. H.; Lynfield, R.; Dumyati, G.; Townes, J. M.; Craig, A. S.; Zell, E. R.; Fosheim, G. E.; McDougal, L. K.; Carey, R. B.; Fridkin, S. K. Invasive methicillin-resistant Staphylococcus aureus infections in the united states J. Am. Med. Assoc. 2007, 298, 1763-1771
2. Rodvold, K. A.; McConeghy, K. W. Methicillin-resistant Staphylococcus aureus therapy: Past, present, and future Clin. Infect. Dis. 2014, 58, S20-S27
3. Dietrich, L. E. P.; Teal, T. K.; Price-Whelan, A.; Newman, D. K. Redox-active antibiotics control gene expression and community behavior in divergent bacteria Science 2008, 321, 1203-1206
4. Price-Whelan, A.; Dietrich, L. E. P.; Newman, D. K. Rethinking "secondary metabolism: physiological roles for phenazine antibiotics Nat. Chem. Biol. 2006, 2, 71-78
5. Borrero, N. V.; Bai, F.; Perez, C.; Duong, B. Q.; Rocca, J. R.; Jin, S.; Huigens Iii, R. W. Phenazine antibiotic inspired discovery of potent bromophenazine antibacterial agents against Staphylococcus aureus and Staphylococcus epidermidis Org. Biomol. Chem. 2014, 12, 881-886
6. Imlay, J. A. The molecular mechanisms and physiological consequences of oxidative stress: Lessons from a model bacterium Nat. Rev. Microbiol. 2013, 11, 443-454
7. Wondrak, G. T. Redox-directed cancer therapeutics: Molecular mechanisms and opportunities Antioxid. Redox Signal. 2009, 11, 3013-3069
8. Parkinson, E. I.; Bair, J. S.; Cismesia, M.; Hergenrother, P. J. Efficient NQO1 substrates are potent and selective anticancer agents ACS Chem. Biol. 2013, 8, 2173-2183
9. Bair, J. S.; Palchaudhuri, R.; Hergenrother, P. J. Chemistry and biology of deoxynyboquinone, a potent inducer of cancer cell death J. Am. Chem. Soc. 2010, 132, 5469-5478
10. Dharmaraja, A. T.; Alvala, M.; Sriram, D.; Yogeeswari, P.; Chakrapani, H. Design, synthesis and evaluation of small molecule reactive oxygen species generators as selective Mycobacterium tuberculosis inhibitors Chem. Commun. 2012, 48, 10325-10327
11. Vilchèze, C.; Hartman, T.; Weinrick, B.; Jacobs, W. R. Mycobacterium tuberculosis is extraordinarily sensitive to killing by a vitamin C-induced Fenton reaction Nat. Commun. 2013, 4, 1881
12. Miller, M. J.; Walz, A. J.; Zhu, H.; Wu, C.; Moraski, G.; Mollmann, U.; Tristani, E. M.; Crumbliss, A. L.; Ferdig, M. T.; Checkley, L.; Edwards, R. L.; Boshoff, H. I. Design, synthesis, and study of a mycobactin-artemisinin conjugate that has selective and potent activity against Tuberculosis and Malaria J. Am. Chem. Soc. 2011, 133, 2076-2079
13. Yano, T.; Kassovska-Bratinova, S.; Teh, J. S.; Winkler, J.; Sullivan, K.; Isaacs, A.; Schechter, N. M.; Rubin, H. Reduction of clofazimine by mycobacterial Type 2 NADH: Quinone oxidoreductase a pathway for the generation of bactericidal levels of reactive oxygen species J. Biol. Chem. 2011, 286, 10276-10287
14. Shan, M.; Sharif, E. U.; ODoherty, G. A. Total synthesis of jadomycin A and a carbasugar analogue of jadomycin B Angew. Chem., Int. Ed. 2010, 49, 9492-9495
15. Khodade, V. S.; Dharmaraja, A. T.; Chakrapani, H. Synthesis, reactive oxygen species generation and copper-mediated nuclease activity profiles of 2-aryl-3-amino-1,4-naphthoquinones Bioorg. Med. Chem. Lett. 2012, 22, 3766-3769
16. Jakeman, D. L.; Bandi, S.; Graham, C. L.; Reid, T. R.; Wentzell, J. R.; Douglas, S. E. Antimicrobial activities of jadomycin B and structurally related analogues Antimicrob. Agents Chemother. 2009, 53, 1245-1247
17. Hillard, E. A.; de Abreu, F. C.; Ferreira, D. C. M.; Jaouen, G.; Goulart, M. O. F.; Amatore, C. Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds Chem. Commun. 2008, 2612-2628
18. Sharma, K.; Iyer, A.; Sengupta, K.; Chakrapani, H. INDQ/NO, a bioreductively activated nitric oxide prodrug Org. Lett. 2013, 15, 2636-2639
19. Trung Pham, H.; Marquetty, C.; Pasquier, C.; Hakim, J. Luminol assay for microdetermination of superoxide dismutase activity: Its application to human fetal blood Anal. Biochem. 1984, 142, 467-472
20. Maruyama, A.; Kumagai, Y.; Morikawa, K.; Taguchi, K.; Hayashi, H.; Ohta, T. Oxidative-stress-inducible qorA encodes an NADPH-dependent quinone oxidoreductase catalysing a one-electron reduction in Staphylococcus aureus Microbiology 2003, 149, 389-398
21. Georgiou, C. D.; Papapostolou, I.; Grintzalis, K. Superoxide radical detection in cells, tissues, organisms (animals, plants, insects, microorganisms) and soils Nat. Protoc. 2008, 3, 1679-1692
22. Zielonka, J.; Vasquez-Vivar, J.; Kalyanaraman, B. Detection of 2-hydroxyethidium in cellular systems: A unique marker product of superoxide and hydroethidine Nat. Protoc. 2008, 3, 8-21
23. Zhao, H.; Joseph, J.; Fales, H. M.; Sokoloski, E. A.; Levine, R. L.; Vasquez-Vivar, J.; Kalyanaraman, B. Detection and characterization of the product of hydroethidine and intracellular superoxide by HPLC and limitations of fluorescence Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 5727-5732
24. Zhou, M.; Diwu, Z.; Panchuk-Voloshina, N.; Haugland, R. P. A stable nonfluorescent derivative of resorufin for the fluorometric determination of trace hydrogen peroxide: Applications in detecting the activity of phagocyte NADPH oxidase and other oxidases Anal. Biochem. 1997, 253, 162-168
25. Dharmaraja, A. T.; Chakrapani, H. A Small molecule for controlled generation of reactive oxygen species (ROS) Org. Lett. 2014, 16, 398-401
26. Chen, Z.; Yang, H.; Pavletich, N. P. Mechanism of homologous recombination from the RecA-ssDNA/dsDNA structures Nature 2008, 453, 489-494
27. Price-Whelan, A.; Dietrich, L. E. P.; Newman, D. K. Pyocyanin alters redox homeostasis and carbon flux through central metabolic pathways in Pseudomonas aeruginosa PA14 J. Bacteriol. 2007, 189, 6372-6381
28. Kohanski, M. A.; Dwyer, D. J.; Hayete, B.; Lawrence, C. A.; Collins, J. J. A common mechanism of cellular death induced by bactericidal antibiotics Cell 2007, 130, 797-810
29. Liu, Y.; Imlay, J. A. Cell death from antibiotics without the involvement of reactive oxygen species Science 2013, 339, 1210-1213
30. Cottreau, K. M.; Spencer, C.; Wentzell, J. R.; Graham, C. L.; Borissow, C. N.; Jakeman, D. L.; McFarland, S. A. Diverse DNA-cleaving capacities of the jadomycins through precursor-directed biosynthesis Org. Lett. 2010, 12, 1172-1175