Aminoacyl-tRNA synthetase inhibitors as potential antibiotics

European Journal of Medicinal Chemistry

Volumn 46, Issue 11, 2011, Pages 5227-5236

  Vondenhoff, Gaston H M ^a   Van Aerschot, Arthur ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Aminoacyl sulfamoyladenosines; Aminoacyl tRNA synthetase inhibitors; Antibiotics; Drug design

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID; 5 FLUORO 1,3 DIHYDRO 2,1 BENZOXABOROL 1 OL; AMINOACYL TRANSFER RNA INHIBITOR; ANTIBIOTIC AGENT; ASPARTYCIN; BEDEROCIN; BLEOMYCIN A2; CB 432; CD 432; CHUANGXINMYCIN; CYCLOSPORIN A; GLUTAMYCIN; GRAMICIDIN S; GRISEIN; ICOFUNGIPEN; INDOLMYCIN; LIGASE INHIBITOR; PSEUDOMONIC ACID; SB 234764; UNCLASSIFIED DRUG;

AMINOACYLATION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; BACTERIUM ISOLATION; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG SYNTHESIS; ENTEROBACTERIACEAE; ENZYME ACTIVE SITE; ESCHERICHIA COLI; HYDROLYSIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PEPTIDE SYNTHESIS; PSEUDOMONAS FLUORESCENS; REVIEW; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION;

AMINO ACYL-TRNA SYNTHETASES; ANIMALS; ANTI-BACTERIAL AGENTS; DRUG DISCOVERY; ENZYME INHIBITORS; HUMANS;

EID: 80054882325     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.08.049     Document Type: Review

References (84)

1. J.G. Hurdle, A.J. O'Neill, and I. Chopra Prospects for aminoacyl-tRNA synthetase inhibitors as new antimicrobial agents Antimicrob. Agents Chemother. 49 2005 4821 4833 (Pubitemid 41778891)
2. S. Rachakonda, and L. Cartee Challenges in antimicrobial drug discovery and the potential of nucleoside antibiotics Curr. Med. Chem. 11 2004 775 793 (Pubitemid 38380051)
3. K. Bockstael, and A. Van Aerschot Antimicrobial resistance in bacteria Cent. Eur. J. Med. 4 2009 141 155
4. R.C. Moellering Jr. Discovering new antimicrobial agents Int. J. Antimicrob. Agents 37 2011 2 9
5. J.J. Barker Antibacterial drug discovery and structure-based design Drug Discov. Today 11 2006 391 404
6. J. Pohlmann Phenylalanyl-tRNA synthetase as a target for potential new antibacterial agents Drug Future 29 3 2004 243 251 (Pubitemid 38508069)
7. J.A. Krzycki The direct genetic encoding of pyrrolysine Curr. Opin. Microbiol. 8 2005 706 712 (Pubitemid 41643039)
8. P. O'Donoghue, and Z. Luthey-Schulten On the evolution of structure in aminoacyl-tRNA synthetases Microbiol. Mol. Biol. Rev. MMBR 67 2003 550 573
9. C.R. Woese, G.J. Olsen, M. Ibba, and D. Soll Aminoacyl-tRNA synthetases, the genetic code, and the evolutionary process Microbiol. Mol. Biol. Rev. MMBR 64 2000 202 236 (Pubitemid 30143846)
10. P. Schimmel, J. Tao, and J. Hill Aminoacyl tRNA synthetases as targets for new anti-infectives FASEB J. 12 1998 1599 1609 (Pubitemid 28553655)
11. L. Moulinier, S. Eiler, G. Eriani, J. Gangloff, J.C. Thierry, K. Gabriel, W.H. McClain, and D. Moras The structure of an AspRS-tRNA(Asp) complex reveals a tRNA-dependent control mechanism EMBO J. 20 2001 5290 5301 (Pubitemid 32910923)
12. F.L. Rock, W. Mao, A. Yaremchuk, M. Tukalo, T. Crepin, H. Zhou, Y.K. Zhang, V. Hernandez, T. Akama, S.J. Baker, J.J. Plattner, L. Shapiro, S.A. Martinis, S.J. Benkovic, S. Cusack, and M.R. Alley An antifungal agent inhibits an aminoacyl-tRNA synthetase by trapping tRNA in the editing site Science 316 2007 1759 1761 (Pubitemid 46988553)
13. H. Ueda, Y. Shoku, N. Hayashi, J. Mitsunaga, Y. In, M. Doi, M. Inoue, and T. Ishida X-ray crystallographic conformational study of 5′-O- [N-(l-alanyl)-sulfamoyl]adenosine, a substrate analogue for alanyl-tRNA synthetase Biochim. Biophys. Acta 1080 1991 126 134
14. M.J. Brown, L.M. Mensah, M.L. Doyle, N.J. Broom, N. Osbourne, A.K. Forrest, C.M. Richardson, P.J. O'Hanlon, and A.J. Pope Rational design of femtomolar inhibitors of isoleucyl tRNA synthetase from a binding model for pseudomonic acid-A Biochemistry (Mosc) 39 2000 6003 6011 (Pubitemid 30327074)
15. D. Heacock, C.J. Forsyth, K. Shiba, and K. MusierForsyth Synthesis and aminoacyl-tRNA synthetase inhibitory activity of prolyl adenylate analogs Bioorg. Chem. 24 1996 273 289 (Pubitemid 26352682)
16. B. Ruan, H. Nakano, M. Tanaka, J.A. Mills, J.A. DeVito, B. Min, K.B. Low, J.R. Battista, and D. Soll Cysteinyl-tRNA(Cys) formation in Methanocaldococcus jannaschii: the mechanism is still unknown J. Bacteriol. 186 2004 8 14 (Pubitemid 38020280)
17. S.F. Ataide, and M. Ibba Small molecules: big players in the evolution of protein synthesis ACS Chem. Biol. 1 2006 285 297
18. M. Mirande Processivity of translation in the eukaryote cell: role of aminoacyl-tRNA synthetases FEBS Lett. 584 2010 443 447
19. S.T. Rao, and M.G. Rossmann Comparison of super-secondary structures in proteins J. Mol. Biol. 76 1973 241 256
20. U.A. Ochsner, X. Sun, T. Jarvis, I. Critchley, and N. Janjic Aminoacyl-tRNA synthetases: essential and still promising targets for new anti-infective agents Expert Opin. Investig. Drugs 16 2007 573 593 (Pubitemid 46729098)
21. S. Kim, S.W. Lee, E.C. Choi, and S.Y. Choi Aminoacyl-tRNA synthetases and their inhibitors as a novel family of antibiotics Appl. Microbiol. Biotechnol. 61 2003 278 288 (Pubitemid 36683523)
22. J. Levengood, S.F. Ataide, H. Roy, and M. Ibba Divergence in noncognate amino acid recognition between class I and class II lysyl-tRNA synthetases J. Biol. Chem. 279 2004 17707 17714 (Pubitemid 38560536)
23. R. Fukunaga, and S. Yokoyama Structural basis for substrate recognition by the editing domain of isoleucyl-tRNA synthetase J. Mol. Biol. 359 2006 901 912 (Pubitemid 43842049)
24. B.E.A. Alberts Molecular Biology of The Cell fourth ed. 2002 Garland Science New York
25. S.A. Martinis, and M.T. Boniecki The balance between pre- and post-transfer editing in tRNA synthetases FEBS Lett. 584 2010 455 459
26. K. Sheppard, P.M. Akochy, J.C. Salazar, and D. Soll The Helicobacter pylori amidotransferase GatCAB is equally efficient in glutamine-dependent transamidation of Asp-tRNAAsn and Glu-tRNAGln J. Biol. Chem. 282 2007 11866 11873 (Pubitemid 47100670)
27. J.L. Huot, C. Balg, D. Jahn, J. Moser, A. Emond, S.P. Blais, R. Chenevert, and J. Lapointe Mechanism of a GatCAB amidotransferase: aspartyl-tRNA synthetase increases its affinity for Asp-tRNA(Asn) and novel aminoacyl-tRNA analogues are competitive inhibitors Biochemistry (Mosc) 46 2007 13190 13198 (Pubitemid 350086237)
28. C. Balg, M. De Mieri, J.L. Huot, S.P. Blais, J. Lapointe, and R. Chenevert Inhibition of Helicobacter pylori aminoacyl-tRNA amidotransferase by chloramphenicol analogs Bioorg. Med. Chem. 18 2010 7868 7872
29. J.S. Cisar, J.A. Ferreras, R.K. Soni, L.E. Quadri, and D.S. Tan Exploiting ligand conformation in selective inhibition of non-ribosomal peptide synthetase amino acid adenylation with designed macrocyclic small molecules J. Am. Chem. Soc. 129 2007 7752 7753 (Pubitemid 46998163)
30. R. Finking, A. Neumuller, J. Solsbacher, D. Konz, G. Kretzschmar, M. Schweitzer, T. Krumm, and M.A. Marahiel Aminoacyl adenylate substrate analogues for the inhibition of adenylation domains of nonribosomal peptide synthetases Chembiochem: A Eur. J. Chem. Biol. 4 2003 903 906 (Pubitemid 37185706)
31. S. Bernier, D.Y. Dubois, M. Therrien, J. Lapointe, and R. Chenevert Synthesis of glutaminyl adenylate analogues that are inhibitors of glutaminyl-tRNA synthetase Bioorg. Med. Chem. Lett. 10 2000 2441 2444
32. C.M. Thomas, J. Hothersall, C.L. Willis, and T.J. Simpson Resistance to and synthesis of the antibiotic mupirocin Nat. Rev. Microbiol. 8 2010 281 289
33. R.G. Werner, L.F. Thorpe, W. Reuter, and K.H. Nierhaus Indolmycin inhibits prokaryotic tryptophanyl-tRNA ligase Eur. J. Biochem. FEBS 68 1976 1 3
34. J.G. Hurdle, A.J. O'Neill, and I. Chopra Anti-staphylococcal activity of indolmycin, a potential topical agent for control of staphylococcal infections J. Antimicrob. Chemother. 54 2004 549 552 (Pubitemid 39177486)
35. T. Kanamaru, Y. Nakano, Y. Toyoda, K.I. Miyagawa, M. Tada, T. Kaisho, and M. Nakao In vitro and in vivo antibacterial activities of TAK-083, an agent for treatment of Helicobacter pylori infection Antimicrob. Agents Chemother. 45 2001 2455 2459 (Pubitemid 32801895)
36. R.L. Jarvest, J.M. Berge, V. Berry, H.F. Boyd, M.J. Brown, J.S. Elder, A.K. Forrest, A.P. Fosberry, D.R. Gentry, M.J. Hibbs, D.D. Jaworski, P.J. O'Hanlon, A.J. Pope, S. Rittenhouse, R.J. Sheppard, C. Slater-Radosti, and A. Worby Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against gram-positive pathogens J. Med. Chem. 45 2002 1959 1962 (Pubitemid 34477708)
37. I.A. Critchley, C.L. Young, K.C. Stone, U.A. Ochsner, J. Guiles, T. Tarasow, and N. Janjic Antibacterial activity of REP8839, a new antibiotic for topical use Antimicrob. Agents Chemother. 49 2005 4247 4252 (Pubitemid 41400971)
38. A.S. Faqi, S.J. Bell, S. Gill, and D.B. Colagiovanni An intranasal irritation assessment of antibacterial ointment alone or in combination with mupirocin versus Bactroban Nasal in rabbits Regulatory Toxicol. Pharmacol. RTP 55 2009 28 32
39. B. Nare, S. Wring, C. Bacchi, B. Beaudet, T. Bowling, R. Brun, D. Chen, C. Ding, Y. Freund, E. Gaukel, A. Hussain, K. Jarnagin, M. Jenks, M. Kaiser, L. Mercer, E. Mejia, A. Noe, M. Orr, R. Parham, J. Plattner, R. Randolph, D. Rattendi, C. Rewerts, J. Sligar, N. Yarlett, R. Don, and R. Jacobs Discovery of novel orally bioavailable oxaborole 6-carboxamides that demonstrate cure in a murine model of late-stage central nervous system african trypanosomiasis Antimicrob. Agents Chemother. 54 2010 4379 4388
40. K. Ziegelbauer, P. Babczinski, and W. Schonfeld Molecular mode of action of the antifungal beta-amino acid BAY 10-8888 Antimicrob. Agents Chemother. 42 1998 2197 2205 (Pubitemid 28420350)
41. J. Mittendorf, F. Kunisch, M. Matzke, H.C. Militzer, A. Schmidt, and W. Schonfeld Novel antifungal beta-amino acids: synthesis and activity against Candida albicans Bioorg. Med. Chem. Lett. 13 2003 433 436 (Pubitemid 36259708)
42. B. Ruan, M.L. Bovee, M. Sacher, C. Stathopoulos, K. Poralla, C.S. Francklyn, and D. Soll A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases J. Biol. Chem. 280 2005 571 577 (Pubitemid 40165023)
43. D.V.R.N. Bhikshapathi, Y.S. Kumar, Y.M. Rao, and V. Kishan Borrelidin: a prospective drug Indian J. Biotechnol. 9 2010 18 23
44. D.V.R.N. Bhikshapathi, D.R. Krishna, and V. Kishan Anti-HIV, anti-tubercular and mutagenic activities of borrelidin Indian J. Biotechnol. 9 2010 265 270
45. J.S. Reader, P.T. Ordoukhanian, J.G. Kim, V. de Crecy-Lagard, I. Hwang, S. Farrand, and P. Schimmel Major biocontrol of plant tumors targets tRNA synthetase Science 309 2005 1533 (Pubitemid 41266473)
46. J.G. Kim, B.K. Park, S.U. Kim, D. Choi, B.H. Nahm, J.S. Moon, J.S. Reader, S.K. Farrand, and I. Hwang Bases of biocontrol: sequence predicts synthesis and mode of action of agrocin 84, the Trojan horse antibiotic that controls crown gall Proc. Natl. Acad. Sci. USA 103 2006 8846 8851 (Pubitemid 43880345)
47. T. Moriguchi, N. Asai, T. Wada, and M. Sekine Synthesis of nucleotide antibiotics having N-acyl phosphoramidate linkages Nucleic Acids Symp. Ser. 1999 15 16
48. M. Ubukata, H. Osada, and K. Isono Synthesis and biological activity of nucleoside antibiotics, ascamycin and its amino acid analogs Nucleic Acids Symp. Ser. 1985 81 83
49. H. Osada, and K. Isono Mechanism of action and selective toxicity of ascamycin, a nucleoside antibiotic Antimicrob. Agents Chemother. 27 1985 230 233 (Pubitemid 15002437)
50. M. Uramoto, C.J. Kim, K. Shin-Ya, H. Kusakabe, K. Isono, D.R. Phillips, and J.A. McCloskey Isolation and characterization of phosmidosine. A new antifungal nucleotide antibiotic J. Antibiotics 44 1991 375 381
51. M. Sekine, K. Okada, K. Seio, H. Kakeya, H. Osada, T. Obata, and T. Sasaki Synthesis of chemically stabilized phosmidosine analogues and the structure-activity relationship of phosmidosine J. Org. Chem. 69 2004 314 326 (Pubitemid 38101711)
52. G. Benz, T. Schroder, J. Kurz, C. Wunsche, W. Karl, G. Steffens, J. Pfitzner, and D. Schmidt Constitution of the deferriform of the albomycins Delta-1, Delta-2, and epsilon Angew. Chem. Int. Ed. 21 1982 527 528
53. A.L. Stefanska, M. Fulston, C.S. Houge-Frydrych, J.J. Jones, and S.R. Warr A potent seryl tRNA synthetase inhibitor SB-217452 isolated from a Streptomyces species J. Antibiotics 53 2000 1346 1353 (Pubitemid 32042463)
54. H. Paulsen, M. Brieden, and G. Benz Branched and chain-extended sugars.31. Synthesis of the deferri form of the oxygen analog of delta-1-albomycin Liebigs Ann. Chem. 1987 565 575
55. Y.M. Lin, and M.J. Miller Practical synthesis of hydroxamate-derived siderophore components by an indirect oxidation method and syntheses of a DIG-siderophore conjugate and a biotin-siderophore conjugate J. Org. Chem. 64 1999 7451 7458
56. Y. Zeng, H. Roy, P.B. Patil, M. Ibba, and S. Chen Characterization of two seryl-tRNA synthetases in albomycin-producing Streptomyces sp strain ATCC 700974 Antimicrob. Agents Chemother. 53 2009 4619 4627
57. J.F. Garcia-Bustos, N. Pezzi, and E. Mendez Structure and mode of action of microcin 7, an antibacterial peptide produced by Escherichia coli Antimicrob. Agents Chemother. 27 1985 791 797 (Pubitemid 15121993)
58. I.A. Khmel, V.M. Bondarenko, I.M. Manokhina, E.I. Basyuk, A.Z. Metlitskaya, V.A. Lipasova, and Y.M. Romanova Isolation and characterization of Escherichia coli strains producing microcins of B and C types FEMS Microbiol. Lett. 111 1993 269 274 (Pubitemid 23242336)
59. A.Z. Metlitskaya, G.S. Katrukha, A.S. Shashkov, D.A. Zaitsev, T.A. Egorov, and I.A. Khmel Structure of microcin C51, a new antibiotic with a broad spectrum of activity FEBS Lett. 357 1995 235 238
60. T. Farhanullah, E.J. Kang, E.C. Yoon, S. Choi, J. Kim, and Lee 2- [2-Substituted-3-(3,4-dichlorobenzylamino)propylamino]-1H-quinolin-4-one s as Staphylococcus aureus methionyl-tRNA synthetase inhibitors Eur. J. Med. Chem. 44 2009 239 250
61. Z.P. Xiao, X.B. He, Z.Y. Peng, T.J. Xiong, J. Peng, L.H. Chen, and H.L. Zhu Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials Bioorg. Med. Chem. 19 2011 1571 1579
62. D. Ding, Q. Meng, G. Gao, Y. Zhao, Q. Wang, B. Nare, R. Jacobs, F. Rock, M.R. Alley, J.J. Plattner, G. Chen, D. Li, and H. Zhou Design, synthesis, and structure-activity relationship of Trypanosoma brucei leucyl-tRNA synthetase inhibitors as antitrypanosomal agents J. Med. Chem. 54 2011 1276 1287
63. H. Eum, Y. Lee, S. Kim, A. Baek, M. Son, K.W. Lee, S.W. Ko, S. Kim, S.Y. Yun, W.K. Lee, and H.J. Ha Synthesis of substituted imidazolidin-2-ones as aminoacyl-tRNA synthase inhibitors Bull. Korean Chem. Soc. 31 2010 611 614
64. M. Hoffmann, and M. Torchala Search for inhibitors of aminoacyl-tRNA synthases by virtual click chemistry J. Mol. Model. 15 2009 665 672
65. Y. Wu, K. Yu, B. Xu, L. Chen, X. Chen, J. Mao, A. Danchin, X. Shen, D. Qu, and H. Jiang Potent and selective inhibitors of Staphylococcus epidermidis tryptophanyl-tRNA synthetase J. Antimicrob. Chemother. 60 2007 502 509 (Pubitemid 47299863)
66. A.K. Forrest, R.L. Jarvest, L.M. Mensah, P.J. O'Hanlon, A.J. Pope, and R.J. Sheppard Aminoalkyl adenylate and aminoacyl sulfamate intermediate analogues differing greatly in affinity for their cognate Staphylococcus aureus aminoacyl tRNA synthetases Bioorg. Med. Chem. Lett. 10 2000 1871 1874 (Pubitemid 30657626)
67. P. Brown, C.M. Richardson, L.M. Mensah, P.J. O'Hanlon, N.F. Osborne, A.J. Pope, and G. Walker Molecular recognition of tyrosinyl adenylate analogues by prokaryotic tyrosyl tRNA synthetases Bioorg. Med. Chem. 7 1999 2473 2485 (Pubitemid 30122749)
68. H. Belrhali, A. Yaremchuk, M. Tukalo, K. Larsen, C. Berthet-Colominas, R. Leberman, B. Beijer, B. Sproat, J. Als-Nielsen, and G. Grubel Crystal structures at 2.5 angstrom resolution of seryl-tRNA synthetase complexed with two analogs of seryl adenylate Science 263 1994 1432 1436 (Pubitemid 24137830)
69. J. Lee, S.U. Kang, M.K. Kang, M.W. Chun, Y.J. Jo, J.H. Kwak, and S. Kim Methionyl adenylate analogues as inhibitors of methionyl-tRNA synthetase Bioorg. Med. Chem. Lett. 9 1999 1365 1370 (Pubitemid 29232208)
70. M. Ora, M. Murtola, S. Aho, and M. Oivanen Hydrolytic reactions of 3′-N-phosphoramidate and 3′-N-thiophosphoramidate analogs of thymidylyl-3 ′,5′-thymidine Org. Biomol. Chem. 2 2004 593 600
71. D.R. Phillips Structure of the antifungal nucleotide antibiotic phosmidosine J. Org. Chem. 58 1993 854 859 (Pubitemid 23074390)
72. S. Bernier, P.M. Akochy, J. Lapointe, and R. Chenevert Synthesis and aminoacyl-tRNA synthetase inhibitory activity of aspartyl adenylate analogs Bioorg. Med. Chem. 13 2005 69 75 (Pubitemid 39575693)
73. X.Y. Yu, J.M. Hill, G. Yu, W. Wang, A.F. Kluge, P. Wendler, and P. Gallant Synthesis and structure-activity relationships of a series of novel thiazoles as inhibitors of aminoacyl-tRNA synthetases Bioorg. Med. Chem. Lett. 9 1999 375 380 (Pubitemid 29084497)
74. J.Y. Winum, A. Scozzafava, J.L. Montero, and C.T. Supuran Sulfamates and their therapeutic potential Med. Res. Rev. 25 2005 186 228 (Pubitemid 40299846)
75. P. Van de Vijver, G.H. Vondenhoff, S. Denivelle, J. Rozenski, J. Verhaegen, A. Van Aerschot, and P. Herdewijn Antibacterial 5′-O-(N- dipeptidyl)-sulfamoyladenosines Bioorg. Med. Chem. 17 2009 260 269
76. M. Mattiuzzo, A. Bandiera, R. Gennaro, M. Benincasa, S. Pacor, N. Antcheva, and M. Scocchi Role of the Escherichia coli SbmA in the antimicrobial activity of proline-rich peptides Mol. Microbiol. 66 2007 151 163 (Pubitemid 47414795)
77. J.W. Payne, B.M. Grail, S. Gupta, J.E. Ladbury, N.J. Marshall, R. O'Brien, and G.M. Payne Structural basis for recognition of dipeptides by peptide transporters Arch. Biochem. Biophys. 384 2000 9 23
78. D. Weitz, D. Harder, F. Casagrande, D. Fotiadis, P. Obrdlik, B. Kelety, and H. Daniel Functional and structural characterization of a prokaryotic peptide transporter with features similar to mammalian PEPT1 J. Biol. Chem. 282 2007 2832 2839 (Pubitemid 47084338)
79. M. Novikova, A. Metlitskaya, K. Datsenko, T. Kazakov, A. Kazakov, B. Wanner, and K. Severinov The Escherichia coli Yej transporter is required for the uptake of translation inhibitor microcin C J. Bacteriol. 189 2007 8361 8365 (Pubitemid 350178950)
80. A. Metlitskaya, T. Kazakov, G.H. Vondenhoff, M. Novikova, A. Shashkov, T. Zatsepin, E. Semenova, N. Zaitseva, V. Ramensky, A. Van Aerschot, and K. Severinov Maturation of the translation inhibitor microcin C J. Bacteriol. 191 2009 2380 2387
81. T. Kazakov, G.H. Vondenhoff, K.A. Datsenko, M. Novikova, A. Metlitskaya, B.L. Wanner, and K. Severinov Escherichia coli peptidase A, B, or N can process translation inhibitor microcin C J. Bacteriol. 190 2008 2607 2610 (Pubitemid 351466357)
82. P. Van de Vijver, G.H. Vondenhoff, T.S. Kazakov, E. Semenova, K. Kuznedelov, A. Metlitskaya, A. Van Aerschot, and K. Severinov Synthetic microcin C analogs targeting different aminoacyl-tRNA synthetases J. Bacteriol. 191 2009 6273 6280
83. G.H.M. Vondenhoff, S. Dubiley, K. Severinov, J. Rozenski, and A. Van Aerschot Extended targeting potential and improved synthesis of Microcin C analogues as antibacterials Bioorg. Med. Chem. 19 2011 5462 5467
84. M. Messmer, S.P. Blais, C. Balg, R. Chenevert, L. Grenier, P. Lague, C. Sauter, M. Sissler, R. Giege, J. Lapointe, and C. Florentz Peculiar inhibition of human mitochondrial aspartyl-tRNA synthetase by adenylate analogs Biochimie 91 2009 596 603