MraY inhibitors as novel antibacterial agents

Current Topics in Medicinal Chemistry

Volumn 5, Issue 13, 2005, Pages 1221-1236

  Dini, Christophe ^a  

^a Oroxcell   (France)

Author keywords

A 500359A; Amphomycin; Antibacterial; Antibiotic; Caprazamycin; Capuramycin; Corynetoxin; FR 900493; Lipopeptide; Liposidomycin; MraY; Muraymycin; Mureidomycine; Napsamycin; Pacidamycin; Protein E; Ribosamino uridine; Riburamycin; RU75411; Streptovirudin; Translocase; Tunicamycin; Uridylpeptide

Indexed keywords

AMFOMYCIN; ANTIINFECTIVE AGENT; CAPRAZAMYCIN; CAPROLACTAM; CAPURAMYCIN; CARRIER PROTEIN; DIHYDROPACIDAMYCIN D; ENZYME INHIBITOR; FR 900493; LIPOPEPTIDE; LIPOSIDOMYCIN; MRAY INHIBITOR; MURAYMYCIN; MUREIDOMYCIN; MUREIDOMYCIN C; NAPSAMYCIN; NUCLEOSIDE DERIVATIVE; PACIDAMYCIN; PEPTIDE DERIVATIVE; PEPTIDOGLYCAN; POLYPEPTIDE; PROTEIN E; PROTEIN MRAY; RIBOSE; TUNICAMYCIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; URACIL DERIVATIVE; URIDINE DERIVATIVE; URIDYLPEPTIDE DERIVATIVE; VETERINARY DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL INFECTION; BACTERIAL STRAIN; DOSE RESPONSE; DRUG EFFICACY; DRUG HALF LIFE; DRUG MECHANISM; DRUG STRUCTURE; DRUG TARGETING; GRAM NEGATIVE INFECTION; IC 50; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIOSIS; NONHUMAN;

ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; BACTERIAL PROTEINS; MOLECULAR STRUCTURE; NUCLEOSIDES; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFERASES;

EID: 29444456936     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802605774463042     Document Type: Article

References (66)

1. Jones, G. Antimicrobial drug resistance is an increasing, inevitable global problem. Pharmaceutical J., 2004, 273, 124.
2. Meka, V. G.; Pillai, S. K.; Sakoulas, G.; Wennersten, C.; Venkataraman, L.; DeGirolami, P. C.; Eliopoulos, G. M.; Moellering Jr., R. C.; Gold, H. S. Linezolid resistance in sequential Staphylococcus aureus isolates associated with a T2500A mutation in the 23S rRNA gene and loss of a single copy of rRNA. J. Infect. Dis., 2004, 190, 311-317.
3. van Heijenoort, J. Recent advances in the formation of bacterial peptidoglycan monomer unit. Nat. Prod. Rep., 2001, 18, 503-519.
4. Park, J. T.; Johnson, M. J. Accumulation of labile phopshate in Staphyloccus aureus grown in the presence of penicillin. J. Biol. Chem., 1949, 179, 585-592.
5. Heydanek, M. G.; Struve, W. G.; Neuhaus, F. C. On the initial stage in peptidoglycan synthesis. 3. Kinetics and uncoupling of phospho-N-acetylmuramyl-pentapeptide translocase (uridine 5′-phosphate). Biochemistry, 1969, 8, 1214.
6. Neuhaus, F. C. Initial translocation reaction in the biosynthesis of peptidoglycan by bacterial membranes. Acc. Chem. Res., 1971, 4, 297-303.
7. Struve, W. G.; Sinha, R. K.; Neuhaus, F. C. On the initial stage in peptidoglycan synthesis. Phospho-N-acetylmuramyl-pentapeptide translocase (uridine monophosphate). Biochemistry, 1966, 5, 82.
8. Pless, D. D.; Neuhaus, F. C. Initial membrane reaction in peptidoglycan synthesis. Lipid dependence of phospho-n-acetylmuramyl-pentapeptide translocase (exchange reaction). J. Biol. Chem., 1973, 248, 1568-1576.
9. Umbreit, J. N.; Strominger, J. L. Complex lipid requirements for detergent-solubilized phosphoacetylmuramyl-pentapeptide translocase from Micrococcus luteus. Proc. Nat. Acad. Sci., 1972, 69, 1972-1974.
10. Boyle, D. S.; Donachie, W. D. mraY is an essential gene for cell growth in Escherichia coli. J. Bacteriol., 1998, 180, 6429-6432.
11. Inukai, M.; Ishino, F.; Takaitsuki, A. Selective inhibition of the bacterial translocase reaction in peptidoglycan synthesis by mureidomycins. Antimicrob Agents Chemother, 1993, 37, 980-983.
12. Bouhss, A.; Mengin-Lecreulx, D.; Le Beller, D.; van Heijenoort, J. Topological analysis of the MraY protein catalysing the first membrane step of peptidoglycan synthesis. Mol. Microbiol., 1999, 34, 576-585.
13. Bugg, T. D. H.; Brandish, P. E. From peptidoglycan to glycoproteins: common features of lipid-linked oligosaccharides biosynthesis. FEMS Microbiol. Lett., 1994, 119, 255-262.
14. Parodi, A. J.; Behrens, N. H.; Leloir, L. F.; Carminatti, H. The role of polyprenol-bound saccharides as intermediates in glycoprotein synthesis in liver. Proc. Natl. Acad. Sci., 1972, 69, 3268.
15. Scocca, J. R.; Krag, S. S. Sequence of a cDNA that specifies the uridine diphosphate N-acetyl-D-glucosamine:dolichol phosphate N-acetylglycosamine-1-phosphate transferase from Chinese hamster ovary cells. J. Biol. Chem., 1990, 265, 20621.
16. Zara, J.; Lehrman, M. A. Role of the carboxyl terminus in stable expression of hamster UDP-GlcNAc:dolichol-P GlcNAc-1-P transferase. J. Biol. Chem., 1994, 269, 19108-19115.
17. Maas, D.; Pelzer, H. Murein biosynthesis in ether permeabilized Escherichia coli starting from early peptidoglycan precursors. Arch. Microbiol., 1981, 130, 301-306.
18. Dini, C.; Collette, P.; Drochon, N.; Guillot, J. C.; Lemoine, G.; Mauvais, P.; Aszodi, J. Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors. Bioorg. Med. Chem. Lett., 2000, 10, 1839-1843.
19. Brandish, P. E.; Kimura, K.; Inukai, M.; Southgate, R.; Lonsdale, J. T.; Bugg, T. D. H. Modes of action of tunicamycin, liposidomycin B, and mureidomycin A: inhibition of phospho-N-acetylmuramyl-pentapeptide translocase from Escherichia coli. Antimicrob. Agents Chemother., 1996, 40, 1640-1644.
20. Stachyra, T.; Dini, C.; Ferrari, P.; Bouhss, A.; van Heijenoort, J.; Mengin-Lecreulx, D.; Blanot, D.; Biton, J.; Le Beller, D. Fluorescence Detection-Based Functional Assay for High-Throughput Screening for MraY. Antimicrob. Agents. Chemother., 2004, 48, 897-902.
21. Schwartz, R.; Datema, R. Inhibitors of protein glycosylation. Trends Bioch. Sci., 1980, 65-67.
22. Takatsuki, A.; Tamura, G. Tunicamycin, a new antibiotic. III. Reversal of the antiviral activity of tunicamycin by aminosugars and their derivatives. J. Antibiot. (Tokyo), 1971, 24, 232-8.
23. Eckardt, K.; Wetzstein, H.; Thrum, H.; Ihn, W. Streptovirudin and tunicamycin, two inhibitors of glycolipid synthesis. Differentiation by use of gel chromatography, H.P.L.C. and hydrolysis. J. Antibiot. (Tokyo), 1980, 33, 908-10.
24. Vogel, P.; Petterson, D. S.; Berry, P. H.; Frahn, J. L.; Anderton, N.; Cockrum, P. A.; Edgar, J. A.; Jago, M. V.; Lanigan, G. W.; Payne, A. L.; Culvenor, C. C. Isolation of a group of glycolipid toxins from seedheads of annual ryegrass Lolium rigidum Gaud.) infected by Corynebacterium rathayi. Aust. J. Exp. Biol. Med. Sci., 1981, 59, 455-67.
25. Eckardt, K. Tunicamycins, streptovirudins, and corynetoxins, a special subclass of nucleoside antibiotics. J. Nat. Prod., 1983, 46, 544.
26. Takatsuki, A.; Tamura, G. Tunicamycin, a new antibiotic. II. Some biological properties of the antiviral activity of tunicamycin. J. Antibiot. (Tokyo), 1971, 24, 224-31.
27. Edgar, J. A.; Frahn, J. L.; Cockrum, P. A.. Corynetoxins, causative agents of annual ryegrass toxicity; their identification as tunicamycin group antibiotics. J. Chem. Soc., 1982, 4, 222-224.
28. Bugg, T. D. H.; Walsh, C. T. Intracellular steps of bacterial cell wall peptidoglycan biosynthesis: enzymolgy, antibiotics, and antibiotic resistance. Nat. Prod. Rep., 1992, 9, 199.
29. Xu, L.; Appell, M.; Scott, K.; Momany, F. A.; Price, N. P. J. Conformational Anlaysis of Chirally Deutereted Tunicamycin as an Active Site Probe of UDP-N-Acetylhexosamine:polyprenol-P N-Acetylhexosamine-1P-Translocases. Biochemistry, 2004, 43, 1348-55.
30. Isono, K.; Uramoto, M.; Kusakabe, H.; Kimura, K.; Izaki, K.; Nelson, C.; McCloskey, J. A. Liposidomycins: novel nucleoside antibiotics which inhibit bacterial peptidoglycan synthesis. J. Antibiot., 1985, 38, 1617-21.
31. Kimura, K.; Ikeda, Y.; Kagami, S.; Yoshihama, M.; Suzuki, K.; Osada, H.; Isono, K. Selective inhibition of the bacterial peptidoglycan biosynthesis by the new types of liposidomycins. J. Antibiot., 1998, 51, 1099-1104.
32. Takeuchi, T.; Igarashi, M.; Naganawa, H.; Hamada, M. Antibiotic caprazamycins and process for producing the same. WO 2001012643-A1, 1999, Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai, Japan.
33. Takeuchi, T.; Igarashi, M.; Naganawa, H.; Hamada, M. Caprazamycin manufacture with Streptomyces for control of acid-fast bacteria. JP 2003012687, 2001, Meiji Seika Kaisha, Ltd, Japan.
34. Igarashi, M.; Nakagawa, S.; Hattori, S.; Doi, T.; Nasuda, T.; Miyake, M.; Ishizuka, H.; Naganawa, H.; Shomura, T.; S., O.; I., Y.; HamadaM.; T., T. Caprazamycins A-F, novel anti-TB antibiotics, from Streptomyces sp. 42nd Interscience, Conference on Antimicrobial Agents and Chemotherapy, San Diego, California, September 30th, 2002, Abstract F-2031 (p. 232). 2002.
35. Ochi, K.; Ezaki, M.; Iwani, M.; Komori, T.; Kohsaka, M. Antibiotic FR-900493 manufacture with Bacillus. EP-333177, 1989, Fujisawa Pharmaceutical Co., Ltd., Japan.
36. Yoshida, Y.; Yamanaka, H.; Sakane, K. Preparation of uronic acid (FR-900493) derivatives as antibacterial agents. JP05078385, 1993, Fujisawa, Pharma.
37. McDonald, L. A. B., L. R.; Carter, G. T.; Lenoy, E.; Lotvin, J.; Petersen, P. J.; Siegel, M. M.; Singh, G.; Williamson, R. T. Structures of the muraymycins, novel peptidoglycan biosynthesis inhibitors. J. Am. Chem. Soc., 2002, 124, 10260-10261.
38. Dini, C.; Drochon, N.; Guillot, J. C.; Mauvais, P.; Walter, P.; Aszodi, J. Synthesis of analogues of the O-.beta.-D-Ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY. Bioorg. Med. Chem. Lett., 2001, 11, 533-536.
39. Dini, C.; Drochon, N.; Feteanu, S.; Guillot, J. C.; Peixoto, C.; Aszodi, J. Synthesis of analogues of the O-.beta.-D-Ribofuranosyl Nucleoside Moiety of Liposidomycins. Part 1: contribution of the amino group and the Uracil Moiety upon the inhibition of MraY. Bioorg. Med. Chem. Lett., 2001, 11, 529-531.
40. Dini, C.; Didier-Laurent, S.; Drochon, N.; Feteanu, S.; Guillot, J. C.; Monti, F.; Uridat, E.; Zhang, J.; Aszodi, J. Synthesis of submicromolar inhibitors of MraY by exploring the region originally occupied by the diazepanone ring in the liposidomycin structure. Bioorg. Med. Chem. Lett., 2002, 12, 1209-1213.
41. Dini, C.; Stachyra, T.; Braham, K.; Krebs, O.; Lassaigne, P.; Monti, F.; Zhang, J.; Steier, V.; Biton, J. Synthesis and in vitro evaluation of Riburamycin RU75411: Activity against MraY, antibacterial profile, and mechanism of action (MOA) on whole cells. Abstr. Intersci. Confer. Antimicrobial Agents Chemother., 2002, 42, 181.
42. Stachyra, T.; Biton, J.; Dini, C.; Feteanu, S.; Le Beller, D. Development of functional assays based on fluorescence detection to both perform high throughput screening on MraY and precisely quantify lipid I upon enzyme inhibition. Abstracts of the Interscience Conference on Antimicrobial Agents and Chemotherapy, 2002, 42, 192.
43. Inukai, M.; Isono, F.; Takahashi, S.; Enokita, R.; Sakaida, Y.; Haneishi, T. Mureidomycins A-D, novel peptidyl nucleoside antibiotics with spheroplast forming activity. I. Taxonomy, fermentation, isolation and physicochemical properties. J. Antibiot., 1989, 42, 662-6.
44. Chen, R. H.; Buko, A. M.; Whittern, D. N.; McAlpine, J. Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. II. Isolation and structural elucidation. J. Antibiot., 1989, 42, 512-20.
45. Fernandes, P. B.; Swanson, R. N.; Hardy, D. J.; Hanson, C. W.; Coen, L.; Rasmussen, R. R.; Chen, R. H. Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. III. Microbiologic: profile. J. Antibiot., 1989, 42, 521-6.
46. Lee, V. J.; Hecker, S. J. Antibiotic resistance versus small molecules, the chemical evolution. Med. Res. Rev., 1999, 19, 521-542.
47. Boojamra, C. G.; Lemoine, R. C.; Lee, J. C.; Leger, R.; Stein, K. A.; Vernier, N. G.; Magon, A. Stereochemical elucidation and total synthesis of dihydropacidamycin D, a semisyn hetic pacidamycin. J. Am. Chem. Soc., 2001, 123, 870-874.
48. Isono, F.; Katayama, T.; Inukai, M.; Haneishi, T. Mureidomycins A.apprx.D, novel peptidylnucleoside antibiotics with spheroplast forming activity. III. Biological properties. J. Antibiot., 1989, 42, 674-9.
49. Inukai, M.; Isono, F.; Takatsuki, A. Selective inhibition of the bacterial translocase reaction in peptidoglycan synthesis by mureidomycins. Antimicrob. Agents Chemother., 1993, 37, 980-3.
50. Brandish, P. E.; Burnham, M. K.; Lonsdale, J. T.; Southgate, R.; Inukai, M.; Bugg, T. D. H. Slow binding inhibition of phospho-N-acetylmuramyl-pentapeptide-translocase (Escherichia coli) by mureidomycin A. J. Biol. Chem., 1996, 271, 760.
51. Karwowski, J. P. J., M.; Theriault, R. J.; Chen, R. H.; Barlow, G. J.; Maus, M. L. Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. I. Taxonomy of the producing organism and fermentation. J. Antibiot., 1989, 42, 506-11.
52. Chatterjee, S.; Nadkarni, S. R.; Vijayakumar, E. K. S.; Patel, M. V.; Ganguli, B. N.; Fehlhaber, H. W.; Vertesy, L. Napsamycins, new Pseudomonas active antibiotics of the mureidomycin family from Streptomyces sp. HIL Y-82,11372. J. Antibiot., 1994, 47, 595-8.
53. Yamaguchi, H.; Sato, S.; Yoshida, S.; Takada, K.; Itoh, M.; Seto, H.; Otake, N. Capuramycin, a new nucleoside antibiotic. Taxonomy, fermentation, isolation and characterization. J. Antibiotics, 1986, 39, 1047-53.
54. Kimura, K.; Bugg, T. D. H. Recent advances in antimicrobial nucleoside antibiotics targetting cell wall biosynthesis. Nat. Prod. Rep., 2003, 20, 252-273.
55. Hotoda, H.; Miyuki, F.; Furukawa, M.; Daigo, M.; Murayama, K.; Kaneko, M.; Muramatsu, Y.; Ishii, M. M.; Miyakoshi, S.; Takatsu, T.; Inukai, M.; Kakuta, M.; Abe, T.; Harasaki, T.; Fukuoka, T.; Utsuic, Y.; Ohyac, S. Synthesis and Antimycobacterial Activity of Capuramycin Analogues. Part 1: Substitution of the Azepan-2-one Moiety of Capuramycin. Bioorg. Med. Chem. Lett., 2003, 13, 2829-2832.
56. Hotoda, H.; Daigo, M.; Furukawa, M.; Murayama, K.; Hasegawa, C. A.; Kaneko, M.; Muramatsu, Y.; Ishii, M. M.; Miyakoshi, S.; Takatsu, T.; Inukai, M.; Kakuta, M.; Abe, T.; Fukuoka, T.; Utsuic, Y.; Ohyac, S. Synthesis and Antimycobacterial Activity of Capuramycin Analogues. Part 2: Acylated Derivatives of Capuramycin-Related Compounds. Bioorg. Med. Chem. Lett., 2003, 13, 2833-2836.
57. Heinemann, B.; Kaplan, M. A.; Muir, R. D.; Hooper, I. R. Amphomycin-a new antibiotic. Antib. Chemother., 1953, 3, 239.
58. Bodanszky, M.; Sigler, G.; Bodanszky, A. Structure of the peptide antibiotic amphomycin. J. Am. Chem. Soc., 1973, 95, 2352.
59. Tanaka, H.; Iwai, Y.; Oiwa, R.; Shinohara, S.; Shimizu, S.; Oka, T.; Omura, S. Studies on bacterial cell wall inhibitors. II. Inhibition of peptidoglycan synthesis in vivo and in vitro by amphomycin. Biochimica Et Biophysica Acta, 1977, 497, 633-640.
60. Omura, S.; Tanaka, H.; Shinohara, S.; Oiwa, R.; Hata, T. Inhibition of bacterial cell wall synthesis by amphomycin. Chemother. Proc. int. Congr. Chemother. 9th, 1975, 5, 365-369.
61. Tanaka, H.; Oiwa, R.; Matsukura, S.; Omura, S. Amphomycin inhibits phospho-N-acetylmuramyl-pentapeptide translocase in peptidoglycan synthesis of Bacillus. Biochem. Biophys. Res. Commun., 1979, 86, 902.
62. Banerjee, D. K. Amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate. J. Biol. Chem., 1989, 264, 2024.
63. Kang, M.; Spencer, J.; Elbein, A. Amphomycin inhibits the incorporation of mannose and GlcNAc into lipid-linked saccharides by aorta extracts. Biochem. Biophys. Res. Commun., 1978, 82, 568.
64. Kang, M.; Spencer, K.; Elbein, A. Amphomycin inhibition of mannose and GlcNAc incorporation into lipid-linked saccharides. J. Biol. Chem., 1978, 253, 8860.
65. Bernhardt, T. G.; Roof, W. D.; Young, R. Genetic evidence that the bacteriophage X174 lysis protein inhibits cell wall synthesis. Proc. Natl. Acad. Sci. USA, 2000, 97, 4297.
66. Bernhardt, T. G.; Struck, D. K.; Young, R. The Lysis Protein E of fX174 Is a Specific Inhibitor of the MraY-catalyzed Step in Peptidoglycan Synthesis. J. Biol. Chem, 2001, 276, 6093-6097.