Diaza-anthracene Antibiotics from a Freshwater-Derived Actinomycete with Selective Antibacterial Activity toward Mycobacterium tuberculosis

ACS Infectious Diseases

Volumn 1, Issue 4, 2016, Pages 168-174

  Mullowney, Michael W ^a   Hwang, Chang Hwa ^a   Newsome, Andrew G ^a   Wei, Xiaomei ^a   Tanouye, Urszula ^a   Wan, Baojie ^a   Carlson, Skylar ^a   Barranis, Nanthida Joy ^a   Ó Hainmhire, Eoghainín ^a   Chen, Wei Lun ^a   Krishnamoorthy, Kalyanaraman ^b   White, John ^b   Blair, Rachel ^c   Lee, Hyunwoo ^a   Burdette, Joanna E ^a   Rathod, Pradipsinh K ^b   Parish, Tanya ^c   Cho, Sanghyun ^a   Franzblau, Scott G ^a   Murphy, Brian T ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

^c INFECTIOUS DISEASE RESEARCH INSTITUTE   (United States)

Author keywords

actinobacteria; antibiotic; diazaquinomycin; drug discovery; Great Lakes; natural products

Indexed keywords

ANTIBIOTIC AGENT; DIAZAQUINOMYCIN A; DIAZAQUINOMYCIN H; DIAZAQUINOMYCIN J; PROPRANOLOL; QUINOMYCIN; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG; VINBLASTINE;

ACTINOBACTERIA; ANIMAL CELL; ANIMAL EXPERIMENT; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL CLEARANCE; BACTERIAL GENE; BACTERIAL STRAIN; CACO 2 CELL LINE; CELL MEMBRANE PERMEABILITY; CONCENTRATION RESPONSE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG CYTOTOXICITY; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG POTENCY; DRUG RESISTANT TUBERCULOSIS; DRUG SCREENING; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG TOLERANCE; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; FRESHWATER ENVIRONMENT; GENE OVEREXPRESSION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LC50; LIVER MICROSOME; METABOLIC STABILITY; MINIMUM BACTERICIDAL CONCENTRATION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR STABILITY; MOLECULAR WEIGHT; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; OVARIAN CANCER CELL LINE; PRIORITY JOURNAL; SOLUBILITY; THYA GENE; THYX GENE; VERO CELL LINE;

EID: 84969185783     PISSN: None     EISSN: 23738227     Source Type: Journal    
DOI: 10.1021/acsinfecdis.5b00005     Document Type: Article

References (33)

1. Global Tuberculosis Report-2014 (2014), World Health Organization, Geneva, Switzerland, www.who.int/tb.
2. Fischbach, M. A. and Walsh, C. T. (2009) Antibiotics for emerging pathogens Science 325, 1089-1093 10.1126/science.1176667
3. Dorman, S. E. and Chaisson, R. E. (2007) From magic bullets back to the magic mountain: the rise of extensively drug-resistant tuberculosis Nat. Med. 13, 295-298 10.1038/nm0307-295
4. Glaziou, P., Falzon, D., Floyd, K., and Raviglione, M. (2013) Global epidemiology of tuberculosis Semin. Respir. Crit. Care Med. 34, 3-16 10.1055/s-0032-1333467
5. Newman, D. J. and Cragg, G. M. (2012) Natural products as sources of new drugs over the 30 years from 1981 to 2010 J. Nat. Prod. 75, 311-335 10.1021/np200906s
6. Fenical, W. and Jensen, P. R. (2006) Developing a new resource for drug discovery: marine actinomycete bacteria Nat. Chem. Biol. 2, 666-673 10.1038/nchembio841
7. Murphy, B. T., Maloney, K., and Fenical, W. (2011) Marine microorganisms. In Phytochemistry and Pharmacognosy, Eolss Publishers, Oxford, UK.
8. Olivera, B. M., Cruz, L. J., de Santos, V., LeCheminant, G. W., Griffin, D., Zeikus, R., McIntosh, J. M., Galyean, R., Varga, J., Gray, W. R., and Rivier, J. (1987) Neuronal calcium channel antagonists. Discrimination between calcium channel subtypes using omega-conotoxin from Conus magus venom Biochemistry 26, 2086-2090 10.1021/bi00382a004
9. Rinehart, K. L., Holt, T. G., Fregeau, N. L., Stroh, J. G., Keifer, P. A., Sun, F., Li, L. H., and Martin, D. G. (1990) Ecteinascidins 729, 743, 745, 759A, 759B, and 770: potent antitumor agents from the Caribbean tunicate Ecteinascidia turbinata J. Org. Chem. 55, 4512-4515 10.1021/jo00302a007
10. Pettit, G. R., Herald, C. L., Boyd, M. R., Leet, J. E., Dufresne, C., Doubek, D. L., Schmidt, J. M., Cerny, R. L., Hooper, J. N., and Rützler, K. C. (1991) Isolation and structure of the cell growth inhibitory constituents from the western Pacific marine sponge Axinella sp J. Med. Chem. 34, 3339-3340 10.1021/jm00115a027
11. Newton, R. J., Jones, S. E., Eiler, A., McMahon, K. D., and Bertilsson, S. (2011) A guide to the natural history of freshwater lake bacteria Microbiol. Mol. Biol. Rev. 75, 14-49 10.1128/MMBR.00028-10
12. Carballeira, N. M., Pagan, M., Shalabi, F., Nechev, J. T., Lahtchev, K., Ivanova, A., and Stefanov, K. (2000) Two novel iso-branched octadecenoic acids from a Micrococcus species J. Nat. Prod. 63, 1573-1575 10.1021/np000305r
13. Carlson, S., Tanouye, U., Ómarsdóttir, S., and Murphy, B. T. Phylum-specific regulation of resistomycin production in a Streptomyces sp. via microbial coculture. J. Nat. Prod. 2015, DOI: 10.1021/np500767u (accessed Jan 7, 2015).
14. Ashforth, E. J., Fu, C., Liu, X., Dai, H., Song, F., Guo, H., and Zhang, L. (2010) Bioprospecting for antituberculosis leads from microbial metabolites Nat. Prod. Rep. 27, 1709-1719 10.1039/c0np00008f
15. Collins, L. and Franzblau, S. G. (1997) Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium Antimicrob. Agents Chemother. 41, 1004-1009
16. Franzblau, S. G., Witzig, R. S., McLaughlin, J. C., Torres, P., Madico, G., Hernandez, A., Degnan, M. T., Cook, M. B., Quenzer, V. K., Ferguson, R. M., and Gilman, R. H. (1998) Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay J. Clin. Microbiol. 36, 362-366
17. Mullowney, M. W., Ó hAinmhire, E., Shaikh, A., Wei, X., Tanouye, U., Santarsiero, B. D., Burdette, J. E., and Murphy, B. T. (2014) Diazaquinomycins E-G, novel diaza-anthracene analogs from a marine-derived Streptomyces sp Mar. Drugs 12, 3574-3586 10.3390/md12063574
18. Tsuzuki, K., Yokozuka, T., Murata, M., Tanaka, H., and Omura, S. (1989) Synthesis and biological activity of analogues of diazaquinomycin A, a new thymidylate synthase inhibitor J. Antibiot. 42, 727-737 10.7164/antibiotics.42.727
19. Cho, S. H., Warit, S., Wan, B., Hwang, C. H., Pauli, G. F., and Franzblau, S. G. (2007) Low-oxygen-recovery assay for high-throughput screening of compounds against nonreplicating Mycobacterium tuberculosis Antimicrob. Agents Chemother. 51, 1380-1385 10.1128/AAC.00055-06
20. Maskey, R. P., Grun-Wollny, I., and Laatsch, H. (2005) Isolation and structure elucidation of diazaquinomycin C from a terrestrial Streptomyces sp. and confirmation of the akashin structure Nat. Prod. Res. 19, 137-142 10.1080/14786410410001704741
21. Omura, S., Iwai, Y., Hinotozawa, K., Tanaka, H., Takahashi, Y., and Nakagawa, A. (1982) OM-704 A, a new antibiotic active against gram-positive bacteria produced by Streptomyces sp J. Antibiot. 35, 1425-1429 10.7164/antibiotics.35.1425
22. Omura, S., Nakagawa, A., Aoyama, H., Hinotozawa, K., and Sano, H. (1983) The structures of diazaquinomycins A and B, new antibiotic metabolites Tetrahedron Lett. 24, 3643-3646 10.1016/S0040-4039(00)88190-3
23. Clinical and Laboratory Standards Institute (CLSI). (2014) Performance Standards for Antimicrobial Susceptibility Testing, 24th Informational Supplement, CLSI Document M100-S24, CLSI, Wayne, PA, USA.
24. Omura, S., Murata, M., Kimura, K., Matsukura, S., Nishihara, T., and Tanaka, H. (1985) Screening for new antifolates of microbial origin and a new antifolate AM-8402 J. Antibiot. 38, 1016-1024 10.7164/antibiotics.38.1016
25. Murata, M., Miyasaka, T., Tanaka, H., and Omura, S. (1985) Diazaquinomycin A, a new antifolate antibiotic, inhibits thymidylate synthase J. Antibiot. 38, 1025-1033 10.7164/antibiotics.38.1025
26. Myllykallio, H., Lipowski, G., Leduc, D., Filee, J., Forterre, P., and Liebl, U. (2002) An alternative flavin-dependent mechanism for thymidylate synthesis Science 297, 105-107 10.1126/science.1072113
27. Chernyshev, A., Fleischmann, T., and Kohen, A. (2007) Thymidyl biosynthesis enzymes as antibiotic targets Appl. Microbiol. Biotechnol. 74, 282-289 10.1007/s00253-006-0763-1
28. Hunter, J. H., Gujjar, R., Pang, C. K., and Rathod, P. K. (2008) Kinetics and ligand-binding preferences of Mycobacterium tuberculosis thymidylate synthases, ThyA and ThyX PLoS One 3 e2237 10.1371/journal.pone.0002237
29. Songsumanus, A., Tanasupawat, S., Igarashi, Y., and Kudo, T. (2013) Micromonospora maritima sp. nov., isolated from mangrove soil Int. J. Syst. Evol. Microbiol. 63, 554-559 10.1099/ijs.0.039180-0
30. Galagan, J. E., Minch, K., Peterson, M., Lyubetskaya, A., Azizi, E., Sweet, L., Gomes, A., Rustad, T., Dolganov, G., Glotova, I., Abeel, T., Mahwinney, C., Kennedy, A. D., Allard, R., Brabant, W., Krueger, A., Jaini, S., Honda, B., Yu, W. H., Hickey, M. J., Zucker, J., Garay, C., Weiner, B., Sisk, P., Stolte, C., Winkler, J. K., Van de Peer, Y., Iazzetti, P., Camacho, D., Dreyfuss, J., Liu, Y., Dorhoi, A., Mollenkopf, H. J., Drogaris, P., Lamontagne, J., Zhou, Y., Piquenot, J., Park, S. T., Raman, S., Kaufmann, S. H., Mohney, R. P., Chelsky, D., Moody, D. B., Sherman, D. R., and Schoolnik, G. K. (2013) The Mycobacterium tuberculosis regulatory network and hypoxia Nature 499, 178-183 10.1038/nature12337
31. Goude, R. and Parish, T. (2008) Electroporation of mycobacteria J. Vis. Exp. 15 e761 10.3791/761
32. Ollinger, J., Bailey, M. A., Moraski, G. C., Casey, A., Florio, S., Alling, T., Miller, M. J., and Parish, T. (2013) A dual read-out assay to evaluate the potency of compounds active against Mycobacterium tuberculosis PLoS One 8 e60531 10.1371/journal.pone.0060531
33. Sirgel, F. A., Wiid, I. J., and van Helden, P. D. (2009) Measuring minimum inhibitory concentrations in mycobacteria Methods Mol. Biol. 465, 173-186 10.1007/978-1-59745-207-6-11