Rational Drug Design, Synthesis and Biological Evaluation of Dihydrofolate Reductase Inhibitors as Antituberculosis Agents

References

• Dye C , ScheeleS, DolinP, PathaniaV, RaviglioneMC. Consensus statement. Global burden of tuberculosis: estimated incidence, prevalence, and mortality by country. WHO Global Surveillance and Monitoring Project. JAMA282 (7), 677–686 (1999).
   PubMed Web of Science ®Google Scholar
• Globaltuberculosisreport http://apps.who.int.
   Google Scholar
• Zignol M , HosseiniMS, WrightAet al. Global incidence of multidrug-resistant tuberculosis. J. Infect. Dis.194 (4), 479–485 (2006).
   PubMed Web of Science ®Google Scholar
• Schnell JR , DysonHJ, WrightPE. Structure, dynamics, and catalytic function of dihydrofolate reductase. Ann. Rev. Biophys. Biomol. Strut.33, 119–140 (2004).
   PubMedGoogle Scholar
• Berman EM , WerbelLM. The renewed potential for folate antagonists in contemporary cancer chemotherapy. J. Med. Chem.34 (2), 479–485 (1991).
   PubMed Web of Science ®Google Scholar
• Gerum AB , UlmerJE, JacobusDP, JensenNP, ShermanDR, SibleyCH. Novel Saccharomyces cerevisiae screen identifies WR99210 analogues that inhibit Mycobacteriumtuberculosis dihydrofolate reductase. Antimicrob. Agents Chemother.46 (11), 3362–3369 (2002).
   PubMed Web of Science ®Google Scholar
• Li R , SirawarapornR, ChitnumsubPet al. Three-dimensional structure of M. tuberculosis dihydrofolate reductase reveals opportunities for the design of novel tuberculosis drugs. J. Mol. Biol.295 (2), 307–323 (2000).
   PubMed Web of Science ®Google Scholar
• El-Hamamsy MH , SmithAW, ThompsonAS, ThreadgillMD. Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis. Bioorg. Med. Chem.15 (13), 4552–4576 (2007).
   PubMed Web of Science ®Google Scholar
• Reynolds RC , CampbellSR, FairchildRGet al. Novel boron-containing, nonclassical antifolates: Synthesis and preliminary biological and structural evaluation. J. Med. Chem.50 (14), 3283–3289 (2007).
   PubMed Web of Science ®Google Scholar
• Kumar A , SiddiqiMI. Virtual screening against Mycobacterium tuberculosis dihydrofolate reductase: Suggested workflow for compound prioritization using structure interaction fingerprints. J. Mol. Graph.27 (4), 476–488 (2008).
   Google Scholar
• Kumar M , VijayakrishnanR, Subba RaoG. In silico structure-based design of a novel class of potent and selective small peptide inhibitor of Mycobacterium tuberculosis Dihydrofolate reductase, a potential target for anti-TB drug discovery. Mol. Divers.14 (3), 595–604 (2010).
   PubMed Web of Science ®Google Scholar
• Bag S , TawariNR, DeganiMS. Insight into inhibitory activity of mycobacterial dihydrofolate reductase inhibitors by in silico molecular modeling approaches. QSAR Comb. Sci.28 (3), 296–311 (2009).
   Google Scholar
• Tawari NR , BagS, DeganiMS. A review of molecular modelling studies of dihydrofolate reductase inhibitors against opportunistic microorganisms and comprehensive evaluation of new models. Curr. Pharm. Des.17 (7), 712–751 (2011).
   PubMed Web of Science ®Google Scholar
• Bag S , TawariNR, QueenerSF, DeganiMS. Synthesis and biological evaluation of biguanide and dihydrotriazine derivatives as potential inhibitors of dihydrofolate reductase of opportunistic microorganisms. J. Enzyme Inhib. Med. Chem.25 (3), 331–339 (2010).
   PubMed Web of Science ®Google Scholar
• Degani MS , BagS, BairwaR, TawariNR, QueenerSF. Novel 2-hydrazino-pyrimidin-4(3H)-one derivatives as potential dihydrofolate reductase inhibitors. J. Heterocycl. Chem.47 (3), 558–563 (2010).
   Web of Science ®Google Scholar
• Bag S , TawariNR, DeganiMS, QueenerSF. Design, synthesis, biological evaluation and computational investigation of novel inhibitors of dihydrofolate reductase of opportunistic pathogens. Bioorg. Med. Chem.18 (9), 3187–3197 (2010).
   PubMed Web of Science ®Google Scholar
• Raju A , KhedkarMA, DeganiMS. Optimization of Mycobacterium tuberculosis DHFR production from recombinant Saccharomyces cerevisiae. Int. J. Curr. Microb. App. Sci.2 (6), 70–79 (2013).
   Google Scholar
• Raju A , DeganiMS, KhedkarMA, NiphadkarSA. Novel affinity chromatographic technique for purification of dihydrofolate reductase from recombinant yeast. Int. J. Drug Des. Discov.4 (1), 994–997 (2013).
   Google Scholar
• Maestro, version 8.0 Schrödinger, LLC , NY, USA (2007).
   Google Scholar
• LigPrep, version 3.0, Schrödinger, LLC , NY, USA (2008)., User manual.
   Google Scholar
• Glide, Version 5.0, Schrödinger, LLC , NY, USA (2008), User manual.
   Google Scholar
• ZINC database. http://zinc.docking.org.
   Google Scholar
• Bairwa R , KakwaniM, TawariNRet al. Novel molecular hybrids of cinnamic acids and guanylhydrazones as potential antitubercular agents. Bioorg. Med. Chem. Lett.20 (5), 1623–1625 (2010).
   PubMed Web of Science ®Google Scholar
• Palomino JC , MartinA, CamachoM, GuerraH, SwingsJ, PortaelsF. Resazurin microtiter assay plate: Simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrob. Agents Chemother.46 (8), 2720–2722 (2002).
   PubMed Web of Science ®Google Scholar
• Freshney R L . J. Heterocyclic ChemistryCulture of Animal Cells: A Manual of Basic Techniques (4th Edition). Willy-LISS, (2000).
   Google Scholar
• Khan A , SarkarS, SarkarD. Bactericidal activity of 2-nitroimidazole against the active replicating stage of Mycobacterium bovis BCG and Mycobacterium tuberculosis with intracellular efficacy in THP-1 macrophages. Int. J. Antimicrob. Agents.32, 40–45 (2008).
   PubMed Web of Science ®Google Scholar
• Singh U , AkhtarS, MishrA, SarkarD. A novel screening method based on menadione mediated rapid reduction of tetrazolium salt for testing of anti-mycobacterial agents. J. Microbiol. Methods84, 202–207 (2011).
   PubMed Web of Science ®Google Scholar
• Sarkar S , SarkarD. Potential use of nitrate reductase as a biomarker for the identification of active and dormant inhibitors of Mycobacterium tuberculosis in a THP1 Infection Model. J. Biomol. Screen.17 (7), 966–973 (2012).
   PubMedGoogle Scholar
• White EL , RossLJ, CunninghamA, EscuyerV. Cloning, expression, and characterization of Mycobacterium tuberculosis dihydrofolate Reductase. FEMS Microbiol. Lett.232, 101–105 (2004).
   PubMed Web of Science ®Google Scholar
• Hillcoat BL , NixonPF, BlakleyRL. Effect of substrate decomposition on the spectrophotometric assay of dihydrofolate reductase. Anal. Biochem.21, 178–189 (1967).
   PubMed Web of Science ®Google Scholar
• Topliss JG . A manual method for applying the Hansch approach to drug design. J. Med. Chem.20 (4), 463–469 (1977).
   PubMed Web of Science ®Google Scholar