Bacterial RNA polymerase inhibitors: An organized overview of their structure, derivatives, biological activity and current clinical development status

Current Medicinal Chemistry

Volumn 16, Issue 4, 2009, Pages 430-454

  Mariani, Riccardo ^a   Maffioli, S I ^b  

^a Gentium SpA   (Italy)

^b NAICONS Srl   (Italy)

Author keywords

Antibacterial agents; Antibiotics; Inhibitors; Rifamycins; RNA polymerase; RNAP; SAR

Indexed keywords

ABI 0043; ANTIINFECTIVE AGENT; CALOTHRIXIN; CLOSTOMICIN; CORALLOPYRININE DERIVATIVE; DAUNORUBICIN; ETNANGIEN; GE 23077; HAPALINDOLE ISONITRILE; LIPIARMYCIN; MARCELLOMYCIN; MICROCIN; MIXOPYRONIN DERIVATIVE; PAROMOMYCIN; PYRROTHINE DERIVATIVE; RIFABUTIN; RIFALAZIL; RIFAMPICIN; RIFAMYCIN; RIFAPENTIN; RIPOSTATIN DERIVATIVE; RNA POLYMERASE INHIBITOR; SALINAMIDE; SORANGICIN; STREPTOLYDIGIN; TAGETITOXIN; TIACUMICIN B; TIACUMICIN DERIVATIVE; TOLYPOMYCIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; UREIDOTHIOPHENE; DNA DIRECTED RNA POLYMERASE; ENZYME INHIBITOR;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; BACTERIAL INFECTION; BACTERIAL STRAIN; CLINICAL TRIAL; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG RESPONSE; DRUG SCREENING; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTEIN TARGETING; REVIEW; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; AMINO ACID SEQUENCE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; GENETICS; METABOLISM; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; DNA-DIRECTED RNA POLYMERASES; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 63449096360     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709787315559     Document Type: Review

References (173)

1. Karam, G. H.; Heffner, J. Emerging Issues in Antibiotic Resistance in Blood-borne Infections. Am. J. Resp. Crit. Care Med., 2000, 162, 1610-6.
2. Yoneyama, H.; Katsumata, R. Antibiotic resistance in bacteria and its future for novel antibiotic development. Biosci. Biotechnol. Biochem., 2006, 70(5), 1060-75.
3. Werner, F.; Floranta, J.J.; Weinzierl, R.O.J. Archeal RNA polymerase subunits F and P are bona fide homologs of eukaryotic RPB4 and RPB12. Nucl. Ac. Res., 2000, 28, 4299-305.
4. Werner, F.; Weinzierl, R.O.J. A recombinant RNA polymerase II-like enzyme capable of promoter-specific transcription. Mol. Cell, 2002, 10, 635-46.
5. Landick, R. A Long time in the making - the nobel prize for RNA polymerase. Cell, 2006, 127, 1087-90.
6. Vassylyev, D.G.; Artsimovitch, I. Tracking RNA Polymerase,One Step at a Time. Cell, 2005, 123, 977-9.
7. Campbell, E.A.; Westblade, L.F.; Darst, S.A. Regulation of bacterial RNA polymerase s factor activity: A structural perspective. Curr. Opin. Microbiol., 2008, 11, 121-7.
8. Burgess, R.; Anthony, L. How sigma docks to RNA polymerase and what sigma does. Curr. Opin. Microb., 2001, 4, 126-31.
9. Darst, S. Bacterial RNA polymerase. Curr. Opin. Struct. Biol., 2001, 11, 155-62.
10. Cramer, P. Multisubunit RNA polymerases. Curr. Opin. Struct. Biol., 2002, 12, 89-97.
11. Spirin, A.S. RNA polymerase as a molecular machine. Mol. Biol., 2002, 36(2), 153-9.
12. Borukhov, S.; Nudler E. RNA polymerase holoenzyme: Structure, function and biological implications. Curr. Opin. Microb., 2003, 6, 93-100.
13. Murakami, K.; Darst, S. Bacterial RNA polymerases: The wholo story. Curr. Opin. Struct. Biol., 2003, 13, 31-9.
14. Landick, R. Active-site dynamics in RNA polymerases. Cell, 2004, 116, 35-3.
15. Vassylyev, D.G. TimeTracking RNA Polymerase, One Step at a Time. Cell, 2005, 123, 977-9.
16. Landick R. A long time in the making - the nobel prize for RNA polymerase. Cell, 2006, 127, 1087-90.
17. Roberts, J.W. RNA polymerase, a scrunching machine. Science, 2006, 314, 1097-8.
18. Darst, S.E. New inhibitors targeting bacterial RNA polymerase. Trends Biochem. Sc., 2004, 29, 159-62.
19. Zorov, S.D.; Yuzenkova, J.V.; Severinov, K.V. Low-molecular-weight inhibitors of bacterial DNA-dependent RNA polymerase. Mol. Biol., 2006, 40, 875-84.
20. Chopra, I. Bacterial RNA polymerase: A promising target for the discovery of new antimicrobial agents. Curr. Op. Invest. Drugs., 2007, 8, 600-7.
21. Villain-Guillot, P.; Bastide, L.; Gualtieri, M.; Leonetti, J-P. Progress in targeting bacterial transcription. Drugs Discov. Today, 2007, 12, 200-8.
22. Domecq, C.; Trinh, V.; Langelier, M-F.; Archambault, J.; Coulombe, B. Inhibitors of multisubunit RNA polymerases as tools to study transcriptional mechanisms in prokaryotes and eukaryotes. Curr. Chem. Biol., 2008, 2, 21-32.
23. Agarwal, A.K.; Johnson, E.P.; Fishwick, C.W.G. Synthesis of de novo designed small-molecule inhibitors of bacterial RNA polymerase. Tetrahedron, 2008, 64, 10049-54
24. Higashide, C.; Asai, M.; Ootsu, K.; Tanida, S.; Kozai, Y.; Hasegawa, T.; Kishi, T.; Sugino, Y.; Yoneda, M. Ansamitocin, a group of novel maytansinoid antibiotics with antitumour properties from Nocardia. Nature, 1977, 270, 721-2.
25. Deboer, C.; Meulman, P.; Wnuk, R.J.; Peterson, D.H. Geldanamycin. A new antibiotic. J. Antibiot., 1970, 23, 442-7.
26. Williams T.H. Naphthomycin, a novel ansa macrocyclic antimetabolite, proton NMR spectra and structure elucidation. J. Antibiot., 1975, 28, 85-6.
27. Brufani, M.; Cellai, L.; Keller-Schierlein, W. Degradation studies of Naphthomycin. J. Antibiot., 1979, 32, 167-8.
28. Keller-Schierlein, W.; Meyer M.; Zeeck, A.; Damberg, M.; Machinek, R.; Zahner, H.; Lazar, G. Isolation and structural elucidation of Naphthomycin B and C. J. Antibiot. 1983, 36, 484-92.
29. Yamazaki, H.; Mizuno, S.; Nitta, K.; Utahara, R.; Umezawa, H. Biochemical mechanism of action of substance B44P J. Antibiot., 1968, 21, 63-5.
30. Rinehart, K.L.Jr.; Maheshwari, M.L.; Antosz, F.Z.; Mathur, H.H.; Sasaki, K.; Schacht, R.J. Chemistry of the Streptovaricins. VIII. Structures of Streptovaricins A, B, D, E, F, and G. J. Am. Chem. Soc., 1971, 93, 6273-4.
31. Logan, K.; Zhang, J.; Davis, E.A., Ackerman, S. Drug inhibitors of RNA polymerase II transcription. DNA, 1989, 8, 595-604.
32. Brockmann, W.W.; Carter, W.A.; Li, L.H.; Reusser, F.; Nichol, F.R. Streptovaricins inhibit RNA dependent DNA polymerase present in an oncogenic RNA virus. Nature, 1971, 230, 249-50
33. Sensi, P.; Timbal, M.T.; Maffii, G. Two new antibiotics of rifamycin family: Rifamycin S and rifamycin SV. Preliminary report. Experentia, 1960, 16, 412-4.
34. Sensi, P. History of the development of Rifampin. Rev. Infect. Dis., 1983, 5, S402-6.
35. Margalith, P.; Beretta, G. Rifamycin XI: Taxonomic study on Streptomyces mediterranei nov. sp. Mycopathol. Mycol. Appl., 1960, 13, 321-30.
36. Thiemann, J.E.; Zucco, G.; Pelizza, G. A protoplast for the transfer of Streptomyces mediterranei to the genus Nocardia mediterranei. Comb. Nov. Arch. Mikrobiol., 1969, 67, 147-55.
37. Lechevalier, M.P.; Prauser, H.; Labeda, D.P.; Ruan, J.S. Two new genera of nocardioform actinomycetes: Amycolata gen. nov. and Amycolatopsis gen. nov. Int. J. Syst. Bacteriol., 1986, 32, 29-37.
38. Floss, H.G.; Yu, T.W. Rifamycins mode of action, resistance, and biosynthesis. Chem. Rev., 2005, 105, 621-32.
39. Bellomo, P.; Brufani, M.; Marchi, E.; Mascellani, G. Melloni, W.; Montecchi, L.; Stanzani, L. Synthesis and antibacterial activity of some derivatives of tolypomycinone. Relationship between structure and activity in ansamycins. J. Med. Chem., 1977, 20, 1287-91.
40. Ganguly, A.K.; Liu, Y.T.; Sarre, O.Z. Szmulewicz, S. Structure of Halomicins A and C. J. Antibiot., 1977, 30, 625-7
41. Arora, S.K.; Kook, A.M. Structure and Conformation of Halomycin B in Solid State and Solution. J. Org. Chem., 1987, 52, 1530-5.
42. Brizzi, V.; Brufani, M.; Celai, L.; Segre, A. Chemical modifications of the aliphatic bridge of ansamycins. Synthesis and activity of 25-deacetoxy-25-epi-hydroxyRifamycins S. J. Antibiot., 1983, 36, 516-21.
43. Brufani, M.; Cellai, L.; Cozzella, L.; Federici, M.; Guiso, M.; Segre, A. Chemical modifications of the aliphatic bridge of Ansamycins 3. Synthesis and activity of 21-epi-Rifamycin S. J. Antibiot., 1985, 38, 1359-62.
44. Brufani, M.; Cecchini, G.; Cellai, L.; Federici, M.; Guiso, M.; Segre, A.L. Chemical modifications of the aliphatic bridge of ansamycins. 2. Synthesis and activity of 23-epi-25-deacetylrifamycin S. J. Antibiot., 1985, 38, 259-62.
45. Quan, S.; Imai, T.; Mikami, Y.; Yazawa, K.; Dabbs, E.R.; Morisaki, N.; Iwasaki, S.; Hashimoto, Y.; Furihata, K. ADP-Ribosylation as an Intermediate Step in Inactivation of Rifampin by a Mycobacterial Gene. Antimicrob. Agents Chemother., 1999, 43, 181-4
46. Marsili, L.; Franceschi, G.; Ballabio, M.; Oronzo, G.; Vigevani, A.; Ungheri, D.; DellaBruna, C.; Sanfilippo, A. Novel rifamycins. III: Synthesis and antibacterial activity of 3-amidino- and of 4-aminoimidazolo [4,5-c]rifamycin derivatives. J. Antibiot., 1983, 36, 1495-501.
47. Marsili, L.; Franceschi, G.; Ballabio, M.; Vioglio, S.; Vigevani, A.; Ungheri, D.; DellaBruna, C.; Sanfilippo, A. Novel Rifamycins IV. 3-Aminomethylaazinomethylrifamycins, a new class of Rifamycins, endowed with remarkable antibacterial activity. J. Antibiot., 1984, 37, 1209-12.
48. Bellomo, P.; Marchi, E.; Mascellani, G.; Brufani, M. Synthesis and Antibacterial Activity of Some esters, Amides, and Hydrazides of 3-Carboxyrifamycin S. Relationship between Structure and Activity of Ansamycins. J. Med. Chem., 1981, 24, 1310-4.
49. Bartolucci, C.; Cellai.; Martuccio, C.; Rossi. A.; Segre, A.L.; Savu, S.R.; Silvestro, L. Synthesis of Glycosylrifamycins, a New Type of Semisynthetic Rifamycins. Helv. Chim. Acta, 1996, 79, 1611-9.
50. Jarvis, B.; Lamb, H.M. Rifapentin. Drugs, 1998, 56, 607-16.
51. Dimov, D.; Nedyalkova, Z.; Haladjova, S.; Schuurmann, G.; Makenyan, O. QSAR modeling of antimycobacterial activity and activity against other bacteria of 3-formyl rifamycin SV derivatives. Quant. Struct.-Act. Relat., 2001, 20, 298-318.
52. 1H-NMR. Mol. Pharmacol., 1984, 27, 103-8.
53. Marchi, E.; Montecchi, L.; Venturini, A.P.; Mascellani, G.; Brufani, M. 4-Deoxypyrido[1′,2′:1,2] imidazo [5,4-c]rifamycin SV derivatives. A new series of semisynthetic rifamycins with high antibacterial activity and low gastroenteric absorption. J. Med. Chem., 1985, 28, 960-3.
54. Cellai, L.; Cerrini, S.; Segre, A.L.; Battistoni, C.; Cossu, G.; Mattogno, G.; Brufani, M.; Marchi, E.; Venturini, A.P. Structure-Activity Relationships in 4-deoxypyrido[1′,2′-1,2]imidazo[5,4-c]rifamycin SV derivatives. Il FARMACO, 1989, 44, 97-107.
55. Cavalleri, B.; Turconi, M.; Tamborini, G.; Occelli, E.; Cietto, G.; Pallanza, R.; Scotti, R.; Berti, M.; Romano, G.; Parenti, F. Synthesis and Biological Activity of Some derivatives of Rifamycin P. J. Med. Chem., 1990, 33, 1470-6.
56. Della Bruna, C.; Schioppacassi, G.; Ungheri, D.; Jabes, D.; Morvillo, E.; Sanfilippo, A.; LM 427, a new spiropiperidylrifamycin: in vitro and in vivo studies. J. Antibiot., 1983, 36, 1502-6.
57. Adachi, J.A.; DuPont, H.L. Rifaximin: A novel nonabsorbed rifamycin for gastrointestinal disorders. Clin. Infect. Dis., 2006, 42, 541-7.
58. Robins G.W.; Wellington, K.; Rifaximin. A review of its use in the management of traveller's diarrhoea. Drugs, 2005, 65, 1697-713.
59. Brodgen, R.N.; Fitton, A. Rifabutin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs, 1994, 47, 983-1009.
60. Rothstein, D.M.; Shalish, C.; Murphy, C.K.; Sternlicht, A.; Campbell, L.A. Development potential of rifalazil and other benzoxazinorifamycins. Expert Opin. Investig. Drugs, 2006, 15, 603-23.
61. Dietze, R.; Teixeira, L.; Rocha, L. M.; Palaci, M.; Johnson, J.L.; Wells, C.; Rose, L.; Eisenach, K.; Ellner, J.J. Safety and bactericidal activity of rifalazil in patients with pulmonary tuberculosis. Antimicrob. Agents Chemother., 2001, 45, 1972-6.
62. Rothstein, D.M.; Hartman, A.D., Cynamon, M.H.; Eisenstein, B.I.; Development potential of rifalazil. Expert Opin. Investig. Drugs, 2003, 12, 255-71.
63. Suchland R.J.; Bourillon, A.; Denamur, E.; Stamm, W.E.; Rothstein, D.M. Rifampin-resistant RNA polymerase mutants of Chlamydia trachomatis remain susceptible to the ansamycin rifalazil. Antimicrob. Agents Chemother., 2005, 49, 1120-26.
64. Yang, B.; Koga, H.; Ogawa, K.; Fukuda, M.; Hirakata, Y.; Maesaki, S.; Tomono, K.; Tashiro, T.; Kohno, S. Relationship between antimycobacterial activities of rifampicin, Rifabutin and KRM-1648 and rpoB mutations of Mycobacterium tubercolosis. J. Antimicrob. Chemother., 1998, 42, 621-8.
65. Wichelhaus, T.A.; Schafer, V.; Brade, V.; Boddinghaus, B. Differential effect of rpoB mutations on antibacterial activities of rifampicin and KRM-1648 against Staphylococcus aureus. J. Antimicrob. Chemother., 2001, 47, 153-6.
66. Murphy, C.M.; Mullin, S.; Osburne, M.S.; Van Duzer, J.; Siedlecki, J.; Yu, X.; Kerstein, K.; Cynamon, M.; Rothstein, D.M. In vitro Activity of Novel Rifamycins against Rifamycin-Resistant Staphylococcus aureus. Antimicrob. Agents Chemother., 2006, 50, 827-34.
67. Trampuz, A.; Murphy, C.K.; Rothstein, D.M.; Widmer, A.F.; Landmann, R.; Zimmerli, W. Efficacy of a Novel Rifamycin Derivative, ABI-0043, against Staphylococcus aureus in an Experimental Model of Foreign-Body Infection. Antimicrob. Agents Chemother., 2007, 51, 2540-5.
68. Rothstein, D.M.; Farquhar, R.S.; Sirokman, K.; Sondergaard, K.L.; Hazlett, C.; Doye, A.A.; Gwathwey, J.K.; Mullin, S.; Van Duzer, J.; Murphy, C.K. Efficacy of Novel Rifamycin Derivatives against Rifamycin-Sensitive and -Resistant Staphylococcus aureus Isolates in Murine Models of Infection. Antimicrob. Agents Chemother., 2006, 50, 3658-64.
69. Barluenga, J.; Aznar, F.; Garcia, A.B.; Cabal, M.P.; Palacios, J.J.; Menéndez, M.A., New rifabutin analogs: Synthesis and biological activity against Mycobacterium tuberculosis. Biorg. Med. Chem. Lett., 2006, 16, 5717-22.
70. Kim, I.H.; Combrick, K.D.; Ma, Z.; Chapo, K.; Yan, D.; Renick, P.; Morris, T.W.; Pulse, M.; Simecka, J.W.; Ding, C.Z. Synthesis and antibacterial evaluation of a novel series of rifabutin-like spirorifamycins. Bioorg. Med. Chem. Lett., 2007, 17, 1181-4.
71. Li, J.; Ma, Z.; Chapo, K.; Yan, D.; Lynch, A.S.; Ding, C.Z. Preparation in vitro anti-staphylococcal activity of novel 11-deoxy-11-hydroxyiminorifamycins. Bioorg. Med. Chem. Lett., 2007, 17, 5510-3.
72. Combrink, K.D.; Denton, D.A.; Harran, S.; Ma, Z.; Chapo, K.; Yan, D.; Bonentre, E.; Roche, E.; Doyle, T.B.; Robertson, G.T.; Lunch, A.S. New C25 carbamate rifamycin derivatives are resistant to inactivation by ADP-ribosyl transferases. Bioorg. Med. Chem. Lett., 2007, 17, 522-6
73. Sippel, A.; Hartmann, G. Mode of action of rifamycin on the RNA polymerase reaction. Biochim. Biophys. Acta, 1968, 157, 218-9.
74. Boyd, D.H.; Zillig, W. Reference mutations for the beta subunit of RNA polymerase. Mol. Gen. Genet,. 1974, 130, 315-20
75. Kawai, M.; Ishihama, A.; Yura, T. RNA polymerase mutants of Escherichia coli. III. A temperature-sensitive rifampicin-resistant mutant. Mol. Gen. Genet., 1976, 143, 233-41.
76. Ovchinnikov, Y.A.; Monastyrskaya, G.C.; Guriev, S.O.; Kalinina, N. F.; Sverdlov, E.D.; Gragerov, A.L.; Bass, I.A.; Kiver, I.F.; Moiseyeva, E.P.; Igumnov, V.N. RNA polymerase rifampicin resistance mutations in Escherichia coli: Sequence changes and dominance. Mol. Gen. Genet., 1983, 190, 344-8.
77. Severinov, K.; Soushko, M.; Goldfarb, A.; Nikiforov, V. Rifampicin Region Revisited. J. Biol. Chem., 1993, 268, 14820-5.
78. Severinov, K.; Soushko, M.; Goldfarb, A.; Nikiforov, V. RifR mutations in the beginning of the Escherichia coli rpoB gene. Mol. Gen. Genet., 1994, 244, 120-6.
79. Jin, D.J.; Gross, C.A. Mapping and sequencing of mutations in the E. coli rpoB gene that lead to rifampicin resistance. J. Mol. Biol., 1988, 202, 45-8.
80. Campbell, E.A.; Korzheva, N.; Mustaev, A.; Murakami, K.; Nair, S.; Goldfarb, A.; Darst, S.A. Structural mechanism for rifampicin inhibition of bacterial RNA polymerase. Cell, 2001, 104, 901-12.
81. Brufani, M.; Cellai, L.; Cerrini, S.; Fedeli, W.; Segre, A.; Vaciago, A. Structure-Activity Relationships in the Ansamycins. Molecular Structure and Activity of 3-Carbomethoxy Rifamycin S. Mol. Pharmacol., 1982, 21, 394-9.
82. Wehrli, W.; Staehelin, M. The rifamycins - relation of chemical structure and action on RNA polymerase. Biochim. Biophys. Acta, 1969, 182, 24-9.
83. Artsimovitch, I.; Vassylyeva, M.N.; Svetlov, D.; Svetlov, V.; Perederina, A.; Igarashi, N.; Matsugaki, N.; Wakatsuki, S.; Tahirov, T.H.; Vassylyev, D.G. Allosteric modulation of the RNA polymerase catalytic reaction is an essential component of transcription control by rifamycins. Cell, 2005, 122, 351-63.
84. Artsimovitch, I.; Vassylyev, D.G. Is it easy to stop RNA polymerase? Cell Cycle, 2006, 5, 399-404.
85. 2+ to the RNA polymerase active center. Proc. Natl. Acad. Sci. USA, 2008, 105, 14820-5.
86. Parenti, F.; Pagani, H.; Beretta, G. Lipiarmycin, a new antibiotic from Actinoplanes I. Description of the producer strain and fermentation studies. J. Antibiot., 1975, 28, 247-52.
87. Coronelli, C.; White, R.J.; Lancini, G.C.; Parenti, F. Lipiarmicin, a new antibiotic from Actinoplanes II. Isolation, chemical, biological and biochemical characterization. J. Antibiot., 1975, 28, 253-9.
88. Somma, S.; Pirali, G.; White, R.; Parenti, F. Lipiarmycin, a new antibiotic from Actinoplanes III. Mechanism of action. J. Antibiot., 1975, 28, 543-9.
89. Osburne, M.; Sonhensein, A. Inhibition by lipiarmycin of bacteriophage growth in Bacillus subtilis. J. Virol., 1980, 33, 945-53.
90. Sonenshein, A.; Alezander, H.; Rothstein, D.; Fisher, S. Lipiarmycin-resistant ribonucleic acid polymerase mutants of Bacillus subtilis. J. Bacteriol., 1977, 132, 73-9.
91. Gualtieri, M.; Villain-Guillot, P.; Latouche, J.; Leonetti, J-P.; Bastide, L. Mutation in the Bacillus subtilis RNA polymerase β subunit confers resistance to lipiarmycin. Antimicrob. Agents Chemother., 2006, 50, 401-2.
92. Johnson, A. Drug evaluation: OPT-80, a narrow-spectrum macrocyclic antibiotic. Curr. Opin. Invest. Drugs., 2007, 8, 168-73.
93. Ciciliato, I.; Corti, E.; Sarubbi, E.; Stefanelli, S.; Gastaldo, L.; Montanini, N.; Kurz, M.; Losi, D.; Marinelli, F.; Selva, E. Antibiotics GE23077, novel inhibitors of bacterial RNA polymerase I. taxonomy, isolation and characterization. J. Antibiotics, 2004, 57, 210-17.
94. Sarubbi, E.; Monti, F.; Corti, E.; Miele, A; Selva, E. Mode of action of the microbial metabolite GE23077, a novel potent and selective inhibitor of bacterial RNA polymerase. Eur. J. Biochem., 2004, 271, 3146-54.
95. Marazzi, A.; Kurz, M.; Stefanelli, S.; Colombo, L. Antibiotics GE23077, Novel Inhibitors of Bacterial RNA Polymerase II. Structure Elucidation. J. Antibiotics, 2005, 58, 260-7.
96. Mariani, R.; Granata, G.; Maffioli, S. I.; Serina, S.; Brunati, C.; Sosio, M.; Marazzi, A.; Vannini, A.; Patel, D.; White, R.; Ciabatti, R. Antibiotics GE23077, novel inhibitors of bacterial RNA polymerase. Part 3: Chemical derivatization. Biorg. Med. Chem. Lett., 2005, 15, 3748-52.
97. Siddhikol, C.; Erbstoeszer, J. W.; Weisblum, B. Mode of Action of Streptolydigin. J. Bacteriol., 1969, 9, 151-5.
98. Eble, T. E.; Large, C. M.; De Vries, W. H.; Crum, G. F.; Shell, J. W. Antibiotic Annual (1955-1956), Welch, H. and Marti-Ibanez, Ed.; Medical Encyclopedia, Inc.: New York, 1956; II, pp. 893-896.
99. Cassani, G.; Burgess, R. R.; Goodman, H. M.; Gold L. Inhibition of RNA polymerase by streptolydigin. Nat. New Biol., 1971, 230, 197-200.
100. McClure, W. R. On the Mechanism of Streptolydigin Inhibition of Escherichia coli RNA Polymerase. J. Biol. Chem., 1980, 255, 1610-6.
101. Heisler, L. M.; Suzuki, H.; Landick, R.; Gross, C. A. Four contiguous amino acids define the target for streptolydigin resistance in the β subunit of Escherichia coli RNA polymerase. J. Biol. Chem., 1993, 268, 25369-75.
102. Severinov, K.; Soushko, M.; Goldfarb, A.; Nikiforov, V. Rifampicin region revisited. J. Biol. Chem., 1993, 268, 14820-5.
103. Yang, X.; Price, C. W. Streptolydigin resistance can be conferred by alterations to either the β or β subunits of Bacillus subtilis RNA polymerase. J. Biol. Chem., 1995, 270, 23930-3.
104. Severinov, K.; Markov, D.; Severinova, E.; Nikiforov, V.; Landick, R.; Darst, S. A.; Goldfarb, A. Streptolydigin-resistant Mutants in an Evolutionarily Conserved Region of the β' Subunit of Escherichia coli RNA Polymerase. J. Biol. Chem., 1995, 270, 23926-29.
105. Vassylyev, D. G.; Sekine, S.; Laptenko, O.; Lee, J.; Vassylyeva, M. N.; Borukhov, S.; Yokoyama, S. Crystal structure of a bacterial RNA polymerase holoenzyme at 2.6 Å resolution. Nature, 2002, 417, 712-9.
106. Temiakov, D.; Zenkin, N.; Vassylyeva, M. N.; Perederina, A.; Tahirov, T. H.; Kashkina, E.; Savkina, M.; Zorov, S.; Nikiforov, V.; Igarashi, N.; Matsugaki, N.; Wakatsuki, S.; Severinov, K.; Vassylyev, D. G. Structural basis of transcription inhibition by antibiotic streptolydigin. Mol. Cell, 2005, 19, 655-66.
107. Tuske, S.; Sarafianos, S. G.; Wang, X.; Hudson, B.; Sineva, E.; Mukhopadhyay, J.; Birktoft, J. J.; Leroy, O.; Ismail, S.; Clark, A. D. Jr.; Dharia, C.; Napoli, A.; Laptenko, O.; Lee, J.; Borukhov, S.; Ebright, R. H.; Arnold, E. Inhibition of bacterial RNA polymerase by streptolydigin: Stabilization of a straight-bridge-helix activecenter conformation. Cell, 2005, 122, 541-52.
108. Xu, M.; Zhou, Y. N.; Goldstein, B. P.; Jin, D. J. Cross-Resistance of Escherichia coli RNA Polymerases Conferring Rifampin Resistance to Different Antibiotics. J. Bacteriol., 2005, 187, 2783-92.
109. Kyzer, S.; Zhang, J.; Landick, R. Inhibition of RNA Polymerase by Streptolydigin: No Cycling Allowed. Cell, 2005, 494-6.
110. Matsuo, K.; Kimura, M.; Kinuta, T.; Takai, N.; Tanaka, K. Synthesis and Antimicrobial Activities of 3-Acyltetramic Acid Derivatives. Chem. Pharm. Bull., 1984, 32, 4197-204.
111. Matsuo, K.; Kitaguchi, I.; Takata, Y.; Tanaka, K. Structure-activity relationships in tetramic acids and their copper (II) complexes. Chem. Pharm. Bull., 1980, 28, 2494-502.
112. Rosen, T.; Fernandes, P. B.; Marovich, M. A.; Shen, L.; Mao, J.; Pernet, A. G. Aromatic Dienoyl Tetramic Acids. Novel Antibacterial Agents with Activity against Anaerobes and Staphylococci. J. Med. Chem., 1989, 32, 1062-9.
113. Jansen, R.; Wray, V.; Irschik, H.; Reichenbach, H.; Hofle, G. Isolation and spectroscopic structure elucidation of sorangicin A, a new type of macrolide-polyether antibiotic from gliding bacteria. Tetrahedron Lett., 1985, 26, 6031-4.
114. Jansen, R.; Irshik, H.; Reichenbach, H.; Schomburg, D.; Wray, V.; Hofle, G. Antibiotics from gliding bacteria. XXXVII. Sorangicin A, a highly active antibiotic with novel macrocicle-polyether structure from Sorangium cellulosum, So cel2: Spectroscopic structure elucidation, crystal and solution structure. Leibigs Ann. Chem., 1989, 111-19.
115. Irshik, H.; Jansen, R.; Gerth, K.; Höfle, G.; Reichenbach, H. The sorangicins, novel and powerful inhibitors of eubacterial RNA polymerase isolated from myxobacteria. J. Antibiotics, 1985, 40, 7-13.
116. Campbell, E. A.; Pavlova, O.; Zenkin, N.; Leon, F.; Irschik, H.; Jansen, R.; Severinov, K.; Darst, S. Structural, functional, and genetic analysis of sorangicin inhibition of bacterial RNA polymerase. EMBO J, 2005, 24, 674-682.
117. Xu, M.; Zhou, Y. N.; Goldstein, B. P.; Jin, D. J. Cross-Resistance of Escherichia coli RNA Polymerases Conferring Rifampin Resistance to Different Antibiotics. J. Bacteriol., 2005, 187, 2783-92.
118. Römmele, G.; Wirz, G.; Solf, R.; Vosbeck, K.; Gruner, J.; Wehrli, W. Resistance of Escherichia coli to rifampicin and sorangicin A - a comparison. J. Antibiotics, 1990, 43, 88-91.
119. Jansen, R.; Schummer, D.; Irshik, H.; Hoefle, G. Antibiotics from gliding bacteria XLII. Chemical modification of Sorangicin A and structure-activity relationship I: Carboxy and hydroxyl group derivatives. Liebigs Ann. Chem., 1990, 975-88.
120. Salomon, R.A.; Farias, R.N. Microcin 25, a Novel Antimicrobial Peptide Produced by Escherichia coli. J. Bacteriol., 1992, 174, 7428-35.
121. Blond, A.; Péduzzi, J.; Goulard, C.; Chiuchiolo, M.J.; Barthélémy, M.; Pringent, Y.; Salomon, R.A.; Farias, R.N.; Moreno, F.; Rebuffat, S. The cyclic structure of microcin J25, a 21-residue peptide antibiotic from Escherichia coli. Eur. J. Biochem., 1999, 259, 747-55.
122. Blond, A.; Cheminant, M.; Ségalas-Milazzo, I.; Péduzzi, J.; Barthélémy, M.; Goulard, C.; Salomon, R.A.; Moreno, F.; Farias, R.N.; Rebuffat, S. Solution structure of microcin J25, the single acrocyclic antimicrobial peptide from Escherichia coli. Eur. J. Biochem., 2001, 268, 2124-33.
123. Wilson, K.A.; Kalkum, M.; Ottesen, J.; Yuzenkova, J.; Chait, B.T.; Landick, R.; Muir, T.; Severinov, K.; Darst, S.A. Structure of Microcin J25, a Peptide Inhibitor of Bacterial RNA Polymerase, is a Lassoed Tail J. Am. Chem. Soc., 2003, 125, 12475-83.
124. Rosengren, K.J.; Clark, R.J.; Daly, N.L.; Goransson, U.; Jones, A.; Craik, D.J: Microcin J25 has a threaded sidechain-to-backbone ring structure and not a head-to-tail cyclized backbone. J. Am. Chem. Soc., 2003, 125, 12464-74.
125. Bayro, M.J.; Mukhopadhyay, J.; Swapna, G.V.T.; Huang, J.Y.; Ma, L.C.; Sineva, E.; Dawson, P.E.; Montelione, G.T.; Ebright, R.H. Structure of Antibacterial Peptide Microcin J25: A 21-Residue Lariat Protoknot. J. Am. Chem. Soc., 2003, 125, 12382-3.
126. Bellomio, A.; Vincent, P.A.; de Arcuri, B.F.; Salomon, R.A.; Morero, R.D.; Farias, R.N. The microcin J25 β-hairpin region is important for antibiotic uptake but not for RNA polymerase and respiration inhibition. Biochem. Biophys. Res. Comm., 2004, 325, 1454-8.
127. Mukhopadhyay, J.; Sineva, E.; Knight, J.; Levy, R.M.; Ebright, R.H. Antibacterial peptide microcin J25 inhibits transcription by binding within and obstructing the RNA polymerase secondary channel. Mol. Cel., 2004, 14, 739-51.
128. Adelman, K.; Yuzenkova, J.; La Porta, A.; Zenkin, N.; Lee, J.; Lis, J.T.; Borukhov, S.; Wang, M.D.; Severinov, K. Molecular mechanism of transcription inhibition by peptide antibiotic microcin J25. Mol. Cell, 2004, 14, 753-62.
129. Yuzenkova, J.; Delgado, M.; Nechaev, S.; Savalia, D.; Epshtein, V.; Artsimovitch, I.; Mooney, R.A.; Landick, R.; Farias, R.N.; Salomon, R.; Severinov, K. Mutations of bacterial RNA polymerase leading to resistance to microcin J25. J. Biol. Chem. 2002, 277, 50867-75.
130. Kresge, N.; Ebright, R.H. Peptide's 'Cork in a Bottle' mechanism may lead to new generation of antibiotics. ASBMB Today, 2004, 9, 8.
131. Artsimovitch, I.; Chu, C.; Lynch, A. S.; Landick, R. A new class of bacterial RNA polymerase inhibitor affects nucleotide addition. Science, 2003, 30, 650-4.
132. Artsimovitch, I.; Svetlov, V.; Anthony, L.; Burgess, R. R.; Landick, R. RNA polymerases from Bacillus subtilis and Escherichia coli differ in recognition of regulatory signals In vitro. J. Bacteriol., 2000, 182, 6027-35.
133. Irschik, H.; Augustiniak, H.; Gerth, K.; Hofle, G.; Reichenbach, H. Ripostatins, novel inhibitors of eubacterial RNA polymerase isolated from Myxobacteria. J. Antibiotics, 1995, 48(8), 787-92.
134. O'Neill, A.; Oliva, B.; Storey, C.; Hoyle, A.; Fishwick, C.; Chopra, I. RNA Polymerase Inhibitors with Activity against Rifampin-Resistant Mutants of Staphylococcus aureus. Antimicrob. Agents Chemother., 2000, 44, 3163-66.
135. Arhin, F.; Bélanger, O.; Ciblat, S.; Dehbi, M.; Delorme, D.; Dietrich, E.; Dixit, D.; Lafontaine, Y.; Lehoux, D.; Liu, J.; McKay, G. A.; Moeck, G.; Reddy, R.; Rose, Y.; Srikumar, R.; Tanaka, K. S. E.; Williams, D. M.; Gros, P.; Pelletier, J.; Parr, T. R. Jr.; Far, A. R. A new class of small molecule RNA polymerase inhibitors withactivity against Rifampicin-resistant Staphylococcus aureus. Bioorg. Med. Chem., 2006, 14, 5812-32.
136. Sabnis, R. W.; Ragnekar, D. W.; Sonawane, N. D. J. 2-Aminothiophenes by the Gewald Reaction. Heterocyclic Chem., 1999, 36, 333-45.
137. André, E.; Bastide, L.; Villain-Guillot, P.; Latouche, J.; Rouby, J.; Leonetti, J-P. A multiwell assay to isolate compounds inhibiting the assembly of the prokaryotic RNA polymerase. Assay Drug Dev. Techn., 2004, 2(6), 629-35.
138. André, E.; Bastide, L.; Michaux-Charachon, S.; Gouby, A.; Villain-Guillot, P.; Latouche, J.; Bouchet, A.; Gualtieri, M.; Leonetti, J. P. Novel synthetic molecules targeting the bacterial RNA polymerase assembly. J. Antimicrob. Chemother., 2006, 57, 245-51.
139. Gualtieri, M.; Bastide, L.; Villain-Guillot, P.; Michaux-Charachon, S.; Latouche, J.; Leonetti, J-P. In vitro activity of a new antibacterial rhodanine derivative against Staphylococcus epidermidis biofilms. J. Antimicrob. Chemother., 2006 58, 778-83.
140. Villain-Guillot, P.; Gualtieri, M.; Bastide, L.; Roquet, F.; Martinez, J.; Amblard, M.; Pugniere, M.; Leonetti, J-P. Structure-activity relationships of phenyl-furanyl-rhodanines as inhibitors of RNA polymerase with antibacterial activity on biofilms. J. Med. Chem., 2007, 50, 4195-204.
141. Wieser, J.; Mitsch, A.; Jomaa, H.; Schiltzer, M.; Structure-activity relationships of novel anti-malarian agents. Part 7: N-(3-benzoyl-4- tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides with polar moieties. Bioorg. Med. Chem. Lett., 2003, 13, 2159-61.
142. Zhang, G. Ligand-free Suzuki-Miyaura reaction catalysed bu Pd/C at room temperature. J. Chem. Res., 2004, 593-5.
143. Irshik, H.; Gerth, K.; Höfle, G.; Kohl, W.; Reichenbach, H. The Myxopyronins, new inhibitors of bacterial RNA synthesis from Myxococcus fulvus (Myxobacteriales). J. Antibiotics, 1983, 36, 1651-8.
144. Hu, T.; Schaus, J.V.; Lam, K.; Palfreyman, M.G.; Wuonola, M.; Gustafson, G.; Panek, J.S. Total Synthesis and Preliminary Antibacterial Evaluation of the RNA Polymerase Inhibitors (±)-Myxopyronin A and B. J. Org. Chem., 1998, 63, 2401.
145. Doundoulakis, T.; Xiang, A.X.; Lira, R.; Agrios, K.A.; Webber, S.E.; Sisson, W.; Aust, R.M.; Shah, A.M.; Showalter, R.E.; Appleman, J.R.; Simonsen, K.B. Myxopyronin B analogs as inhibitors of RNA polymerase, synthesis and biological evaluation. Bioorg. Med. Chem. Lett., 2004, 14, 5667-72.
146. Lira, R.; Xiang, A.X.; Doundoulakis, T.; Biller, W.T.; Agrios, K.A.; Simonsen, K.B.; Webber, S.E.; Sisson, W.; Aust, R.M.; Shah, A.M.; Showalter, R.E.; Banh, V.N.; Steffy, K.R.; Appleman, J.R. Syntheses of novel Myxopyronin B analogs as potential inhibitors of bacterial RNA polymerase. Bioorg. Med. Chem. Lett., 2007, 17, 6797-800.
147. Irshik, H.; Jansen, R.; Hofle, G.; Gerth, K.; Reichenbach, H. The Corallopyronins, new inhibitors of bacterial RNA synthesis from Myxobacteria. J. Antibiotics, 1985, 38, 145-52
148. Mitchell, R.; Durbin, R. D. Tagetitoxin, a toxin produced by Pseudomonus syriizgae pv. tagetis: Purification and partial characterization, Physiol. Plant Pathol., 1981, 18, 157-68.
149. Steinberg, T. H.; Mathews, D. E.; Durbin, R. D.; Burgess, R. R. Tagetitoxin: A New Inhibitor of Eukaryotic Transcription by RNA Polymerase III. J. Biol. Chem., 1990, 265, 499-505.
150. Mathews, D. E.; Durbin, R. D. Mechanistic aspects of tagetitoxin inhibition of RNA polymerase from Escherichia coli. Biochemistry, 1994, 33, 11987-92.
151. Mitchell, R. E.; Coddington, J. M.; Young, H. A revised structure for Tegetitoxin Tetrahedron Lett., 1989, 30, 501-4
152. Dent, B. R.; Furneaux, R. H.; Gainsford, G. J.; Lynch, G. P. Synthesis Studies of Structural Analogues of Tagetitoxin: 4-O-Acetyl- 3-amino-1,6-anhydro-3-deoxy-D-gulose 2-Phosphate. Tetrahedron, 1999, 55, 6977-96.
153. Gronwald, J. W.; Plaisance, K. L.; Marimanikkuppam, S.; Ostrowski, B. G. Tagetitoxin purification and partial characterization. Phys. Mol. Plant Pathol., 2005, 67, 23-32.
154. Vassylyev, D. G.; Svetlov, V.; Vassylyeva, M. N.; Perederina, A.; Igarashi, N.; Matsugaki, N.; Wakatsuki, S.; Artsimovitch, I. Structural basis for transcription inhibition by tagetitoxin. Nat. Struct. Mol. Biol., 2005, 12, 1086-93.
155. Plet, J. R. H.; Porter, M. J. Synthesis of the bicyclic core of tagetitoxin. Chem. Comm., 2006, 1197-99.
156. Ettlinger, L.; Gaumann, E.; Hutter, R.; Keller-Schierlein, W.; Kradlofer, F.; Neipp, L.; Prelog, V.; Zahner, H. Stoffwechselprodukte von actinomyceten, holomycin. Helv. Chim. Acta, 1959, 42, 563-9.
157. Seneca, H.; Kane, J.H.; Rockenbach, J. Bactericidal, protozoicidal and fungicidal properties of thiolutin. Antibiot. Chemother., 1952, 2, 357-60.
158. Khachatourians, G.G.; Tipper, D.J. Inhibition of messenger ribonucleic acid synthesis in Escherichia coli by thiolutin J. Bacteriol., 1974, 119, 795-804.
159. Sivasubramanian, N.; Jayaraman, R. Thiolutin resistant mutants of Escherichia coli are they RNA chain initiation mutants? Mol. Gen. Genet., 1976, 145, 89-96.
160. Oliva, B.; O'Neill, A.; Wilson, J.M.; O'Hanlon, P.J.; Chopra, I. Antimicrobial properties and mode of action of the pyrrothine holomycin. Antimicrob. Agents Chemother., 2001, 45, 532-9
161. Tipper, D.J. Inhibition of yeast ribonucleic acid polymerases by thiolutin. J. Bacteriol., 1973, 116, 245-256.
162. O'Neill, A.; Oliva, B.; Storey, C.; Hoyle, A.; Fishwick, C.; Chopra, I. RNA polymerase inhibitors with activity against rifampin- resistant mutants of Staphylococcus aureus. Antimicrob. Agents Chemother., 2000, 44, 3163-6.
163. Hjelmgaard, T.; Givskov, M.; Nielsen, J. Expedient total synthesis of pyrrothine natural products and analogs. Org. Biomol. Chem., 2007, 5, 344-8.
164. Irschik, H.; Schummer, D.; Hofle, G.; Reicherbach, H.; Steinmetz, H.; Jansen, R. Etnangien, a macrolide-polyene antibiotic from Sorangium cellulosum that inhibits nucleic acid polymerases. J. Nat. Prod., 2007, 70, 1060-3.
165. Doan, N.T.; Stewart, P.R.; Smith, G.D. Inhibition of bacterial RNA polymerase by the cyanobacterial metabolites 12-epi-hapalindole E isonitrile and calothrixin A. FEMS Microbiol. Lett., 2001, 196, 135-9.
166. Doan, N.T.; Rickards, R.W.; Rothschild, J.M.; Smith, G.D. Allelopathic actions of the alkaloid 12-epihapalindole E isonitrile and calothrixin A from cyanobacteria of the genera Fischerella and Calothrix. J. Appl. Phycol., 2000, 12, 409-16.
167. Rickards, R.W.; Rothschild, J.M.; Willis, A.C.; de Chazal, N.M.; Kirk, J.; Kirk, K.; Saliba, K.J.; Smith, G.D. Calothrixins A and B, novel pentacyclic metabolites from calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells. Tetrahedron, 1999, 155, 13513-520.
168. Trischman, J.A.; Tapiolas, D.M.; Jensen, P.R.; Dwight, R.; Fenical, W. Salinamides A and B: Anti-inflammatory depsipeptides from a marine Streptomycete. J. Am. Chem. Soc., 1994, 116, 757-8.
169. Miao, S.; Anstee, M.R.; LaMarco, K.; Matthew, J.; Huang, L.H.T.; Brasseur, M.M. Inhibition of bacterial RNA polymerases. Peptide metabolites from the cultures of Streptomyces sp. J. Nat. Prod., 1997, 60, 858-61.
170. Moore, B.S.; Trischman, J.A.; Seng, D.; Kho, D.; Jensen, P.R.; Fenical, W. Salinamides, antiinflammatory depsipeptides from a Marine Streptomycete. J. Org. Chem., 1999, 64, 1145-50.
171. Tan, L.; Ma, D. J. Total Synthesis of Salinamide A: A Potent anti-inflammatory bicyclic depsipeptide. Angew. Chem. Int. Ed., 2008, 47, 3614-7.
172. Kriebardisz, T.; Meng, D.; Aktipis, S. Inhibition of the RNA Polymerase-catalyzed Synthesis of RNA by Daunomycin. J. Biol. Chem., 1988, 262, 12632-40.
173. Kriebardisz, T.; Aktipis, S. Inhibition of the RNA Polymerase-catalyzed Synthesis of RNA by Marcellomycin. J. Biol. Chem., 1988, 263, 6960-3.