Aminoacyl-tRNA synthetases and their inhibitors as a novel family of antibiotics (original) (raw)
Antonio M, McFerran N, Pallen MJ (2002) Mutations affecting the Rossman fold of isoleucyl-tRNA synthetase are correlated with low-level mupirocin resistance in Staphylococcus aureus. Antimicrob Agents Chemother 46:438-442 ArticleCASPubMed Google Scholar
Arnez JG, Moras D (1997) Structural and functional considerations of the aminoacylation reaction. Trends Biochem Sci 22:211–216 ArticleCASPubMed Google Scholar
Baines PJ, Mellows G, Swaisland AJ, Tasker TC (1984) Mupirocin: its chemistry and metabolism. In: Mupirocin a novel topical antibiotic. Royal Society of Medicine, London, pp 13–22
Beecham Group PLC (1989) Antibacterial 1-normon-2-yl-heterocyclic compounds. US patent 4,861,788
Beecham Group PLC (1991) Antibacterial monic acid derivatives. US patent 5,041,567
Berge JM, Copley RC, Eggleston DS, Hamprecht DW, Jarvest RL, Mensah LM, O'Hanlon PJ, Pope AJ (2000) Inhibitors of bacterial tyrosyl tRNA synthetase: synthesis of four stereoisomeric analogues of the natural product SB-219383. Bioorg Med Chem Lett 10:1811–1814 ArticleCASPubMed Google Scholar
Broom NJ, Cassels R, Cheng HY, Elder JS, Hannan PC, Masson N, O'Hanlon PJ, Pope A, Wilson JM (1996) The chemistry of pseudomonic acid. 17. Dual-action C-1 oxazole derivatives of pseudomonic acid having an extended spectrum of antibacterial activity. J Med Chem 39:3598–3600 Article Google Scholar
Brown P, Eggleston DS, Haltiwanger RC, Jarvest RL, Mensah L, O'Hanlon PJ, Pope AJ (2001) Synthetic analogues of SB-219383. Novel C-glycosyl peptides as inhibitors of tyrosyl tRNA synthetase. Bioorg Med Chem Lett 11:711–714 ArticleCASPubMed Google Scholar
Burbaum JJ, Schimmel P (1991) Structural relationships and the classification of aminoacyl-tRNA synthetases. J Biol Chem 266:16965–16968 CASPubMed Google Scholar
Carcanague DR (1997) Novel derivatives of pseudomonic acid. Bioorg Med Chem Lett 7:2805–2808 ArticleCAS Google Scholar
Class YJ, Deshong P (1995) The pseudomonic acid. Chem Rev 95:1483–1857 Google Scholar
Cookson BD (1998) The emergence of mupirocin resistance: a challenge to infection control and antibiotic prescribing practice. J Antimicrob Chemother 41:11–18 ArticleCASPubMed Google Scholar
Cubist Pharmaceuticals Inc (1998a) Aminoacyl adenylate minics as novel antimicrobial and antiparasitic agents. US patent 5,726,195
Cubist Pharmaceuticals Inc (1998b) Aminoacyl sulfamides for the treatment of hyperproliferative disorders. WO 98/41215
Cubist Pharmaceuticals Inc (2000a) Condensed imidazolidinones as tRNA synthetase inhibitors. WO 00/18772
Cubist Pharmaceuticals Inc (2000b) Tetracyclic heterocycles as antimicrobial. WO 00/17206
Desjardins M, Garneau S, Desgagnes J, Lacoste L, Yang F, Lapointe J, Chenevert R (1998) Glutamyl adenylate analogues are inhibitors of glutamyl-tRNA synthetase. Bioorg Chem 26:1–13 ArticleCAS Google Scholar
Eriani G, Delarue M, Poch O, Gangloff J, Moras D (1990) Partition of tRNA synthetases into two classes based on mutually exclusive sets of sequence motifs. Nature 347:203–206 CASPubMed Google Scholar
Farmer TH, Gilbart J, Elson SW (1992) Biochemical basis of mupirocin resistance in strains of Staphylococcus aureus. J Antimicrob Chemother 30:587-596 CASPubMed Google Scholar
Finn J, Hill J, Ram S, Morytko M, Yu X, Gimi R, Silverman J, Stein R, Lim A, Mak E, Gallant P, Wendler P, Rose S, Stevens A, Keith D (2001) Novel antibacterial agents targeting methionyl-tRNA synthetase: a chemlnformatic approach to convert HTS data into quality medicinal chemistry leads. In: Proceedings of the 41st Annual Interscience Conference on Antimicrobial Agents and Chemotherapy Chicago, Ill.
Forrest AK, Jarvest RL, Mensah LM, O'Hanlon PJ, Pope AJ, Sheppard RJ (2000) Aminoalkyl adenylate and aminoacyl sulfamate intermediate analogues differing greatly in affinity for their cognate Staphylococcus aureus aminoacyl tRNA synthetases. Bioorg Med Chem Lett 10:1871–1874 ArticleCASPubMed Google Scholar
Fraser TH, Rich A (1975) Amino acids are not all initially attached to the same position on transfer RNA molecules. Proc Natl Acad Sci USA 72:3044–3048 CASPubMed Google Scholar
Frugier M, Florentz C, Schimmel P, Giege R (1993) Triple aminoacylation specificity of a chimerized transfer RNA. Biochemistry 32:14053–14061 CASPubMed Google Scholar
Heacock D, Forsyth CJ, Shiba K, Musiter-Forsyth K (1996) Synthesis and aminoacyl-tRNA synthetase inhibitory of prolyl adenylate analogs. Bioorg Chem 24:273–289 ArticleCAS Google Scholar
Hill J, Finn J, Wang Z, Silverman J, Oliver N, Gallant P, Wender P, Keith D (2001) Synthesis and activity of spirocyclic tetrahydrofurans as inhibitors of phenylalanine tRNA synthetase. In: Proceedings of the 41st Annual Interscience Conference on Antimicrobial Agents and Chemotherapy Chicago, Ill.
Houge-Frydrych CS, Readshaw SA, Bell DJ (2000a) SB-219383, a novel tyrosyl tRNA synthetase inhibitor from a Micromonospora sp. II. Structure determination. J Antibiot (Tokyo) 53:351–356
Houge-Frydrych CS, Gilpin ML, Skett PW, Tyler JW (2000b) SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp. II. Structure determination. J Antibiot (Tokyo) 53:364–372 Google Scholar
Hughes J, Mellows G (1980) Interaction of pseudomonic acid A with Escherichia coli B isoleucyl-tRNA synthetase. Biochem J 191:209–219 CASPubMed Google Scholar
Ibba M, Morgan S, Curnow AW, Pridmore DR, Vothknecht UC, Gardner W, Lin W, Woese CR, Soll D (1997) A euryarchaeal lysyl-tRNA synthetase: resemblance to class I synthetases. Science 278:1119–1122 CASPubMed Google Scholar
Jarvest RL, Berge JM, Houge-Frydrych CS, Janson C, Mensah LM, O'Hanlon PJ, Pope A, Saldanha A, Qiu X (1999) Interaction of tyrosyl aryl dipeptides with S. aureus tyrosyl tRNA synthetase: inhibition and crystal structure of a complex. Bioorg Med Chem Lett 9:2859–2862 ArticleCASPubMed Google Scholar
Jarvest RL, Berge JM, Berry V, Boyd HF, Brown MJ, Elder JS, Forrest AK, Fosberry AP, Gentry DR, Hibbs MJ, Jaworski DD, O'Hanlon PJ, Pope AJ, Rittenhouse S, Sheppard RJ, Slater-Radosti C, Worby A (2002) Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against gram-positive pathogens. J Med Chem 45:1959–1962 ArticleCASPubMed Google Scholar
Klein LL, Yeung CM, Kurath P, Mao JC, Fernandes PB, Lartey PA, Pernet AG (1989) Synthesis and activity of nonhydrolyzable pseudomonic acid analogues. J Med Chem 32:151–160 CASPubMed Google Scholar
Konishi M, Nishio M, Saitoh K, Miyaki T, Oki T, Kawaguchi H (1989) Cispentacin, a new antifungal antibiotic. I. Production, isolation, physico-chemical properties and structure. J Antibiot (Tokyo) 42:1749–1755 Google Scholar
Konrad I, Roschenthaler R (1977) Inhibition of phenylalanine tRNA synthetase from Bacillus subtilis by ochratoxin A. FEBS Lett 83:341–347 ArticleCASPubMed Google Scholar
Leberman R, Hartlein M, Cusack S (1991) Escherichia coli seryl-tRNA synthetase: the structure of a class 2 aminoacyl-tRNA synthetase. Biochim Biophys Acta 1089:287–298 CASPubMed Google Scholar
Lee J, Kang SU, Kang MK, Chun MW, Jo YJ, Kwak JH, Kim S (1999) Methionyl adenylate analogues as inhibitors of methionyl-tRNA synthetase. Bioorg Med Chem Lett 9:1365–1370 ArticleCASPubMed Google Scholar
Lee J, Kang SU, Kim SY, Kim SE, Jo YJ, Kim S (2001) Vanilloid and isovanilloid analogues as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases. Bioorg Med Chem Lett 11:965–968 ArticleCASPubMed Google Scholar
Merck & Co Inc (2000a) Novel prolines as antimicrobial agents. WO 00/66119
Merck & Co Inc (2000b) Novel catechols as antimicrobial agents. WO 00/66120
Morton TM, Johnston JL, Patterson J, Archer GL. (1995) Characterization of a conjugative staphylococcal mupirocin resistance plasmid. Antimicrob Agents Chemother 39:1272–1280 CASPubMed Google Scholar
Nass G, Poralla K, Zahner H (1969) Effect of the antibiotic Borrelidin on the regulation of threonine biosynthetic enzymes in E. coli. Biochem Biophys Res Commun 34:84–91 CASPubMed Google Scholar
Ogilvie A, Wiebauer K, Kersten W (1975) Inhibition of leucyl-transfer ribonucleic acid synthetasymol. Biochem J 152:511–515 CASPubMed Google Scholar
Parr I, Hill J, Finn J, Yang D, Silverman J, Oliver N, Gallant P, Mak E, Stein R, Lim A, (2001) Synthesis and biological activity of novel di-alkylated thiazolidinone phenylalanyl-tRNA synthetase inhibitors. In: Proceedings of the 41st Annual Interscience Conference on Antimicrobial Agents and Chemotherapy Chicago, Ill.
Ribas de Pouplana L, Schimmel P (2001) Two classes of tRNA synthetases suggested by sterically compatible dockings on tRNA acceptor stem. Cell 104:191–193 PubMed Google Scholar
Ruff M, Krishnaswamy S, Boeglin M, Poterszman A, Mitschler A, Podjarny A, Rees B, Thierry JC, Moras D (1991) Class II aminoacyl transfer RNA synthetases: crystal structure of yeast aspartyl-tRNA synthetase complexed with tRNA(Asp). Science 52:1682–1689 Google Scholar
Schimmel P, Giege R, Moras D, Yokoyama S (1993) An operational RNA code for amino acids and possible relationship to genetic code. Proc Natl Acad Sci USA 90:8763–8768 CASPubMed Google Scholar
Schmitz FJ, Lindenlauf E, Hofmann AC, Fluit AC, Verhoef J, Heinz HP, Jones ME (1998) The prevalence of low- and high-level mupirocin resistance in staphylococci from 19 European hospitals. J Antimicrob Chemother 42:489–495 ArticleCASPubMed Google Scholar
Sissler M, Eriani G, Martin F, Giege R, Florentz C (1997) Mirror image alternative interaction patterns of the same tRNA with either class I arginyl-tRNA synthetase or class II aspartyl-tRNA synthetase. Nucleic Acids Res 25:4899–4906 Google Scholar
SmithKline Beecham PLC (1996a) (Hetero)-aryl ketones derivatives with antibacterial properties. US patent 5,536,745
SmithKline Beecham PLC (1997a) Mupirocinsulfamates with antibacterial activity. WO 97/05126
SmithKline Beecham PLC (1997b) Compounds with a sulfamoyl group and pharmaceutical compositions containing them. WO 97/35859
SmithKline Beecham PLC (1998a) Sulfamate derivatives with t-RNA synthetase inhibiting activity. WO 98/32765
SmithKline Beecham PLC (1998b) Enzymatic preparation of monic acids. US patent 5,726,049
SmithKline Beecham PLC (1999) Quinolones used as MRS inhibitors and bactericides. WO 99/55677
SmithKline Beecham PLC (2000a) 2-NH-Pyridones and pyrimidones as MRS inhibitors. WO 00/71524 A.
SmithKline Beecham PLC (2000b) Benzimidazole derivatives and their use as methionyl-tRNA synthetase inhibitors. WO 00/71522 A1
SmithKline Beecham PLC (2000c) Quinolones as t-RNA synthetase inhibitors and antibacterial agents. WO 00/21949
Stefanska AL, Fulston M, Houge-Frydrych CS, Jones JJ, Warr SR (2000a) A potent seryl tRNA synthetase inhibitor SB-217452 isolated from a Streptomyces species. J Antibiot (Tokyo) 53:1346–1353 Google Scholar
Stefanska AL, Cassels R, Ready SJ, Warr SR (2000b) SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp. I. Fermentation, isolation and properties. J Antibiot (Tokyo) 53:357–363
Tanaka K, Tamaki M, Watanabe S (1969) Effect of furanomycin on the synthesis of isoleucyl-tRNA. Biochim Biophys Acta 195:244–245 CASPubMed Google Scholar
Yu XY, Hill JM, Yu G, Wang W, Kluge AF, Wendler P, Gallant P(1999) Synthesis and structure-activity relationships of a series of novel thiazoles as inhibitors of aminoacyl-tRNA synthetases. Bioorg Med Chem Lett 9:375–380 ArticleCASPubMed Google Scholar
Yu XY, Hill JM, Yu G, Yang Y, Kluge AF, Keith D, Finn J, Gallant P, Silverman J, Lim A (2001) A series of quinoline analogues as potent inhibitors of C. albicans prolyl tRNA synthetase. Bioorg Med Chem Lett 11:541–544 ArticleCASPubMed Google Scholar
Yun HJ, Lee SW, Yoon GM, Kim SY, Choi S, Lee YS, Choi EC, Kim S (2003) Prevalence and mechanisms of low- and high-level mupirocin resistance in staphylococci isolated from a Korean Hospital. J Antimicrob Chemother (in press)