Novel phytochemical–antibiotic conjugates as multitarget inhibitors of Pseudomononas aeruginosa GyrB/ParE and DHFR

References

• Breidenstein EB de la Fuente-Núñez C Hancock RE Pseudomonas aeruginosa: all roads lead to resistance Trends Microbiol 2011 19 8 419 426 21664819
   PubMed Web of Science ®Google Scholar
• Lister PD Wolter DJ Hanson ND Antibacterial-resistant Pseudomonas aeruginosa: clinical impact and complex regulation of chromosomally encoded resistance mechanisms Clin Microbiol Rev 2009 22 4 582 610 19822890
   PubMed Web of Science ®Google Scholar
• Mesaros N Nordmann P Plésiat P Pseudomonas aeruginosa: resistance and therapeutic options at the turn of the new millennium Clin Microbiol Infect 2007 13 6 560 578 17266725
   PubMed Web of Science ®Google Scholar
• Traugott KA Echevarria K Maxwell P Green K Lewis JS2nd Monotherapy or combination therapy? The Pseudomonas aeruginosa conundrum Pharmacotherapy 2011 31 6 598 608 21923444
   PubMed Web of Science ®Google Scholar
• Johnson SJ Ernst EJ Moores KG Is double coverage of gramnegative organisms necessary? Am J Health Syst Pharm 2011 68 2 119 124 21200057
   PubMed Web of Science ®Google Scholar
• Pokrovskaya V Baasov T Dual-acting hybrid antibiotics: a promising strategy to combat bacterial resistance Expert Opin Drug Discov 2010 5 9 883 902 22823262
   PubMed Web of Science ®Google Scholar
• Zimmermann GR Lehár J Keith CT Multi-target therapeutics: when the whole is greater than the sum of the parts Drug Discov Today 2007 12 1–2 34 42 17198971
   PubMed Web of Science ®Google Scholar
• Hopkins AL Network pharmacology: the next paradigm in drug discovery Nat Chem Biol 2008 4 11 682 690 18936753
   PubMed Web of Science ®Google Scholar
• Bremner JB Ambrus JI Samosorn S Dual action-based approaches to antibacterial agents Curr Med Chem 2007 14 13 1459 1477 17584056
   PubMed Web of Science ®Google Scholar
• Morphy R Rankovic Z Designing multiple ligands – medicinal chemistry strategies and challenges Curr Pharm Des 2009 15 6 587 600 19199984
   PubMed Web of Science ®Google Scholar
• Morphy R Kay C Rankovic Z From magic bullets to designed multiple ligands Drug Discov Today 2004 9 15 641 651 15279847
   PubMed Web of Science ®Google Scholar
• Pokrovskaya V Belakhov V Hainrichson M Yaron S Baasov T Design, synthesis, and evaluation of novel fluoroquinolone-aminoglycoside hybrid antibiotics J Med Chem 2009 52 8 2243 2254 19301822
   PubMed Web of Science ®Google Scholar
• Ball AR Casadei G Samosorn S Conjugating berberine to a multidrug efflux pump inhibitor creates an effective antimicrobial ACS Chemi Biol 2006 1 9 594 600
   Web of Science ®Google Scholar
• Labischinski H Cherian J Calanasan C Boyce RS Inventors Hybrid antimicrobial compounds and their use United States patent US WO/2010/025906 3 11 2010
   Google Scholar
• Ma XH Shi Z Tan C In-silico approaches to multi-target drug discovery: computer aided multi-target drug design, multi-target virtual screening Pharm Res 2010 27 5 739 749 20221898
   PubMed Web of Science ®Google Scholar
• O’Boyle NM Banck M James CA Morley C Vandermeersch T Hutchison GR Open Babel: an open chemical toolbox J Cheminform 2011 3 33 21982300
   PubMed Web of Science ®Google Scholar
• Koch W Holthausen MC A Chemist’s Guide to Density Functional Theory Weinheim, Germany Wiley-VCH 2000
   Google Scholar
• Zhao YH Abraham MH Le J Rate-limited steps of human oral absorption and QSAR studies Pharm Res 2002 19 10 1446 1457 12425461
   PubMed Web of Science ®Google Scholar
• Sander T Freyss J von Korff M Reich JR Rufener C OSIRIS, an entirely in-house developed drug discovery informatics system J Chem Inf Model 2009 49 2 232 246 19434825
   PubMed Web of Science ®Google Scholar
• Thomsen R Christensen MH MolDock: a new technique for high-accuracy molecular docking J Med Chem 2006 49 11 3315 3321 16722650
   PubMed Web of Science ®Google Scholar
• Wang R Fang X Lu Y Wang S The PDBbind database: collection of binding affinities for protein-ligand complexes with known three-dimensional structures J Med Chem 2004 47 12 2977 2980 15163179
   PubMed Web of Science ®Google Scholar
• Krieger E Darden T Nabuurs SB Finkelstein A Vriend G Making optimal use of empirical energy functions: force-field parameterization in crystal space Proteins 2004 57 4 678 683 15390263
   PubMed Web of Science ®Google Scholar
• Essmann U Perera L Berkowitz ML Darden T Lee H Pedersen LG A smooth particle mesh Ewald method J Chem Phys 1995 103 19 8577 8593
   Web of Science ®Google Scholar
• Klamt A Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena J Phys Chem 1995 99 7 2224 2235
   Web of Science ®Google Scholar
• Jakalian A Jack DB Bayly CI Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. parameterization and validation J Comput Chem 2002 23 16 1623 1641 12395429
   PubMed Web of Science ®Google Scholar
• Wang J Wolf RM Caldwell JW Kollman PA Case DA Development and testing of a general amber force field J Comput Chem 2004 25 9 1157 1174 15116359
   PubMed Web of Science ®Google Scholar
• Hooft RW Sander C Vriend G Positioning hydrogen atoms by optimizing hydrogen-bond networks in protein structures Proteins 1996 26 4 363 376 8990493
   PubMed Web of Science ®Google Scholar
• Krieger E Nielsen JE Spronk CA Vriend G Fast empirical pKa prediction by Ewald summation J Mol Graph Model 2006 25 4 481 486 16644253
   PubMed Web of Science ®Google Scholar
• Xie L Xie L Kinnings SL Bourne PE Novel Computational approaches to polypharmacology as a means to define responses to individual drugs Annu Rev Pharmacol Toxicol 2012 52 1 361 379 22017683
   PubMed Web of Science ®Google Scholar
• Spina M Cuccioloni M Mozzicafreddo M Mechanism of inhibition of wt-dihydrofolate reductase from E. coli by tea epigallocatechin-gallate Proteins 2008 72 1 240 251 18214969
   PubMed Web of Science ®Google Scholar
• Gradisar H Pristovsek P Plaper A Jerala R Green tea catechins inhibit bacterial DNA gyrase by interaction with its ATP binding site J Med Chem 2007 50 2 264 271 17228868
   PubMed Web of Science ®Google Scholar
• Bradbury BJ Pucci MJ Recent advances in bacterial topoisomerase inhibitors Curr Opin Pharmacol 2008 8 5 574 581 18555745
   PubMed Web of Science ®Google Scholar
• Jayaraman P Sakharkar KR Sing LC Chow VT Sakharkar MK Insights into antifolate activity of phytochemicals against Pseudomonas aeruginosa J Drug Target 2011 19 3 179 188 20429775
   PubMed Web of Science ®Google Scholar
• Sakharkar MK Jayaraman P Soe WM Chow VT Sing LC Sakharkar KR In vitro combinations of antibiotics and phytochemicals against Pseudomonas aeruginosa J MicrobioI Immunol Infect 2009 42 5 364 370
   Web of Science ®Google Scholar
• Marques SM Enyedy EA Supuran CT Krupenko NI Krupenko SA Santos MA Pteridine-sulfonamide conjugates as dual inhibitors of carbonic anhydrases and dihydrofolate reductase with potential antitumor activity Bioorg Medicinal Chem 2010 18 14 5081 5089
   Web of Science ®Google Scholar
• Brvar M Perdih A Oblak M Masic LP Solmajer T In silico discovery of 2-amino-4-(2,4-dihydroxyphenyl)thiazoles as novel inhibitors of DNA gyrase B Bioorg Med Chem Lett 2010 20 3 958 962 20045642
   PubMed Web of Science ®Google Scholar
• Lerner MG Bowman AL Carlson HA Incorporating dynamics in E. coli dihydrofolate reductase enhances structure-based drug discovery J Chem Inf Model 2007 47 6 2358 2365 17877338
   PubMed Web of Science ®Google Scholar
• Schechner M Sirockin F Stote RH Dejaegere AP Functionality maps of the ATP binding site of DNA gyrase B: generation of a consensus model of ligand binding J Med Chem 2004 47 18 4373 4390 15317451
   PubMed Web of Science ®Google Scholar
• Manly CJ Chandrasekhar J Ochterski JW Hammer JD Warfield BB Strategies and tactics for optimizing the hit-to-lead process and beyond – a computational chemistry perspective Drug Discov Today 2008 13 3–4 99 109 18275907
   PubMed Web of Science ®Google Scholar
• Matter H Baringhaus KH Naumann T Klabunde T Pirard B Computational approaches towards the rational design of drug-like compound libraries Comb Chem High Throughput Screen 2001 4 6 453 475 11562252
   PubMed Web of Science ®Google Scholar
• Lipinski CA Lead- and drug-like compounds: the rule-of-five revolution Drug Discov Today Technol 2004 1 4 337 341
   PubMedGoogle Scholar
• Veber DF Johnson SR Cheng HY Smith BR Ward KW Kopple KD Molecular properties that influence the oral bioavailability of drug candidates J Med Chem 2002 45 12 2615 2623 12036371
   PubMed Web of Science ®Google Scholar
• Maiti R Van Domselaar GH Zhang H Wishart DS SuperPose: a simple server for sophisticated structural superposition Nucleic Acids Res 2004 32 Web Server issue W590 W594 15215457
   PubMed Web of Science ®Google Scholar
• Lessa JA Mendes IC da Silva PR 2-Acetylpyridine thiosemicarbazones: cytotoxic activity in nanomolar doses against malignant gliomas Eur J Med Chem 2010 45 12 5671 5677 20884094
   PubMed Web of Science ®Google Scholar
• Liu XH Chen PQ Wang BL Li YH Wang SH Li ZM Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor Bioorg Med Chem Lett 2007 17 13 3784 3788 17512731
   PubMed Web of Science ®Google Scholar
• Nascimento EC Martins JB Electronic structure and PCA analysis of covalent and non-covalent acetylcholinesterase inhibitors J Mol Model 2011 17 6 1371 1379 20839017
   PubMed Web of Science ®Google Scholar
• Oblak M Kotnik M Solmajer T Discovery and development of ATPase inhibitors of DNA gyrase as antibacterial agents Curr Med Chem 2007 14 19 2033 2047 17691945
   PubMed Web of Science ®Google Scholar
• Bellon S Parsons JD Wei Y Crystal structures of Escherichia coli topoisomerase IV ParE subunit (24 and 43 kilodaltons): a single residue dictates differences in novobiocin potency against topoisomerase IV and DNA gyrase Antimicrob Agents Chemother 2004 48 5 1856 1864 15105144
   PubMed Web of Science ®Google Scholar
• Cody V Schwalbe CH Structural characteristics of antifolate dihydrofolate reductase enzyme interactions Crystallogr Rev 2006 12 4 301 333
   Google Scholar
• Agarwal P Searls DB Literature mining in support of drug discovery Brief Bioinform 2008 9 6 479 492 18820304
   PubMed Web of Science ®Google Scholar
• Yang Y Adelstein SJ Kassis AI Target discovery from data mining approaches Drug Discov Today 2009 14 3–4 147 154 19135549
   PubMed Web of Science ®Google Scholar
• Park K Kim D Binding similarity network of ligand Proteins 2008 71 2 960 971 18004762
   PubMed Web of Science ®Google Scholar
• Durrant JD Amaro RE Xie L A multidimensional strategy to detect polypharmacological targets in the absence of structural and sequence homology PLoS Comput Biol 2010 6 1
   Web of Science ®Google Scholar
• Jayaraman P Sakharkar MK Lim CS Tang TH Sakharkar KR Activity and interactions of antibiotic and phytochemical combinations against Pseudomonas aeruginosa in vitro Int J Biol Sci 2010 6 6 556 558 20941374
   PubMed Web of Science ®Google Scholar
• Gibbons S Moser E Kaatz GW Catechin gallates inhibit multidrug resistance (MDR) in Staphylococcus aureus Planta Med 2004 70 12 1240 1242 15643566
   PubMed Web of Science ®Google Scholar
• Hemaiswarya S Kruthiventi AK Doble M Synergism between natural products and antibiotics against infectious diseases Phytomedicine 2008 15 8 639 652 18599280
   PubMed Web of Science ®Google Scholar
• Cushnie TP Lamb AJ Antimicrobial activity of flavonoids Int J Antimicrob Agents 2005 26 5 343 356 16323269
   PubMed Web of Science ®Google Scholar
• Harvey AL Natural products in drug discovery Drug Discov Today 2008 13 19–20 894 901 18691670
   PubMed Web of Science ®Google Scholar
• Lewis K Ausubel FM Prospects for plant-derived antibacterials Nat Biotechnol 2006 24 12 1504 1507 17160050
   PubMed Web of Science ®Google Scholar
• Bermingham A Derrick JP The folic acid biosynthesis pathway in bacteria: evaluation of potential for antibacterial drug discovery Bioessays 2002 24 7 637 648 12111724
   PubMed Web of Science ®Google Scholar
• Hawser S Lociuro S Islam K Dihydrofolate reductase inhibitors as antibacterial agents Biochem Pharmacol 2006 71 7 941 948 16359642
   PubMed Web of Science ®Google Scholar
• Köhler T Kok M Michea-Hamzehpour M Multidrug efflux in intrinsic resistance to trimethoprim and sulfamethoxazole in Pseudomonas aeruginosa Antimicrob Agents Chemother 1996 40 10 2288 2290 9036831
   PubMed Web of Science ®Google Scholar
• Chusri S Villanueva I Voravuthikunchai SP Davies J Enhancing antibiotic activity: a strategy to control Acinetobacter infections J Antimicrob Chemother 2009 64 6 1203 1211 19861335
   PubMed Web of Science ®Google Scholar
• Rogers GB Carroll MP Bruce KD Enhancing the utility of existing antibiotics by targeting bacterial behaviour? Brit J Pharmacology 2012 165 4 845 857
   Web of Science ®Google Scholar