Atropisomeric dihydroanthracenones as inhibitors of multiresistant staphylococcus aureus

Journal of Medicinal Chemistry

Volumn 56, Issue 8, 2013, Pages 3257-3272

  Bara, Robert ^a   Zerfass, Ilka ^a   Aly, Amal H ^a   Goldbach Gecke, Heike ^a   Raghavan, Vijay ^b   Sass, Peter ^a   Mándi, Attila ^c   Wray, Victor ^d   Polavarapu, Prasad L ^b   Pretsch, Alexander ^e   Lin, Wenhan ^f   Kurtán, Tibor ^c   Debbab, Abdessamad ^a   Brötz Oesterhelt, Heike ^a   Proksch, Peter ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b VANDERBILT UNIVERSITY   (United States)

^c UNIVERSITY OF DEBRECEN   (Hungary)

^d HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^e SeaLife Pharma GmbH   (Austria)

^f PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; FLAVOMANNIN A; FLAVOMANNIN B; FLAVOMANNIN C; FLAVOMANNIN D; TALAROMANNIN A; TALAROMANNIN B; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL CHROMOSOME; BACTERIAL GROWTH; BACTERICIDAL ACTIVITY; CHIRALITY; CIRCULAR DICHROISM; DNA DEGRADATION; DNA REPAIR; DNA STRUCTURE; DRUG SOLUBILITY; ENDOPHYTE; ENTEROCOCCUS FAECIUM; FLUORESCENCE MICROSCOPY; HYDROGEN BOND; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR WEIGHT; NONHUMAN; REPORTER GENE; SENNA OCCIDENTALIS; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS AGALACTIAE; STREPTOCOCCUS PYOGENES; TALAROMYCES;

ALOE; ANIMALS; ANTHRACENES; ANTI-BACTERIAL AGENTS; BALB 3T3 CELLS; CELL LINE, TUMOR; DNA, BACTERIAL; DRUG RESISTANCE, MULTIPLE, BACTERIAL; ENDOPHYTES; EUROTIALES; HUMANS; MICE; MICROBIAL SENSITIVITY TESTS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SOS RESPONSE (GENETICS); STAPHYLOCOCCUS AUREUS; STEREOISOMERISM;

EID: 84876835724     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301816a     Document Type: Article

References (92)

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 JAMA, J. Am. Med. Assoc. 2007, 298, 1763-1771
2. MacDougall, C.; Powell, J. P.; Johnson, C. K.; Edmond, M. B.; Polk, R. E. Hospital and community fluoroquinolone use and resistance in Staphylococcus aureus and Escherichia coli in 17 US hospitals Clin. Infect. Dis. 2005, 41, 435-440
3. Knight, G. M.; Budd, E. L.; Whitney, L.; Thornley, A.; Al-Ghusein, H.; Planche, T.; Lindsay, J. A. Shift in dominant hospital-associated methicillin-resistant Staphylococcus aureus (HA-MRSA) clones over time J. Antimicrob. Chemother. 2012, 67, 2514-2522
4. Delero, F. R.; Otto, M.; Kreiswirth, B. N.; Chambers, H. F. Community-associated methicillin-resistant Staphylococcus aureus Lancet 2010, 375, 1157-1168
5. Ruef, C. Epidemiology and clinical impact of glycopeptide resistance in Staphylococcus aureus Infection 2004, 32, 315-327
6. Cui, L.; Tominaga, E.; Neoh, H. M.; Hiramatsu, K. Correlation between reduced daptomycin susceptibility and vancomycin resistance in vancomycin-intermediate Staphylococcus aureus Antimicrob. Agents Chemother. 2006, 50, 1079-1082
7. Tenover, F. C.; Moellering, R. C., Jr. The rationale for revising the Clinical and Laboratory Standards Institute vancomycin minimal inhibitory concentration interpretive criteria for Staphylococcus aureus Clin. Infect. Dis. 2007, 44, 1208-1215
8. Tenover, F. C. Characterization of a Staphylococcus aureus strain with progressive loss of susceptibility to vancomycin and daptomycin during therapy Int. J. Antimicrob. Agents 2009, 33, 564-568
9. Gould, D. M.; David, M. Z.; Esposito, S.; Garau, J.; Mazzei, T.; Peters, G. New insight into methicillin-resistant Staphylococcus aureus (MRSA) pathogenesis, treatment and resistance Int. J. Antimicrob. Agents 2012, 39, 96-104
10. Aly, A. H.; Debbab, A.; Kjer, J.; Proksch, P. Fungal endophytes from higher plants: a prolific source of phytochemicals and other bioactive natural products Fungal Diversity 2010, 41, 1-16
11. Debbab, A.; Aly, A. H.; Lin, W. H.; Proksch, P. Bioactive compounds from marine bacteria and fungi J. Microb. Biotechnol. 2010, 3, 544-563
12. Aly, A. H.; Debbab, A.; Proksch, P. Fungal endophytes: unique plant inhabitants with great promises Appl. Microbiol. Biotechnol. 2011, 90, 1829-1845
13. Debbab, A.; Aly, A. H.; Proksch, P. Bioactive secondary metabolites from endophytes and associated marine derived fungi Fungal Diversity 2011, 49, 1-12
14. Eichelbaum, M.; Gross, A. S. Stereochemical aspects of drug action and disposition Adv. Drug Res. 1996, 28, 1-64
15. Evans, D. A.; Dinsmore, C. J.; Watson, P. S.; Wood, M. R.; Richardson, T. I.; Trotter, B. W.; Katz, J. L. Nonconventional stereochemical issues in the design of the synthesis of the vancomycin antibiotics: challenges imposed by axial and nonplanar chiral elements in the heptapeptide aglycons Angew. Chem., Int. Ed. 1998, 37, 2704-2708
16. Shah, R. R.; Midgley, J. M.; Branch, S. K. Stereochemical origin of some clinically significant drug safety concerns: lessons for future drug development Adverse Drug React. Toxicol. Rev. 1998, 17, 145-190
17. Wagenaar, M. M.; Gibson, D. M.; Clardy, J. Akanthomycin, a new antibiotic pyridone from the entomopathogenic fungus Akanthomyces gracilis Org. Lett. 2002, 4, 671-673
18. LaPlante, S. R.; Edwards, P. J.; Fader, L. D.; Jakalian, A.; Hucke, O. Revealing atropisomer axial chirality in drug discovery ChemMedChem 2011, 6, 505-513
19. LaPlante, S. R.; Fader, L. D.; Fandrick, K. R.; Fandrick, D. R.; Hucke, O.; Kemper, R.; Miller, S. P. F.; Edwards, P. J. Assessing atropisomer axial chirality in drug discovery and development J. Med. Chem. 2011, 54, 7005-7022
20. Lloyd-Williams, P.; Giralt, E. Atropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics Chem. Soc. Rev. 2001, 30, 145-157
21. Li, E.; Jiang, L.; Guo, L.; Zhang, H.; Che, Y. Pestalachlorides A-C, antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta Bioorg. Med. Chem. 2008, 16, 7894-7899
22. Nicolaou, K. C.; Simmons, N. L.; Chen, J. S.; Haste, N. M.; Nizet, V. Total synthesis and biological evaluation of marinopyrrole A and analogues Tetrahedron Lett. 2011, 52, 2041-2043
23. Debbab, A.; Aly, A. H.; Edrada-Ebel, R. A.; Wray, V.; Pretsch, A.; Pescitelli, G.; Kurtan, T.; Proksch, P. New anthracene derivatives-structure elucidation and antimicrobial activity Eur. J. Org. Chem. 2012, 1351-1359
24. Muniz-Medina, V. M.; Jones, S.; Maglich, J. M.; Galardi, C.; Hollingsworth, R. E.; Kazmierski, W. M.; Ferris, R. G.; Edelstein, M. P.; Chiswell, K. E.; Kenakin, T. P. The relative activity of "function sparing" HIV-1 entry inhibitors on viral entry and CCR5 internalization: is allosteric functional selectivity a valuable therapeutic property? Mol. Pharmacol. 2009, 75, 490-501
25. Aly, A.; Debbab, A.; Clements, C.; Edrada-Ebel, R.; Orlikova, B.; Diederich, M.; Wray, V.; Lin, W. H.; Proksch, P. NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum Bioorg. Med. Chem. 2011, 19, 414-421
26. Ebrahim, W.; Aly, A. H.; Mandi, A.; Totzke, F.; Kubbutat, M. H. G.; Wray, V.; Lin, W. H.; Dai, H.; Proksch, P.; Kurtan, T.; Debbab, A. Decalactone derivatives from Corynespora cassiicola, an endophytic fungus of the mangrove plant Laguncularia racemosa Eur. J. Org. Chem. 2012, 3476-3484
27. Hammerschmidt, L.; Wray, V.; Lin, W. H.; Kamilova, E.; Proksch, P.; Aly, A. H. New styrylpyrones from the fungal endophyte Penicillium glabrum isolated from Punica granatum Phytochem. Lett. 2012, 5, 600-603
28. Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach, 3rd ed.; John Wiley & Sons Ltd: Baffins Lane, Chichester, England, 2009; pp 104.
29. Atherton, J.; Bycroft, B. W.; Roberts, J. C.; Roffey, P.; Wilcox, M. E. Studies in mycological chemistry. XXIII. The structure of flavomannin, a metabolite of Penicillium wortmanni Kloeck J. Chem. Soc. C 1968, 2560-2564
30. Ren, X.; Dong, Y.; Zhang, H.; Lu, X.; Zheng, Z.; Liu, M.; He, J. Study on aldose reductase inhibitor F01-195A produced from fermentation broth of microorganism J. Hebei Univ. Nat. Sci. Ed. 2006, 26, 7-10
31. Antonowitz, A.; Gill, M.; Morgan, P. M.; Yu, J. Coupled anthraquinones from the toadstool Dermocybe icterinoides Phytochemistry 1994, 37, 1679-1683
32. Gill, M.; Morgan, P. M. Pigments of fungi. Part 73. Absolute stereochemistry of fungal metabolites: icterinoidins A1 and B1, and atrovirins B1 and B2 ARKIVOC 2004, 152-165
33. Beattie, K.; Elsworth, C.; Gill, M.; Milanovic, N. M.; Prima-Putra, D.; Raudies, E. Austrocolorins A1 and B1: atropisomeric 10,10′-linked dihydroanthracenones from an Australian Dermocybe sp Phytochemistry 2004, 65, 1033-1038
34. Elsässer, B.; Krohn, K.; Flörke, U.; Root, N.; Aust, H.-J.; Draeger, S.; Schulz, B.; Antus, S.; Kurtán, T. X-ray structure determination, absolute configuration and biological activity of phomoxanthone A Eur. J. Org. Chem. 2005, 4563-4570
35. Polavarapu, P. L.; Jeirath, N.; Kurtán, T.; Pescitelli, G.; Krohn, K. Determination of the absolute configurations at stereogenic centers in the presence of axial chirality Chirality 2009, 21, E202-E207
36. Gill, M.; Gimenez, A.; McKenzie, R. W. Pigments of fungi, part 8. Bianthraquinones from Dermocybe austroveneta J. Nat. Prod. 1988, 51, 1251-1256
37. Takeda, N.; Seo, S.; Ogihara, Y.; Sankawa, U.; Iitaka, I.; Kitagawa, I.; Shibata, S. Studies on fungal metabolites-XXXI: Anthraquinonoid colouring matters of Penicillium islandicum sopp and some other fungi (-)luteoskyrin, (-)rubroskyrin, (+)rugulosin and their related compounds Tetrahedron 1973, 29, 3703-3719
38. Elsworth, C.; Gill, M.; Giménez, A.; Milanovic, N. M.; Raudies, E. Pigments of fungi. Part 50. Structure, biosynthesis and stereochemistry of new dimeric dihydroanthracenones of the phlegmacin type from Cortinarius sinapicolor Cleland J. Chem. Soc., Perkin Trans. 1 1999, 119-126
39. Arai, K.; Aoki, Y.; Yamamoto, Y. Asperinines A and B, dimeric tetrahydroanthracene derivatives from Aspergillus ruber Chem. Pharm. Bull. 1989, 37, 621-625
40. Gill, M.; Gimenez, A.; Jhingran, A. G.; Smrdel, A. F. Pigments of fungi. Part 10. Dihydroanthracenones from Dermocybe splendida and related fungi Phytochemistry 1989, 28, 2647-2650
41. Gill, M.; Gimenez, A.; Jhingran, A. G.; Palfreyman, A. R. Pigments of fungi. Part 19. A degradative method for the determination of central chirality in naturally occurring 3-hydroxy-3-methyl-3,4-dihydroanthracen-1(2 H)-ones: application to pigments of the flavomannin type Tetrahedron 1990, 1, 621-634
42. Gill, M.; Saubern, S.; Yu, J. Pigments of fungi. LXVI. The gentiobiosides of (R)- and (S)-torosachrysone from Australian toadstools and methods for assaying the enantiomeric purity of natural torosachrysone Aust. J. Chem. 2000, 53, 213-220
43. Gill, M.; Morgan, P. M. New fungal anthraquinones ARKIVOC 2001, 7, 145-156
44. Müller, M.; Lamottke, K.; Steglich, W.; Busemann, S.; Reichert, M.; Bringmann, G.; Spiteller, P. Biosynthesis and stereochemistry of phlegmacin-type fungal pigments Eur. J. Org. Chem. 2004, 4850-4855
45. Wanjohi, J. M.; Yenesew, A.; Midiwo, J. O.; Heydenreich, M.; Peter, M. G.; Dreyer, M.; Reichert, M.; Bringmann, G. Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica Tetrahedron 2005, 61, 2667-2674
46. Takahashi, S.; Kitanaka, S.; Takido, M.; Sankawa, U.; Shibata, S. Phlegmacins and anhydrophlegmacinquinones: dimeric hydroanthracenes from seedlings of Cassia torosa Phytochemistry 1977, 14, 999-1002
47. Endo, M.; Naoki, H. Antimicrobial and antispasmodic tetrahydroanthracenes from Cassia singueana Tetrahedron 1980, 36, 2449-2452
48. Kitanaka, S.; Takido, M. Two new bitetrahydroanthracenes from roots of Cassia occidentalis L Chem. Pharm. Bull. 1989, 37, 511-512
49. Dreyer, D. L.; Arai, I.; Bachman, C. D.; Anderson, W. R., Jr.; Smith, R. G.; Daves, G. D., Jr. Toxins causing noninflammatory paralytic neuronopathy. Isolation and structure elucidation J. Am. Chem. Soc. 1975, 97, 4985-4990
50. Rivas, V.; Cuevas, G.; Garza, L.; Waksman, N. Isolation and evaluation of the cytotoxic properties of peroxisomicine isomers from Karwinskia parvifolia ARKIVOC 2005, 224-233
51. Salazar, R.; Rivas, V.; González, G.; Waksman, N. Antimicrobial activity of coupled hydroxyanthracenones isolated from plants of the genus Karwinskia Fitoterapia 2006, 77, 398-400
52. Stierle, A.; Strobel, G. A.; Stierle, D. Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew Science 1993, 260, 214-216
53. Kusari, S.; Lamshöft, M.; Zühlke, S.; Spiteller, M. An endophytic fungus from Hypericum perforatum that produces hypericin J. Nat. Prod. 2008, 71, 159-162
54. Kusari, S.; Zühlke, S.; Kosuth, J.; Cellarova, E.; Spiteller, M. Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis J. Nat. Prod. 2009, 72, 1825-1835
55. Lin, L.-C.; Chou, C.-J.; Kuo, Y.-C. Cytotoxic principles from Ventilao leiocarpa J. Nat. Prod. 2001, 64, 674-676
56. Lee, N.-J.; Choi, J.-H.; Koo, B.-S.; Ryu, S.-Y.; Han, Y.-H.; Lee, S.-I.; Lee, D.-U. Antimutagenicity and cytotoxicity of the constituents from the aerial parts of Rumex acetosa Biol. Pharm. Bull. 2005, 28, 2158-2161
57. Tan, J.-H.; Zhang, Q.-X.; Huang, Z.-S.; Chen, Y.; Wang, X.-D.; Gu, L.-Q.; Wu, J. Y. Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives Eur. J. Med. Chem. 2006, 41, 1041-1047
58. Liu, F.; Cai, X.-L.; Yang, H.; Xia, X.-K.; Guo, Z.-Y.; Yuan, J.; Li, M.-F.; She, Z.-G.; Lin, Y.-C. The bioactive metabolites of the mangrove endophytic fungus Talaromyces sp. ZH-154 isolated from Kandelia candel (L.) druce Planta Med. 2010, 76, 185-189
59. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, 8th ed.; Approved Standard M7-A8; Clinical and Laboratory Standards Institute (CLSI), 2008.
60. Bandow, J. E.; Brötz, H.; Leichert, L. I.; Labischinski, H.; Hecker, M. Proteomic approach to understanding antibiotic action Antimicrob. Agents Chemother. 2003, 47, 948-955
61. Freiberg, C.; Brunner, N.; Macko, L.; Fischer, H. P. Discovering antibiotic efficiacy biomarkers: toward mechanism-specific high content compound screening Mol. Cell. Proteomics 2006, 5, 2326-2335
62. Brötz-Oesterhelt, H.; Beyer, D.; Kroll, H.-P.; Endermann, R.; Ladel, C.; Schroeder, W.; Hinzen, B.; Raddatz, S.; Paulsen, H.; Henninger, K.; Bandow, J. E.; Sahl, H.-G.; Labischinski, H. Dysregulation of bacterial proteolytic machinery by a new class of antibiotics Nature Med. 2005, 11, 1082-1087
63. Freiberg, C.; Fischer, H. P.; Brunner, N. A. Discovering the mechanism of action of novel antibacterial agents through transcriptional profiling of conditional mutants Antimicrob. Agents Chemother. 2005, 49, 749-759
64. Sass, P.; Josten, M.; Famulla, K.; Schiffer, G.; Sahl, H.-G.; Hamoen, L.; Brötz-Oesterhelt, H. Antibiotic acyldepsipeptides activate ClpP peptidase to degrade the cell division protein FtsZ Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 17474-17479
65. Wenzel, M.; Patra, M.; Albrecht, D.; Chen, D. Y.; Nicolaou, K. C.; Metzler-Nolte, N.; Bandow, J. E. Proteomic signature of fatty acid biosynthesis inhibition available for in vivo mechanism-of-action studies Antimicrob. Agents Chemother. 2011, 55, 2590-2596
66. Urban, A.; Eckermann, S.; Fast, B.; Metzger, S.; Gehling, M.; Ziegelbauer, K.; Rübsamen-Waigmann, H.; Freiberg, C. Novel whole-cell antibiotic biosensors for compound discovery Appl. Environ. Microbiol. 2007, 73, 6436-6443
67. + gene Biochimie 1992, 74, 755-762
68. Delumeau, O.; Lecointe, F.; Mutel, J.; Guillot, A.; Guédon, E.; Monnet, V.; Hecker, M.; Becher, D.; Polard, P.; Noirot, P. The dynamic protein partnership of RNA polymerase in Bacillus subtilis Proteomics 2011, 11, 2992-3001
69. Mascher, T.; Zimmer, S. L.; Smith, T.-A.; Helmann, J. D. Antibiotic-inducible promoter regulated by the cell envelope stress-sensing two-component system LiaRS of Bacillus subtilis Antimicrob. Agents Chemother. 2004, 48, 2888-2896
70. Pietiäinen, M.; Gardemeister, M.; Mecklin, M.; Leskelä, S.; Sarvas, M.; Kontinen, V. P. Cationic antimicrobial peptides elicit a complex stress response in Bacillus subtilis that involves ECF-type sigma factors and two-component signal transduction systems Microbiology 2005, 151, 1577-1592
71. Wolf, D.; Kalamorz, F.; Wecke, T.; Juszczak, A.; Mäder, U.; Homuth, G.; Jordan, S.; Kirstein, J.; Hoppert, M.; Voigt, B.; Hecker, M.; Mascher, T. In-depth profiling of the LiaR response of Bacillus subtilis J. Bacteriol. 2010, 192, 4680-4693
72. Torres, C.; Galián, C.; Freiberg, C.; Fantino, J. R.; Jault, J. M. The YheI/YheH heterodimer from Bacillus subtilis is a multidrug ABC transporter Biochim. Biophys. Acta 2009, 1788, 615-622
73. Lazarevic, V.; Dusterhoft, A.; Soldo, B.; Hilbert, H.; Mauel, C.; Karamata, D. Nucleotide sequence of the Bacillus subtilis temperate bacteriophage SPbetac2 Microbiology 1999, 145, 1055-1067
74. Au, N.; Kuester-Schoeck, E.; Mandava, V.; Bothwell, L. E.; Canny, S. P.; Chachu, K.; Colavito, S. A.; Fuller, S. N.; Groban, E. S.; Hensley, L. A.; O'Brien, T. C.; Shah, A.; Tierney, J. T.; Tomm, L. L.; O'Gara, T. M.; Goranov, A. I.; Grossman, A. D.; Lovett, C. M. Genetic composition of the Bacillus subtilis SOS system J. Bacteriol. 2005, 187, 7655-7666
75. Yasbin, R. E. DNA repair in Bacillus subtilis. II. Activation of the inducible system in competent bacteria Mol. Gen. Genet. 1977, 153, 218-225
76. Yasbin, R. E. DNA repair in Bacillus subtilis. I. The presence of an inducible system Mol. Genet. 1977, 153, 211-218
77. Yasbin, R. E.; Andersen, B. J. DNA repair in Bacillus subtilis: the identification of a strain temperature inducible for SOS functions. In Molecular Cloning and Gene Replication in the Bacilli; Ganesan, A. T.; Hoch, J.; Chang, S., Eds.; Academic Press Inc.: New York, 1982; pp 237-247.
78. Love, P. E.; Yasbin, R. E. Genetic characterization of the inducible SOS-like system of Bacillus subtilis J. Bacteriol. 1984, 160, 910-920
79. Drlica, K.; Zhao, X. DNA gyrase, topoisomerase IV, and the 4-quinolones Microbiol. Mol. Biol. Rev. 1997, 61, 377-392
80. Polavarapu, P. L.; Shanmugam, G. A comparison of mid-infrared Fourier transform vibrational circular dichroism measurements with single and dual polarization modulations Chirality 2011, 23, 801-807
81. Debbab, A.; Aly, A. H.; Edrada-Ebel, R.; Wray, V.; Mueller, W. E.; Totzke, F.; Zirrgiebel, U.; Schaechtele, C.; Kubbutat, M. H.; Lin, W. H.; Mosaddak, M.; Hakiki, A.; Proksch, P.; Ebel, R. Bioactive metabolites from endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium J. Nat. Prod. 2009, 72, 626-631
82. Kjer, J.; Debbab, A.; Aly, A. H.; Proksch, P. Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products Nature Protoc. 2010, 5, 479-490
83. Burkholder, P. R.; Giles, N. H. Induced biochemical mutations in Bacillus subtilis Am. J. Bot. 1947, 34, 345-348
84. Hiramatsu, K.; Hanaki, H.; Ino, T.; Yabuta, K.; Oguri, T.; Tenover, F. C. Methicillin-resistant Staphylococcus aureus clinical strain with reduced vancomycin susceptibility J. Antimicrob. Chemother. 1997, 40, 135-136
85. Klare, I.; Heier, H.; Claus, H.; Böhme, G.; Marin, S.; Seltmann, G.; Hakenbeck, R.; Antanassova, V.; Witte, W. Enterococcus faecium strains with vanA -mediated high-level glycopeptide resistance isolated from animal foodstuffs and fecal samples of humans in the community Microb. Drug Resist. 1995, 1, 265-272
86. Henrichfreise, B.; Wiegand, I.; Sherwood, K. J.; Wiedemann, B. Detection of VIM-2 metallo-beta-lactamase in Pseudomonas aeruginosa from Germany Antimicrob. Agents Chemother. 2005, 49, 1668-1669
87. Stülke, J.; Hanschke, R.; Hecker, M. Temporal activation of beta-glucanase synthesis in Bacillus subtilis is mediated by the GTP pool J. Gen. Microbiol. 1993, 139, 2014-2045
88. Miller, J. H. Experiments in Molecular Genetics; Laboratory Press: Cold Spring Harbor, NY, 1972.
89. MacroModel; Schrödinger LLC, 2009; http://www.schrodinger.com/ Products/macromodel.html.
90. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E., Jr.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford CT, 2010.
91. Stephens, P. J.; Harada, N. ECD cotton effect approximated by the Gaussian curve and other methods Chirality 2010, 22, 229-233
92. Varetto, U. MOLEKEL 5.4; Swiss National Supercomputing Centre: Manno, Switzerland, 2009.