Erratum: Designed Small-Molecule Inhibitors of the Anthranilyl-CoA Synthetase PqsA Block Quinolone Biosynthesis in Pseudomonas aeruginosa (ACS Chemical Biology (2016) 11:11 (3061?3067) DOI: 10.1021/acschembio.6b00575);Designed small-molecule inhibitors of the anthranilyl-CoA synthetase PqsA block quinolone biosynthesis in pseudomonas aeruginosa

ACS Chemical Biology

Volumn 11, Issue 11, 2016, Pages 3061-3067

  Ji, Cheng ^a   Sharma, Indrajeet ^a   Pratihar, Debarshi ^a   Hudson, L Lynn ^b   Maura, Damien ^c   Guney, Tezcan ^a   Rahme, Laurence G ^c,d,e   Pesci, Everett C ^b   Coleman, James P ^b   Tan, Derek S ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b EAST CAROLINA UNIVERSITY   (United States)

^c MASSACHUSETTS GENERAL HOSPITAL   (United States)

^d HARVARD MEDICAL SCHOOL   (United States)

^e SHRINERS HOSPITALS FOR CHILDREN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HEPTYL 4 HYDROXYQUINOLINE; 3,4 DIHYDROXY 2 HEPTYLQUINOLINE; ANTHRANILYL AMS; ANTHRANILYL AMSN; ANTHRANILYL AVSN; ANTHRANILYLIN COA SYNTHETASE PQSA; ANTIBIOTIC AGENT; BENZOYL AMS; LIGASE INHIBITOR; LONG CHAIN FATTY ACID COENZYME A LIGASE; PYOCYANINE; QUINOLONE; QUINOLONE DERIVATIVE; SALICYL AMS; SALICYL AMSN; SALICYL AVSN; UNCLASSIFIED DRUG; COENZYME A LIGASE; ENZYME INHIBITOR; MOLECULAR LIBRARY;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; PSEUDOMONAS AERUGINOSA; QUORUM SENSING; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; MOLECULAR LIBRARY;

COENZYME A LIGASES; ENZYME INHIBITORS; PSEUDOMONAS AERUGINOSA; QUINOLONES; SMALL MOLECULE LIBRARIES;

EID: 84996773778     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/acschembio.9b00298     Document Type: Erratum

References (78)

1. Page, M. G. P. and Heim, J. (2009) Prospects for the next anti-Pseudomonas drug Curr. Opin. Pharmacol. 9, 558-565 10.1016/j.coph.2009.08.006
2. Gomez, M. I. and Prince, A. (2007) Opportunistic infections in lung disease Curr. Opin. Pharmacol. 7, 244-251 10.1016/j.coph.2006.12.005
3. Bonomo, R. A. and Szabo, D. (2006) Mechanisms of multidrug resistance in Acinetobacter species and Pseudomonas aeruginosa Clin. Infect. Dis. 43, S49-S54 10.1086/504477
4. Zavascki, A. P., Carvalhaes, C. G., Picao, R. C., and Gales, A. C. (2010) Multidrug-resistant Pseudomonas aeruginosa and Acinetobacter baumannii: Resistance mechanisms and implications for therapy Expert Rev. Anti-Infect. Ther. 8, 71-93 10.1586/eri.09.108
5. O'Connell, K. M. G., Hodgkinson, J. T., Sore, H. F., Welch, M., Salmond, G. P. C., and Spring, D. R. (2013) Combating multidrug-resistant bacteria: Current strategies for the discovery of novel antibacterials Angew. Chem., Int. Ed. 52, 10706-10733 10.1002/anie.201209979
6. Galloway, W. R. J. D., Hodgkinson, J. T., Bowden, S., Welch, M., and Spring, D. R. (2012) Applications of small molecule activators and inhibitors of quorum sensing in Gram-negative bacteria Trends Microbiol. 20, 449-458 10.1016/j.tim.2012.06.003
7. Heras, B., Scanlon, M. J., and Martin, J. L. (2015) Targeting virulence not viability in the search for future antibacterials Br. J. Clin. Pharmacol. 79, 208-215 10.1111/bcp.12356
8. LaSarre, B. and Federle, M. J. (2013) Exploiting quorum sensing to confuse bacterial pathogens Microbiol. Mol. Biol. Rev. 77, 73-111 10.1128/MMBR.00046-12
9. Nadal Jimenez, P., Koch, G., Thompson, J. A., Xavier, K. B., Cool, R. H., and Quax, W. J. (2012) The multiple signaling systems regulating virulence in Pseudomonas aeruginosa Microbiol. Mol. Biol. Rev. 76, 46-65 10.1128/MMBR.05007-11
10. Williams, P. and Camara, M. (2009) Quorum sensing and environmental adaptation in Pseudomonas aeruginosa: A tale of regulatory networks and multifunctional signal molecules Curr. Opin. Microbiol. 12, 182-191 10.1016/j.mib.2009.01.005
11. Pesci, E. C., Milbank, J. B. J., Pearson, J. P., McKnight, S., Kende, A. S., Greenberg, E. P., and Iglewski, B. H. (1999) Quinolone signaling in the cell-to-cell communication system of Pseudomonas aeruginosa Proc. Natl. Acad. Sci. U. S. A. 96, 11229-11234 10.1073/pnas.96.20.11229
12. Xiao, G., Deziel, E., He, J., Lepine, F., Lesic, B., Castonguay, M.-H., Milot, S., Tampakaki, A. P., Stachel, S. E., and Rahme, L. G. (2006) MvfR, a key Pseudomonas aeruginosa pathogenicity LTTR-class regulatory protein, has dual ligands Mol. Microbiol. 62, 1689-1699 10.1111/j.1365-2958.2006.05462.x
13. Calfee, M. W., Coleman, J. P., and Pesci, E. C. (2001) Interference with Pseudomonas quinolone signal synthesis inhibits virulence factor expression by Pseudomonas aeruginosa Proc. Natl. Acad. Sci. U. S. A. 98, 11633-11637 10.1073/pnas.201328498
14. Cao, H., Krishnan, G., Goumnerov, B., Tsongalis, J., Tompkins, R., and Rahme, L. G. (2001) A quorum sensing-associated virulence gene of Pseudomonas aeruginosa encodes a LysR-like transcription regulator with a unique self-regulatory mechanism Proc. Natl. Acad. Sci. U. S. A. 98, 14613-14618 10.1073/pnas.251465298
15. Deziel, E., Lepine, F., Milot, S., He, J., Mindrinos, M. N., Tompkins, R. G., and Rahme, L. G. (2004) Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication Proc. Natl. Acad. Sci. U. S. A. 101, 1339-1344 10.1073/pnas.0307694100
16. Deziel, E., Gopalan, S., Tampakaki, A. P., Lepine, F., Padfield, K. E., Saucier, M., Xiao, G., and Rahme, L. G. (2005) The contribution of MvfR to Pseudomonas aeruginosa pathogenesis and quorum sensing circuitry regulation: Multiple quorum sensing-regulated genes are modulated without affecting lasRI, rhlRI or the production of N-acyl-L-homoserine lactones Mol. Microbiol. 55, 998-1014 10.1111/j.1365-2958.2004.04448.x
17. McGrath, S., Wade, D. S., and Pesci, E. C. (2004) Dueling quorum sensing systems in Pseudomonas aeruginosa control the production of the Pseudomonas quinolone signal (PQS) FEMS Microbiol. Lett. 230, 27-34 10.1016/S0378-1097(03)00849-8
18. McKnight, S. L., Iglewski, B. H., and Pesci, E. C. (2000) The Pseudomonas quinolone signal regulates rhl quorum sensing in Pseudomonas aeruginosa J. Bacteriol. 182, 2702-2708 10.1128/JB.182.10.2702-2708.2000
19. Dulcey, C. E., Dekimpe, V., Fauvelle, D.-A., Milot, S., Groleau, M.-C., Doucet, N., Rahme, L. G., Lepine, F., and Deziel, E. (2013) The end of an old hypothesis: The Pseudomonas signaling molecules 4-hydroxy-2-alkylquinolines derive from fatty acids, not 3-ketofatty acids Chem. Biol. 20, 1481-1491 10.1016/j.chembiol.2013.09.021
20. Dubern, J.-F. and Diggle, S. P. (2008) Quorum sensing by 2-alkyl-4-quinolones in Pseudomonas aeruginosa and other bacterial species Mol. BioSyst. 4, 882-888 10.1039/b803796p
21. Coleman, J. P., Hudson, L. L., McKnight, S. L., Farrow, J. M., III, Calfee, M. W., Lindsey, C. A., and Pesci, E. C. (2008) Pseudomonas aeruginosa PqsA is an anthranilate-coenzyme A ligase J. Bacteriol. 190, 1247-1255 10.1128/JB.01140-07
22. Pistorius, D., Ullrich, A., Lucas, S., Hartmann, R. W., Kazmaier, U., and Mueller, R. (2011) Biosynthesis of 2-alkyl-4(1H)-quinolones in Pseudomonas aeruginosa: Potential for therapeutic interference with pathogenicity ChemBioChem 12, 850-853 10.1002/cbic.201100014
23. Weidel, E., de Jong, J. C., Brengel, C., Storz, M. P., Braunshausen, A., Negri, M., Plaza, A., Steinbach, A., Mueller, R., and Hartmann, R. W. (2013) Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa Infections and elucidation of binding mode by SPR, STD NMR, and molecular docking J. Med. Chem. 56, 6146-6155 10.1021/jm4006302
24. Hinsberger, S., de Jong, J. C., Groh, M., Haupenthal, J., and Hartmann, R. W. (2014) Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections Eur. J. Med. Chem. 76, 343-351 10.1016/j.ejmech.2014.02.014
25. Storz, M. P., Maurer, C. K., Zimmer, C., Wagner, N., Brengel, C., de Jong, J. C., Lucas, S., Muesken, M., Haeussler, S., Steinbach, A., and Hartmann, R. W. (2012) Validation of PqsD as an anti-biofilm target in Pseudomonas aeruginosa by development of small-molecule Inhibitors J. Am. Chem. Soc. 134, 16143-16146 10.1021/ja3072397
26. Storz, M. P., Brengel, C., Weidel, E., Hoffmann, M., Hollemeyer, K., Steinbach, A., Mueller, R., Empting, M., and Hartmann, R. W. (2013) Biochemical and biophysical analysis of a chiral PqsD inhibitor revealing tight-binding behavior and enantiomers with contrary thermodynamic signatures ACS Chem. Biol. 8, 2794-2801 10.1021/cb400530d
27. Storz, M. P., Allegretta, G., Kirsch, B., Empting, M., and Hartmann, R. W. (2014) From in vitro to in cellulo: Structure-activity relationship of (2-nitrophenyl) methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa Org. Biomol. Chem. 12, 6094-6104 10.1039/C4OB00707G
28. Sahner, J. H., Brengel, C., Storz, M. P., Groh, M., Plaza, A., Mueller, R., and Hartmann, R. W. (2013) Combining in silico and biophysical methods for the development of Pseudomonas aeruginosa quorum sensing Inhibitors: An alternative approach for structure-based drug design J. Med. Chem. 56, 8656-8664 10.1021/jm401102e
29. Sahner, J. H., Empting, M., Kamal, A., Weidel, E., Groh, M., Boerger, C., and Hartmann, R. W. (2015) Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa Eur. J. Med. Chem. 96, 14-21 10.1016/j.ejmech.2015.04.007
30. Zender, M., Witzgall, F., Drees, S. L., Weidel, E., Maurer, C. K., Fetzner, S., Blankenfeldt, W., Empting, M., and Hartmann, R. W. (2016) Dissecting the multiple roles of PqsE in Pseudomonas aeruginosa virulence by discovery of small tool compounds ACS Chem. Biol. 11, 1755-1763 10.1021/acschembio.6b00156
31. Lu, C., Kirsch, B., Zimmer, C., de Jong, J. C., Henn, C., Maurer, C. K., Muesken, M., Haeussler, S., Steinbach, A., and Hartmann, R. W. (2012) Discovery of antagonists of PqsR, a key player in 2-alkyl-4-quinolone-dependent quorum sensing in Pseudomonas aeruginosa Chem. Biol. 19, 381-390 10.1016/j.chembiol.2012.01.015
32. Klein, T., Henn, C., de Jong, J. C., Zimmer, C., Kirsch, B., Maurer, C. K., Pistorius, D., Mueller, R., Steinbach, A., and Hartmann, R. W. (2012) Identification of small-molecule antagonists of the Pseudomonas aeruginosa transcriptional regulator PqsR: Biophysically guided hit discovery and optimization ACS Chem. Biol. 7, 1496-1501 10.1021/cb300208g
33. Lu, C., Maurer, C. K., Kirsch, B., Steinbach, A., and Hartmann, R. W. (2014) Overcoming the unexpected functional inversion of a PqsR antagonist in Pseudomonas aeruginosa: An in vivo potent antivirulence agent targeting pqs quorum sensing Angew. Chem., Int. Ed. 53, 1109-1112 10.1002/anie.201307547
34. Lu, C., Kirsch, B., Maurer, C. K., de Jong, J. C., Braunshausen, A., Steinbach, A., and Hartmann, R. W. (2014) Optimization of anti-virulence PqsR antagonists regarding aqueous solubility and biological properties resulting in new insights in structure-activity relationships Eur. J. Med. Chem. 79, 173-183 10.1016/j.ejmech.2014.04.016
35. Zender, M., Klein, T., Henn, C., Kirsch, B., Maurer, C. K., Kail, D., Ritter, C., Dolezal, O., Steinbach, A., and Hartmann, R. W. (2013) Discovery and biophysical characterization of 2-amino-oxadiazoles as novel antagonists of PqsR, an important regulator of Pseudomonas aeruginosa virulence J. Med. Chem. 56, 6761-6774 10.1021/jm400830r
36. Ilangovan, A., Fletcher, M., Rampioni, G., Pustelny, C., Rumbaugh, K., Heeb, S., Camara, M., Truman, A., Chhabra, S. R., Emsley, J., and Williams, P. (2013) Structural basis for native agonist and synthetic inhibitor recognition by the Pseudomonas aeruginosa quorum sensing regulator PqsR (MvfR) PLoS Pathog. 9, e1003508 10.1371/journal.ppat.1003508
37. Starkey, M., Lepine, F., Maura, D., Bandyopadhaya, A., Lesic, B., He, J., Kitao, T., Righi, V., Milot, S., Tzika, A., and Rahme, L. (2014) Identification of anti-virulence compounds that disrupt quorum-sensing regulated acute and persistent pathogenicity PLoS Pathog. 10, e1004321 10.1371/journal.ppat.1004321
38. Thomann, A., de Mello Martins, A. G. G., Brengel, C., Empting, M., and Hartmann, R. W. (2016) Application of dual inhibition concept within looped autoregulatory systems toward antivirulence agents against Pseudomonas aeruginosa infections ACS Chem. Biol. 11, 1279-1286 10.1021/acschembio.6b00117
39. Kasper, S. H., Bonocora, R. P., Wade, J. T., Musah, R. A., and Cady, N. C. (2016) Chemical inhibition of kynureninase reduces Pseudomonas aeruginosa quorum sensing and virulence factor expression ACS Chem. Biol. 11, 1106-1117 10.1021/acschembio.5b01082
40. Kim, K., Kim, Y. U., Koh, B. H., Hwang, S. S., Kim, S.-H., Lepine, F., Cho, Y.-H., and Lee, G. R. (2010) HHQ and PQS, two Pseudomonas aeruginosa quorum-sensing molecules, down-regulate the innate immune responses through the nuclear factor-κB pathway Immunology 129, 578-588 10.1111/j.1365-2567.2009.03160.x
41. Müsken, M., Di Fiore, S., Dötsch, A., Fischer, R., and Häussler, S. (2010) Genetic determinants of Pseudomonas aeruginosa biofilm establishment Microbiology 156, 431-441 10.1099/mic.0.033290-0
42. Lesic, B., Lepine, F., Deziel, E., Zhang, J., Zhang, Q., Padfield, K., Castonguay, M.-H., Milot, S., Stachel, S., Tzika, A. A., Tompkins, R. G., and Rahme, L. G. (2007) Inhibitors of pathogen intercellular signals as selective anti-infective compounds PLoS Pathog. 3, e126 10.1371/journal.ppat.0030126
43. Komor, U., Bielecki, P., Loessner, H., Rohde, M., Wolf, K., Westphal, K., Weiss, S., and Haeussler, S. (2012) Biofilm formation by Pseudomonas aeruginosa in solid murine tumors-A novel model system Microbes Infect. 14, 951-958 10.1016/j.micinf.2012.04.002
44. Gulick, A. M. (2009) Conformational dynamics in the acyl-CoA synthetases, adenylation domains of non-ribosomal peptide synthetases, and firefly luciferase ACS Chem. Biol. 4, 811-827 10.1021/cb900156h
45. Ferreras, J. A., Ryu, J.-S., Di Lello, F., Tan, D. S., and Quadri, L. E. N. (2005) Small-molecule inhibition of siderophore biosynthesis in Mycobacterium tuberculosis and Yersinia pestis Nat. Chem. Biol. 1, 29-32 10.1038/nchembio706
46. Lun, S., Guo, H., Adamson, J., Cisar, J. S., Davis, T. D., Chavadi, S. S., Warren, J. D., Quadri, L. E. N., Tan, D. S., and Bishai, W. R. (2013) Pharmacokinetic and in vivo efficacy studies of the mycobactin biosynthesis inhibitor salicyl-AMS in mice Antimicrob. Agents Chemother. 57, 5138-5140 10.1128/AAC.00918-13
47. Cisar, J. S., Ferreras, J. A., Soni, R. K., Quadri, L. E. N., and Tan, D. S. (2007) Exploiting ligand conformation in the selective inhibition of non-ribosomal peptide synthetase amino acid adenylation with designed macrocyclic small molecules J. Am. Chem. Soc. 129, 7752-7753 10.1021/ja0721521
48. Lu, X., Zhang, H., Tonge, P. J., and Tan, D. S. (2008) Mechanism-based inhibitors of MenE, an acyl-CoA synthetase involved in bacterial menaquinone biosynthesis Bioorg. Med. Chem. Lett. 18, 5963-5966 10.1016/j.bmcl.2008.07.130
49. Lu, X., Zhou, R., Sharma, I., Li, X., Kumar, G., Swaminathan, S., Tonge, P. J., and Tan, D. S. (2012) Stable analogues of OSB-AMP: Potent inhibitors of MenE, the o-succinylbenzoate-CoA synthetase from bacterial menaquinone biosynthesis ChemBioChem 13, 129-136 10.1002/cbic.201100585
50. Matarlo, J. S., Evans, C. E., Sharma, I., Lavaud, L. J., Ngo, S. C., Shek, R., Rajashankar, K. R., French, J. B., Tan, D. S., and Tonge, P. J. (2015) Mechanism of MenE inhibition by acyl-adenylate analogues and discovery of novel antibacterial agents Biochemistry 54, 6514-6524 10.1021/acs.biochem.5b00966
51. Ferreras, J. A., Stirrett, K. L., Lu, X., Ryu, J.-S., Soll, C. E., Tan, D. S., and Quadri, L. E. N. (2008) Mycobacterial phenolic glycolipid virulence factor biosynthesis: Mechanism and small-molecule inhibition of polyketide chain initiation Chem. Biol. 15, 51-61 10.1016/j.chembiol.2007.11.010
52. Lu, X., Olsen, S. K., Capili, A. D., Cisar, J. S., Lima, C. D., and Tan, D. S. (2010) Designed semisynthetic protein inhibitors of Ub/Ubl E1 activating enzymes J. Am. Chem. Soc. 132, 1748-1749 10.1021/ja9088549
53. Olsen, S. K., Capili, A. D., Lu, X., Tan, D. S., and Lima, C. D. (2010) Active site remodelling accompanies thioester bond formation in the SUMO E1 Nature 463, 906-912 10.1038/nature08765
54. Finking, R., Neumueller, A., Solsbacher, J., Konz, D., Kretzschmar, G., Schweitzer, M., Krumm, T., and Marahiel, M. A. (2003) Aminoacyl adenylate substrate analogues for the inhibition of adenylation domains of nonribosomal peptide synthetases ChemBioChem 4, 903-906 10.1002/cbic.200300666
55. Koroniak, L., Ciustea, M., Gutierrez, J. A., and Richards, N. G. J. (2003) Synthesis and characterization of an N-acylsulfonamide inhibitor of human asparagine synthetase Org. Lett. 5, 2033-2036 10.1021/ol034212n
56. Brown, P. H. and Beckett, D. (2005) Use of binding enthalpy to drive an allosteric transition Biochemistry 44, 3112-3121 10.1021/bi047792k
57. Branchini, B. R., Murtiashaw, M. H., Carmody, J. N., Mygatt, E. E., and Southworth, T. L. (2005) Synthesis of an N-acyl sulfamate analog of luciferyl-AMP: A stable and potent inhibitor of firefly luciferase Bioorg. Med. Chem. Lett. 15, 3860-3864 10.1016/j.bmcl.2005.05.115
58. May, J. J., Finking, R., Wiegeshoff, F., Weber, T. T., Bandur, N., Koert, U., and Marahiel, M. A. (2005) Inhibition of the D-alanine:D-alanyl carrier protein ligase from Bacillus subtilis increases the bacterium's susceptibility to antibiotics that target the cell wall FEBS J. 272, 2993-3003 10.1111/j.1742-4658.2005.04700.x
59. Somu, R. V., Boshoff, H., Qiao, C., Bennett, E. M., Barry, C. E., III, and Aldrich, C. C. (2006) Rationally designed nucleoside antibiotics that inhibit siderophore biosynthesis of Mycobacterium tuberculosis J. Med. Chem. 49, 31-34 10.1021/jm051060o
60. Miethke, M., Bisseret, P., Beckering, C. L., Vignard, D., Eustache, J., and Marahiel, M. A. (2006) Inhibition of aryl acid adenylation domains involved in bacterial siderophore synthesis FEBS J. 273, 409-419 10.1111/j.1742-4658.2005.05077.x
61. Pfleger, B. F., Lee, J. Y., Somu, R. V., Aldrich, C. C., Hanna, P. C., and Sherman, D. H. (2007) Characterization and analysis of early enzymes for petrobactin biosynthesis in Bacillus anthracis Biochemistry 46, 4147-4157 10.1021/bi6023995
62. Tian, Y., Suk, D.-H., Cai, F., Crich, D., and Mesecar, A. D. (2008) Bacillus anthracis o-succinylbenzoyl-CoA synthetase: Reaction kinetics and a novel inhibitor mimicking its reaction intermediate Biochemistry 47, 12434-12447 10.1021/bi801311d
63. Ciulli, A., Scott, D. E., Ando, M., Reyes, F., Saldanha, S. A., Tuck, K. L., Chirgadze, D. Y., Blundell, T. L., and Abell, C. (2008) Inhibition of Mycobacterium tuberculosis pantothenate synthetase by analogues of the reaction intermediate ChemBioChem 9, 2606-2611 10.1002/cbic.200800437
64. Arora, P., Goyal, A., Natarajan, V. T., Rajakumara, E., Verma, P., Gupta, R., Yousuf, M., Trivedi, O. A., Mohanty, D., Tyagi, A., Sankaranarayanan, R., and Gokhale, R. S. (2009) Mechanistic and functional insights into fatty acid activation in Mycobacterium tuberculosis Nat. Chem. Biol. 5, 166-173 10.1038/nchembio.143
65. Drake, E. J., Duckworth, B. P., Neres, J., Aldrich, C. C., and Gulick, A. M. (2010) Biochemical and structural characterization of bisubstrate inhibitors of BasE, the self-standing nonribosomal peptide synthetase adenylate-forming enzyme of acinetobactin synthesis Biochemistry 49, 9292-9305 10.1021/bi101226n
66. Sikora, A. L., Wilson, D. J., Aldrich, C. C., and Blanchard, J. S. (2010) Kinetic and inhibition studies of dihydroxybenzoate-AMP ligase from Escherichia coli Biochemistry 49, 3648-3657 10.1021/bi100350c
67. Ueda, H., Shoku, Y., Hayashi, N., Mitsunaga, J., In, Y., Doi, M., Inoue, M., and Ishida, T. (1991) X-ray crystallographic conformational study of 5′-O-[N-(L-alanyl)-sulfamoyl]adenosine, a substrate analog for alanyl-tRNA synthetase Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1080, 126-134 10.1016/0167-4838(91)90138-P
68. Waller, C. W., Patrick, J. B., Fulmor, W., and Meyer, W. E. (1957) The structure of nucleocidin. I J. Am. Chem. Soc. 79, 1011-1012 10.1021/ja01561a076
69. Morton, G. O., Lancaster, J. E., Van Lear, G. E., Fulmor, W., and Meyer, W. E. (1969) Structure of nucleocidin. III. Revised structure J. Am. Chem. Soc. 91, 1535-1537 10.1021/ja01034a046
70. Isono, K., Uramoto, M., Kusakabe, H., Miyata, N., Koyama, T., Ubukata, M., Sethi, S. K., and McCloskey, J. A. (1984) Ascamycin and dealanylascamycin, nucleoside antibiotics from Streptomyces sp J. Antibiot. 37, 670-672 10.7164/antibiotics.37.670
71. Qiao, C., Wilson, D. J., Bennett, E. M., and Aldrich, C. C. (2007) A mechanism-based aryl carrier protein/thiolation domain affinity probe J. Am. Chem. Soc. 129, 6350-6351 10.1021/ja069201e
72. Sundlov, J. A., Shi, C., Wilson, D. J., Aldrich, C. C., and Gulick, A. M. (2012) Structural and functional investigation of the intermolecular interaction between NRPS adenylation and carrier protein domains Chem. Biol. 19, 188-198 10.1016/j.chembiol.2011.11.013
73. Morrison, J. F. (1969) Kinetics of the reversible inhibition of enzyme-catalyzed reactions by tight-binding inhibitors Biochim. Biophys. Acta, Enzymol. 185, 269-286 10.1016/0005-2744(69)90420-3
74. Williams, J. W. and Morrison, J. F. (1979) The kinetics of reversible tight-binding inhibition Methods Enzymol. 63, 437-467 10.1016/0076-6879(79)63019-7
75. Lepine, F., Deziel, E., Milot, S., and Rahme, L. G. (2003) A stable isotope dilution assay for the quantification of the Pseudomonas quinolone signal in Pseudomonas aeruginosa cultures Biochim. Biophys. Acta, Gen. Subj. 1622, 36-41 10.1016/S0304-4165(03)00103-X
76. Kesarwani, M., Hazan, R., He, J., Que, Y., Apidianakis, Y., Lesic, B., Xiao, G., Dekimpe, V., Milot, S., Deziel, E., Lepine, F., and Rahme, L. G. (2011) A quorum sensing regulated small volatile molecule reduces acute virulence and promotes chronic infection phenotypes PLoS Pathog. 7, e1002192 10.1371/journal.ppat.1002192
77. Davis, T. D., Gerry, C. J., and Tan, D. S. (2014) General platform for systematic quantitative evaluation of small-molecule permeability in bacteria ACS Chem. Biol. 9, 2535-2544 10.1021/cb5003015
78. Welsh, M. A. and Blackwell, H. E. (2016) Chemical genetics reveals environment-specific roles for quorum sensing circuits in Pseudomonas aeruginosa Cell Chem. Biol. 23, 361-369 10.1016/j.chembiol.2016.01.006